• Failed entrepreneurship

• Experiments with different kinds of work through volunteer opportunities and variety of jobs

• A lot of reading and thinking with no particular destination in mind

• Honest conversations with my wife about personal finances.

None of it looked like progress. It produced nothing visible for a long time, and in fact looked like indulgent exploration. But all of it built the conviction that made decisive action possible when my moment came.

That slow, invisible accumulation was the hard thing. The job search was just the execution.

There is almost always a hard thing and an easy thing. The easy thing is visible, measurable, and comfortable. The hard thing is slow, ambiguous, and almost impossible to justify to anyone watching. And yet the hard thing is almost always the one that matters.

The load bearing constraint.

That’s what this essay is about: how to find it, why we avoid it, and why it’s imperative for you to find out what it is if you lead a team. If you’re a leader, this is addressed to you directly.

But if you’re an individual contributor at any level, understanding this will help you see what good leadership looks like, and what you have every right to expect from the people above you.

1. Background

How did I understand what the load bearing constraint was behind my career pivot? I think it all started in my first year of law school.

That first semester at Northwestern, I worked harder than I ever did at anything else in my life. I read every single case; highlighted the facts, holdings, etc.; built meticulous outlines; bought all the supplements (I had an unlimited budget for E&Es). By the time finals came round I felt thoroughly prepared.

Unfortunately, my grades told a different story.

So the following semester, I went back to basics. I asked for meetings with my professors & walked through my exam answers, understood where they broke down, and asked what I should do differently. The feedback was consistent: stop passively studying and start simulating the finals experience. Do practice exams under timed conditions. Write the answers. Then go back and analyze what you wrote and where your reasoning failed.

So that’s exactly what I did. And guess what? Second semester my grades improved, despite actually working less hard than I did the first semester.

Turns out that all the highlighting & outlining had felt like preparation. The practice exams felt uncomfortable and exposed. But only one of them was actually building toward the outcome that mattered. That is the pattern I keep coming back to.

In almost any system, there is a load-bearing constraint: the thing that actually determines the outcome. And there is everything else, which can feel rigorous and necessary but doesn’t move the number that matters. The hard part is not the execution. The hard part is correctly identifying which is which, because the work that feels most like progress is often not the work that produces it.1

2. The Load-Bearing Constraint

It would be convenient to blame the law school failure mode on lack of awareness. But when I think back, I remember people telling me to do practice exams. I knew. I just didn’t do it. The hard thing was obvious. It was also uncomfortable, time-consuming, and humbling. So I found other things to do that felt productive.

That’s usually how it works. Most people, in most contexts, have a sense of what the hard thing is. The problem isn’t ignorance. It’s that the work that actually produces results is unpleasant to do, easy to defer, and hard to justify in the moment. So it waits.

In law school, at least you have professors to tell you what matters. Nobody is going to do that for you in a business. The differentiating activity, the “hard thing” in your market (the equivalent of doing practice exams) is something you have to figure out yourself.

Example from my sales career

Having seen this pattern play out at three different scaling startups, the same dynamic shows up every time. Many sales reps believe their closing ability is the load-bearing constraint, and that it’s hard to find.

Sometimes that’s true. A rep who can build trust quickly, navigate a complex buying process, and close in a competitive situation is genuinely valuable and not easy to find. But sometimes the closing ability is less rare than it appears.

The tell is whether the environment was doing the work. When you’re at a company with strong inbound lead flow and a recognized brand, closing feels like the skill. But take that same rep and put them somewhere with thin pipeline and no brand, and the results often tell a different story. The leads were doing the heavy lifting. Closing the deal was just the last step.

So how do you identify whether something is actually the load-bearing constraint? A few questions worth asking:

• Can many people with similar backgrounds do it?

• Can it be hired for reliably?

• Does the skill transfer across environments?

If the answer to those is yes, it is probably not the constraint. The question is never whether the sales rep can close deals; it’s how hard it is to find someone else who closes just as well.

This is why you should pay attention to other organizations

If you look around your market and see that everyone struggles with the same thing, that is a strong signal you are looking at the load-bearing constraint. In startup sales, that’s usually reliable pipeline/lead generation—not closing ability. Hiring a bunch of “strong closers” likely won’t get you the results you want.

Again, just like in law school: if every student is highlighting cases and outlining everything and still struggling on exams, those activities are probably not the bottleneck. They’re not the load-bearing constraint.2

The true source of leverage is wherever the scarce, non-commoditized work lives, and that is almost always upstream. Every system has a load-bearing constraint: the one step that actually determines the outcome. Everything else can be optimized, staffed for, outsourced.3

3. The Leadership Obligation

Identifying the load-bearing constraint is one thing, translating it into organizational behavior is the leadership one. And there, the stakes are much higher.

I’ll use an example from GTM/sales to illustrate what I mean:

Individual sales reps gravitate toward legible work. And the most legible metric in any sales organization is revenue. Which is why reps fight over inbound leads and easy opportunities: when they close them, they generate revenue—the result is visible and the credit is clear. It appears they are valuable. And in a narrow sense, they are.

But the system rarely rewards the difficult-to-measure but far more valuable early indicators: the quality of outreach, the discipline of qualification, the work of building pipeline from scratch in an unresponsive market. These are harder to track, slower to show results, and easy to deprioritize.

And yet if everyone focused on them, the business would be in a fundamentally stronger position.

This is the leadership failure. No one is doing this maliciously. It’s that the organization leadership has not been able to translate the illegible hard thing into something measurable, hireable, coachable, and compensated. The organization defaults to optimizing what it can see.

Key corollary:

The more senior you are, the more your job is thinking: specifically, thinking about what actually matters so that the people working hardest are not working hardest for nothing. Your teammates are grinding. They are doing everything asked of them, often heroically. The question is whether you have given them the right hill to climb.

What good leadership actually requires: identify the constraint with specificity, translate it into something measurable and coachable, build incentive structures and hiring profiles around it, and protect the team’s time and energy for that thing above all others. Then, when the constraint shifts, do the diagnostic again.

4. Conclusion: Slow Down To See Clearly

This is my message to leaders: The individual contributor’s job is to execute well. Your job is to make sure that execution is aimed at the right thing. These are fundamentally different jobs, and yours requires a different kind of work and a certain way of approaching problem.

Your most valuable work doesn’t show up on a timesheet. It doesn’t generate a visible output. It will sometimes look, from the outside, like you are digging into irrelevant details, connecting abstract ideas, and thinking more than executing.

Do it anyway.

The most important investment a leader can make is time spent observing the system before optimizing inside it. Step out of execution mode and ask: what is the actual load-bearing constraint right now? Is the team working on it? Are the incentives aligned to it? This is not a quarterly planning exercise. It is an ongoing discipline.

Two important questions worth building into your diagnostic process:

• Where does everyone else consistently fall short?

This is harder to answer than it sounds. Competitors don’t publish their GTM/sales failures. Legal teams at other companies don’t talk about their struggles. The answer requires inference: off-the-record conversations, pattern recognition across interactions, understanding the why behind where the industry struggles, not just the what.

Resist the temptation to copy the moves of whoever looks most successful. The load-bearing constraint for a mature, well-resourced market leader is completely different from the one for a small scaling upstart. Their current constraints are not your current constraints. You need a mental model built from first principles, not from mimicking someone else’s motion.

• Where are your people spending disproportionate time, and what is the ROI of that activity?

If your team is grinding hardest on a low-return activity, you have missed the forest for the trees and are rowing hard to stay in place. The goal is to find the valuable gap: the constraint that is hard, that matters, and that the market hasn’t solved.

Identifying this requires more than dashboards. You have to talk to everyone: your team, your customers, your partners. Seek out the scuttlebutt, the off-hand frustrations, the patterns that don’t show up in any report. This is itself the illegible non-scalable leadership work.

It is actually the most diagnostic thing you can do. Feed everything into your mental model. The model is never finished. It gets revised as the market moves and the business matures.

• For leaders of legal departments the question is similar: where is the team spending its time, and is it on the work that actually reduces risk and enables the business? If the team is buried in routine contract review while consequential business decisions are being made without legal at the table, that is a constraint misidentification problem. The most important activity rarely comes from knowing more law or working 100-hour weeks. It comes instead from the business partners who will tell you, early on—before problems arise, where they actually need help.4

The goal isn’t to work harder or smarter in the abstract. It’s to ensure that the hardest, smartest work is aimed at the right thing. A leader who does this well gives their team something more valuable than a tight process or a well-resourced budget: they give them the confidence that the hill they are climbing is the right hill.

Everything else is just tidying the house.

Although the article is largely optimistic, the underlying tone was that my pivot was essentially a failure, and that I was now switching to a more enjoyable path. My expectations were low—I thought I was choosing lifestyle over meaning.

What’s clearer to me today, ten years later, is that something else was actually happening. Up until that point, I had chosen work based on perceived status and financial stability. In the summer of 2016, I decided to begin a new chapter where I’d focus on finding work I actually enjoyed.2

What I thought I knew in 2016

In the years leading up to that moment, I had already gone through a few different versions of what I thought my career was supposed to look like. I started out clerking for a federal judge, which was an incredible experience. I thought it would translate well to my role as a litigation associate at Sullivan & Cromwell. On paper, it was about as clear and rewarding a path as you could have.

But even early on, something didn’t quite click. I’ve written publicly about this before, but the underlying problem was that I didn’t feel like I was using my superpowers or building toward anything. Instead, I felt like I was paying my dues, waiting to be someday “chosen” for more significant work.

When I left to join a plaintiffs’ firm, I thought I’d fixed the problem by choosing a smaller organization with less bureaucracy. However, for multiple reasons, that job didn’t work out, and I found myself being let go. That’s when I decided to open my own solo practice.

Owning my own business was the first time I had full control over how I worked. And to be fair, parts of it worked. I enjoyed talking to clients. I liked figuring out how to position my services and generate interest. There were moments where things seemed to come together—but they didn’t last.

What I couldn’t figure out was how to turn all that activity into something financially sustainable. From my 10-year-old article:

I knew I was making a financial sacrifice. And know I said I wasn’t in it for the money. But still. IT SUCKS. In the twelve months that I worked as a solo, I would have generated more profit by working a full-time hourly document review job. I could have taken the most lifestyle-focused legal job and had great hours, earn a good living, and enjoy full medical benefits, matching 401k, etc. And if I was still working in Biglaw? I’d be working hard, sure, but I’d also be making over $300,000 this year. Damn that really hurts just to type out.

At the time, I didn’t think of my solo practice and my law firm jobs as connected experiences. Each one had its own explanation, its own set of circumstances. I could sense what wasn’t working, but I couldn’t quite put my finger on what tied them together.

On my bad days, I told myself that maybe I just wasn’t meant to achieve professional success—that I’d be better off focusing on other parts of life that might make me happier.

Looking back now, that was the wrong narrative.

The reality of the situation

It took me a long time to see what was actually going on.

In Biglaw, success came from executing careful, detail-oriented tasks as a small part of a larger plan designed by someone much more senior. At the plaintiffs’ firm, there were fewer layers, but what was required day-to-day was similar. And in my own practice, where I had the most control, I couldn’t figure out how to make the economics work.

To be clear, at each step I learned a lot and got better at what was being asked of me. The problem was that my day-to-day was painful. I had to put in an extraordinary amount of effort just to get ordinary results.

It was too exhausting to end up being merely average.

Parts of the job felt right, but none of it carried forward. The more I progressed, the harder it got. I was working, learning, and improving—but it didn’t add up to momentum.

However, there was one thing I wrote back then that I think I got right: My problems stemming from choosing career paths based on how easy it is explain to other people:

Let’s say you just met me and I tell you I’m headed to law school. You might say Oh that’s pretty cool, you’ll have a stable job and make some money. You must be Headed In The Right Direction.

Now you really have no idea whether I’m actually headed in the right direction. I might be taking out hundreds of thousands of dollars in student debt with no serious job prospects. But for the purposes of that conversation, I have successfully convinced you that I’m Headed In The Right Direction without having to expend any real effort explaining how or why . . .

What I didn’t fully grasp then was that my instinct, in 2016 on the heels of a series of setbacks, to then move in a highly uncertain direction—was the best possible decision I could’ve made.3

I needed to stop worrying about explaining to people that I was Headed In The Right Direction.

At the time the “right direction” wasn’t obvious. Me joining a tech startup didn’t look like a step forward. It looked like me drifting. I wasn’t a technical person. I had no sales experience. I didn’t look or act like the other people on the sales team. A well-meaning friend even warned me early on to be prepared to get fired.

But for the first time, I found myself in an environment where the things I was naturally drawn to actually mattered. The things I felt naturally good at—winning over clients, coming up with strategic plans, connecting ideas across multiple parts of the business—were part of the job.4

And because of that, something started to feel different. The same instincts that had felt peripheral before started to carry weight. Conversations led to opportunities. Small wins built into larger ones.

It felt easier—and far more sustainable. In retrospect, that was the real difference.

Conclusion

Ten years ago, I was working hard to meet the expectations of the system I was in. Then I stopped trying to map out the “right” path. I didn’t have a clear plan—I just moved toward things that felt interesting, even if they didn’t make much sense on paper.

That meant letting go of the need to justify what I was doing. It meant shedding the burden of forcing myself to stay the course. Ultimately, that’s what helped me creat space to explore what actually made sense.

At the time, I thought I was choosing a “lifestyle” path. Pivoting turned out to be the most important step toward figuring out where I belonged. My takeaway, having lived through the decade that followed, is this:

Sometimes moving forward feels like drifting. But stepping into uncertainty can open doors you didn’t even know were there.5

Share

Look, it’s a lot of money. And yet clients are all willing to pay it. So I think you’ve got to accept that clients aren’t paying $3,400 an hour for some lawyer to draft a few memos they can generate from some junior lawyer + AI.

They are paying for effective Risk Transfer.

Clients hire these elite firms to transfer regulatory risk, litigation risk, and reputational exposure to an institution whose judgment they trust. In the legal ecosystem, the product isn’t “outcomes” in the way most AI commentators describe it.

Instead, it’s the credible transfer of consequential risk.

A Venture Bet on AI-Native Agencies

Recently I came across this request for startups on Y Combinator’s website. Basically, they are looking to incubate AI-native law firm startups. I thought it was interesting that they grouped law firms with other types of agencies:1

Agencies have always been crazy hard to scale. Low margins, slow manual work, and the only way to grow is to add more people. But AI changes this. Now instead of selling software to customers to help them do the work, you can charge way more by using the software yourself and selling them the finished product at 100x the price.

Think of a design firm that uses AI to produce custom design work for clients upfront, to win the business before the contract is even signed. Or an ad agency that uses AI to create stunning video ads without the time and expense of setting up a physical shoot. Or a law firm that uses AI to write legal docs in minutes, rather than weeks.

That’s why agencies of the future will look more like software companies, with software margins. And they’ll scale far bigger than any agencies that exist in these fragmented markets today.

My friend, and long-time Off The Record reader Matt Wheatley, saw the same thing and wrote a thoughtful post on LinkedIn and shared my article from last week, leading me to leave the following comment:

I’m always fascinated by what YC does because it’s usually a leading indicator of what the VC world/tech community is thinking about legal innovation. Here, at its core, this drive towards AI-enabled firms is a margin expansion thesis.2

The thinking goes like this: If AI dramatically increases individual productivity, then smaller, leaner teams can produce more output. Fixed costs compress, leading to expanded gross margins. Implicit to this theory: Distribution becomes the primary lever.

The question is whether this strategy will work in the legal ecosystem. To paraphrase Alex Rampell from Andreesen Horowitz, can these startups figure out distribution (via Risk Transfer) before incumbents figure out how to incorporate AI?

The Legal Industry Works Differently

You won’t be surprised to hear my take here. In marketing, design, or other creative services, outcomes are iterative and downside exposure is limited. Clients can experiment. Efficiency translates quickly into adoption.

Lawyers operate under a completely different structural constraint.

The stakes are asymmetric. Liability is real. A regulatory misstep, an adverse ruling, or a poorly structured transaction can create consequences that far exceed the legal bill itself. When those stakes are present, clients are not simply purchasing work product.

They are purchasing Judgment Under Uncertainty, and the reassurance that the matter has been placed in credible hands.

Productivity has never been the governing variable

Technology has consistently improved execution, from legal research databases to document automation to e-discovery platforms. Yet the firms commanding $3,400 an hour are not simply the most efficient. They are the ones that clients believe can carry risk. Or as my friend Zach Abramowitz put it succinctly:

They are the ones who are trusted.

Building that kind of trust is extraordinarily difficult.

Trust in legal does not come from a glossy brand campaign. It doesn’t come from PR announcements of the latest valuation. It certainly doesn’t come from using tried-and-true go-to-market playbooks that work for selling marketing tech or CRM software.

It is earned slowly, through repeated exposure to high-stakes matters and consistent internal standards.

Just look at how law firms got to where they are today

Organizationally, they look very little like startups. They are deeply de-centralized and are highly partner-driven. Clients often trust specific individuals whose judgment has been validated over the course of decades.

That external trust transfer only works if those partners themselves trust the institution: Its leadership, its standards, its governance. When partners feel aligned and empowered, they extend institutional credibility outward. When internal trust fractures, external trust weakens.

Startups, on the other hand, rely on a command-and-control structure. They organized like the Navy while law firms are organized like a group of pirates.3

Trust requires internal alignment

That dynamic is hard to replicate in a newly formed, unproven institution, like a AI native law firm startup.

Trust compounds slowly. It requires full buy-in from the operating team. It requires autonomy for professionals who themselves feel supported by leadership. Without internal cohesion, it is difficult to convincingly intermediate risk for clients.

This is the messy part that many investor-led models rarely capture.

The open question for AI-native firms is not whether they can deliver high-quality work. Many likely will. In fact, I’ve heard that some are innovating on pricing as well, offering flat fees and volume-based fees (e.g. $X per contract up to 1,000 contracts) I believe these innovations are much needed for the legal ecosystem.

The open (and more) interesting question is whether these AI native firm startups can build the institutional support to deliver external trust at scale. Will they bring on trusted advisors with reputations the startup can borrow? Or will they bring on mercenary GTM operators with minimal accountability to their customer base?

Conclusion

The AI-native agency thesis assumes that legal services can be rebuilt primarily around mechanical optimization and expanded margins.

The historical dynamics of legal markets suggest something more complex: efficiency matters, but it is subordinate to Risk Transfer—which itself depends on deep institutional credibility.

None of this means AI-native firms cannot succeed. They very well may. It just means they are operating in a market where the binding constraint is not feature velocity, but trust velocity.

There, the underlying currency remains institutional credibility. And that currency compounds more slowly than many outsiders might think.

These big announcements show no signs of stopping any time soon. And it’s reaching all corners of the ecosystem, which prompted me to write a two part piece on AI and its intersection with the ALSP world last summer (see here and here). Today I’d like to make the case that while AI certainly has had a big impact—it hasn’t changed how legal decision makers adopt innovation.

Which is through trust & accountability.

