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: