It was the kind of group you’d expect at an event like that. A bunch of highly accomplished professionals in their 30s from lots of different industries, not just law. There was one guy in particular who had done extremely well in the tech world, who I had always known casually but never had a long 1-1 conversation with.

At some point, he and I were catching up—and as is typical of conversations in these places, the topic shifted to what we we did for work.

I started to explain that I had stopped practicing law to pivot to sales at a legal tech startup. But then I felt something unexpected. The words wouldn’t come out of my mouth easily.

I had been in the business development representative (BDR) role for about six months at that point, and thus far had really only spent time spent most of that time around my closest friends. My goal was to stay focused without having to worry about explaining my career pivot to people who didn’t know me well.

With the lawyers in the group I wasn’t concerned about talking about my job. I could say I was doing “business development” for a startup, and that would land fine. Different enough from law to seem interesting, not so different as to require much elaboration. Nobody in that group knew exactly what business development meant at an early-stage company.

A tech person, on the other hand, knows exactly what a BDR is. There is no sugarcoating it. A BDR is a junior, entry-level sales role meant for 22 year olds straight out of college. You’re cold calling, you’re prospecting, you’re the person at the bottom of the sales org whose job is to get meetings for someone else to close. You get paid $50k/year salary.

In the hierarchy of tech jobs, it’s just about as low as you could go on the org chart. In the context of my former career ladder—a law review editor from Northwestern Law, former federal law clerk, and Sullivan and Cromwell associate—this wasn’t just one step down. It was literally at the ground.

The words came out awkwardly.

“I’m … just a BDR at a startup.”

He nodded, asked a couple of follow-up questions, and was completely gracious about it. Genuinely curious, even, especially about the legal industry and its receptiveness to technology. Then the conversation moved on.

The embarrassment I felt lived entirely in my head.

The bachelor party was about six months into a decision I’d spend the next several years living out. Despite how painful that conversation was, I knew I hadn’t ended up in that role by accident. Being a BDR was the byproduct of my conscious decision to organize my career around a specific philosophy around preserving boundaries at work.

And it was a mindset and approach I arrived at the hard way.

Origins of the Philosophy

For most of my legal career, it felt like I dedicated 99% of my time & energy to career advancement, making it my primary project. I’ve written about this before. I went to law school to reinvent myself, and I did. Ended up building the kind of resume that was supposed to be a golden ticket to future success.

I have written about what happened next in other places (see here and here) so I won’t get into details. The short version is that it didn’t work. Just a few years after amassing a star-studded “golden” resume, I found myself shutting down a solo practice I’d only opened up a year earlier, having generated less revenue than I would have earned doing first level doc review.

What I took from that experience was a specific lesson about concentration. I had put too many chips on a single bet that being a successful lawyer would make me … well, happy.

My response to experience those setbacks was to spread the risk around differently. Specifically, I wanted to reduce the amount of time and energy organized around career advancement, so that a career failure would be less devastating. Instead it would be just a small setback in a highly diversified, satisfying life.

So when I ended up in the BDR role, I made a deliberate decision to do the job well and protect time outside of my 40 hours a week. As any prudent lawyer would do, I kept my expectations low. My guess was that by being a legal tech salesman, I probably would never earn more than a first year Biglaw associate, if that much.

I knew you could earn a lot in tech sales, but I didn’t have a lot of confidence that lawyers would turn out to be good tech buyers. I could see a version of my future where I worked in legal tech sales for a long time, never making meaningful money.

I decided I could live with that. Career disappointment, and embarrassment even, had zero real-world impact on the other aspects of life that I valued. What I genuinely could not tolerate was time risk. Spending the next decade pouring everything into advancement and having it not work out again. The memory of what that felt like was too fresh.

Over time this approach calcified into something more meaningful, almost like a mantra that I used to reassure myself whenever I dealt with career crossroads or work related dilemmas. “It’s just work. Make sure it doesn’t affect the other important things in your life.” I kept repeating it to myself.

The Mantra: Don’t spend too much time at work

A few years into my journey, I became a father, and the calculus shifted even more.

I had already organized things around protecting time, but fatherhood clarified something I wasn’t able to articulate. It wasn’t just about the hours. It when the hours took place, about the flexibility of schedule, energy levels at the end of a day, and the mental & emotional load a job leaves behind even after you’ve closed your laptop.

On the surface, this retelling of my journey reads like a cliched story about someone who had a demanding career, became a parent, and decided to protect his time. This is not an uncommon decision, especially among highly successful lawyers.

The story usually conveys the message that it’s a zero sum trade: less ambition in exchange for more work life balance.

However in my case, that wasn’t the whole story.

What I learned about myself

Despite the philosophy, I could not stop myself from filling up free time with work. I was doing my BDR job. Finishing my calls, hitting my activity targets, logging my notes. I got good at the role and the time it took me to hit my outreach targets went from 40 hours a week, to 30, to less than 20 hours a week.

And then, with the extra time that came from not organizing my entire life around the work, I found myself doing things at work nobody had asked me to do. Bear with me in this next section as it gets kind of granular, but I’ll explain how it ties together later on.

The extra work

Instead of taking long lunches or leaving work early, I instead spent my extra free time pulling up old Salesforce reports and reading through them carefully. What I was looking for was where our sales process had distinct segments. We were selling to extremely busy lawyers who did not have expertise with evaluating technology solutions.

And so I took a magnifying glass to past sales cycles where things worked, didn’t work, and where the choke points were. A cold email that never received a reply was a very different problem from converting that reply into a meeting. Getting the meeting on the calendar was a different problem from getting them to show up. And so on.

What I found, when I looked closely enough, was that a single sales cycle was not really one long continuous, coherent thing. It was a succession of five to seven individual, narrow steps, each with unique dynamics and bottlenecks. You could isolate each one and study it separately.

Nobody had told me to think about it that way. I had just started to see it, because I had spent my time reading sales books, listening to podcasts, and just absorbing general sales tactics so I could apply them to legal.

Why did I do all this extra work?

I learned something about myself in that period. Protecting time was not about creating balance in the conventional sense. It was about creating room for the right kind of work. When I wasn’t grinding to fill every hour with visible activity, I started filling the space with things I genuinely wanted to understand.

It was out of curiosity instead of obligation.

Crucially, this self-directed work never crept into the time I had carved out for my friends and family. That stayed protected. But within my working hours (and even on Saturday mornings when I had time to myself) the bandwidth I had created meant I could follow my own interests inside the job. Those interests turned out to matter more than I knew.

The impact of time as a constraint

Over time I started to notice that having time as a genuine constraint was forcing me to do things I wouldn’t have done otherwise.

The first was to prioritize one-to-many outreach.

I recognized that I needed to put myself on stage more often. I needed more efficient ways of spreading my sales/marketing messages without corresponding increases in time spent on the work. That meant more speaking opportunities, more posting on LinkedIn, more activity on social media. All these tasks felt cringey and uncomfortable in a similar way the bachelor party convo was. But it would give me operating leverage to preserve my time.

The second was learning to build systems I wasn’t at the center of.

This is where the Salesforce work paid off in ways I hadn’t anticipated.

• When I was later running a sales organization at my second startup and needed to build an outbound motion from scratch, I took a different approach than many other senior sales execs. Those execs (often from bigger companies with more established brand) diagnose problems by reaching back to experiences at previous companies rather than by (limited) evidence at the current company.

• This is natural because they either haven’t done the entry-level work before, or they had decades ago. Because I had taken the time reading Salesforce reports and broken down the sales process for lawyers into their individual steps, I could see exactly where the choke points were—even with limited information.

• My first step was to do the outreach myself, even though I was a Director and Head of Sales. In parallel, I asked an intern to mimic my activities to see where things broke down. The intern’s efforts led to mixed results but it told me something specific about where the process was breaking.

• Then I proceeded in a specific sequence: First, bringing in a 10+ year experience BDR contractor to validate that the approach could work when executed well (it did). Then I hired a full-time rep with 2 years of experience to see if the results could be replicated again. Results were mixed, but now I knew which step was the bottleneck.

That sequenced approach was only possible because I understood the process at the level of its individual parts. And I understood it that way because I had spent time at the bottom of the org paying close attention when nobody was asking me to.

That was only possible because I had the energy, interest, and bandwidth to study how things worked—which was only possible because I made a conscious decision to protect my time.

Conclusion: This is not a formula

I want to be honest about something before I close.

My career journey benefitted from a huge amount of luck. The particular window of time I was operating in, the sequence of roles that gave me both the foundation and the flexibility — I can’t claim that all of it was purely by design. A lot of it was timing. A lot of it was being in the right conversation at the right time.

What I can say is that the way I had organized my work prepared me to act when future pivotal moments arrived. I wasn’t overcommitted and burned out. I had mental energy. And I had genuine interest in the work itself.

So looking back to that time as a BDR, I see things differently. At the time I thought I was making a trade, ie. less advancement for more time. Less legible success for more sustainability.

What I didn’t understand was that the structure I was building my work inside would itself become the thing that mattered. The bachelor party was uncomfortable, and saying the words out loud was harder than I expected, and then it passed.

What didn’t pass were the skills I built and the judgment I developed.

I don’t know if this path is replicable, and if it would work for you. I’m genuinely not sure the specific sequence of events that shaped it could be engineered in advance.

But I do think the underlying question is worth considering, especially if you’re in a moment where stepping back feels like the only option, or where the thing you’re considering looks worse on paper than what you’re leaving behind. You might be underestimating what could go right if you stopped organizing your life around how your career “should” look like.

Best of luck my friends.1

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Law firm proprietary AI

Kirkland & Ellis announced that it has committed $500 million to develop its own proprietary AI platform. The announcement was notable because the firm opted to build their own tech vs. buy from an existing vendor (e.g. Harvey or Legora) which appears to be the more common approach.

The build vs. buy decision is common among conventional businesses. There are tradeoffs in either direction. I suspect that K&E is taking the “build” approach for strategic reasons. The world now realizes that data is the long-term moat, and K&E recognizes that they’re sitting on a trove of historical transaction data.

Correction: As pointed out in the comments, K&E is also currently using third party AI tools like Harvey & others … this does not appear to be a build vs. buy situation, but perhaps a build and buy situation. Thanks to Nikki Shaver for the correction!

Time will tell if the execution risk of developing proprietary AI outweighs the risk of outsourcing AI design to a vendor, even if they appear to be highly capable. Makes me wonder if this is why Freshfields decided to partner directly with Anthropic to develop their own proprietary AI.

Relatedly, this week Fried Frank announced that it’s launched a proprietary AI platform focused on asset management & private equity practice areas. The platform, called FundAssist, is designed for internal use and will help firm attorneys pull templates, conduct deep queries from massive documents, and leverage agentic AI to engage in complex drafting.

After seeing so many PR announcements of firms adopting Harvey or Legora, it’s been fascinating to see firms start rolling out their own capabilities. I asked a friend of mine in Biglaw if he thinks if “building” is a broader trend. My friend noted that his firm tried to do this 3-4 years ago but execution was difficult—and wondered if the foundational models today have made it easier.

Non-lawyer ownership of law firms

Just yesterday, Bloomberg reported that LA based firm Massumi + Consoli has sold a stake of its firm to private equity. Regulations prohibit non-lawyers from owning law firms so the sale was structured by creating a separate entity (called a Managed Services Organization, ie. MSO) that only handles back-office work.

The move to carve out a MSO from law firms has become super popular. It’s the structure of many of the newest AI-native law firms that have sprouted up over the past year or two. MSOs allow for investors to plow capital (indirectly) into law firms in the hopes that they’ll become more efficient—which is a legit strategy given how quickly AI has been improving.

As a general rule, lawyers are great at lawyering, but not always great at business and operational efficiency. I can see how specialization (attorneys focusing on law, MSO focusing on ops) can lead to better results overall for the firm. Interestingly, allowing for non-lawyer ownership may lead to some interesting second-order effects.

For example, businesses themselves may start acquiring law firms. Two weeks ago, we saw how private capital platform Carta acquired UK-based AI native law firm Avantia Law. Avantia isn’t structured as a MSO, but instead operates under an alternative business structure, ie. ABS, that allows for non-lawyer ownership.

On paper, the combo seems to make perfect sense—Carta and Avantia have significant overlap in their ideal client/customer base. Both work with private equity, private credit, and VC asset managers. This acquisition allows Carta to deliver services on top of all the products they offer.

It’ll be interesting to see how all of this non-lawyer ownership impacts clients. Many commentators have observed a troubling parallel: enabling indirect ownership of physician practices led to patient decisions being made based on financial considerations, with negative impact on patient treatment & experience.