1. AI Has Already Had A Huge Impact

For years, commentators debated whether AI would meaningfully change legal work. Not any more. The mechanics of how tasks get completed have already shifted. It’s all led to massive growth and incredible valuations for the top players in the space. Just last week Harvey announced that it was raising yet another round of funding at an incredible $11 billion valuation, prompting me to share this niche tongue-in-cheek post that surprisingly received heavy engagement from tech/VC communities:

It’s not just Harvey though. It’s the steady stream of new startups backed by top VCs, all seeming to raise $5-$10M out of the gate. AI-native firms are the most recent signal of this change. They aren’t just layering tools onto legacy processes; they are designing their operating models around the assumption that intelligence is embedded internally from the start. From Nikki Shaver:

Are AI-native and AI-first firms simply another iteration of boutique experimentation, or are they early manifestations of the kind of disruptive force Clayton Christensen described in The Innovator’s Dilemma? When viewed through that lens, these firms look less like curiosities and more like early fabric-change signals—indicators that the underlying architecture of the legal market may be beginning to shift in ways incumbent firms are structurally ill-prepared to respond to.

Nikki points out that there are at least 20 of these new AI firms out there; it also appears that there are 3 in the most recent Y Combinator cohort alone. (Richard Tromans,, who calls them “NewMod” startups, wrote a great summary of the YC phenomenon here) From Richard:

As AL explored last year, NewMods are certain to make more of an impact this year as the realities of combining fixed fees, super-structured workflows, curated data, lots of AI, as well as experienced lawyers, all in one package, starts to filter through the market. If it were just AI alone, then naturally you would need a legal team to leverage that tech and data. But, with lawyers as part of the offering, then we have a whole different ball game.

That’s a significant development. All this suggests that legal work can indeed be structured differently and potentially delivered with far fewer human bottlenecks than before.

But here’s my point: These changing org structures is just the first step towards change. Faster production—even if promised and delivered to the client—does not automatically translate into widespread adoption. Innovation does not move through the legal ecosystem the way it does in other industries. They move through relationships, risk thresholds, budget cycles, and organizational politics.

AI may be changing how the work gets done. It has not changed how legal decision makers decide where it’s used.

2. Distribution in Legal Is Earned, Not Announced

In many industries, distributing innovation is a function of visibility and scale. Raise a big round from a Tier 1 VC, build a shiny new brand, hire proven go-to-market executives, and land lots of new customer accounts. This is a proven formula.

This approach isn’t quite as effective in a trust-based ecosystem like legal.

In legal, distribution is less about announcements and more about credibility. It almost always starts narrowly, perhaps a single engagement, which only expands if the experience builds confidence. Not merely confidence in the vendor brand, but confidence in how the work was handled when stakes were real (if small). I wrote about this a few weeks ago in a post:

New logos and revenue are positive signs, but increased usage & wallet share over time are probably far more relevant. My experience in the ALSP world suggests that the initial buy decision provides a mixed signal. For example: A legal department may take the first step of “buying” an engagement attorney who’s great at spotting legal issues—but ultimately adds little value to the organization. As it turns out, it’s not enough to be able to merely give good legal answers; you have to also be embedded within the organizational context you operate in.

Growth rarely comes from the first signed contract with the customer. It comes from being invited back. A matter goes well, or even just predictably. Communication is clear. Escalations are handled thoughtfully. Judgment aligns with the client’s risk tolerance. Months later, another matter surfaces. Then a slightly larger one. Over time, scope expands not because of a feature set, but because of familiarity and trust.

That is how wallet share grows in institutional markets: incrementally, through repetition.

This is why distribution in legal compounds quietly. It runs through relationships, clear & constant communication of feedback, and the day-to-day rhythms of legal teams. It is shaped as much by organizational politics and internal alignment as by technical capability. Press releases and announcements move faster than trust. But trust, once established, creates permission—permission to handle more work, more sensitive matters, and eventually more consequential decisions.

And that permission is what durable distribution looks like.1

3. Legal Institutions Embrace Innovation Through People

Legal departments and law firms don’t innovate in the abstract. They adopt new processes and technologies through people they already trust. You need someone credible to stand behind it. Or “internal champions” in sales parlance. When the innovation is dramatic and has significant change management implications for the organization, the champion needs something more.

They need a partner on the outside they trust & who has deep accountability.

Contrast this with sales or marketing tech. You can hire a junior sales rep to schedule & sell software over the phone. I remember at my first legal tech startup, our VP of Sales told me that he regularly purchases software he learns about from people cold calling him. I was shocked. Because that went against my own (lawyer-trained) instincts about how to buy software.

I think it’s also because if you mess up sales or marketing tech, it’s not a big deal. In those worlds you have to move fast and break things, you work and develop through iteration. So the stakes are lower up front—you can be imperfect in selecting tools or innovation, and still be ok in the end.

Legal work couldn’t be more different. Not only is there little room for error—the lawyers themselves are viewed as shock absorbers for all types of problems. When a lawyer is asked for his/her opinion on the matter, it’s not just the substance that’s relevant—it’s also their credibility; the fact that they are reputable practitioner with extensive experience. Or as Kevin Roose once told me, they are “moral crumple zones.”2

Further complicating these dynamics is the fact that not all players in the ecosystem assesses innovation the same way. A conservative global law firm evaluates change differently than a fast-growing startup. A Fortune 500 legal department operates under different pressures than a well funded scale-up. A west coast firm thinks differently than an east coast firm.

Distribution across the spectrum of legal firm types requires far more than mere product capability. It requires proximity to how each type of client thinks — about risk, about timing, about optics, about internal buy-in. The closer you are to those conversations, the more effective you can be at introducing change.

The upshot of all this: Innovative firms that distribute effectively tend to reflect the personalities & beliefs of the markets they serve. They aren’t built from a single archetype. They bring together operators with different professional backgrounds, different styles, different instincts about risk and speed. That internal range creates a closer read on the client’s reality. It makes it easier to introduce innovation gradually, without forcing the customer/client to absorb an immense amount of uncertainty all at once.

In institutional markets, technology doesn’t spread because it is powerful. It spreads because someone trusted made it feel safe.3

Conclusion

If legal work can be decomposed, accelerated, and systematized at scale, then the architecture of the industry will inevitably shift in some form. The question is not whether the mechanics will improve. They already have.

The more interesting question is how that improvement travels through institutions that are, by design, cautious.

Legal departments and law firms are not blank slates. They are layered systems of incentives, history, relationships, and risk management. When change happens, it tends to move through those layers unevenly: Expanding in some corners, stalling in others, accelerating where trust is already deep.

Maybe the next phase won’t be about who builds the most powerful models, but who earns the right to deploy them in increasingly consequential contexts. In high-risk markets, innovation doesn’t just need to work. It needs to feel safe.

And safety, unlike speed, rarely scales overnight.

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The underlying problem isn’t effort or ability. It’s that the very traits that drive early success in their legal careers eventually start producing the opposite effect in the business world. These high achievers rely on personal effort to excel at every level until they reach a point where they can no longer increase their impact through individual contribution alone.

That moment is an inflection point. Continuing to grow scope and influence requires a fundamentally different lens on the job: delegating work to others, aligning stakeholders, and tolerating ambiguity or temporary underperformance. You can’t simply work harder and expect a quick road to superior results.

This shift is uniquely difficult for lawyers who were all-stars early on in their careers. Much of it stems from professional training in law firms and the legal profession’s implicit values, rules, and standards of behavior—many of which are deeply ingrained and almost impossible to unlearn.

The insights I’ll share come from the entirety of my professional experience practicing law at two law firms, hundreds of conversations with in-house & law firm lawyers, and working at 3 different high growth startups.

This is not about changing jobs. It’s about changing what your effort is optimized for.

Law Firms: Where the Habit Is Learned

Law firms are not structured the way most business are; they usually don’t have resale value so they don’t have any enterprise value.

In most companies, there’s an incentive to design operations around systems and processes because it increases the company’s resale value. This resale value, ie. “enterprise value” is often shared among owners, employees, and stakeholders through equity.

Law firms, on the other hand, operate under a different incentive structure. The economics are driven by annual profits that are distributed each year rather than by long-term, capitalized value. There is little direct upside to making work more repeatable or less dependent on specific individuals.

As a result, there is also little downside to over-relying on those individuals. Reliability and responsiveness are rewarded immediately, while building systems that reduce dependence is deprioritized. When something breaks, stepping in personally is not just encouraged—it is rational. Even if the work is low value.1

Why Heroics Make Sense

Working late, absorbing problems, and being the safety net all make sense when value is measured by individual throughput rather than the durability of the system. These “heroics” are not a cultural accident. They are the predictable result of the unique dynamics at law firms.

This is why many high-achieving lawyers default to personal effort as the only solution to all problems. If something is broken, the fastest and most reliable response is personal intervention.

To be sure, there are some exceptions. Some firms are intentionally designed around process, e.g. the apocryphal small firm that relies on a few managing lawyers to oversee process & paralegals to complete the work. Firms like these are more similar to typical companies than law firms.

But they are the exception rather than the rule.

Personality Versus Incentives

It’s tempting to explain this broader pattern as a matter of personality. Perhaps it’s not incentives; instead, it’s that law attracts people who are more risk-averse and therefore prefer certainty and control.

It’s possible that personality-driven behavior has some effect. But I’d argue that it’s a function of the law firm economic model. We all know plenty of lawyers who are willing to take risk when the structure rewards it.2 In my experience lawyers have similar views to risk as other high performing professionals.

In my view, incentives encourage the development of habits and values that work extremely well inside firms. High-achieving lawyers learn from day one that personal excellence solves most problems, and that reliability is the highest form of value. When something is broken, the right response is to absorb it yourself.

Those habits produce success in environments that reward personal throughput vs. system throughput. The problem begins when lawyers move into environments that reward something else. Let’s talk about what happens when these lawyers move in-house.

In-House: Where Effort Stops Translating Into Influence

Corporate legal teams are not viewed the same way as revenue-generating functions are. They are cost centers by design. That framing is more than just a label, it impacts how work is described, how lack of bandwidth is addressed, and more.

Because the legal department is not directly tied to growth, the value an individual in-house lawyer brings is often unclear. In that vacuum, responsiveness and availability become proxies for usefulness. Being fast, helpful, and accommodating is the safest way to signal contribution.

Many in-house lawyers respond to this dynamic by taking on more work personally. They stay extremely close to the business, absorb extra context, and step in wherever ambiguity appears. The effort they put in is very real.

But the returns here are very limited.

When Responsiveness Replaces Leverage

While legal teams grapple with these challenges, the overall business continues to grow. Demand for legal increases but corresponding headcount doesn’t: Legal is expected to keep up with demand without proportional investment.

Once again, personal effort typically fills the gap. The legal team could establish internal SLAs, leverage AI/tech, or rely on outside providers like law firms or ALSPs. But it’s just much simpler to just work longer hours. The company keeps moving forward with no added costs and with no interruption in service.

But the system does not improve.

The deeper problem is that prevented problems don’t earn any credit. No one gets credit for the “dog that never barked.” What gets noticed is speed, or lack thereof, in the moment.

This is usually is where frustration sets in. Despite long hours and high responsiveness, legal is looped in late, bypassed entirely, or treated as an afterthought. In house lawyers are viewed as a bottleneck that needs to be overcome.

Who Actually Breaks Through

In practice, there is only one reliable path for in-house lawyers who want to increase influence: expanding their scope.

Those who break through this barrier shed the“lawyer” label. They take on adjacent responsibilities and become accountable for more than legal output. The modern CLO role can sometimes include ownership of HR, compliance, risk, or other functions that sit closer to the business’s core operations.

This is a relatively new trend that’s just starting to take off. From this column on Bloomberg Law last year:

This shift has led to the “GC Plus” model—in which GCs assume multiple C-suite roles, such as chief human resources officer or chief operating officer . . . As companies increasingly rely on GCs to balance risk, strategy, and operations, the boundaries of the role continue to shift. Rather than operating as isolated legal advisers, GCs are integrating legal expertise with broader business priorities.3

To effectively expand your scope, you need to absorb more work.

Learning To Delegate

You cannot take on additional functions while continuing to operate business as usual. At some point, the constraint is no longer legal judgment on an individual issue/contract but time, attention, and decision capacity.

Expanding scope forces a shift away from personally executing every task and toward setting priorities, designing interfaces, and building systems that allow others to operate effectively. This is why scope expansion and delegation are inseparable.4

One is not possible without the other—and resisting that shift is often what causes otherwise capable in-house lawyers to stall just as their responsibilities begin to grow. This is often exactly where in-house lawyers feel burnout.

The irony is that many burned out lawyers leave to take a business role at a startup, in order to escape these constraints—only to encounter a sharper version of them there.

Startups: When Indispensability Becomes a Ceiling

Early-stage startups reward team members who can do everything. Jack of all trades. Knowledge of the broader operating context matters more than specialized expertise. Speed matters more than structure. The people who thrive are those who step in, figure things out, and keep the company moving.

For lawyers-turned-operators coming from firms or in-house roles, this can feel familiar (and extremely validating!). Personal excellence works again. Being indispensable is a huge asset at this stage of a startup.

In the early days, that’s exactly what the organization needs. But not for long.

Where the Pattern Breaks

As the startup grows, the constraints change. Volume of work in a wide range of domains skyrockets The organization adds a ton of new people. Capital suddenly becomes available which provides immense resources.

The bottleneck is no longer effort; it is now coordination.

A familiar pattern begins to emerge. An highly valued early employee learns the business deeply, earns trust, and becomes highly influential as a result. Work moves faster when they are involved. Problems get solved. Seems like all good news so far, right?

The Ceiling Appears

At some point, leadership faces a different question: is it better for the organization to promote and elevate that early employee? Or keep them where they are and hire a senior, experienced leader from the outside?

Too often, the answer is external. Not because the early employee lacks ability, but because they are too embedded in execution of the lower-level work to step back. They have become critical to too many day-to-day decisions.

In the cases where early employees do get elevated, one condition is almost always present: they are not so indispensable in execution that they cannot be removed from it. In a scaling company, work has to succeed without any single person as the point of failure.5

The Subtle Trap

This is what makes the trap hard to see. The behaviors that create early momentum are the same ones that eventually cap growth.

Staying close to the work feels responsible. Delegating feels risky. Letting go of decisions feels premature. But without that shift, indispensability becomes a ceiling rather than a strength.

For high achievers, this is often the first time personal excellence stops being enough.

Moving Up a Layer: From Individual Heroics to Systems

When processes don’t scale, high achievers step in to do the work. They fix what’s broken, smooth over friction, and keep things moving. In the short term, this works. The organization appears to be high functioning. But it’s not.

That’s because when high achievers consistently solve problems through individual heroics, system and process failures stop surfacing. And without visible failure, organizations don’t learn where there’s fragility. The very competence that keeps things running also prevents those systems from improving.6

What makes all this uniquely hard: Most organizations instinctively *want to* celebrate individual heroics. Leadership spotlights the person who stays up until 3 AM fixing a crisis is easy to recognize and easy to reward. Personal sacrifice is legible to the entire company. It reassures everyone that someone capable is paying attention.

For high-achieving lawyers, this form of contribution feels natural. It aligns with how value has been signaled throughout their careers in various contexts. When something breaks, stepping in personally feels like responsibility, not overreach.

How Heroics Hold Systems Back

I saw this play out at Logikcull, the first legal tech startup I worked at. There, we’d created an internal system of “Logik Props” to publicly recognize teammates who stepped up during unexpected emergencies. The intent was good. But eventually, an engineer correctly pointed out the flaw:

As an organization, we were incentivizing people to act heroically to cover up process gaps instead of fixing them.

There’s a relevant analog here: When high performers intervene consistently, system failures stop surfacing. And without visible failure, there is no pressure to redesign the system.

Letting Problems Surface

Moving up a layer requires tolerating short-term messiness. Problems have to emerge. Work that was once handled by an A player is now done by someone less capable. Quality dips. Edge cases are mishandled. Issues become visible in ways they weren’t before.

Those problems are not regressions. They are diagnostics.

The temptation to step back in—to “just fix it”—is constant. But each rescue reinforces the same pattern: the organization leans on you, and the system never matures. Over time, you become indispensable in exactly the role you need to leave in order to grow.

What ultimately happens is that your day-to-day work doesn’t disappear; it changes. There are fewer visible wins and fewer hero moments. Feedback is delayed. Credit is diffuse.

You are designing for a system where the dog never barks.

But this messy period is exactly the point at which your personal effort starts to compound and grow. Moving up a layer is not about withdrawing effort. It is about redirecting it—from solving the same problems over and over to preventing them from occurring through a process/system based solution.7

The Inflection Point

The pivotal moment is when you realize that incremental personal effort no longer results in corresponding gains. Instead you realize that the system now rewards leverage more than personal throughput.8

Gaining leverage is critical in scaling organizations. And the measure of whether or not a leader is using leverage properly is by evaluating the total output of the group he/she oversees.

This is not a concept I invented, by the way. It comes from Andy Grove’s masterpiece High Output Management:

The question then becomes, what can managers do to increase the output of their teams? Put another way, what specifically should they be doing during the day when a virtually limitless number of possible tasks calls for their attention?

To give you a way to answer the question, I introduce the concept of managerial leverage, which measures the impact of what managers do to increase the output of their teams. High managerial productivity, I argue, depends largely on choosing to perform tasks that possess high leverage.

When that realization sets in, you face a choice. You can remain indispensable in your current role, or you can begin the slower, less visible work of making yourself less necessary—so that you may focus on the higher leverage activities of the job at the next level up.

One of the hardest parts of this shift is that the work you do becomes less visible. When you stop stepping in personally, it can look—especially from the outside—like you’ve taken your foot off the gas. That perception gap is real, and it doesn’t close on its own.

Communication & Organizational Values

As your work shifts toward system design, prioritization, and leverage, you have to take the time to explain what you’re doing and why it matters. Without that explanation, stakeholders default to the most obvious interpretation: that you’re doing less.

This is especially true in environments that have historically rewarded visible effort over durable outcomes. Communicating the shift isn’t about self-promotion. It’s about shedding light on what appears to be work that would otherwise be invisible.

How this transition goes also depends on your organization’s self-awareness. Your leadership team needs to recognize and rewards it.

If leadership values heroics over durability, the system will keep pulling you back into execution. No amount of personal discipline can override that for long. The incentives will always win.9

Reclaiming momentum is not about opting out of the work. It’s about opting into a different definition of value—one that prioritizes compounding impact over immediate relief.

Conclusion: Operate At A Higher Layer By Managing Tradeoffs

Unfortunately there is no flip to switch. No magic bullet that suddenly shifts you from heroics to systems. No checklist, no playbook, no clean handoff where everything just works.

What actually exists are tensions—between speed and durability, visibility and leverage, control and scale. Learning to operate at a higher layer means learning to live inside those tradeoffs rather than trying to eliminate them.

Tension #1: Striking the right balance between doing the work yourself vs. delegating to others

That’s why this transition feels so hard. You’re not replacing one set of problems with another. You’re changing which problems you’re responsible for. At the same time, you can’t delegate everything on day one. During the adjustment period, heroics don’t disappear—they coexist with system-building.

There will be moments when you still have to step in personally. When the cost of failure is too high. When the system isn’t ready yet. That doesn’t mean you’re doing it wrong. It means you’re in transition.

The mistake is not using heroics temporarily. The mistake is letting them become permanent again.

Tension #2: Creating an imperfect metric that approximates measurement of your main objective

One of the hardest parts of moving away from heroics is knowing whether things are actually working. When you’re personally involved in everything, feedback is immediate. You feel productive. You feel useful.

When you step back, those signals disappear. In their place, ambiguity creeps in—and with it, the temptation to judge performance based on whether others are working the way you would.

This is why some form of objective measurement becomes critical. Metrics and KPIs help separate system performance from personal style. They give you a way to tell whether outcomes are improving even when execution looks messier than it used to.

