What I learned at Evisort

Why I decided to join a relatively unknown AI startup back in 2019 and what I took away from the entire experience

Last week I learned that Evisort was acquired by Workday. This is the second time something like this has happened to me; just last summer my first startup was acquired, which I wrote about here. Hearing the news led to lots of text messages this week between me and a few old friends from Evisort.

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

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

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

Joining an unknown startup

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

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

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

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

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

I decided to jump on board.

“If I was running things”

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

Now I had a chance to do exactly that.

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

All in all it felt risky.

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

This is me at the happy hour we hosted at the 2019 ACC in Phoenix. It was the company’s first time sponsoring the ACC conference and to say that it was a chaotic doesn’t even begin to describe the experience.

Making my mark

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

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

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

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

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

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

Seeing the bigger picture

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

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

I joined Evisort right after they raised a seed round; you can see how scalability and predictability of sales matters to unlock the next level. Source

This visual from Elad Gil shows how showing that sales could be scalable increases the valuation of the company. Source

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

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

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

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

I snapped this picture of our intern as we made those cold calls. That intern by the way—who was at the time a law student—ended up starting his own legal tech startup that was eventually acquired a few years later. I’d like to think that he used some of the tactics we developed in our calling campaign.

Good news for the company, bad news for me

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

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

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

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

All company picture we took at HQ right before announcing the Series A

More time to develop expertise on how to sell to lawyers

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

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

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

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

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

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

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

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

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

Epilogue

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

Basically Ironclad offered me a unicorn job.

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

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

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

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

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

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

1. Here’s coverage from Bob Ambrogi about me joining Evisort. It was the first time I ever had to deal with PR and journalists, and I was incredibly nervous.

2. Related point: I have always been surprised by how many lawyers are interested in working for “hot” startups. To me the real opportunity is at small, unknown companies that haven’t figured things out yet. Otherwise, why don’t you just join a big company or established firm? I suspect the truth is that most lawyers overindex on employer branding, to the extent that they’ll take a smaller opportunity in comp or responsibility, to associate themselves with a hot startup. After all it’s likely how they built their resumes; having gone to top schools and worked at top firms. So they focus on the wrong signals when choosing a startup.

3. If you’re new around here, feel free to look at my old articles detailing my experience at Logikcull.

4. For any salesperson looking to work for a startup, I would say product market fit is the most important thing. Most sales jobs are relatively straightforward—you know there are buyers out there, and your job is to find them. For startups though, there’s usually another hurdle to overcome. Do people actually want or need the product, so much so that they’re willing to pay for it? For many startups the answer is no—and yet lackluster sales are often blamed on ineffective sales teams. Truth is, if your company doesn’t have product market fit, no amount of magic sales words and clever tricks will get you the revenue you need.

5. Notably the company did not have a job posting for a head of sales. Instead, they had an opening for a relatively junior salesperson (which I found on AngelList). Instead of applying for that role, I instead reached out to the CEO directly via LinkedIn. At the time I knew I had a unique background and set of experiences, so I fully expected that there would be very few companies who even knew to look for someone like me. That’s why I always recommend lawyers looking to transition to startups to directly reach out to CEO; you never know what they need and how they might find a way to use you. You certainly won’t find that unicorn role posted on a job board.

6. If you talk to any junior level sales rep, e.g. BDRs and SDRs, you’ll find that a big part of their job is cleaning lists and prospecting. It’s not actually selling. And yet many top-down sales orgs believe that merely adding headcount will add to sales pipeline. You get far more ROI by handling the list building/cleaning process centrally so the BDRs/SDRs can focus only on outbound calls and emails. Remember, as a general rule, people who are interested in sales jobs are often not detail oriented and struggle with tasks requiring detail orientation, like building lists. Evisort actually was ahead of the curve in this respect; they invested in sales ops to set up a working infrastructure for the sales team very early on. And it showed in our results.

7. It’s incredibly important to know what you’re selling, and to who. In contracting, it may appear that you’re selling your tech to in house lawyers, but the true buyer may be procurement, IT, operations, or some other group. If that’s the case, you absolutely do not need to hire ex-lawyers to sell your product. On the other hand, if you’re selling something more specific like legal research software, it may not be enough to hire an ex lawyer—what you need is an ex litigator. To get a sense of what I’m talking about, look at all of Casetext’s former sales reps vs. your typical CLM or ELM (enterprise legal management). It’s very likely that the latter has successful AEs who come from a wide range of professional backgrounds. But that probably wouldn’t work when selling niche legal products with innovative features, like AI powered legal research.

8. I also launched a podcast for Evisort and helped the marketing team launch a webinar program that add hundreds of registrants to our list. Because we had such a lean team I was forced to do things that didn’t scale, like produce/edit our episodes or manually add registrants from LinkedIn comments. It sucked at the time, but it helped me learn so much.

9. Around this time I was also recruited to a tiny legal tech startup called “Litty” as its head of growth because they came across me on Tik Tok. Even though I got along with the founders and felt like they were on to something, I declined the opportunity. In my mind, I could more easily judge the early iterations of my social media experiments if all the other market dynamics were familiar to me. If I’d joined Litty, I’d need to navigate a completely new market while running experiments; that was too many variables. It was far preferable for me to stay in CLM. Around the time I left Evisort, Litty decided to rebrand and changed their name to EvenUp. Things really took off thereafter. Just last week The Information reported that EvenUp’s about to raise their next round of funding at a $1 billion valuation. I try not to think about counterfactuals too much but this one will probably weigh on me for a while.