My take is that it will wholly depend on the firm and the non-lawyer ownership that acquires the firm. Carta has done much over the years to build an incredible brand among its users, and I doubt they’ll try to monetize Avantia in a way that hurts the client experience. But if a private equity buyer who only looks at financial ROI numbers indirectly buys a law firm, I can see that going south quickly.

Quick favor: my book needs reviews!

Thanks everyone for buying a copy of my new book, Talk Less Win More: How Lawyers in Business Development Roles Can Turn Meetings Into Revenue. If you could please take a few minutes to leave me a review on Amazon, that would do wonders for my book’s visibility. Shout out to the 7 people who already left me reviews—thank you!

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I wasn’t.

What I eventually figured out, after all the ups and downs of being a sales rep, sales manager, and eventually CRO—and through all the wins and losses was this:

The instincts that make us lawyers good at our law jobs work against us when it comes to business development. Your preparation, your expertise, and the fundamental urge to demonstrate both. You walk into the meeting ready to impress your listeners.

And yet that’s not what potential clients want. They want to feel heard.

The gap between you and the person you’re trying to convince is precisely what Talk Less Win More is about.

It’s a short book—just thirty-five pages. It’s designed to be a quick read. The argument I make is simple: lawyers generate better business development results by listening more than talking, and in very specific ways.

I wrote it for lawyers who are in sales or business development roles, because that’s my background. But it could be useful for law firm partners or recruiters who are trying to pitch other lawyers as well.

I just published the book via Kindle Direct Publishing.

If you buy the book (it’s priced at $4.99) and find it useful, I’d genuinely appreciate a review. Reviews in the first 30 days are what determines whether a book gets discovered by the Amazon algorithm. Even just a sentence or two makes a real difference.

Here’s the link to the book.

Thank you! And hope you have a wonderful long weekend.

Alex

And yet something isn’t translating in the current state of your career. The workload feels unending, and there’s no light at the end of the tunnel. You’re burning out from doing all of the things you were told to do, and that’s what makes it disorienting.

If this sounds familiar, the gap is worth examining. Because the problem usually isn’t effort or ability. It’s something subtler, and almost invisible to those who have spent their entire careers practicing law.

1. Discovering the problem

There’s a version of this I hear often from lawyers who’ve moved into revenue or performance based roles. Sometimes it’s someone who moved into sales, but other times it comes from a newly promoted partner who suddenly needs to do more biz dev.

It’s a common fact pattern: This lawyer wlil describe getting on the phone with a potential client and feeling completely at ease. They know the subject matter, can handle tough questions, stay organized, and inspire confidence. When the phone rings, they’re outstanding. It’s not surprising then that they almost always tell me:

“Just get me on the phone with a client and I will close the deal!”

What they are completely blind to is that getting the phone to ring in the first place is the actual job! The calls where they perform brilliantly represent a tiny part of the valuable work. The main part is figuring out who to call, why they might care, how to reach them, when to push and when to let go, and which opportunities are worth pursuing versus which ones appear to look like opportunities.

Or, to borrow a term I used in a previous article, the ability to get on lots of client calls is the load bearing constraint.

That layer of the job requires a fundamentally different skill: using business judgment to assess what actually matters, and actively declining to focus on what doesn’t. Legal training develops many things, but this particular skill, prioritization judgment in a commercial context, is largely absent from it.

2. How legal work is assigned

When you’re coming up as a lawyer, someone more senior than you, a managing partner, a general counsel, a senior associate, looks at the full landscape of problems and decides which ones require attention, which are urgent, what the priorities are. Then they hand you a piece of it.

Your job, from that point forward, is to execute as thoroughly as possible on what you’ve been given: research it completely, draft it carefully, review it meticulously. The work that reaches you has already been filtered. You are working on a pre-selected set of problems, and thoroughness on that set feels like doing the whole job. It isn’t. The prioritization happened upstream, and someone else was responsible for it.

This division makes sense in legal contexts. The judgment required to triage a docket or decide which contractual risks matter for a specific client in a specific transaction takes years to develop, and handing it to junior lawyers before they’ve earned it would be a mistake.