Importantly, this doesn’t require perfect metrics. Even clearly articulated goals—what success should look like over a given period—create an external reference point.

Without that, it’s easy to fall into the trap of assuming the team is underperforming simply because they aren’t engaging in the same heroics you once did.

Tension #3: Aligning stakeholders with different perspectives & incentives who may never agree

None of this works without stakeholder alignment and leadership trust.

As your work shifts, your personal output becomes less visible. If expectations aren’t reset, that shift can look like a decline in performance rather than a change in contribution. People may conclude you’re disengaged when you’re actually working at a different layer.

You also need to make sure senior leadership recognizes the reality of the situation on the ground. Information from the front lines about realistic projections, bandwidth and capacity, and changing conditions have to make their way up.

On the flip side, you also need to make sure the front lines understand how their work fits into organization-wide objectives. That allows them to make the right tradeoffs, and helps them act autonomously to the benefit of the collective.

Alignment is key to all this. You need clarity with leadership about what your success looks like now, and trust that the organization will reward leverage rather than just effort. Without that, the system will always pull you back into execution no matter how disciplined you are.

—

Moving up a layer isn’t about finding better answers. It’s about developing judgment—knowing when to step in, when to step back, and when to tolerate short-term discomfort in service of long-term momentum.

There’s no magic bullet. Just a set of tensions you get better at managing over time. That’s the job now.

Good luck, my friends.

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There was a time in my mid to late twenties when I thought my biggest career wins—making law review, landing a job at Sullivan & Cromwell, securing a federal clerkship—were proof that hard work could overcome anything. I saw them as moments where I just happened to push harder than everyone else. And to be clear, luck and privilege played a role. I had access, timing, and support that many people don’t, and I don’t want to pretend otherwise.

But now that I’m in my early forties, looking back, I can clearly see that all those wins share the same origin story. They didn’t happen because I was the most gifted person in the room. They happened because of strengths I didn’t know how to articulate yet: The ability to connect with people, read & interpret unspoken dynamics, and nudge people toward decisions.

For years, I treated those strengths as irrelevant to my career. It wasn’t until much later that I realized they were the through-line of my entire career; and that every so-called “pivot,” including moving into sales, was really just a return to what I’d always been good at.

This article attempts to describe how I figured that out and why, if you’ve ever felt slightly out of place in your own career, hopefully you’ll end up seeing your path differently by the end.

The First Signs My Real Strength Was Something Else

It all started during my first year of law school. I met a classmate—let’s call him Jack—who was friendly & chill, and seemed like a good person to study with. I spent hours preparing for our first session together. I took meticulous notes during class, outlined everything we covered, used every supplement I could find, and put in hours of prep just for that meeting.

Jack showed up with nothing prepared. No notes, no outlines. He casually talked through every concept off the top of his head, with a level of clarity that made my preparation look pointless. When I asked how he remembered it all, he shrugged and said he just listened carefully in class. For me, it was a devastating revelation: The first person I happened to work with was operating at a level I couldn’t touch, even with massive effort.1

As the weeks went on, I realized my class was full of people like Jack. People who absorbed black letter law instantly and wrote thousands of words under time pressure effortlessly. I didn’t have that.So I defaulted to what I knew—sacrificing my social life and working really hard.

But while I was fixated on what I didn’t have, I completely missed the talents I did bring to the table. They didn’t show up on exams, but they were very real. I could gain people’s trust quickly, and make friends from different groups easily. I naturally made people feel comfortable in an environment that was anything but. I could rally people to go out for drinks (or stay in to watch NBA games) without significant effort.2

In hindsight, those were signs of unique interpersonal skills; just a completely different kind of talent than what law school rewarded. And while it didn’t help me much during the hyper-competitive 1L year, it became invaluable later in my career.

Those early moments planted a seed, even if I didn’t see it at the time: my strengths weren’t in mastering the law. They were instead persuasion in the broadest sense—connecting with people, earning trust, and moving individuals & groups toward action. It would take me years to understand how important that distinction actually was.

Hustle Was a Signal, Not Just a Survival Tactic

Coming out of my first year, I carried a simple & neat story about myself: I wasn’t naturally talented, so I had to rely on effort. Anytime I broke through, I credited it to working harder. Looking back, I now recognize that wasn’t the full picture. The moments where I advanced weren’t just about grinding out academic results—they were moments where I leaned into strengths I didn’t realize I had.

An instructive example was during on campus interviews (OCI). My GPA was below the cutoff for Sullivan & Cromwell, so on paper I shouldn’t have had a shot.3 By that point, I had just written onto law review rather than qualifying by my grades. Law review was an important credential that helped me get in the door, but it also fed a quiet insecurity. Internally I felt like an imposter who had somehow acquired credentials I didn’t deserve. I distinctly remember walking into OCI interviews convinced the firms would eventually see right through me.

I knew I had to do something different. Showing up and just talking about myself—the advice I’d received from 3Ls and other well-meaning people—didn’t feel sufficient. So for S&C, I decided to arrive at the “hospitality suite” where interviews took place, and talked to anyone I could. I ended up chatting with a junior associate who was tasked with greeting people. Most candidates ignored her because she wasn’t a decision-maker, but I thought her story was interesting. So we talked like normal people, without all the forced formality of an interview.

When I then interviewed with the partner, the conversation felt unremarkable. We had little in common, and I walked out assuming it was over. But later that evening I learned I’d been selected to advance to the “callback” stage, where they’d invite me to meet with more lawyers at their NYC office. At S&C, a “callback” meant that the offer was yours to lose.4

As it turned out, the reason wasn’t my grades or some brilliant interview moment—it was that the associate had championed me. She told the hiring partner that my personality came through in a way that mattered, and it outweighed the credential gap.5

At the time, I thought I’d gotten lucky. But looking back, it wasn’t luck alone. It was the ability to connect with someone and make them feel at ease—even while I was quietly terrified of being exposed. What I had always labeled “hustle” was really something else: understanding people, spotting unexpected opportunities, and creating momentum from zero.

Law school didn’t reward those skills directly, but every time the stakes were high, they showed up. And over time, those moments formed a pattern—one that hinted my strengths were never about legal acumen. They were about connection and persuasion long before I ever considered a career in sales.

Where I Misread My Own Strength

Even as these patterns started to appear, I didn’t know how to interpret them. I kept assuming my advantages were temporary or accidental. And because I didn’t understand what my real strengths were, I kept putting myself into situations where those strengths didn’t actually matter.

A perfect example was when I ran for Editor-in-Chief of the law review. I treated the whole thing like a persuasion exercise—building support, talking to the 3Ls on the editorial board, thinking it was a popularity contest I could “win.” What I completely misread was the structure of the game. It wasn’t a broad election at all. The outgoing EIC was the real decision-maker; everything else was theater.6

On top of that, there was some self-delusion mixed in. The application process required us to rank our interest in various editorial board roles. I convinced myself that saying that I’d take any job they offered would somehow increase my chances of getting the top one. I even convinced myself I would genuinely be happy with anything. When I lost, the result made the reality clear: they didn’t give me my second choice, or third, or even fourth—they gave me the role I had ranked dead last. Which I immediately realized I didn’t want.

My summer associate experience had a similar dynamic. Instead of leaning into the strengths that had helped me up to that point—curiosity, connection, showing personality—I tried to blend in. Some of it was the culture shock of being at S&C. I was surrounded by people from extremely privileged backgrounds, and even though there were plenty of Asian associates, I still felt a cultural distance from everyone that I couldn’t quite define.7 My instinct was to avoid rocking the boat. The result was predictable: I didn’t stand out. I worked hard, fit in fine, but that was it.

Both situations had the same root problem. I was applying my strengths in the wrong arena, and sometimes in the wrong way. I kept trying to play games I shouldn’t have been playing—games optimized for credentials and prestige—when my edge lived somewhere else entirely.

The Moment I Could Finally Name It

For most of my early career, I kept trying to succeed on terms that weren’t mine. I chased the roles, credentials, and validation that the legal world told me mattered, and every time something didn’t click, I assumed it was because I needed to work harder or make bigger sacrifices.

The first real clue came from something I initially treated as insignificant: becoming my class’ graduation speaker. It wasn’t based on grades or by appointment; it was based on an election. On a whim I decided to run. It wasn’t a coveted role like law review leadership, and I certainly didn’t see it as career-defining. I just thought it might be something cool and fun to do.

There were two stages to that experience.

• The first was campaigning for the position itself. Unlike the law review process, which had a single decision-maker, the graduation speaker appointment depended on a broad base of support. It was an election. Nearly twenty classmates ran, and I immediately grasped the implications. If I could mobilize my friends from all the different groups quickly, I could immediately secure a plurality of support.8 What started casually became something I pursued with real focus and intensity, even if I didn’t yet understand why.

• The second stage was preparing the speech. This part scared me far more than running in the election. Standing in front of a thousand people made me acutely aware of the responsibility that came with the platform. I felt a deep fear of wasting everyone’s time. Anyone who’s gone to a couple of graduations knows that student speeches can be painful. I vowed to deliver a speech that was both entertaining and memorable.
  
  So I took the speechwriting process seriously. I kept the message simple and personal—how I ended up at Northwestern Law and how hard it had been to get there. I studied what worked, watched other graduation speeches on Youtube, borrowed structures, tested jokes, and practiced it in front of focus groups of friends from different circles. The goal wasn’t to impress. It was to respect the audience.

You can find the speech here, on Youtube. My delivery was imperfect and I was incredibly nervous throughout. Once I was done, I immediately walked off the stage because I wasn’t sure if people would clap very much—and I wanted to get back to my seat quickly before it died down. But when I got off the stage and looked up, I saw that every single one of my classmates were applauding.

And not just that—they were all standing.

The standing ovation wasn’t just gratifying. It unlocked unexpected upside. One of my professors, who had taught at the school for decades, remarked to me afterwards: “I have never seen a student speaker receive a standing ovation.” The professor then told me that he planned to call up his former student—whose nomination to the federal bench was pending—to recommend me as his first law clerk.

That was the moment the pattern became impossible to ignore. When the work revolved around persuasion in its broadest sense—people, trust, clarity, and decision-making—everything felt easier and my performance was superlative. Over time, it became clear that the same instincts that helped with my graduation speaker experience showed up elsewhere in my career in domains ranging from sales, to social media, to leadership/management.

Alignment, Not Reinvention

Once I saw that pattern clearly, it reshaped how I understood my career—and how I made decisions going forward. Law review opened short-term doors. S&C shaped my work habits and standards. The clerkship gave me a mentor and showed me how to combine high performance with kindness. Not a single one of those experiences were wasted.

But the realization underneath all of them also clarified something else. I didn’t need to keep playing the same games other people were playing just because they came with gold stars or impressed strangers. That insight directly informed my decision to eventually pivot into startup sales in 2016—and to remain in the legal ecosystem rather than abandon it entirely.

At times, it’s still hard to explain to people what exactly it is that I do. Most lawyers understand, but a lot of people (especially outside of the legal industry) don’t quite know how to put me in a box. “You’re a lawyer—but you decided to work in … legal staffing?” But over time I’ve come to believe there’s more real satisfaction—and more real glory—in doing excellent work in your chosen domain (no matter what it is) than trying to gain prestige for its own sake.

Pivoting out of law didn’t feel like a leap. It felt like alignment. Once I realized that, everything that came afterward was easier to understand.

Conclusion

Luck and privilege matter. Timing matters. I benefited from all three. But so does paying attention to patterns.

In my case, the achievements I was proud of early in my career—law review, S&C, the clerkship—didn’t happen because I mastered substantive law faster than everyone else. They happened because of strengths I had been using my whole life: persuasion, connection, trust, and an instinct for how decisions actually get made.

The moment I started focusing on those strengths, my career stopped feeling like a tug-of-war and started feeling like alignment. I didn’t reinvent myself. I recognized what had been true all along.

Here’s the takeaway from my long and meandering story: If you feel stuck or out of place, I highly recommend that you to look backward before you look forward. Look at where things felt easy. Where opportunities appeared that couldn’t be explained by credentials or randomness. You might find that the path you’re meant to take isn’t a sharp turn at all. but the one you’ve been walking toward for years, waiting for you to finally name it.

Good luck my friends.

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But a bigger part of the reason I’m writing on this theme of being underrated today, is because of an unrelated spot-on comment from Lulu Cheng Meservey on Jack Altman’s podcast that popped up on my feed:

So today I’m going to share a few thoughts on how to manage your PR by being underrated and share my own personal experiences being viewed as underrated and as overrated. I’ll then end with some takeaways for individuals and organizations.

What exactly does being overrated mean

To me, being overrated is when you appear to collect all the rewards up front before you’ve earned them. It sets you up for backlash when a setback happens. In fact, you sometimes the setback doesn’t even need to take place. Even when you rack up wins, the haters lurk in the background.

When you’re underrated, the opposite dynamic plays out. When I joined Logikcull, my first legal tech startup, I was obviously overqualified for the job. I was a 33 year old lawyer with an elite resume, starting over as an entry level salesperson.

Despite my job title, colleagues sensed that I was extremely competent. So when I eventually became the fastest-promoted SDR in company history, I didn’t experience backlash; instead I became “the people’s champion” where everyone up and down the org chart celebrated my success.

How exactly do you become underrated?

There is no formula. But generally speaking you need to do two things:

• Work in the shadows for a long time

• Eventually gain recognition through some type of public success

It’s not enough to work in the shadows. For example, plenty of people work with no recognition. However, many of them (probably?) deserve the lack of recognition because they are average. So the fact that they do not gain public attention for their achievements is generally a fair result.1 It’s deserved.

Obscurity on its own does not make you underrated.

The challenge is that many people on the field are reputational Karens. This is exactly what we are seeing with Harvey and how things are playing out. There is a ton of noise out there, but from the comments it seems that many people—some of whom have toiled in obscurity for years with zero attention—gleefully piling on.

The best defense to haters is to ignore them. The second best defense though, is to maintain a reputation for being underrated.

The key to that? You’ve got to pair “work in the shadows” with real, concrete progress. That’s the only way to compound your own capabilities to the point where when public recognition hits, you have grown sufficiently to appear to deserve the success.

That will keep the haters at bay.

My personal experiences

I experienced both sides of the coin when I was in law school.

• Being underrated: During 1L year I worked in the shadows because I was insecure. On the basis of a strong LSAT score, I ended up at one of the top law schools in the country. Yet I didn’t possess the strong work ethic and academic prowess of my classmates, all of whom had top GPAs on top of their similarly strong LSAT scores. So I was super low key, never really speaking up in class or talking about my ambitions, while spending all of my time in the library. The summer after 1L year, I ended up writing on to law review, it surprised a lot of people. However they all celebrated my success; many of them saw how hard I worked and so they saw my win as very fair.

• Being overrated: However, at the beginning of 2L year, something changed. By then my persona went from “humble 1L” to “law review editor.” Then, I landed a summer associate job at Sullivan & Cromwell, which was a very public win. Right around then I began to realize that some of my closest friends perceived my ascent as fundamentally unfair; that my success was an undeserved aberration because I gamed the system. They weren’t entirely wrong. I did prepare intensely for OCI interviews & networked aggressively (unlike many of my peers) which was a big part of the reason why I punched above my weight. But that experience made me realize that when you land public wins faster than others’ expectations, it’ll lead to them wanting to tear you down.

These were not lone instances; I had in fact throughout my life had been experiencing backlash to what people perceived as undeserved success. As someone who probably cares too much about what other people think, it was all very painful.

History repeats itself

The same “being overrated” experience happened again a few years ago when I achieved social media notoriety in legal tech circles. At the time I was a salesperson who made funny video skits during the pandemic, and going massively viral and building a large niche audience was incredible for my job performance. But as my name spread across the Internet, I began coming across haters.

Turns out a lot of legal tech commentators had been working in the shadows in the space for a long time with almost no attention. And yet here I was, a young sales guy who exploded on the scene by making dumb jokes and comments, commanding far more attention than them.

I was tempted to dismiss the haters. But after reflecting on it some more, I took a different approach. I decided to slow down my own audience growth and made strategic pivots to something more substantive. Examples:

• I stopped trying to grow views and followers, and instead tried to be more thoughtful with my posts instead of just dropping hot takes.

• I launched this newsletter and started to write on substantive topics ranging from sales/marketing to legal ecosystem trends.

• I declined to pursue sponsored posts/influencer marketing deals, even though they paid generously.

• I instead focused on biz dev related consulting/advisor engagements, even though they drew no attention and sometimes paid less

The goal was to do more work in the shadows and make real, concrete progress. Over time I began to see my own follower/view count metrics plateau. I witnessed other creators with smaller audiences or who started later than me grow quickly and at times surge past me. Part of me felt like I was falling behind. But another part of me realized that their goals and mine were likely very different.

I was on a different path.

My unsolicited advice

There are a lot of implications for individuals and companies. I’m by no means an expert. And I recognize the irony of a “social media guy” writing an entire article sent to thousands of readers about why you should avoid the limelight. If you can set all that aside, here’s what I’d (humbly) recommend.

If you’re a company:

• Consider *not* making a name for yourself via splashy fundraises or high valuations. It’s ok to announce these wins, but they should not be the centerpiece of your public persona.

• If you do want to drive attention, let your employees or clients/customers do it for you. Enable your people to speak out on social media—even if it’s not *exactly* what you’d say, give them that freedom. This is how you gain trust, which is critical in this space.

• Focus on achieving quiet, concrete progress over the course of years. Solve hard problems in the shadows. And then be selective about what PR announcements you decide to share on traditional/social channels.

If you’re an individual:

• Aspire to be someone that others call underrated. Yes, I get that we all want to announce our career wins on LinkedIn (I’m very guilty of this) but similar to companies, be selective of what you decide to share

• Avoid general networking or personal brand building. Knowing people is important, and you definitely should not “just put your head down and do good work.” But don’t becomes someone who is viewed as a lightweight.

• Work every day at improving your craft. Make mistakes, learn from them & others, and maintain a growth/abundance mindset. Not everyone will like you but make sure at least they respect you.

There’s a lot of noise out there and truly a ton of “reputational Karens” out there. Haters are just a fact of life. And the best solution may be to just ignore them. But at the same time, these haters can be check on yourself to make sure you’re not overly hyping yourself and drinking too much of your own Kool Aid.

Best of luck my friends!

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In this article, I’ll make the case that alternative legal services providers (ALSPs) are uniquely positioned to fill that role. ALSPs are embedded in client workflows where AI can make the biggest difference, are funded from budgets clients already understand, and trusted by the decision makers who matter.1

Here’s what I’ll cover:

1. Why ALSPs Are Natural Distribution Channels

2. It Happened in E-Discovery

3. The Coming Wave (AI Agents)

4. Traits of the Ideal ALSP Partner

5. Where the Market Is Headed

6. Conclusion

Before I get into it, I want to cover two important points (that I also shared last time) that I’ll share again::

• In this piece, I refer to “AI” generally, but my focus is on generative and agentic AI.

• These are my own views, and do not represent the views of Latitude Legal, Stanford Law School, or any other organization I’m a part of.

1. Why ALSPs Are Natural Distribution Channels

The barriers that slow AI adoption in legal—unclear budgets, long procurement cycles, and client skepticism—are the exact areas where ALSPs have an edge. Their positioning, incentives, and track record with legal buyers make them uniquely suited to act as distribution channels for AI.

A. They’re Already Embedded in Workflows

ALSPs are engaged directly in the streams of legal work where outcomes depend on coordinating multiple tasks—commercial contracting, technology implementations, litigation support, document-heavy investigations, etc. They don’t just deliver tools; they put people inside these processes to ensure the work gets done.

That positioning makes them uniquely suited to introduce AI. By contrast, many AI tools today are marketed as abstract generalists, e.g. “AI legal assistant.” That label may spark imagination, especially from outsiders/investors, but they don’t map cleanly onto how legal work is actually structured.2

Legal tasks are interdependent and outcome-driven. Buyers don’t want a free-floating assistant; they want assurance that a specific workflow gets done correctly. ALSPs are already inside those processes, which allows them to deploy AI in a way that feels specific, contextual, and safe.

B. There’s Budget Alignment

ALSP engagements are funded from budget categories legal departments already rely on—outside counsel and professional services. These budgets are stable and recurring, and are relatively uncontroversial.

By contrast, legal technology is often funded from fleeting experimental AI resources or shared budget from other departments. At first, these resources appear significant. But the dollars rarely sustain over time. Once they shrink, startups whose product is attached to them face stalled renewals and declining net dollar retention3 because clients don’t know who should own the spend.

ALSPs avoid this trap by tying AI to commonly accepted categories of spend that have existed for years. To the client’s CFO, spend on AI doesn’t require “new money” that needs to be justified; it simply fits into buckets of dollars the legal department was already planning to spend.

C. They Have the Ability to Drive Innovation

ALSPs, by their very nature, had to prove themselves as innovators from day one. Unlike law firms, they couldn’t lean on legacy brand power or the safety of precedent. They had to persuade cautious, risk-averse clients to move work outside the traditional model.

That meant demonstrating why their approach was not only more cost-effective, but also safer, faster, and more reliable. In doing so, they built a unique organizational skill: the ability to make change feel safe for conservative legal buyers.

That same skill translates directly to AI. Where a startup pitching an “AI assistant” can sound abstract and untested, an ALSP can leverage their sales and marketing teams to frame AI as a practical extension of existing services. That shift in framing makes a huge difference.

Now don’t get me wrong. Relying on ALSPs for distribution isn’t a magic bullet. The client still needs to run security and risk review, and approve the AI for internal use. You can’t sneak AI through the back door by having an ALSP use it for client matters without any vetting.

But here’s the upshot: AI deployed through ALSPs will be viewed very differently at the outset. Instead of clients reacting to an AI startup with: “Who are you and why should we trust you with our data?” the framing becomes, “Your partner’s been doing sensitive work for us for years—help us understand how your technology helps them be even more efficient.”

I’m not making this up—there’s already some precedent for this.

2. It Happened in E-Discovery

There’s some historical precedent for what I’m articulating.4 In e-discovery, Relativity didn’t become the dominant platform because every firm/legal department rushed to buy licenses directly. They didn’t raise a ton of money at the outset, have flashy marketing, or advertise monstrous valuations.

Their go-to-market was instead designed around how lawyers viewed technology. They didn’t want to deal with the hassle of standing up servers, training staff, or taking on the risk of a new system. The lawyers recognized that all that was outside their core competency.

Instead, adoption spread through a fragmented ecosystem of local vendors who hosted, customized, and supported the platform. To the clients, it felt like they were simply using a vendor they trusted, not “adopting Relativity.” That helped the technology scale in those early days, and quickly become a necessary tool in the lawyers’ day to day.

Now like many other providers that outsourced distribution at first, Relativity did eventually build their own direct distribution. But that was a deliberate strategic choice made years after they’d already become the market leader.

ALSPs are positioned to go further

It’s worth noting that the work many lit support vendors do, by their nature, is highly reactive. Generally, they only get pulled in by a law firm after a litigation or investigation is already underway. Other ALSPs, by contrast, may sit closer to the origin point of legal work. For example:

• At law firms: Instead of merely standing up a doc review environment when the litigator receives a production from opposing counsel, a higher end ALSP might be involved during the pleading stage.

• At legal departments: Instead of merely reviewing NDAs that the commercial team sends over, a higher end ALSP might be involved in developing playbooks and SLAs with the in-house lawyer’s internal clients.

All that early stage visibility gives the AI-enabled ALSP the opportunity to proactively reshape downstream work. You don’t want AI to incrementally improve traditional processes designed for a pre-AI world.

The takeaway is this: The winners in the legal AI arms race are the ones who can drive adoption of redesigned workflows. To do that they need to be trusted by the client, and have early visibility into processes that take place upstream. This is absolutely critical for anyone building AI agents designed for legal.

Which brings me to my next point.

3. The Coming Wave

If the first wave of generative AI felt disruptive, imagine what the next wave will feel like. Agentic AI doesn’t just produce text—it goes ahead and “acts” on your behalf.

Imagine an agent that redlines a contract against playbook terms, circulates it to the right stakeholders, and logs the approval into the CLM. Or one that monitors regulatory changes, compares them against policies, drafts suggested updates, and pushes them to compliance.

Or in the law firm context, picture an agent that pulls precedent from the DMS, drafts a first-pass motion, cites relevant authorities, and sources comments from a senior associate, before passing it on to a partner.

These aren’t discrete tasks. They’re multi-step workflows that look and feel like real legal work done by a human being.

Legal work is different from other types of work

The leaps that AI agents promise dramatically raises the stakes. And this is what many outsiders don’t understand about the fundamental nature of legal work.

When a sales-focused agentic AI gets something wrong, the cost is minimal—maybe you send out the wrong e-mail, or maybe you fail to schedule a sales appointment. Annoying but not catastrophic.

When legal-focused agentic AI takes the wrong step—like accidentally filing the wrong version with the SEC or sending privileged documents to opposing counsel—the consequences are devastating.

As a result, the primary question about agentic AI isn’t “does it work?” It’s “how do we make sure that never happens?” And potentially even more important: “who is ultimately accountable when something terrible happens?”

Ensuring that a trusted human is involved

This is where ALSPs come in. They regularly deliver outcomes to clients, and their people are already accountable for the work. Embedding agents into this system doesn’t look or feel like a scary leap; it may not even be noticeable.

Humans—contractors, employees, and staff of ALSPs, can design escalation points, validate outputs, and ultimately stand behind their results. Which makes agentic AI feel like a seamless extension of existing services.

I truly believe that’s how agents will rapidly scale in the legal vertical. Yes, some of it will happen through direct adoption by pure AI companies. But a ton of it will just happen through intermediaries who make the agents seem invisible. Which brings me to the next question:

Which intermediaries are likely to be most effective in this new world?

4. Traits of the Ideal ALSP Partner

All ALSPs have some potential to play a significant role in AI adoption. But certain traits make some especially well-suited to lead the way. These characteristics don’t just make distribution possible; they make it smoother, faster, and more credible in the eyes of clients. Here are 4 examples of key traits of the “ideal” ALSP to partner with:

A. Already Embedded in High-End Workflows

The first trait is being embedded in high-end workflows. If an ALSP is doing associate-level or interim counsel-level work (drafting, negotiating, advising) AI can be slotted into those workflows seamlessly. The tasks that make up those workflows can be shifted around to address the high level goals of the legal work itself.

By contrast, ALSPs focused on lower-end tasks are too far from upstream factors to shape workflows and influence how/where AI fits in. Example: An ALSP specializing in first level doc review or data hosting will have limited opportunities to drive efficiency. Conversely, an ALSP that has exposure to early negotiations during the discovery process of litigation has the potential to impact what files/documents get exchanged by the parties.

Which ALSP do you think AI startups would rather partner with?

B. Trusted by Senior Decision Makers

The second trait is trust with senior decision makers. Nothing moves in legal without a senior in-house counsel or law firm partner giving the green light. An ALSP that has already delivered sensitive, high-stakes work has built credibility with that exact audience, which will accelerate adoption.

As a result, clients won’t see AI enablement as an unfamiliar or risky proposal. Instead it’ll be viewed as a recommendation from a trusted third party who has already proven reliability on highly sensitive matters. The technology review process is still there, but will be guided by confidence in the relationship rather than doubt about the messenger.

C. Lawyer-In-The-Loop Accountability

The third trait is having a licensed attorney involved in overseeing the work AI helps with. Theoretically, any competent professional can do this. But licensed lawyers face consequences that go far beyond a bad outcome—they can lose their license and derail their entire career. That reality raises the stakes and creates a heightened threshold of trust.

When experienced attorneys are involved, clients know there’s someone who is betting their license on validating the AI’s outputs, monitoring escalations, and managing risk. This layer of professional responsibility makes AI adoption feel less like an experiment and more like a mere extension of existing legal services.

D. Quiet, Outcome-Focused Delivery

Finally, the best distributors lead with quality work—not marketing driven hype. Legal buyers generally don’t see themselves as loud early adopters. They view themselves as more traditional types who quietly do good work. Accordingly, the market positioning of ALSPs that will be most effective might take a more understated approach.

Personally, I think it’s better if the AI operates in the background early on. The marketing pitch should revolve around faster turnaround times, better outcomes, and consistently high quality. The AI will be there, but working in the background. Adoption becomes a foregone conclusion because it feels less like change management and more like organic improvement.

Eventually, after the AI has been de-risked, and the technology has moved from the early adopter phase to the early majority phase—startups can re-evaluate.

The ALSPs that combine these traits—embedded in high-value work, trusted at the executive level, accountable for results, and quietly focused on outcomes—are the ones positioned to become the most effective distribution channels for AI.

5. Where the Market Is Headed

We’re already seeing signs that tech and services are starting to converge. First, multiple providers on both sides, ie. AI startups and ALSPs, have begun to partner with one another.5 Second, some startups are already pushing AI-enabled services directly to clients. These developments suggest that services will increasingly play a large role in early adoption of legal AI.

However, the ALSP-first distribution strategy I’ve been describing here is *not* the most popular one right now. I mentioned this briefly in my previous article, but it’s worth re-emphasizing: The current strategy in legal AI go-to-market right now is the social proof/valuation-led approach. Which I’ll admit, can be incredibly effective in the legal vertical. From Ken Priore:

While competitors chased demos, press releases, and conference buzz, Harvey quietly cracked the code on BigLaw's actual decision-making process. The insight? Law firms don't buy technology—they buy social proof. "What other firms are using this?" isn't just the first question; it's often the only question that matters in the initial evaluation. Harvey recruited former BigLaw partners who understood this psychology, then methodically secured Allen & Overy, Paul Weiss, and PwC as early adopters. No flashy marketing. No thought leadership campaigns. Just strategic relationship-building with the right insiders at the right firms.

I think this is right, but only if you combine it with Harvey’s continuous stream of fundraising announcements. No one *really* knows if their product is better, but everyone’s aware that they raised $500M from leading VCs and are worth $5 billion, just a few years after founding.

Harvey clearly knows what its doing here—their approach to the market has helped them achieve $100M in ARR in record time. But consider the more relevant question for everyone else: What happens to the second, third, fourth etc. startup that follows the same playbook? Will they be able to beat Harvey (and Sequoia, Kleiner Perkins, etc.) at their own game?6

Conclusion

The biggest risk for founders, employees, and investors of legal AI companies, isn’t whether they can build a good product. They probably can. It’s whether these technologies can find their way to this group of conservative, risk averse lawyers.

Most of today’s startups are betting on direct sales, hiring teams of AEs and SDRs, and flooding the same handful of conferences and marketing channels. That playbook looks familiar, but in legal it’s brutally expensive, slow, and rarely sustainable.

To me, the overlooked channel is ALSPs. They already sit in the workflows where AI matters most, already pull from budgets that legal departments know how to spend, and already have the trust of the executives who make the calls.

And if they become an intermediate layer for AI, then they will ultimately be the ones who define adoption velocity. And startups would be mistaken not to partner with them.

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But here’s the reality: building AI is no longer the hard part. Distribution is.

Thanks to foundation models, the technical barriers to creating legal tools have dropped dramatically. Most startups now build on the same platforms. The user interfaces look and feel the same. The core capabilities appear to be increasingly interchangeable.

What used to be a product challenge is now a go-to-market one. It’s not about who can build the best AI tool—it’s about who can actually get people to use it.

This article explores why existing channels—startups, legacy vendors, and law firms—are struggling to deliver AI at scale. I’ll then talk about the traits of an ideal channel, and explain why. And then at the very end, I’ll share a teaser of where I think that distribution channel can be found.

Two important points before I dive in:

• In this piece, I refer to “AI” generally, but my focus is on the kinds of systems that are reshaping legal work most aggressively in 2025: generative and agentic AI. One generates content. The other takes action. More on the difference here.

• The opinions I share are my own views colored by my personal experience. They are my own, and do not represent the views of Latitude Legal, Stanford Law School, or any other organization I’m a part of.

Startups Can Build, But Can’t Reach

Coming up with new legal AI tools has never been easier. Most startups today are built on top of the same handful of foundation models—OpenAI, Anthropic, etc—with nearly identical capabilities. User interfaces have largely converged, too: the workflows center around contract review, chatbots, and summarization tools that look and feel remarkably similar across products.

Some teams claim differentiation through proprietary data or fine-tuned models. While this can matter at the edges, the differences are often invisible to legal buyers and hard to prove. The capabilities may be slightly different but they all *feel* interchangeable.

That wasn’t always the case. Historically, B2B SaaS products in the legal space had some differentiation: in feature set, product vision, and philosophy on workflows. Startups took unique approaches, validated early usage, and used that traction to raise meaningful seed rounds. The goal was to build a product worth trying out, then use that validation to raise funding and build distribution from scratch.1

Today, that formula is widely known—and widely copied when it comes to legal AI. Everyone raises money to fund growth.2 But the larger the round, the more the go to market approach starts to look the same: AE/CSM model, outbound SDRs, sales engineers, premium sponsorships at the same 3-5 conferences, saturating the same digital advertising channels, etc.

The only things that seem differentiated are how much money was raised and who invested.

Think about why some startups have been able to draw disproportionate attention right now: is it really product quality that commands headlines? Or is it the valuation, the investor roster, and the resulting hype?

Consider why lawyers immediately think of Harvey when discussing legal AI. Is it because of anything about the product itself or is it because they’re backed by OpenAI, Sequoia, & Kleiner Perkins, and reached a $5B valuation within just a few years?3

(For a breakdown of funding/hype based advantages, check out Zach Abramowitz’s fantastic article Has Harvey Already Won?)

Legacy Giants Were Built for a Different Era

If startups struggle to scale and law firms lack go-to-market infrastructure, what about the legacy legal tech giants?

For decades, Thomson Reuters and Lexis have defined legal tech distribution. Their dominance came from a potent combination of brand trust, embedded access, and control over proprietary legal content. They reached users early—starting in law school—and remained central to core legal workflows like research, citation, and compliance.4

But AI doesn’t fit neatly into their model.

These companies are built to distribute static tools into familiar workflows—tools that lawyers already know how to use, often procured top-down by centralized law firm buyers or IT. The latest iterations of generative or agentic AI by contrast, requires behavioral change, uncertainty tolerance, and iterative refinement. It’s dynamic and messy, not structured.5

One reason may be strategic: TR’s true long-term advantage isn’t AI—it’s data. Its moat is built around proprietary legal content, annotations, analytics, and decades of structured information.6 That’s where it has pricing power and defensibility. If AI tools commoditize, TR is incentivized to treat them as wrappers around its core data—not as standalone innovations that could undermine it.

The legacy giants’ dynamic makes sense from a business perspective—but it also reveals the limits of relying on legal tech incumbents to usher in AI transformation. They may invest in AI, but they’re unlikely to be the ones to restructure how the work gets done.7

What About Biglaw?

Compared to legacy giants, BigLaw may seem like the ideal channel for legal AI. Firms are deeply trusted by corporate clients, embedded in critical workflows, and highly effective at expanding services through lateral hiring, cross-selling, and geographic or practice-area growth.

Some firms are starting to show real promise. By now, many already use AI for client matters. A few have successfully launched their own subsidiary service providers, invested in proprietary AI initiatives, or even begun commercializing internal tools.8

But these remain outliers.9

The reality is that Biglaw is built to sell legal advice—not novel products. Evangelizing innovation requires a different kind of muscle. You can’t just give clients what they already ask for; you have to reframe problems, guide workflow changes, and navigate long sales cycles.

Driving AI adoption requires coordination, sustained investment, and repeatable sales infrastructure. Most law firms aren’t structured for that. They typically lack

• Incentives that reward experimentation or go to market investment

• CRM systems or visibility into client buying patterns pre-revenue

• Professional sellers & marketers with expertise on how to pitch novel solutions to old problems

• Unilateral decision-making authority necessary to move quickly to direct firmwide investment

There’s also a key blind spot: while BigLaw can influence corporate buyers, it has limited leverage with peer firms. Distribution within the firm’s client base is possible—but across the broader legal market remains unsolved.

What Makes a Strong Distribution Channel for Legal AI?

Rather than immediately come up with a solution, what we should do instead is to ask: “Well what traits actually make a distribution channel effective for legal AI?” I don’t have all the answers, but here are a few that quickly come to mind:

1. Embedded in the Work

Startups often treat the sale as the finish line, but in legal, the buying decision is just the beginning. Without ongoing support and integration, much of the technology becomes shelfware. This is especially true for tools that require behavioral change—those that introduce entirely new workflows, rather than improved versions of existing ones.

As a litigation associate, I used to be surprised by how many of my colleagues struggled with newer, better doc review platforms or resisted abandoning Boolean search. But that experience reflects a deeper truth: in law, even incremental change can feel disruptive.

Adoption is far easier when the tool is delivered by someone already doing the work. Rather than selling AI as a standalone tool, the most promising distribution models wrap it inside services already being delivered—making adoption nearly invisible—but nevertheless impactful.

2. Trusted by Senior Decision Makers

The first step in any legal AI adoption is a senior decision maker choosing to move forward. That means the person introducing the tool must have peer-level trust with CLOs or law firm equity partners—leaders who think in terms of resourcing, risk, and strategic outcomes.10

Salesforce beat its competitors not because it was easier to use, but because it sold directly to sales leaders who understood the problem and had authority to act.11 In legal, it’s a similar situation: ease of use helps with adoption. But economic buyers and senior decision makers must first determine that the tool drives outcomes that matter to the business.

Many startup GTM staff (sellers) lack the credibility to deliver that message. They’re often recent grads or generalist reps without legal experience, unable to speak to senior stakeholders in their language or context.

By the way, agentic AI heightens this trust requirement—it’s not just summarizing or drafting, it’s acting on behalf of the lawyers. That makes peer-level trust from clients even more important, especially when accountability and risk are shared.

3. Internal Operating Maturity

There’s no playbook for distributing legal AI—so success depends on learning fast through structured trial and error. That means tracking what’s working, what’s not, and why.

Startups often have the infrastructure in place: CRMs, analytics tools, and scalable databases. But they struggle with data hygiene and sample size—sales notes are inconsistent, outcomes go untracked, and insights don’t scale. Without clean, consistent inputs, you can’t generalize lessons or build repeatable motions.12

It also requires training. Sellers and delivery teams need to know how to talk about AI credibly—what it can do, what it can’t, and how it fits into legal work. And importantly, what that means for the end clients.

Without that baseline, even the most groundbreaking AI features get lost in translation.

4. Incentive to Scale

Distribution only works when the people involved have a reason to make it succeed. That’s where many law firms fall short—selling legal advice generates cash flow, but it doesn’t build enterprise value. There’s limited motivation to invest in scaling something that doesn’t fundamentally change the firm’s economics.13

Startups are structurally better positioned, but their incentives often drift. Once they gain initial traction in legal, many start chasing larger TAM in other verticals or add features outside their core competency. That may make sense for product development—but for distribution, it creates whiplash.