But the consequence is that lawyers can spend years, sometimes entire careers, developing extraordinary execution skills without ever being asked to develop the judgment that sits upstream of execution. When they move into business roles, the pre-filtering disappears. No one hands them a clear task list with the hard prioritization decisions already made. They get the whole pile, and thoroughness alone stops being sufficient.1

What makes this particularly hard to see is that it’s not a junior lawyer problem

Hot take: Many of the most outwardly accomplished lawyers, GCs, CLOs, partners with decades of experience, never fully developed this skill either. Their careers advanced on the strength of execution, relationships, and subject matter depth, all of which are real and valuable, but none of which are the same as business judgment.

Title is not evidence of prioritization ability. You can advance very far in a legal career, and in many cases in a business career, without ever developing the ability to accurately distinguish high-value from low-value work in a commercial context.

A concrete example: I’ve seen senior in-house lawyers spend considerable time getting a company’s press release exactly right, sharpening the precision of a nuanced position on a controversial topic, ensuring no word could be misconstrued. Technically, the work was excellent. What got missed was the actual purpose of the release, which was to pledge loyalty and endear the company to its core buyer demographic.

The audience for that document was not a judge or a regulator. It was a customer who needed to feel seen—which means you need to take a stand and alienate some other group of people. Judgment means actively choosing to make that tradeoff instead of sending out a communication that feels “safe” but wins over no one.

The lawyer experienced this as doing their job well. The business experienced it as legal getting in the way and simply “not getting it.”

That pattern repeats across functions and seniority levels. It’s the underlying reason the business finds legal so difficult to work with. The problem has less to do with risk aversion (in my opinion) than with consistently answering the question asked instead of the question that matters.

3. My personal experience

I struggled as a young associate. I felt that I was genuinely good at one of the main core aspects of a litigator’s job which was evaluating reasoning across conflicting opinions, to produce a synthesized rule that helped the client. There were moments I did that better than partners who had been practicing for decades.

But I was terrible at keeping my head down. I couldn’t stop evaluating which work mattered and which didn’t. While colleagues moved efficiently through their assigned task lists with a temperamental ease I couldn’t replicate, I was distracted by the question of whether the task list itself was right.

That made me slower and less reliable on execution, and genuinely less valuable in an environment where the billable hour treated all work equally.

My colleagues, on the other hand, were well-suited to that system. Their instinct toward thoroughness and precision was exactly what law firms needed from junior associates, and they were rewarded accordingly. My instinct, to lift my head up, question priorities, figure out what actually mattered, was a liability in an environment where someone else was supposed to be doing that.

Ten years later after leaving the practice of law, I see the other side of that equation. The traits that cost me in law turns out to be the core of what business actually requires. Making tradeoffs and prioritizing objectives. And I can now see that many of the lawyers I who struggle in commercial roles are struggling precisely because they were excellent associates.

The habits that produced their success in law are the same ones creating friction now.

I wrote about a related version of this pattern in The Hidden Ceiling, which looked at why high-achieving lawyers stall out in corporate environments. That piece was about the trap of heroics: doing too much yourself, staying indispensable, never building systems.

This article is about something that sits upstream of that. Before you can figure out how to do work at the right level, you need to figure out which work is worth doing at all.

4. Self diagnosis

So what does this gap actually look like in practice, and how do you know if you have it?

• The clearest signal is a mismatch between effort and recognition. You’re working hard, producing thorough output, and the business still seems frustrated or underwhelmed.

• A second signal is that your contributions tend to resolve the question in front of you without changing how decisions get made.

• A third is that you find yourself surprised, regularly, by what leadership actually cares about, as if the priorities you’re working from and the priorities that matter to the organization are operating on different frequencies.

The underlying pattern in all three is the same: you’re executing well on a task list you didn’t fully analyze. The prioritization judgment that should sit upstream of the execution hasn’t been developed, not because you’re incapable of it, but because nothing in your training required it.

Developing it is possible, but it requires stepping deliberately outside the frame of your daily work often enough that a different kind of attention starts to become natural.

The legal career path selects against this skill, systematically and without malice.

The system that produces excellent lawyers, rigorous training, careful supervision, thorough execution, also produces professionals who’ve had the prioritization layer done for them at every stage.

Some lawyers develop it anyway, usually because something in their career forced the question: a role without close supervision, an environment that punished over-lawyering visibly enough that the feedback was impossible to ignore, a mentor who named the gap explicitly.

But many don’t, and those who don’t tend to find that at some point, whether they’re a fifth-year associate, a ten-year in-house counsel, or a General Counsel with a seat at the table, the effort stops translating in ways they can’t fully explain.