To succeed in legal, you need a focused, repeatable go-to-market motion. Constantly shifting messaging, features, and positioning makes it harder to build trust and momentum with buyers.

Conclusion

If legal AI is going to scale, it needs a new type of distribution channel—one that’s embedded, trusted, and built for outcomes. Most startups focus on building their own distribution, but struggle with execution. Established categories of distribution channels—legacy giants & Biglaw firms—all come up short in some way.

This article has largely focused on the limits of those existing channels and the traits held by high potential channels. In my next article, I’ll explore where the real opportunity may lie: service businesses that already work with law firms & legal departments and have firsthand exposure to workflows.

They’re called “alternative legal services providers.” And that’s who I will be talking about next time.

Stay tuned, my friends!

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The book is called Talk Less Win More: How Lawyers in Business Development Roles Can Turn Meetings Into Revenue and comes in at just under 10,000 words.

Originally I was far more ambitious and wanted to share everything I could think of about sales. But after getting some feedback, I realized that it made sense to scale back my ambitions. And keep it succinct to make it easily digestible.

I’ll share with you the introductory chapter below, which explains my motivations for writing the book and who I think will benefit most from it. After that, I’ll share a Gumroad link that contains the table of contents, and how you can gain access the whole draft (spoiler alert: it’ll cost you $5).

Finally, I’d like to give a special thank you and shout out for the many of you who provided high quality valuable feedback over the months. Lots of people volunteered to review the draft, but only a few left comments and constructive feedback—which I truly appreciated.

Shout out to everyone who put in the work to help me get this draft finished.

Without further ado, here’s the intro!

Introduction

When I first left the practice of law to join an e-discovery startup as a sales rep, I didn’t think I needed help with my business development meetings. All I needed to do was to explain my background as a highly credentialed former Biglaw lawyer, and come across as a subject matter expert on our e-discovery product. It would only be a matter of time before I started closing lots of deals.

Right?

Well, no. I’d have all these meetings with prospective clients, and come out of them feeling pretty good about how the conversation went. But afterwards, they’d all ghost me. Not only would I *not* close the deal–my prospects would ignore all of my emails and calls afterwards. All of my follow ups would go unanswered.

What the heck was going on?

It took me a few weeks of running my head into a brick wall before I decided something needed to change. Like any good lawyer, the first thing I did was to do my homework and read as many sales books as possible. Then, I went out and talked to all the sales veterans on my team.

This process taught me a ton about sales and business development. I began to work these tactics into my routine.

Problem was, most of the things I tried didn’t work. It seemed that most sales books and veterans are used to selling to a general audience–not lawyers. So some of the advice I got that sounded really good in theory simply didn’t work on a legal audience. The lawyers were too skeptical and impatient.

Undeterred, I kept trying different things and running mini experiments in my meetings. Eventually, I learned that while most things I tried didn’t work–a few things did. In fact, these tactics worked *really* well–especially when I combined them. My numbers began to tick up, and I started outperforming my peers–all of whom were seasoned sales professionals.

At one point, I closed a software deal with a law firm partner without even having to show him a product demo.

Management took notice. I was immediately promoted to a leadership role to train a group of new sales reps. After about a year, I left that e-discovery startup to join a contract AI startup as its head of sales and was able to replicate my previous success. Interestingly, my training was especially helpful to the former lawyers on the sales team.

So what exactly was this new approach that changed everything for me?

Basically it boiled down to this: I stopped trying to impress buyers with my resume or knowledge and instead focused on positioning my offering as a specific solution to my prospect’s specific problem.

This is all much easier said than done. Especially for lawyers who are used to heavy research and preparation. It can be very difficult to anticipate what your prospect cares about. How do you prepare for a pitch when it’s impossible to know what their top challenges are? Do you just guess? How do you know if your pitch actually landed? And how do you do it all without coming across like a used car salesman?

Questions like these are exactly why I decided to write this book.

My target audience is any lawyer who wants to be able to effectively sell products/services to other lawyers. That’s who I am and what I’ve done over the past decade, so that’s what I know best. I have firsthand knowledge of how hard the transition from practicing law to pure biz dev can be. Especially when you’re selling to other lawyers.

However, I hope that the lessons I share in this book are also helpful to anyone who sells products/services to legal buyers.

The book is designed to be succinct, and filled with tactical advice. I use stories to help illustrate my broader points. My goal is to put all of my ideas in a short guide that you can refer back to quickly whenever you need–even if it’s 5 minutes before a client meeting.

Here’s what I’ll cover in this book:

• How to quickly identify the most urgent problems facing your prospect. You should spend most of the time in your meeting listening, and probing for what’s most important or pressing to your prospect.

• Why it’s important to always “make the ask” at the end of your meeting. If they say yes, you’ve won the deal more quickly than you otherwise would. But even if they say no, that is valuable feedback to enable you to pivot or move on to a different prospect.
  

• What words or phrases to use to advance the conversation. Maybe you already know exactly what to do, but you’re hesitant because you don’t know how to say/ask it without making things weird. I’ll share examples of how to phrase these statements/questions.

A few things to keep in mind as progress through the book:

1. Some tactics may not work in your situation. My professional experience has been as a lawyer-turned-sales executive at companies offering products/services to other lawyers. I have never been a partner at a law firm. If that’s you, I’m sure things work differently in your world vs. mine. Keep an open mind about what you read, because maybe some of it is applicable.
   

2. Some of my suggestions will feel awkward the first few times you do it. That’s to be expected. If these tactics come naturally to most people, then everyone would do it too–and there would be no way to separate yourself! Being a strong revenue generator requires you to do things outside your comfort zone. Embrace it! It all gets easier with practice.

3. Don’t worry about implementing 100% of the advice all at once. I added each of these individual tactics to my skillset over the course of months and years. If you could just implement 1 or 2 of them in the short run, you should feel an immediate impact–even if the revenue doesn’t materialize immediately. Over time you’ll develop habits and start to see an impact on the revenue side.

Gumroad Link

If you’d like to see the full table of contents, please visit the link here.

You’ll also be able to access a PDF copy of the entire draft (for $5). Thank you all! I truly appreciate everyone’s support.

Background: I’ve spent a lot of time at startups watching them struggle with this challenge when trying to scale sales/revenue. There’s usually one or two Evangelist-Sellers who have driven most of the startup’s early success. They usually fit a common profile: deep domain/subject matter expert, great at building trust with sales prospects, and extremely creative in getting the deal done.

However, as the startup grows and revenue targets increase—there’s top-down pressure to add even more sellers. That leads to hiring a large number of new employees who fit a very different profile than the Evangelist-Seller. For example, it may be a sales professional with limited/no knowledge about the industry. Generalizing broadly, these sales professionals tend to be process oriented & disciplined but lack expertise and aren’t as adaptable to fluid scenarios.

I’ve witnessed this play out at multiple startups/scale-ups. Struggling to scale is a necessary growing pain of any fast-growing company. After seeing how it’s played out and having contributed to some of these teams—I’ve developed a framework on how to tackle these challenges.

It’s a 3 step process that hopefully can be applied to your own situation.

Step 1: Break down valuable work into its most essential pieces

The first step is to take a step back and deeply understand every little thing that goes into the larger process. At one legal tech startup, I saw how our top Evangelist-Seller, “Greg” generate revenue effortlessly. After watching Greg work his magic for a few months, I was able to roughly divide his day-to-day into 6 types of tasks:

1. Meet with buyers who fit our ideal customer profile

2. Effectively ask them for a one on one sales meeting

3. Figure out what the buyer’s biggest challenges at work are

4. Frame our product as a solution to those specific challenges

5. Directly ask the buyer to sign a sales contract

6. Provide technical guidance post-sale to increase usage

These six individual tasks weren’t obvious to anyone who wasn’t looking carefully. When I asked Greg to break down his process, he said he didn’t really have one. “You just gotta know the product cold,” he’d say.

But when you watched Greg work deal after deal, you could see that product knowledge wasn’t the secret sauce. It was something else. Greg didn’t necessarily take the same approach every time, but somehow he’d always complete all 6 tasks. The newer/weaker sellers on the team often skipped/omitted one or more of these tasks.1

The question then became, which of Greg’s 6 tasks could be outsourced, delegated, or automated—and which ones were most valuable, and should remain untouched.

Step 2: Figure out where the magic happens

How do you figure out what task is most valuable? By process of elimination. In short, you should try to delegate & automate everything, and see where you run into roadblocks. You’ll find that most tasks can be outsourced—but maybe 1 or 2 cannot.

That’s where the magic happens.

At that legal tech startup, it took a while to figure out which one of the 6 tasks was most valuable. Right after we raised a large round of funding, company leadership suddenly found themselves with a huge amount of resources to increase sales. Here’s what they did:

• Try and outsource tasks 1 & 2—more meetings with ICPs—by doing two things: (a) hiring BDRs (full-time staff to generate sales appointments) and (b) increasing investment in new marketing channels.

• Try and outsource tasks 3-5—selling effectively—by hiring new account executives and provide rigorous sales training for them

• Try and outsource task 6—post sale technical guidance—by hiring new customer success managers (ie. account managers) and provide rigorous technical training for them.

Within a month or two, we saw a flood of meetings and increased capacity for post sale technical support. However, revenue continued to stall. As it turned out, tasks 3-5 were not easily outsourced. And it was a bottleneck to new revenue. Turns out that it’s quite difficult to find account executives to effectively convert leads to signed contracts.

That was the first time I realized that that’s likely where the magic happens. Looking back to Greg, the reason why he was so effective was partly because he had a unique mix of the right personality & temperament, domain knowledge, and sales drive—to maximize conversion rates from leads to closed contracts.

When we tried to hire from the outside to replicate Greg, it was incredibly difficult. You needed domain experience to address buyer’s challenges. But you couldn’t just rely on a technical expert, you needed someone with sales drive to connect challenges to features, and boldly close the deal. Even hiring from competitors didn’t solve the problem; they were always flawed in some way.

As a result, by process of elimination, we recognized that account executive hiring was the big bottleneck—and likely where the magic happens.

Step 3: Protect the magic while outsourcing everything else

It’s likely that you have a sense of “where the magic happens” in your own team’s processes. Once you discover & validate it, don’t try to immediately outsource it. Instead, your first step should be to aggressively outsource everything else.

That means hiring junior people or adopting technology/AI to tackle low value tasks. For sales teams, that could be list building or prospecting/coming up with target lists. For legal teams, that could be contracting workflows and email/approvals. It’ll be different depending on what function you lead, but the general principle remains the same.

Once you’ve outsourced everything else, what should remain is the “magic” work that can’t be easily scaled/replicated. As a leader you need to protect the magic, and—importantly—take the time to deeply understand how & why it works.

At the legal tech startup, we ended up hiring & firing a ton of account executives. In the end, leadership decided to try something unprecedented for them. Instead of hiring veterans from the outside, they decided to hire from within.

The thinking was that the most effective junior sales reps (who were largely responsible for scheduling appointments) were likely also those who had domain knowledge, sales drive, and culture fit. This seems obvious in hindsight, but at the time—the conventional advice was to always hire from the outside. Which is what we did.

That was partly how I ended up being promoted from BDR to account executive in record time. It didn’t escape leadership that I had domain experience as a former lawyer. But they saw that I also had the potential to convert leads to signed contracts, just by watching me generate appointments for other account executives. The same was true of one of my colleagues—a tenured BDR who wasn’t a lawyer.

The two of us were promoted to jobs that were stacked in our favor. We ended up outperforming external hires, and ended up moving up quickly. It accelerated our careers, all while enabling the company to reach higher and higher levels of revenue.

Look—the lesson isn’t that you can never scale the magical part of your workflow. Eventually you will need to operationalize it. However, your solution will very likely be highly unique to your company and the market it serves. It won’t come from a cookie cutter playbook from investors, ie. “just hire a bunch of sales reps” or “just use legal AI to outsource all the work.”

Takeaways

To sum it up, scaling requires you to deeply understand your workflow and make calculated bets on what’s most easily outsourced. Protect the magic at all costs, and be creative about how to scale that side of the house.

Before I wrap up the article I do want to provide some qualifiers. For example, it may be that your organization has an accelerated timeline to scale, such that it’s necessary to simply add headcount/technology. In that situation, I would simply make sure to assess your tasks in parallel. Hire/outsource, but try and understand what is happening in real time to identify bottlenecks quickly.

Another example, you may believe that all tasks in your team’s workflow are magical and cannot be outsourced. If that’s how you feel, I’d suggest that you take a deeper dive into how your team members spend their day to day. There’s definitely going to be admin/logistical bottlenecks that benefit from a junior resource or technology—it’s just not obvious.

In the end you may find that scaling/operationalizing processes doesn’t actually require a ton of resources. It just requires re-designing workflows and daily schedule; and perhaps even the org chart.

Good luck!

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I know I haven’t written as much as I used to in recent months. Life and work have been busy! But I thought I’d take a moment to share a few updates on what’s been happening in my professional life. It may not surprise you that in addition to my day job, I have been keeping busy with adjacent projects and creating content—although perhaps in a different format than I have in the past.

Today I’ll share with you the big 3 things that occupy my mind: (1) my new partnership with Stanford Law; (2) my Chief Revenue Officer role at Latitude Legal; and (3) the book about legal sales that I’m working on.

Partnership with Stanford Law

As some of you may have seen on LinkedIn, I recently became a fellow at Stanford Law School! I’m partnering with its fledging executive education program (led by the incomparable Adam Sterling) to develop content and programming to improve lawyers’ business acumen. It all came about when Adam reached out to me a few months ago.

Adam is truly a pioneer in this space. He spent 9 years building up the executive education program at Berkeley Law, and achieved all sorts of recognition and accolades during his tenure. We decided to meet over coffee, and immediately hit it off. All sorts of ideas emerged from that meeting, including building digital content, roundtables, summits, and even teaching opportunities.

We decided to kick things off with launching a video podcast/program that’s eligible for CLE credit. Stanford Law, in partnership with PLI, is launching a series of interviews with academics & industry veterans hosted by yours truly. The show will be called Under Review (with Alex Su), and the audio will be made available to everyone publicly via podcast feeds. For those interested in the full video episodes, it’ll be accessible to PLI members on their platform.

This past Friday, we recorded the first episode down in Palo Alto.1 Our featured guest was Kristin Sverchek, the former President (and former General Counsel) of Lyft. We recorded the content at Stanford’s own studio, which was a really cool experience. I learned so much from the conversation with Kristin that was applicable to my own career, and I suspect it’ll be eye opening for all of our listeners.

In addition to the conversation with Kristin, we will also be including in the episode interviews on topics related to Delaware corporate law and generative AI for teaching purposes. Adam and I will be speaking with Stanford Law professors and academics to have them help explain some of these developments.

Honestly, this whole thing has felt surreal. Years ago when I first joined a startup as a BDR to cold call lawyers, I never imagined I’d end up with this type of opportunity. My original goals were to simple: Do work I enjoyed, become good at it, and work with people I liked.

It goes towards what I’ve written before about unicorn jobs. Follow your instincts on your interests & superpowers, and don’t worry about prestige or status. Do good work and be generous with people. Many of the opportunities I’ve received (including Stanford) came from friends & acquaintances saying incredibly generous things about me behind my back.

I hope my journey is helpful to all of you who are considering making a pivot yourself. Not because you can follow my career path to a T—that would be unrealistic. But to show that the journey often includes unexpected stops and detours but (to quote Conan O’Brien) if you work hard and are kind, amazing things will happen.2

One year anniversary at Latitude

I recently hit my one-year anniversary at Latitude Legal and shared a few thoughts about it on LinkedIn. It’s been an amazing ride and I couldn’t be more proud to work with such a talented team. Not to mention having such incredible support from my CEO, executive team, and the board. I’ve worked at places where I’ve had none of that so I am definitely not taking all of that for granted.

Back when I first started the job a year ago, I wrote a few words about what I thought I’d be focused on, and I thought that it would be interesting to share how it actually worked out. From 12 months ago:

As Latitude’s new CRO, my goal will be to lean on our competitive advantages, and help us take things to the next level by: (1) driving awareness of our offerings via my personal brand and social media audience; (2) supporting sales and marketing by sharing best practices from the legal tech startups I’ve worked with; and (3) help advise on operational initiates to help prepare the company to scale.

Looking back, all of that has played out largely as expected. I’ve felt incredibly supported by our team at all levels of the organization. Scaling systems, processes, and org structure is a lot and I’ve been amazed at how so many members of the team have come together to push it all forward.

Another interesting observation is how things have played out since last year when I explained my thinking about why I was joined a flex talent provider vs. some “hot” legal AI startup. Again, from that same article:

It’s not clear to me who’s going to be the big winner in legal AI. However, it *is* clear to me that AI will have a dramatic impact on the future of legal work and how legal teams are structured. Especially amidst the changes taking place in the industry, where the balance of power in the value chain is shifting to clients.

This has played mostly as expected, although I underestimated how much investor appetite there would be for legal AI startups. Seems like even more startups have come on to the scene with huge fundraising announcements.

Although AI for legal dominates the headlines, it’s still not clear who the winners will be. (I have since learned to be skeptical of fundraising amounts as a proxy for customer traction—some investors are incredibly susceptible to unrealistic narratives & hype)

On the other side of things, corporate clients have increasingly relied on ALSPs (like Latitude, but others as well). Demand for legal work continues to skyrocket and as law firms continue to raise rates, there will be plenty of opportunity for other types of providers that can meet that demand. The evidence isn’t just anecdotal—Thomson Reuters recently published a report highlighting the sharp growth of the ALSP market.

As for me, the next 6-12 months will be dedicated to driving growth to the Latitude. A big part of that is infrastructure—training, data, org planning, etc. But a big part of that is also hiring for specific roles that will help us scale. This is not a novel undertaking—every company that’s reached a certain size has also gone through this process. But I do think for us it will require a unique hiring profile, someone who is experienced in law, but has the right mindset to handle biz dev for a fast-growing legal services provider.

It’s an incredibly exciting to help drive growth through this next phase of Latitude.

Book project update

Last thing—as some of you may have seen a few weeks ago, I’ve started working on a passion project of mine: A book on sales for lawyers. Many of you graciously volunteered to serve as reviewers for the first draft, and after working on the project on and off during nights and weekends—I just finalized the second draft this weekend.

The book’s scope ended up being more narrow than I anticipated when I first wrote it. Instead of being a general guide to sales, it’s about how to run biz dev meetings for lawyers who sell to other lawyers. I realized from the feedback that that’s where I need to focus on for now, and to carve out the rest of the content for a future book.

I’ve also been using this super cool web-based software called helpthisbook to gather highly specific, real-time feedback on certain passages and sentences. It helps me determine where people get lost and confused, or passages that readers find compelling (see screenshot above).

If you’d like to be a reviewer of the book, I would love to get your comments! Just make sure you fit into the target audience as described below.

This book is meant to help lawyers who sell products/services to other lawyers . . . In my conversations with law firm partners and sellers of legal products & services, I’ve realized that many do not run tightly focused meetings that drive towards a revenue-focused outcome. As a result they are disappointed with the results of their activity.

If that’s you, my hope is that this book will help.

A quick note on who this book is written for: Lawyers who sell products/services to other lawyers. That’s the core of my personal and professional experience. So if you’re a general sales professional who sells to the legal industry, or a lawyer who sells products/services to a non-legal audience–the tactical advice in this book may not apply to you.

Then, shoot me an email telling me a little about your background and why you’re interested in the book. Note: I am less interested at this point in hearing from readers who want to “teach” and more interested in readers who want to “learn” if that makes sense.

Once I finish this phase of review I will reach out to subject matter experts to get their thoughts on the substantive content.

Conclusion

Alright this email update has turned out to be far longer than I expected. Thanks for reading the whole thing. And hope you all have a wonderful week!

Until next time,
Alex

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Before I get into why, let me first explain what the essay is about. Cedric’s main point is something like this:

Businesses often incorrectly position their product/service from their own perspective. Instead, they must frame it in terms of their buyers’ wants & needs.

How does this play out in the legal industry? The simplest example is from your classic Biglaw partner who pitches clients by talking about the firm’s resume and credentials. Over the years I’ve heard countless corporate clients complain about these kinds of pitches. The main complaint is that the pitch fails to address what the client actually needs.1

It’s not just Biglaw partners who make this mistake by the way. Legal providers like AI startups, recruiters, services companies, all do the same thing

• “Made by lawyers, for lawyers”

• Backed by [insert name-brand venture capital fund]

• Founded/led by [name] who formerly practiced at [name brand firm]

Now these pitches are not necessarily entirely ineffective. As I’ve written about before, credentials are an extremely useful proxy for quality in the legal world, where outcomes are difficult to judge. However, they are only valuable signals to the extent they cannot be replicated by competitors. Wachtell and Cravath can differentiate based on credentials, the other 198 firms in the AmLaw 200 need something more.

So what exactly is that something more? I’ll share three general strategies below, and use my experience in the legal tech space to illustrate the principles.

Basic: What does my target audience care about?

When I first got into CLM (contract lifecycle management) sales, I quickly realized that my company—Evisort—talked about our offering in a vacuum. All of our marketing material discussed our software’s features but failed to connect it to some key aspect of our buyers’ needs. To borrow Cedric’s terminology, we weren’t sufficiently attuned to demand.

Instead, sales were done in an ad-hoc way based on our founders & early employees’ personal relationships. We led off heavily with Evisort’s credentials (using a variety of the example value props described in the earlier section). Often, that was enough, since we didn’t need a ton of sales in the early days.

But as we scaled, we quickly realized that our marketing message wasn’t landing. There were more and more CLMs coming to market, and many of them used similar language as us. In such a crowded market, how could we find a way to break through the noise?

I ended up stumbling into a solution in a completely unexpected way. This was mid-2020, during the early days of the pandemic, and I was starting to try posting different types of content on social media. I posted a joke video skit making fun of first year associates at Biglaw firms. I thought our target market of in-house lawyers might find it amusing, but probably irrelevant to what Evisort offered.

Instead it was the complete opposite. All the in-house lawyers found it relatable. Many senior decision makers at in-house legal departments were themselves former first year associates. Even those who never worked in Biglaw could laugh about it because they dealt with them as outside counsel.

Eventually, some of these in-house lawyers started reaching out to me for sales conversations about Evisort’s CLM.

This experience made me realize that by leading off with our offering, my company was missing out on a huge opportunity to be relevant to our target audience. Our buyers cared about contracts and CLM, but they also cared about a lot of other things, like exorbitant fees charged by Biglaw firms, or the unique nature of Biglaw recruiting & training.

By talking about something that our audience cared about that was less connected to what we were selling—I was able to cut through the noise and generate sales leads. As Cedric wrote in his essay, “You need to pick a topic that is interesting to your target customer.”

Intermediate: Where else can I find them?

A few years later, after I’d developed a niche following through my social media content, I found myself at a crossroads. I had spent the previous two years getting dialed in on content marketing on LinkedIn for in house lawyers. The problem was that I was starting to see diminishing returns. The word was out and it seemed like every legal tech startup was leveraging LinkedIn/short form video now.

This was around 2022, around the time that things started opening up in the real world post-pandemic. I remember that was the year I started attending live events again, like meetups and conferences. By then I was working at my second CLM company, and had shifted my role from generalist, to more of a specialized marketing role.

What I found “in the real world” was that my key audience of in-house professionals on LinkedIn was somewhat saturated. Most of the people who were online were likely familiar with my Tik Toks and memes. However, there was an equally large audience of in-house lawyers who were not active online, who had never heard of me.

It dawned upon me that this was a critical segment I needed to start getting in front of more. I already understood the profile; they were virtually identical to the typical in-house professional on LinkedIn—they just didn’t spend that much time online. So I didn’t have to do a ton of additional research to make myself relevant to this audience. I just needed to get out there and meet them in the real world.

It was around this time I decided to make a pivotal change to how I approached social media. It became obvious to me that even if I dedicated myself to growing my online audience even more—it would likely produce minimal business ROI. Meanwhile, huge swaths of the in-house community remained unaware of me, my company, and our offerings.

Cedric’s point about the difference between being an effective content marketer vs. effective marketer in general hits home here:

Next, you figure out how to reach customers with those properties. If you are a content marketer, this will look like asking: “now that I know my target audience (i.e. folks with similar properties to our best customers) what do they read?” And then: “let’s plot a content schedule around that.”

. . . Hmm, interesting. Maybe these folks don’t read. Never mind. Where else can I find them?” This might be specific conferences, or ads in airport terminals, or LinkedIn cold outreach, or specific types of podcasts. You can then spin up tightly scoped initiatives — with small budgets! — for those channels.

Advanced: What segments of the audience are best for us?

This final piece will be highly anecdotal and a bit complicated. I’m still trying to figure out how to articulate it—in fact, it’s a growth area for me. The goal though, is fairly simple: How do you specifically target potential buyers with the highest likelihood of being valuable to your company long-term?

I’ll share a story from my Evisort days that helps illustrate the concept. Some background first: Evisort’s product strengths (at least in 2020-21) were in post-signature contract management. We were not good at pre-signature, ie. streamlining the approval/collaboration process of getting a new contract signed. Instead, we were strong in identifying what was in your executed contracts automatically (using our proprietary AI).

So when we marketed ourselves to buyers as a “CLM” we often pulled in two unique segments: (1) pre-signature prospects and (2) post-signature prospects. The second group had shorter sales cycles, larger average deal sizes, etc. It quickly became obvious that the second group was a much better target for us.

But how could we market to them effectively? By talking about our offering in the language most familiar to us we were obfuscating our true value. Telling in-house lawyers that we were a “end to end CLM” was counterproductive because it funneled buyers into evaluating us where we were weak. On the flip side, telling them that we were primarily a “post-signature CLM” was confusing because it was vendor-centric language that was unfamiliar to the buyer.

I’m not sure we ever came up with a complete solution to this conundrum. However, in the months before my departure (to Ironclad, the second CLM company I worked for) I started to see some opportunity. For example, instead of using “post signature” language in our marketing, we could say something like “are you tired of missing auto-renewing contracts?”

Missing auto-renewals was a huge problem for our target audience. These were understaffed legal teams that were increasingly relying on software subscriptions that they’d planned to cancel but instead accidentally let lapse. Because they had auto-renewal clauses, the buyers’ company would be on the hook for 5 to 6 figure annual contracts they didn’t need. Legal would often get blamed.

I didn’t realize how potent this messaging was until we sort of stumbled into it. One of our paid ads led to an unusually large deal that closed unusually quickly. It just so happened that the buyer was one of my customers, so I took some time to better understand how they found us and why they moved forward quickly.

And it ended up being the exact fact pattern above. The company had accidentally auto-renewed on a massive subscription contract, which led to the CFO greenlighting a huge budget for CLM.

A few months later I ended up leaving Evisort so I don’t know if they ever fully leveraged this learning. The marketing team was stretched thin, and was being asked to do a million things by the executive leadership team. I’m not sure if they ever had a chance to dig in deep into stories, anecdotes, and data.

Conclusion

All of this stuff is hard! Sales and marketing can be complicated and often involves so many details, data points, and incomplete data. However, you can overcome a ton of challenges if you just focus on the demand side of the equation—instead of focusing on your offering.

For anyone who’s interested in generating more revenue or business for themselves or their organization, I highly recommend checking out Cedric’s essay. I’m also a big fan of his other work around career moats and business.

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How law firms do it

Expanding your corporate brand will lead to lots of good things. You will sell more services/product; retain more clients/customers, and have an enormous recruiting advantage. However, in the beginning of your journey, you likely have an unknown corporate brand and cannot solely rely on it to produce all of these good things. Instead you have to borrow from the collective personal brands of your employees.

That’s how law firms built their own brands over decades. There were specific individuals within those firms that, by sheer force of will, put the firms’ corporate brand on the map. I often cite Wachtell as a classic example of a distinct law firm brand; in the beginning they were completely unknown and had to rely on individual partners’ reputations.

Over time Wachtell was able to build a unique position in the market. They’re known to recruit only top students from top schools; to have their attorneys work insanely long hours, but have the chance to do extremely high level work; to compensate their people more generously than almost every other firm out there. But in the firm’s early days that wasn’t there; instead, it was all about the specific individuals who were part of the firm.

The word “Wachtell” meant nothing to clients.

This is a long way of saying, building up an institutional brand requires the organization to place focus on individuals. There is a very specific reason why that is. Which brings me to my next point.

Transferred trust

An organization’s reputation is built bit by bit over a long period of time, based on unique experiences of their clients and employees. However, until the brand is established, the organization must rely on the reputation of its people—employees for companies, and partners/associates for firms. Clients and new recruits cannot fully process the quality of the organization, but will make snap judgments and assumptions based on the people who are associated with it.

This is exactly how I size up Biglaw firms. It’s not the best way to evaluate brands, but I always think back to which of my law school classmates ended up going where—and impute their reputation to the firm they joined. I hate to admit it, but these brand associations last for a really long time—even if they have limited basis in reality. I still judge Kirkland by that one guy they hired as a summer back in 08.1

The same is true in legal tech. When I first started selling e-discovery software, the vast majority of our buyers had not heard of our product. However, some of them had favorable views of Logikcull because they saw that I worked for the company. “If Alex joined, he’s probably looked at the pros/cons of the tech, and it’s probably decent,” they thought.

They made this assumption because they just don’t have the bandwidth to investigate 100% of the information out there about Logikcull. Lawyers are busy, and they have a lot going on in their lives. So it’s super easy to just rely on this “transferred trust” to make quick decisions. Some of them needed e-discovery software, shot me a DM, and were able to get up and running without needing to undergo a lengthy evaluation process.

My friends knew that if the product ended up being terrible, they could always call me out on it directly. And most importantly, they knew that I knew that as well. There is a level of accountability here that doesn’t exist if the institution doesn’t live up to its promises.2

Conveying trust beyond your friends

What I wrote above holds true even beyond your immediate social circle. As a salesperson, I quickly realized that the number of personal connections I had was limited. It was rare that one of my hundred or so friends needed my product. However, my friends knew even more people, ie. my second degree connections, who might have a need.3

As a result, most of my sales came from that second concentric circle of my network. And the approach I took there was slightly different. I couldn’t merely rely on my personal reputation; I had to communicate that I was trustworthy. And the best way to do that was to convey that the buyer and I had shared values.

Conveying shared values requires more than just saying a few magic words. It requires you to quickly demonstrate them. For lawyers specifically, you need to convey that you are detail oriented and responsible. That you have a healthy respect for their limited, non-billable time. That means you have to start/end meetings on time, send typo-free emails, and respond to their inquiries quickly—even if it’s just to confirm receipt.4

The most interesting thing was that my managers failed to grasp this concept. They thought that all I had to do was to lead off my sales meetings by telling clients that I had a law degree, and the rest would take care of itself. I was trained to make lots of small talk with the buyer before diving into business.

My well meaning managers simply did not understand our potential clients’ values. Some of them came from the HR tech industry where buyers prioritized different values, like friendliness and personal rapport. As a result, many of my sales colleagues lost their buyers’ trust within minutes because all they did was talk about sports and the weather instead of getting to the point quickly.

What was really happening was that our sellers were sending the wrong message; that Logikcull did not respect their clients’ time. They were not equipped to serve as ambassadors to our target audience.

Ambassadorship

This brings me to my final point which I think is a critical one. You have to remember that your client facing employees are ambassadors to the markets you serve. Corporate/firm leaders have to be incredibly careful about who they select to serve as an ambassador, because you can send the wrong message.

I’m reminded of a specific contracts tech company (Acme) who chose the wrong ambassadors. It was a competitor of Ironclad so I spent a lot of time thinking about it. Essentially, Acme sold to legal but focused their hiring on “sales bros.” While they were able to land some quick deals, Acme quickly lost trust among many GCs/CLOs because these sales bros used high pressure tactics that do not work in this market.5

Ironclad, on the other hand, took a more nuanced approach. Their client facing people were either lawyers, from the legal industry, or were more thoughtful analytical types vs. action-oriented sales bros. You won’t be surprised to hear that this approach was highly effective. Yes, some deals were lost in the short term because Ironclad sales team members avoided high pressure tactics. But over time, the corporate brand became known for quality and client-focus, which led to long term success in sales/recruiting.6

It’s rare for legal AI startups to recognize this concept of ambassadorship. One company that seems to understand it well these days is Harvey AI. They have been hiring ex-Biglaw lawyers to serve as strategic sellers. It probably doesn’t escape them that their potential clients—most of whom are either working in Biglaw or *used* to work in Biglaw—will notice. Harvey’s client facing employees are very likely serving as effective ambassadors to this audience.7

Conclusion

Now that I’ve shared some principles behind how to bootstrap an institutional brand via your people, what takeaways are there for you, as a stakeholder or leader of a firm/company?

• Decide who you want to serve. Instead of thinking about who you want to hire first, start with figuring out which communities you want to target. This is a highly nuanced, strategic decision you have to make up front. Do you want to go after the “high end/luxury” segment of the market? Or do you want to go after the “innovator/misfit” segment? How is your target market structured, and is there an order of operations that makes the most sense? (For AI startups, may want to consult the technology adoption curve and map out your buyer personas to it.)

• Find the right ambassadors. Once you figure out which audience you want to evangelize to, you have to select the right people to carry the message on your behalf. The most effective ambassadors may likely look and act very differently from you. Because their shared values line up with your target audience instead of your firm/company. That could lead to organization indigestion, so you have to be careful when you choose. On the other hand, someone who is *too* similar to your existing culture will likely be ineffective at reaching your target audience.

• Expand your definition of what works. If you’re attempting to reach new audiences, you have to temporarily suspend your own conclusions about what is or isn’t effective. My old sales managers could not comprehend that the tactics used in HR tech sales were very different than what we should do when selling to time-constrained lawyers. Once you’ve chosen your ambassador you have to give them the freedom to guide you on the best path forward. Now you do need some type of objective measure to evaluate whether they are carrying your message across. It can be metrics/KPIs tied to your other organization goals. Whatever it is, make sure you give your ambassadors enough time and freedom to be successful.

Best of luck my friends!

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Game Selection describes the act of making a deliberate decision about where you work and what you do. The goal is to find an environment where you have unfair advantages. If you’re a high achiever in the wrong environment, at some point you will reach a place where you have no competitive advantages—because every day you’re going up against other high achievers who look/act just like you. It’s incredibly hard to stand out playing that kind of game.

The principles I share today are applicable beyond individual career development too. CEOs of companies and Managing Partners of major firms all need to make sure they’ve chosen the right game for their organizations. Unfortunately, many leaders don’t realize this and instead of approaching Game Selection thoughtfully, they instead choose games by copying their competitors or prioritizing short term considerations.

My goal with this article isn’t necessarily to provide a full explanation of how to approach Game Selection properly. That’s a deep skill that takes decades to master. My aim today is to share a few examples and insights about Game Selection from my own experience that will hopefully illuminate some of the considerations you might want to take into account—both for your own career and the organization you lead.

High Achievers Playing The Wrong Game

Before I get into explaining the the whole concept, I’ll illustrate two made up examples of high achievers who struggle to “make it to the next level” due to poor game selection:

• An in-house lawyer with exceptional legal acumen struggles to be taken seriously by the executives at his high growth consumer startup. All they want is for him to rubber-stamp vendor contracts, but he sees risks everywhere. The in-house lawyer has a knack for identifying unexpected second or third order effects of otherwise innocuous legal positions and has helped the startup dodge several major risks. Instead of appreciating his value, the startup’s execs dismissively refer to him as “the department of no.” This in-house lawyer would do far better at a company with large sales contracts in a highly regulated industry, where his talent for seeing “ahead of the curve” would directly contribute to his organization’s top objectives.

• A superstar law firm associate struggles to make equity partner. She spends the first 7-8 years developing/mastering the core skills of her practice area—and yet the firm refuses to promote her to the partnership. The associate is informed that her lack of confidence around clients is what’s holding her back. The firm’s clients are mostly in a conservative industry where all interactions with outside counsel are extremely formal. The associate—who has a casual, direct style—is constantly nervous that she’s going to say something wrong in that environment. She would do far better at a firm serving the technology startup or venture capital industry, where her professional style matches the clients’ corporate culture.

In each of these examples, both lawyers are highly competent and would do just fine in their existing environments. But they would likely be interested in moving up, and in doing so—would be tempted to change something fundamental about themselves. High achievers are big on self improvement, so the natural tendency is to do things differently. Maybe they decide to make even more personal sacrifices and work harder.

What if there’s another way?

The Upside Of Switching To A Different Game

When you find the right environment it will feel like a breath of fresh air. That’s because when you’re in the wrong environment, you are absorbing all sorts of subtle rules/values that conflict with your personality and strengths. As a result you develop coping mechanisms that weigh on you. For example, I spent a couple of years working at a large, conservative law firm. I thought I did okay—after all, my performance reviews were pretty decent.

At the same time I could tell that something was weighing on me every day I walked into work. I didn’t realize it then, but I had developed all kinds of coping mechanisms to fit myself into the organization. I am not a naturally detail oriented person; I tend to move/act quickly, which can lead to mistakes. So as an associate, I would re-read my emails 10x and even print them out to review them for typos. Doing all this was incredibly taxing and I would be drained after just a few hours of work.

Meanwhile, the real talents I felt I had—socializing with new people, making jokes on the Internet, and public speaking—were all repressed. I mean, yeah I could occasionally post on my personal Facebook or speak at law schools. But none of those things directly contributed to my professional advancement. I had to fundamentally change who I was to fit in and potentially move ahead.

I didn’t fully appreciate how much I repressed until I joined a startup. Suddenly all of my talents were fully aligned with my organization’s top goals. I was able to lean on my natural tendency to move/act quickly. I had shifted to a sales role, which meant engaging with people and public speaking all the time. And somehow I found a way to use social media to make sales prospects laugh (and accept cold requests for meetings) leading to an unfair advantage in my career.

Having this strong alignment between my personality and my organization felt great! But more than that, it helped me avoid some aspects of professional life that I absolutely hated. For example, I did not have to gain credibility by constantly promoting my credentials. Nor did I have to play office politics to get ahead. Being a natural fit for my company meant I was good enough to almost avoid playing those games. Had I struggled in the core aspects of my work, I would’ve certainly had to play up my own credentials & play politics.1

Don’t Copy My Strategy

I know I just wrote a bunch of stuff that makes working at startups sound perfect. Maybe some of you are thinking of copying my own move and leaving the practice of law to become a salesperson at a startup too.

Don’t do it!