That gap between effort and outcome is diagnostic. It suggests that the job may have started requiring something your legal training didn’t prepare you for.

The good news is that the skill is learnable. But you can’t develop what you haven’t named, and the first step is being honest about whether the signals above sound familiar. For those who want to go further, below I’ll share three specific things you can start doing differently.

Read more

What makes this harder is that platform companies don’t just have resource advantages. They have distribution advantages, and they carry a significant amount of institutional trust already. Their brands are recognizable. Their contracts are already in place at most large firms. A lawyer who has spent years using Microsoft products doesn’t need to be convinced to try a Microsoft legal tool. That’s a meaningful head start that no challenger can simply outspend.

Robust distribution is a known competitive advantage in tech. VCs talk about it often. How do you scale sales (sorry, “GTM”), how do you enable your team, how do you build pipeline. And most of that conversation borrows from the broader software playbook: more layers & middle managers, more activity, automated outreach, tighter process.

That thinking has its limits in legal. Spoiler Alert: If you have a GTM team with healthy pipeline, but can’t seem to convert it to revenue, that’s usually a signal that sales activity isn’t the load bearing constraint. Something else is.

The crux of the problem is this: Sales activity and credibility are different things, and only one of them is the bottleneck. You can run a tight process, hit your call targets, have beautiful Salesforce dashboards, and still find that revenue fails to appear. Lawyers are not evaluating your GTM motion. They are evaluating whether you have earned the right to be taken seriously. No amount of pipeline activity closes that gap.

The real limitation is trust. Lawyers extend it to people and institutions they believe genuinely understand their work, their standards, and what happens when something goes wrong. That bar is specific, and it takes time to clear. Platform companies cannot manufacture it at the level of the profession.

For a challenger, it is the one unfair advantage worth building.

I. The evidence

The storied companies that built formidable positions in legal got there by earning the profession’s trust at scale. Most founders/investors miss something fundamental when they first encounter this market: law does not separate easily from the people who practice it. A lawyer’s judgment, their reputation, and the tools they rely on are bound together in a way that has no clean parallel in other areas of tech. When something goes wrong with a legal tool, it lands as an actionable lawsuit and potentially a professional liability problem.

That changes how lawyers evaluate vendors. It changes what it takes to win their confidence.

The standard is even higher when we’re talking about core legal work, or judgment-based tasks. This is where a lawyer’s training and professional standing are directly implicated in the output. It’s less obvious than it sounds. Legal research, for example, might seem like a straightforward support function. But finding the right case requires judgment: does this precedent actually apply, how does it interact with the facts, what weight does it carry.1 That is legal reasoning. Keeping case files organized or routing a contract for approval is different. The distinction is not about complexity. It is about whether professional judgment lives inside the task. (more on this distinction later)

Legal AI, and specifically the recent generation of generative and agentic AI, sits squarely inside this territory. The trust bar is higher here than in other traditional legal tech categories such as CLM, e-discovery, or practice management. Legal AI is asking lawyers to outsource some level of professional judgment to a robot. The companies that have historically done an effective job earning that trust have done so in ways that are specific, observable, and worth examining closely.2

A. Westlaw

Westlaw (e.g. Thomson Reuters) is the oldest example and risks feeling dated, but it points to something deeper and undervalued. Westlaw understood the psychology of the profession well enough to embed themselves before lawyers even graduated. The student rep program meant Westlaw was the first research tool lawyers ever touched. They give free access to federal clerks, among the heaviest power users, to lock in that trust. I know this because I wasn’t a heavy Westlaw user until after my clerkship. By the time I made it to S&C and was given the option of choosing Westlaw vs. Lexis, it was a no brainer. It didn’t feel like a typical vendor relationship.