Blindly copying my approach would be a mistake. In fact, working at a startup can actually be a terrible experience. Your company has zero brand, so you will constantly find yourself struggling to explain what you do to friends & family. Leadership will constantly change directions, and it will feel impossible to see any initiative all the way through. Salary and benefits will likely be worse than if you worked at a mature company.

Sales is also a very difficult job. You spend virtually all of your time begging people for meetings, and the vast majority of your conversations will lead to zero revenue. Meanwhile, your value is tied to how much you sell, and that number resets every week, every month, or every year. Most potential buyers will have zero idea of what your company offers, or what your product/service even does.

I say all of that to dissuade you from copying my exact move. Remember, the whole point of this article is Game Selection, which means you have to choose based on your own skills, talents, and personality. My own career pivot was made during a very specific period of time (in 2016, when cloud technology for e-discovery was in ascendance) and was designed for a very specific personality (me) and mix of assets on my career balance sheet (firsthand experience as a junior-to-mid-level litigator).

Unless all of these factors line up for you, it’s very likely that you will need to make your own choice about what game you should play. Maybe it is with legal startups; but maybe it’s going to a non-profit or government agency. Maybe it’s something creative or completely outside the business world. Whatever it is, it has to be your own choice that’s highly tailored to your unique circumstances.

That’s what Game Selection is all about.

Path Dependency

Like it or not, the game you choose will be heavily influenced by your past decisions. For example, my pivot to legal tech startup sales at the age of 33 was based in part on the fact that I had an extensive network of lawyers and several years of industry experience in the legal field. In other words, my own Game Selection decision in 2016 was overwhelmingly influenced by my decision to apply to law school back in 2006.

If I could “do it all over again” I’m not sure I would end up where I am now. Knowing what I know now about my personality and the world, I might have chosen something completely different coming out of college. Maybe I would’ve gone to a fintech startup, explored the crypto world, etc. I doubt I would’ve ended up in e-discovery software, CLM, or flex talent. Now that doesn’t mean I ended up in a suboptimal place; maybe my relative quick ascent in the alternative legal career path is directly connected to my exposure to Biglaw and having attention to detail hammered into my brain.

Path dependency plays a huge role in Game Selection. The more subtle point here is that you should not choose a game based purely on the optimal choice in a theoretical sense. In 2024, being a data scientist may be the optimal career path for a new college grad. But that doesn’t mean you should pivot to data science if you’ve spent the last 10 years doing M&A. Instead, maybe it makes sense for you to do corp dev in the AI space. Starting from zero—as if you had no work experience whatsoever—would be a big mistake.

This is why it’s so important for you to have a full understanding of what you bring to the table. Otherwise you will be swayed into making decisions based on trends and what the latest hot thing is—and end up worse off than where you started.

Business Applications of Game Selection

What’s true for individuals is also true for organizations. Take a typical successful startup as an example. Maybe they spend several years growing revenue hyper-fast while serving a niche market very well. Then one day they realize they’re starting to plateau. To continue to grow they will have to do one or more of the following: (1) focus on larger buyers in the niche, ie. move upmarket; (2) create new products/services and sell to the same buyers, ie. increase ASP; and/or (3) sell their core offering to an adjacent market, ie. expand TAM.

How do CEOs and their boards make the right choice? It’s incredibly hard. For example, I often see startups making poorly thought out decisions. Maybe they try to mimic the path of some other market leader in their niche. Or maybe they make decisions based on short term financial considerations, like boosting the valuation for an upcoming round of funding. Incidentally this seems to be why all legal tech startups are embedding generative AI into their offerings regardless of whether it makes sense; my sources tell me it helps increase valuation.2

To be clear, I have no idea what path these startups/companies should take instead. If I did, I’d become a CEO myself and make millions! But from what I’ve observed, startup leaders sometimes lack self awareness about what makes their companies unique. I’m not just talking about the product and the people; I’m also talking about the org chart and existing customer base. It’s the corporate version of what I said earlier—you have to take stock of where you are today. You cannot ignore path dependence.

Case Study

I’m reminded of a very specific example I witnessed several years ago as an early employee of Evisort. The founders had created proprietary AI designed to read existing contracts and tag specific clauses automatically. It was all super impressive. However, they made a strategic decision after they raised a Series A to move in a surprising direction. Instead of doubling down on their AI’s “post-signature” capability, Evisort decided to divert its energy towards the creation of a completely new “pre-signature” offering that helped manage contract approval workflows.3

On paper this was a shrewd decision. If you could manage both pre and post signature aspects of contracting, you could double your average sales price (ASP) and potentially own the entire workflow. Plus, Evisort’s biggest competitor at the time, Ironclad, had an outstanding pre-signature workflow product that customers loved.4 And perhaps even more importantly, Ironclad had just gotten a huge revenue multiple on its most recent round of funding. If Evisort could successfully copy Ironclad’s approach, that could potentially lead to dramatic revenue growth & valuation/multiple spike.

Or so we thought. In reality, building a pre-signature workflow was incredibly difficult. It was buggy and lacked key features. Plus, it wasn’t a natural fit for our ideal customer profile, which were largely big companies with lots of old contracts that needed analyzing. (Notably, Ironclad’s customers at the time were mostly startups, for whom contract approvals for sales agreements were of the utmost importance.)5

Maybe this is all a bit of Monday morning quarterbacking. But I distinctly remember having these thoughts while watching all this play out in real time. Evisort first made a splash in the market specifically because its founders were lawyers and data scientists who spent years building a robust AI engine. That founder profile/initial product led to specific choices and tradeoffs made in feature development and org chart design in the early days. It made little sense to copy what worked for someone else, without taking into account the events that led Evisort to where it was.

In my mind, the better decision would be to double down on the post-signature AI capabilities and find use cases beyond the legal vertical, like procurement or finance. They could also laser-focus on larger companies and their specific needs, like being able to index/tag industry specific clauses. Not much would need to change from a product development or sales/marketing perspective—so operational risk would be minimized. I don’t know if going that way would’ve ultimately been successful, but it probably had better odds of success.

Instead they chose the wrong game and likely burned lots of time/resources trying to compete in a place where they had few natural advantages.

Note: Several years later, Evisort was eventually acquired by Workday (Which I wrote about here.) If you take a look at the press release and media coverage, all of it focused on the “contract intelligence” or AI functionality. There is minimal mention of contract workflows. That should tell you all you need to know about whether that initiative succeeded.

Takeaways

Okay so I just spent nearly 3,000 words trying to explain Game Selection. I bet you’re wondering, what does this all mean for me? Here are a few key lessons/thoughts I hope you’ll take away with you:

• Is it time to change the game you’re playing? If you’ve been successful at something for a while, but suddenly feel like you’re hitting a plateau—it may make sense to change environments. Now, it’s possible that you can push past the plateau through skill development or executing better. This is definitely true if you’re early career, or still adjusting to a new environment.6 But that’s why I’ve added the qualifier “if you’ve been successful at something for a while.” That presumes that you have continued to improve and do well, and that now you’re hitting a wall. This is especially true in scenarios where there’s a lot of competitors. In those instances, working even harder is unlikely to get you the results you want.

• Do you know what makes you special? Make sure you take everything into account—including personality quirks, network & contacts, and work experiences. Don’t forget to take path dependence into account. Have friends complimented you for something throughout your entire life? Are there certain tasks that you find easy that other people inexplicably struggle with? Are there certain types of obstacles that bother others, but not you? Understanding what sets you apart is the first step in finding the right game to play.

• Are there “frontiers” where market dynamics are rapidly changing? All things being equal you want to be at a place where you don’t have to “wait in line” to prove yourself. In mature, established industries and sectors, there’s a lot of paying your dues. But in uncharted territory, everyone’s constantly trying to figure things out. Even in a relatively mature industry like legal, there are niches and pockets of activity where no one really knows what’s going on. If you can apply your superpowers there, you can really accelerate things.

• For managers and executives: Is your organization playing the right game? Are your people assigned to the right kinds of work? This is a super complex topic because there are so many moving parts and constantly shifting dynamics. But as an organizational leader, it is incumbent upon you to make sure employees are assigned to tasks they’re suited to doing, and that the ship, so to speak, is headed in the right direction.

Hope all this has been good food for thought. Best of luck my friends.

Today, I’d like to expand upon his ideas and talk more specifically about how they apply to the legal industry—and specifically, to practicing lawyers. We’ve always heard about how Biglaw partners use leverage, ie. associates, to generate vast amounts of wealth. That certainly is one way to do it.

But a lawyer’s job—whether or not they work at a firm—provides many other opportunities to use other types of leverage to have a huge impact. In this article I’m going to share the 3 main types of leverage; describe a few classic examples of lawyers using that kind of leverage; and explain the rising importance of skill & judgment. I will draw upon examples from what I’ve seen and observed during my own career.

Before I get into it, I think it’s important to highlight that you don’t have to use leverage to have an impact. Many lawyers take a craftsman/artisan approach to the work and serve their clients extraordinarily well. The goal with this article, and my discussion of leverage, is to share how to use your limited time/energy to have the biggest impact possible.

Astute readers will also recognize that having a larger impact also often translates to more autonomy and compensation. Again, that may not necessarily be what all lawyers optimize for in their careers—and that’s ok.

With that disclaimer out of the way, let’s talk about the first source of leverage.

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Any startup focused on legal AI needs to recognize that the legal ecosystem is very unique. It’s made up of a bunch of different players with no analog in other industries. It’s not just licensing/bar exam requirements, or the profession’s obsession with gatekeeping work via unauthorized practice of law rules. It’s also a combination of industry quirks that make it impossible for outsiders to disrupt all in one go.

Don’t get me wrong: There will be plenty of disruption in minor pockets of the legal industry. The move to the cloud was not the sexiest of trends (compared to this wave of AI hype) but it definitely transformed a lot of the way lawyers handle contracts, e-discovery, and more. Historical examples abound, like when email or legal research databases came on the scene.

There is no question that legal will be disrupted by tech.

Having said that, my sense is that investors and tech startup founders dramatically overestimate their grasp of how the legal ecosystem operates. Any time a VC/founder has a bad experience with a law firm, they suddenly become motivated to disrupt legal. In fact, that’s Atrium’s founding story.

As a “power user” of legal services over a decade in the startup industry, through the foundation and fundraising of startups like Justin.tv as well as the work he’s done as an investor and advisor to companies through Y Combinator, Kan says he was frustrated by how little technology was being used in the process of interacting with various law firms. (Source)

And as we all know, Atrium—despite it’s huge backing from VC investors, ended up flaming out spectacularly.

Why did that happen? There are a lot of reasons, some of them generalizable, some of them not. But overall the Atrium story does illustrate a common phenomenon in tech circles: Outsiders dramatically underestimate the difficulty of transforming the legal industry’s workflows, and overestimate their own ability to replace lawyers.

In today’s article I’m going to share a few truths that most industry insiders are already aware of but outsiders might not be.

1. High hourly rates are not as big of a problem as they appear

So many legal tech startups are founded under the premise that law firms are too expensive. Most of the discussion revolves around absurdly high hourly rates charged by the largest firms. This is usually presented as the market opportunity: If some $30k/year tech subscription can potentially handle 90% of the work a $1,000/hr second year associate can handle—what client wouldn’t immediately jump on board?

Quote from the TechCrunch article covering my first legal tech startup’s Series A:

The company charges per user, and a small law firm can expect to pay $15k-$30k per year. Expensive yes, but not if the alternative is paying hundreds of extra hours in legal fees at $600 per hour.

Without getting into the specific reasons why law firm services are uniquely valuable in the ecosystem (more on that below) there’s a simpler reason why this is not a problem. Clients generally *do not* have a problem paying those rates. If they’re paying a junior $1,000/hour, they’re likely also paying for a $3,000/hour partner who’s worth far more than that rate.1

Clients aren’t dumb. They look at the whole bill. And when you have a $2 billion matter, you find the best damn law firm you can and pay them whatever they want. Because at that point, paying $20 million or $30 million doesn’t matter; it’s just a rounding error. How the firm decides to allocate the cost is irrelevant—the real question is how much did the whole thing cost relative to the legal exposure involved?

Now it’s true that not all firms get asked to handle these types of matters. Only a select few are tasked with handling bet the company litigation or high stakes M&A. However—all other firms, the ones who handle more routine matters—are *not* in fact charging absurd rates. There, the story is reversed, where clients are pushing back hard on rates.

Doesn’t matter if it’s $300/hour for a junior or $600/hour for a partner. These rates may seem crazy high when hiring an attorney for ourselves—but that’s not the right comparison to make. For corporate clients, that’s not a lot—in fact it may translate to $30k-$100k in legal fees, which is completely fine for routine matters involving millions in potential legal exposure.

Key takeaway is that the absolute amount of legal fees doesn’t matter. The only thing that matters is how much that is relative to the total potential legal exposure. How much you’re paying per hour for each individual lawyer matters even less.

2. Law firms hold a unique position within the legal ecosystem

Another reason why corporate clients are willing to pay outside lawyers so much is because law firms provide more than just the work. They provide the imprimatur of a professional services organization with a gold standard reputation that’s been around for decades if not centuries. It’s similar to why companies will pay consulting firms like McKinsey a heavy premium—it’s not just for the work product itself.

I think most people who lack familiarity with the legal industry are totally unaware of this dynamic. They view law firms similarly to say, a marketing agency that processes work. They think that if technology can replicate 90% of what the outside agency (or law firm) does, at a fraction of the cost, clients will throw themselves at the tech.

That’s just not how things work in the legal industry. Law firms are incredibly unique players in the legal ecosystem because:

• First, law firms solve highly ambiguous problems. To use the earlier example, marketing agencies often operate in relatively unambiguous environments. They run ad campaigns or create landing pages. These are not novel problems that require novel solutions. The work is straightforward. They either solved the problem and did a good job, or they didn’t.

  
  Law firms, on the other hand, don’t have such clear cut standards. It’s often hard to tell whether the firm’s lawyers made the right decision. When the client settles a case—could it have been settled for more or less? When the client receives a memo suggesting a well thought out course of action—how can you be sure that there’s a better alternative?
  
  This ambiguity is why the legal industry also focuses so heavily on signals or proxies for quality. It’s why we, as lawyers, are so obsessed with law school and law firm pedigree. We can’t really *tell* how good something is, so we look at the surrounding qualities. It’s why big firms focus maniacally on the details. If you can’t get the little things right, the thinking goes, how can you convince your clients that you can be trusted on the big things?

• Second, corporate legal buyers by and large come from law firms. Every big shot Chief Legal Officer or General Counsel likely started off their career at a large fancy law firm. These firms spend a lot of resources and branding efforts to convince their employees and clients that they are top notch. See, e.g. the existence of summer associate classes, which are less about recruiting and more about brand marketing.
  
  Could you imagine what it would be like if Chief Marketing Officers all went to marketing school and started their careers at a handful of top marketing agencies that spent millions of dollars every year convincing themselves that the agency’s full of amazing marketers? I’d be willing to bet that those agencies would hold a special spot in the marketing ecosystem.

Add up both of these factors, and you start to understand why law firms have such a stranglehold on corporate clients. And to be completely fair to the law firms—it’s often completely justified. Law firms are full of extremely talented lawyers who aren’t just good at the work itself—they also have strong decades-old reputations. Which means there’s a level of accountability that a hot new AI startup doesn’t have.

Which leads me to my final point.

3. Trust matters a lot more than efficiency

This is the one thing that startups could really learn from law firms. Because of the nature of the work, law firms have to be trusted by their clients. Trusted not to merely do good work, but to also do right by them. There are all sorts of professional standards, ethics, and rules that govern the interactions between lawyers and their clients.

The startup world, on the other hand, is like the wild west. I don’t mean that in a purely bad way—in fact, I’ve found that personally, I fit in much better at startups. However, there are some things about the wild west I don’t particularly like—and I suspect corporate clients don’t like either.

There is far less accountability to clients/customers in startupland. People who run and work at typical startups often view themselves as outsiders to the industries they serve. They feel like they belong to the founder community, or the venture capital community, or the tech sales / customer success community. They are often more interested in building long term relationships with their own industry peers—as opposed to building those relationships with their clients.

Now this is definitely not always the case. Many founders and employees are legal professionals themselves, and feel a strong connection with the legal ecosystem. Many founders and investors are lawyers as well. Plenty of successful startups have built strong long term relationships with the community they serve.

However, I’ve seen a lot of bad behavior over time. Like overstating product features to buyers just to get the deal done. Or lying to prospects about the product roadmaps. I have seen this bad behavior from startup people who are lawyers and non-lawyers alike. I think at the end of the day, these people do not care, because they believe that these customers/clients are not people they have to do business with in the future.

So when you have startups engaging in this kind of behavior, legal buyers naturally exercise a ton of skepticism. Whether it’s a law firm buyer or an in-house legal department buyer—everyone’s been burned enough times to know you have to keep your eyes wide open. Or as one potential client said to me at a legal conference last week: “I know you’re going to tell me how great you are—let’s see if your clients say the same thing.” 2

For startups that do want to do right by their buyers—I would recommend this: Tone down on the talk tracks around efficiency, and ramp up the talking points around trust and accountability. Legal buyers will find your candor refreshing—and who knows? You might be able to convince them to sign on the dotted line faster than you otherwise would.

Conclusion

If you’re a legal AI startup founder, employee, or investor—sorry if I’ve offended you! My hope with this article is to convey what legal buyers care about, and why this space is unique and different from other industries. Starting and running a company, or working on the front lines of a startup, all while creating new technology is a tough job. Please don’t get swept up in the disruption talk and make your own job even harder.

Personally, I truly believe AI will change the legal industry for the better. I’m already starting to see it in a lot of places. Usually from technologies focused on solving real problems and products that appeal to law firms/legal departments instead of investors. Sometimes the startups that take this route have a longer journey, with a lot more bumps on the road.

But in the legal industry, longevity matters. Trust and reputation matters. So as long as you do right by your clients, you will end up just fine. Even if it takes a little bit longer than you expected.3

Part of why I’m writing about all this now is because of a particular type of reaction from people when they hear I left the practice of law. They think it was driven by courage or bravery. Often it’s because they’re putting themselves in my shoes, and feel an enormous amount of anxiety around possibly leaving the law themselves.

So anyone who made the leap was somehow able to overcome it. Or so the thinking goes.

But the real reason I ended up making my career pivot had nothing to do with bravery. By the time I left law, I had already suffered through several setbacks—including getting fired and failing at entrepreneurship—and was just looking for a quick win. Anywhere. That’s what led me to join a startup at a fraction of the salary.

The upside of my “bold” move though, was that it gave me the chance to start over, completely anew, without the mental burden or baggage of having my personal identity tied up with being a lawyer.

My goal today is for me to share with you what else was happening in my life that led me to make the change. Spoiler alert: There was no grand plan. Whatever happened, it was far less about bravery and far more about me scrambling to figure out my next steps.

And it all happened because of unique situational factors that took place in my personal life between 2010 and 2015.

This is my story.

The Beginning: Why I decided to be a lawyer

To get a full understanding of how I ended up in law, you have to understand where I came from. My parents are immigrants who struggled with the culture shock and language barrier in their new country. To overcome these challenges they worked insanely hard. Like, all the time. So when I was born, they had such high hopes for me.

My parents could not comprehend how someone who was born in the U.S. without the language/culture challenges they faced—could possibly struggle to do well in school.

But that was me. From elementary school and on, I was a mediocre student. There was a perception that my problems were caused by a lack of work ethic, which was understandably maddening to my parents. Even I believed it. Looking back now, I can see that a lot of it was probably due to ADHD.