B. Casetext

Casetext went further in a different direction. You can find its story detailed in many places, but as someone who knew several people at the company, it was obvious to me that lawyer DNA was baked into every function: sales, marketing, product. One of my closest friends from law school was a successful sales rep there; while some elements of their GTM motion looked like the SaaS playbook, many of them did not. And when they began to release AI features that got to core legal work, ie. Prioritizing cases that were relevant for specific legal points, the GTM motion relied very heavily on the ability of their sales reps (who were lawyers) conveying the trust through credible explanations of the product.3

C. Harvey

This is the most recent example that is still playing out. Harvey came in with significant backing and elite firm endorsements, but there were plenty of well-funded legal AI companies that weren’t able to achieve Harvey has. What appears to have differentiated them was the early GTM motion: hiring ex-Biglaw lawyers, and letting client press releases do the work of social-proof based distribution rather than running a traditional conference plus outbound motion. The result (saw this on social media just yesterday) is a presence in over 50% of AmLaw firms in a remarkably short period of time.

Note on ALSPs as a relevant example

I’ll share a brief word on this since this is the space I play in, and there’s quite a bit of history here. Both Axiom and Ontra (called InCloudCounsel at the time), in their early days, leaned very heavily on trust-based GTM. Both hired teams of former lawyers, often with Biglaw experience or from top schools, as salespeople. It wasn’t clear that they had to take this direction—most other existing ALSPs didn’t, and were still able to scale. But because unlike those other ALSPs, Axiom/Ontra focused on core legal work—so they had a higher bar to clear to earn the client’s trust that they could handle those matters competently.4 With the benefit of hindsight, it was the right decision.

II. Legal-adjacent work

My argument weakens as you move away from products/services focused on work that relates to core legal judgment. These adjacent categories are worth naming quickly:

• CLM (e.g. Ironclad, Icertis, Docusign): Primarily about contracting process. Routing approvals, managing contract repositories, tracking obligations. The lawyer is present in the core workflow but the tool—with the exception of any AI add-ons--is not exercising judgment on their behalf.

• Ediscovery (e.g. Relativity, Everlaw, Disco): Primarily about basic-level filtering of documents. The buying decision is typically shared across legal, IT, and litigation support. The value proposition is operational efficiency at scale, and the sales motion reflects that.

• Practice management (e.g. Clio, MyCase, Smokeball): Supports the operational organization of law practice rather than substantive practice of law. Billing, scheduling, client intake. Closer to vertical SaaS than to anything that requires professional trust to sell.

The nuance worth holding onto is that even these companies have not been able to ignore the legal market entirely on its own terms. Each of them, at some point in their growth, had to develop cultural fluency with lawyers: through the profile of their hires, the structure of their GTM teams, the way they show up in conversations with firm leadership. The trust bar is lower in these categories, but it far from zero. Lawyers are the buyers or at least the influencers in almost every legal tech purchase, and they carry their professional instincts into every vendor evaluation regardless of what is being sold.

What about legal operations as a buyer?

Legal ops has become an increasingly influential buyer across the legal tech market, particularly for the adjacent categories described above. Legal operations professionals often come from outside the law; they are process-oriented, metrics-driven, and in many cases deliberately non-lawyer in their outlook. That is part of what makes them effective in their role. But it also means the trust signals that matter elsewhere in this market apply differently here. Selling to legal operations looks more like a sophisticated SaaS sale than a profession-first motion.

Many legal tech companies are selling to both lawyers and legal operations simultaneously. Legal operations often controls budget and procurement. Lawyers control adoption and renewal. You need both. But one buyer has to have primacy in how you build your GTM motion, your hiring profile, and your product positioning. Try to optimize equally for both and you end up speaking clearly to neither. The founders who navigate this well are honest early about which buyer they are fundamentally building their GTM motions for and treat the other as an important secondary relationship.

IV. The absence of a counterexample

It is worth noting first that there are not many companies selling something that genuinely touches core legal work. The market is thinner than it looks from the outside. That may partly explain why the examples are few. And this is what I believe is the most compelling aspect of my argument.

It is genuinely difficult to identify a company that took a traditional SaaS GTM motion and won in core legal work.5 The kind of significant penetration that Harvey has achieved, or that Westlaw built over decades. That company is hard to find. The absence is worth considering. Is that the absence of evidence? Or is evidence of the absence of evidence, evidence itself? (Don’t answer that question)

My view: The examples that come closest to being counterexamples weaken on inspection. Legal SaaS unicorns: Each of them has scaled meaningfully, but they also sit neatly within the adjacent category already carved out. The work they touch is operational, not judgment-based. Instead of disconfirming the thesis, they instead confirm the boundary.6

V. What trust-scaling looks like in practice

This is where challengers have a structural advantage the giants cannot easily close. The patterns below are observable across the companies that have been able to scale meaningfully in this market. Take these as observations about GTM structure, not rules or requirements. The weight you put on each one depends on your ICP and your product/service.7

A. Pedigree

The profile and background of GTM hires sends a signal before anyone has said a word about the product. When a former Biglaw associate or a HLS grad gets on a call with a senior decision maker, something shifts immediately. (And remember, by the way, that not all Biglaw firms are on the same level in the hierarchy.)

As a result, the relationship does not start as vendor and customer. It starts closer to peer and peer. That is a fundamentally different foundation to build from, and it is difficult to manufacture through training or messaging alone. Lawyers are evaluating credibility quickly and instinctively, and the right hire clears that bar before the conversation has properly begun. The specific pedigree that matters will shift with your buyer by the way. Some care about school, others care about former firm, and still others care about in-house experience. There are different badges of honor but the critical element seems to be having the right badge.

The underlying principle holds across all of these examples: the client should immediately grasp, from background alone, that this person has been where they are—and is an equal.

B. Hiring profile and temperament

The best client-facing people in this market have a particular blend. It is rare and hard to build. They carry genuine sales or customer success instincts; they are motivated to win business, they follow up, they move things forward, while retaining the measured, neutral polish that the legal profession expects from people it takes seriously. (This, by the way, cannot be solved for by just hiring ex-lawyers; many lawyers are not wired this way)

The right combination is partly about individual personality and partly about how someone fundamentally views the world. Lawyers, particularly at the upper end of the market, tend to operate—even thrive—in shades of gray. They are trained to hold complexity, to avoid overstatement, and to be skeptical of anyone who seems too certain. A client-facing person who sees the world in black and white, or who defaults to enthusiasm and urgency as sales tools, will feel off to a senior lawyer even if they cannot articulate exactly why.

Temperament compatibility with legal buyers can be developed at the margins, but the underlying disposition has to already be there. Hire for it. As a rough guide: the higher up the market you are selling, specifically senior partners, high-end GCs, and sophisticated legal teams, the more the neutral, measured end of the spectrum matters. Broader markets tend to tolerate a more traditional GTM temperament, though the baseline of professionalism the legal market expects never fully disappears.

C. Alignment in communication style

Attention to detail, responsiveness, and the quality of written communication are the accumulated texture of every interaction a client has with your company. They are observable, they compound over time, and they are among the clearest signals lawyers use, often without naming them, to decide whether a vendor genuinely understands their world. This dimension can be trained, though changing ingrained communication habits is genuinely hard. What you are looking for is a blend: people with a bias for action who also default to careful, precise communication rather than treating it as a tax on speed.

The calibration here follows the buyer. The more upper-end the client, senior partners, high-end GCs, and sophisticated legal teams, the more that responsiveness, detail orientation, and respect for their time become non-negotiable rather than differentiating. (Hint: 99% of enterprise CLOs are former Biglaw associates, so best to optimize for this cohort’s preferences)

At that level, a slow response or a carelessly written email does real damage. It signals that you do not understand what their time is worth or what their standards are. Lower in the market there is more tolerance for imperfection, but the underlying signal remains the same: every interaction is communicating, quietly, whether you are one of them or not.

VI. Conclusion

The giants will continue to make inroads into legal. Anthropic and Microsoft are already moving, and they will not be the last platform companies to see the opportunity. What their arrival ultimately means for the broader ecosystem, for pricing, for consolidation, for which categories remain viable for challengers, remains to be seen.

What is clearer is that there is a ceiling on how deeply they can embed themselves in the profession. The giants bring mass distribution, established brand, and significant product resources to the table. Those are real advantages and challengers cannot fight them on that ground. Competing on distribution or resources against a platform company is a losing game. The ground has to shift.

The asymmetry worth building is the one the giants structurally cannot close. Showing up as an insider rather than a vendor. That advantage does not announce itself with a large fundraising round or a tier one VC on the cap table. It shows up in the compounding of metrics over time (lower CAC, higher net retention, repeatability of sales) in the depth of relationships where a client is genuinely advocating for the product. That kind of trust has always been built slowly, on the profession’s own terms.

That part has not changed despite all the noise about AI. And I would not be surprised if it continues to be the case as time marches on.

• 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.

Read more

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

Read more

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

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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.

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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.

Read more

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?

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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:

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