In any case, struggling in school led me down a path where I became far more interested in hanging out with friends than getting good grades.

At some point my mentality changed. During my junior year of college I realized that I was tired of being an underachiever. I matured and became more aware of the many sacrifices my parents made to give me the opportunities I had. As a result I decided right then and there to reinvent myself as someone who took his future seriously. I thought that would make my parents proud.

That underlying feeling is what ultimately led me to apply to law school.

Law school gave me the chance to reinvent myself

Don’t get me wrong, wanting to make my parents proud wasn’t the *only* reason why I wanted to be a lawyer. I thought going to law school would make me articulate, polished, and potentially rich. I mean, I didn’t actually know any lawyers but my perception was that it was a fantastic career.

Plus, if I could end up at a top school and work for a fancy firm—that would overshadow all of my academic struggles growing up. As cheesy as it sounds, law gave me a path to bring honor to my family and make my parents’ struggles worth it.

Problem was, I already had terrible college grades which meant it would be very difficult to get into a top school, which would make it nearly impossible to land a fancy pants attorney job at one of the big firms. I was super determined though. And ended up spending a few years locking down, raising my GPA, working/studying for the LSAT, and doing whatever it took to get in. And in the end—it worked!

I got into Northwestern Law.

From that point on I tried to reinvent myself. Right before 1L year started I decided that I’d be a law school superstar. Problem was, you can’t just develop good study habits overnight. It was a struggle to outline and prepare for exams. But I persevered, making law school my life’s top priority, and put everything in my personal life on hold.

It wasn’t easy, but it worked. My resume/grades were strong enough to give me an outside shot at some of the country’s top law firms, and once again, I found a way to hustle/talk my way into opportunities. The summer before my second year, I secured a summer associate offer from Sullivan & Cromwell. I felt like I finally made it.

Of course, I never imagined how I’d feel once I actually started the job.

Realizing that I might have made a mistake

As a summer associate I quickly realized that I just didn’t enjoy the work. Like, I loved the idea of being a summer associate at such a great firm. And I was proud to tell people where I worked. However, spending all those hours actually *at* work was a different matter.

As a summer I sought out real assignments and substantive work (this was during the Great Financial Crisis, so we were all trying to work hard to ensure full time offers at the end of the summer). I got a taste of the work and found that I kind of hated it.

However, I couldn’t imagine leaving to do something different. Certainly not as a summer. So I kept pressing on and did what I was supposed to do: secure a full time offer at the end of the summer.

Something should’ve clued me in that I was headed down the wrong path when, as a 3L, I asked S&C to extend the deadline for my offer so I could apply for a job at the Manhattan DA. After a couple of interviews, I got cold feet, and ended up withdrawing and accepted the S&C offer.

Around that time something else happened that influenced my decision: I met a girl and I completely fell for her. Problem was, she had two more years of medical school in Chicago, which meant we’d have to do long distance after I graduated.

I came up with a long shot plan. Could I somehow figure out a way to land a one or two year judicial clerkship in Chicago? My firm told us that if we ever left the firm for a clerkship, we would always be welcomed back afterwards.

I couldn’t believe my luck when I found out that this one AUSA I admired (and met at an APALSA event) had just been nominated to the federal bench. It dawned upon me that there was a possibility that everything could work out perfectly—if I could convince him to hire me as a law clerk.

Tension between my professional goals and my personal life

I ended up getting the clerkship. There’s an entire story behind it that I’ll write about someday.1 But basically I was the luckiest guy on earth. Not only did I land a clerkship I felt barely qualified for—it fit in *perfectly* with my desire to be nearby my new girlfriend.

I spent 20 incredible months clerking for my judge. It was the best law job I’ve ever had, hands down. As the clerkship came to an end, I was faced with yet another decision. Where should I work afterwards? Should I return to S&C or try to find another job that I might like better?

My immediate reaction was to go somewhere else. I ended up re-interviewing with the Manhattan DA, and also interviewed with a top-end plaintiffs’ class action firm in NYC. But then something unexpected happened.

My girlfriend, who I thought would do her medical residency in NYC unexpectedly matched at a hospital in California. Once again I was faced with a decision point. What should I do next?

To be quite honest, I wasn’t ready to follow her to the west coast—after all I’d just spent two years clerking in a city I didn’t plan to stay in. I was also already licensed in New York. So the plan was to work in New York and see how the next few years played out.

Once I decided to go back to NYC, I had to figure out what job to take. From a career perspective, I had a hunch I’d enjoy being a trial lawyer or plaintiffs’ lawyer far more than working in Biglaw. But taking that path was risky. If those jobs were a bad fit, I’d have very few exit options. And if I did decide to eventually move to California, I’d have even fewer options.

Based on all of these considerations, I decided to return to S&C. I knew it wasn’t a great fit for my personality. But I knew it would preserve a ton of exit options, which given the uncertainty around my future plans, was going to b super important.

That’s how I ended up deliberately choosing to work at a job I knew I’d hate.

What it was like to take a job purely for the exit options

For the next two years my girlfriend and I did the whole long distance thing. Which wasn’t as bad as you might think, given that we were both super busy with our work lives. However these two years were tough on me, mentally and professionally. Because I naturally struggled with focus and attention to detail, I ended up putting in extra hours to make sure my work product didn’t have mistakes.

At the end of my two years, I decided enough was enough. By then I was 30 years old and just exhausted. So I decided to make two huge decisions that would change the course of my life.

First, I decided to move to California. It was not an easy decision, since my family, friends, and network were all in New York. But by then I knew I wanted to marry this girl, and also knew that she loved being in California. In my mind, there wasn’t a question of what the right (geographical) move was.

Second, I decided that my next job would *have* to be something I’d enjoy. No more working for the money or exit options. I was 4 years out of law school, and by then I’d paid off my student loans and saved up enough money for a ring and a modest wedding. Given my struggles at S&C, I decided to not apply to any Biglaw firms.

Setbacks and failures

My decision to relocate to California and step off the Biglaw path had pretty huge ramifications for my future. In the end, it took far longer than I ever expected to get my California bar license. As a result, I ended up getting fired from my next job (which happened to be at a plaintiffs’ firm).

Getting fired unexpectedly led me to rush off to my next venture, which was to open a solo practice. That practice ended up getting shut down a year later, after I struggled to break even financially.

All of my worst career nightmares suddenly became reality. I was 33 years old, six years out of law school. With nothing really to show for it.

And yet now—with the benefit of hindsight—I have come to realize that losing everything that I had that gave me the chance to find something better. My whole life I had struggled with school and work. I chose my career path for many reasons (good reasons) but never based on what I actually thought I might enjoy.

But now I could.2

Conclusion

I’m sharing all of these details because the details played such an important part of my journey that I rarely ever touch upon publicly. As I mentioned in the intro, usually my posts about career pivots are fairly sterile. Narrative: I figured out what I was good at, ran into some setbacks, and then took some risks and ended up in a good place.

Life is a lot messier than that. My feelings and circumstances pushed all of my career decisions in a certain direction that otherwise might not have happened.

I chose a career path that was not aligned with my personality. And when I realized what was happening, instead of leaving—I chose to remain on the wrong path. I felt like I needed exit options, because it would help me down the road if I needed to move to California to be with my girlfriend. All of those decisions led to a spectacular blow up of my legal career.

Let me be clear: I have zero regrets about everything that happened. Because this story did have a fairy tale ending.

I ended up marrying that girl, and we now live in California together with our two beautiful children. On the work front, I now have a unicorn job I truly enjoy. The coolest part is that I’ve been able to tie everything in my past together. I get to work with people, doing sales and marketing—and am still deeply connected to the legal community.

My life isn’t perfect. And I’m not certain where my career will end up. But I can’t deny the fact that the way my work and personal life has played out—I’ve had some pretty good luck. I certainly wouldn’t have everything I have today, had I not gone through all of the ups and downs of the past ten years.

That’s why I’m writing this article. Because I genuinely wish the same thing to all of you. The ups *and* the downs. It’s really hard to say, when something happens, whether that’s actually good or bad for you in the long run.

But if you remain authentic to yourself and trust your instincts on the things you value and want out of life—I truly believe it will all work out.

All those conversations made me reflect on the two years I worked there. Evisort was such a fun and wild ride. I joined as employee #12 back when they’d just raised a seed round.1 The team had been developing their AI product for years, but had just started selling the product a few months prior.

Despite how much I got out of the experience, I rarely talk about my experience at Evisort. A big part of it has to do with the fact that I left the company in 2021 to join one of their biggest competitors, Ironclad. And because my new role at Ironclad involved generating brand awareness for my new employer, I felt that it wouldn’t be right to draw attention to one of its competitors.

But make no mistake about it: My Evisort experience was a huge and significant part of my career journey and I feel a lot of gratitude for my time there. It was a huge step in my career. So today I thought I’d to share a few rambling thoughts from my experience there.

Joining an unknown startup

When I first joined Evisort, I distinctly remember some of the reactions from my friends. “Why Evisort? If you’re going to pick a contracts tech startup, why not join Ironclad instead?” he said. At the time, Ironclad was incredibly hot. They were a Y Combinator startup that just raised $23M from Sequoia, one of Silicon Valley’s legendary venture capital funds.2

Honestly, I’d considered joining Ironclad before. It was early 2019 and I had just spent the previous 3 years climbing the sales career ladder at my first startup, Logikcull. I felt I had a lot to contribute to my next startup—not as a mere individual contributor, but as a sales leader. My time at Logikcull gave me a ton of experience in all types of sales roles, from SDR, to account executive (junior, senior, and strategic), and management.3

However, I was also pretty realistic about how startups viewed me. There was no way a Sequoia-backed startup would give me such a significant level of responsibility. Even though by then I had over 11 years of relevant experience having worked for Sullivan & Cromwell, IBM, and a federal judge—none of my pre-Logikcull experience “counted.” So with just 3 years of “SaaS sales experience” I would be always be perceived as just another inexperienced sales guy.

On the flip side, there was this other company, Evisort. I never heard of them but they appeared to be doing exciting stuff with AI and contracts. But Evisort didn’t have all the expected credentials of a top startup. Their founders didn’t do Y Combinator and the company wasn’t backed by a famous VC fund. I checked in with my industry peers and acquaintances to get a point of view; none of them had ever heard of Evisort.

And yet there was still a lot to like. The founders came from top schools like Harvard Law and MIT which suggested that they were smart, driven, and well connected. And importantly, there were lots of hints that they had achieved some semblance of product market fit—which isn’t as common as you might think.4

I decided to jump on board.

“If I was running things”

During the interview process with Evisort, it quickly became clear that they viewed me as more than just a junior sales guy. They told me I’d be the new head of sales, with enormous autonomy to run sales my way.5 In the past I’d constantly griped to coworkers about management, and how “If I was running things I’d do things differently.”

Now I had a chance to do exactly that.

There were a lot of downsides though. I’d take a short term hit to my cash compensation, compared to my previous role. Evisort offered significant equity and a rich commission plan, but it was unclear how achievable quota was. Plus, I was expected to manage/recruit the team, scale operations, and launch new acquisition channels.

All in all it felt risky.

But it really wasn’t. With the benefit of hindsight I can now unequivocally say that the risk was worth the reward. It turned out to be an enormous opportunity. Beyond the financials, the true upside of working at Evisort was the job itself. If Logikcull was the place where I learned how to sell a product to lawyers, Evisort was the place I learned how to scale sales beyond my own efforts.

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Making my mark

During my two years at Evisort, I had unparalleled opportunities to run experiments, iterate, and launch new channels. For example, I was given the green light to launch a cold call outbound channel. Before I joined, the company generated sales by having their founders and early employees reach out—via email—to their alumni networks (these were HLS grads, remember) and local communities they were part of.

It was a hyper efficient and effective way to generate sales. Mass emails and talking to people you had a loose relationship was very effective. The problem though, was that you couldn’t scale those efforts. We started to run into deliverability problems because of our email volume. Plus, once our people exhausted their initial list of connections or email addresses, they didn’t know what to do next.

That’s what I sought to solve with this new channel. In addition to selling the product myself as a quota carrying rep, I spent the first few months at Evisort methodically building up a barebones cold calling operation. At the time there was a ton of skepticism about the effectiveness of cold calls to lawyers.

To be sure, some of those concerns were legit; after all how many lawyers do you know have bought something off a cold call? But some of the skepticism was due to the fact that most outbound operations at legal startups were poorly run; they had bad lead lists, garbage talk tracks, and sloppy targeting. They didn’t set it up the right way.6

I wanted to do things the right way. Not necessarily because I was sure cold calling would work. No, what we really needed to figure out was—if we made all the correct operational choices—could we possibly add a few sales here and there? If the answer was no, that was ok. We could then simply cross it off the list and avoid sinking more resources into outbound cold calling in the future.

But if the answer was yes? Well, that would have huge implications for how quickly we could grow the company.

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Seeing the bigger picture

What I didn’t realize at the time was that there was another, arguably even more important reason why setting up a cold calling channel was valuable. If we could show hints that it *might* work—perhaps with some early data—that evidence would boost the company’s valuation during the next round of funding. Investors would see hints of a sales machine that could potentially scale revenue.

In other words—the initiative didn’t need to show results right away so long as it showed a reasonable path to future success.

I remember the first week of my experiment, I needed to do it myself to prove out the concept. So I found an old burner flip phone (which has since become a recognizable artifact in my Tik Toks) and sat down with our intern to crank out 200 cold calls to in-house lawyers across the country.

We were able to validate the quality of our contact list, establish some base rates for connects (how often people picked up) and conversion (how often people agreed to a sales meeting).

With that data in hand, we began to scale out our workflows. We upgraded to a better tech stack with more accurate contact info, and leveraged software to automate call logging. Instead of continuing to test with a junior hire, we decided to pay for an expensive month-to-month contract service with an experienced cold caller to test out our scripts.

As we refined the operation, it quickly became clear what a “good” cold caller could produce. We had scripts and base rates for results; so we were able to quickly gauge who was doing well and who wasn’t. Coaching and training could then be deployed to specific cold callers.

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Good news for the company, bad news for me

Meanwhile, Evisort was firing on all cylinders. Our AI product was impressing buyers, and we ended up growing revenue very quickly—so fast in fact, that we ended up raising a large Series A round just 6 months into my tenure. It was such an exciting event for all of us; but what I didn’t realize at the time was that the company’s fast success would have negative implications on my career trajectory.

Simply put, the company had now become too successful to let a relatively inexperienced head of sales like me run things. Evisort hired a gray haired Chief Revenue Officer, who wanted to bring on his own VP of Sales. All of the difficult work I’d done to successfully operationalize outbound cold calls had the unexpected effect of providing justification to replace me with an external hire.

I’m not gonna lie, I was pretty angry when I first realized what was happening. How could they do this to me?! But pretty quickly I realized that the change was actually a positive development. Because honestly while the head of sales job was rewarding from a career perspective, it was incredibly tough on my personal life. I had a new baby at home, and was finding it difficult to juggle fatherhood responsibilities (my wife has a demanding job).

Post Series A, there was an influx of new managers and leaders, so there was no longer a need for me to launch new initiatives. I could instead go back to being to a pure individual contributor. The goodwill I’d create by voluntarily taking a step back could solidify my internal relationships, and free up my time for me to be there for my family.

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More time to develop expertise on how to sell to lawyers

Suddenly my schedule opened up. For a few days I enjoyed my newly earned free time. But then I got restless. I needed to do something productive that let me feel like I was growing.

This was a constant pattern in my life. I just can’t seem to enjoy free time—I end up just working on various things and taking side quests. And that’s exactly what I did in December 2019. I began to collect all of my ideas, observations, and insights about sales and document them. Putting my thoughts into writing helped me solidify my theories on how to sell to lawyers. Some examples:

• The outsized role of language and timing. Specific terms—like “cloud” or “AI” that mean nothing to lawyers early on during the innovation cycle—can actually have a huge impact later on. This is why pitching AI was so hard ten years ago vs. now, after ChatGPT has become ubiquitous. As a seller you need to understand how the words you use are perceived, and how their connotations can change overnight.

• How to craft your elevator pitch. For the longest time Evisort used the phrases “contract intelligence” and “AI for contracts.” None of our prospective customers seemed to understand what that meant. Our competitors used the phrase contract lifecycle management (CLM) but that left something to be desired; our product did far more than just that. Through experimenting and A/B testing, I realized the most effective phrase was “software that automatically extracts insights from your contracts.” It was less “cool” but got to the point immediately.

• Look beyond the person on the other side of your sales call. Often we struggled to close deals where sales prospect initially reacted positively. As it turned out, certain features that the in house lawyers loved were not valued by other internal stakeholders who controlled the tech budget. For example, in house lawyers loved AI that could detect indemnification language; problem was, no one else cared. However, if you highlighted AI that could detect nuances in the termination language, that had huge implications for procurement and finance. It was less impressive to the lawyers but held greater sway to those who held the purse strings.

• The hiring profile for someone who can effectively persuade lawyers. I learned unequivocally that you do not need an ex-lawyer to sell things to legal. However, early stage startups with no established playbook need to hire domain experts who can be adaptable on sales calls. Those with zero legal experience can work—but in those early days you have to keep an eye out for specific traits. You’ll want to avoid bringing on people who talk too much, hyper-optimists (they generate too much buyer skepticism), and sloppy communicators.7

In addition to all these sales epiphanies, I also had the opportunity to develop a personal “grand theory” on social media sales. I’d spent years posting on LinkedIn and was starting to see an uptick in engagement. With all this new time, I began to deliberately try to go viral with my content and grow my following.8

These social media experiments ended up positioning me perfectly right before the pandemic hit. And then months into the pandemic, led me to try all kinds of things. It’s a long winding story, but basically my sales pipeline dried up overnight and despite all of the goodwill I’d generated—I still felt like I was about to be fired. So I doubled down on social media, and experimented with a lot of things that felt uncomfortable.

One of those things was something I had zero previous experience in: making short form video skits. No need for me to rehash this story—I’ve shared it before—but getting on Tik Tok ended up changing the entire trajectory of my career. Overnight I became a mini influencer in the legal industry, which opened up all kinds of doors down the road.

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Epilogue

My experience at Evisort was such a critical part in my career development. And to be clear: It was never in my plan to leave the company after just two years. I still felt like I had a lot to contribute. But in 2021, Ironclad came knocking and offered me a unique opportunity to focus on a developing skill very few in the world had—leveraging social media to drive b2b marketing.9

Basically Ironclad offered me a unicorn job.

However, the unfortunate result of leaving Evisort for a direct competitor—as a quasi public spokesperson—was that Evisort effectively disappeared from my public profile.

Now that I’ve moved on from the CLM space I guess I feel more comfortable sharing my experience. Based on what I know, I’m not at all surprised that the company ended up getting acquired. In the years since I left, I had heard about how they were doing—and despite the fact that there seemed to be ups and downs, the company appeared to continue along its growth trajectory.

I didn’t expect the eventual acquirer to be Workday, but having spent two years working closely with Evisort’s early employees and founding team—it was obvious to me that they were going to make a big impact. Everyone on that team worked incredibly hard. They were smart, but also adaptable and scrappy. They truly operated on “founder mode.”

I am proud to have had the chance to work alongside them.

The main thing for me now, is this immense feeling of gratitude. They were the ones who gave me the chance to lead the team in the first place. No matter what happened afterwards, I will always look back fondly at my time at Evisort. What I learned there served as the foundational experience for everything good that happened to me afterwards.

And in the end, I suppose that’s what working for startups is all about.

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