Why I Left E-Discovery For Contracts

A quick overview about my thought process back in 2019 when I made the jump

You all know about the fateful decision I made to leave law for legal tech sales. I’d joined an e-discovery startup, which I felt comfortable with because I had been a litigator. But I’ve never really talked about my pivot to the contracts tech space, three years in. As it turned out, my timing was pretty good, because that’s right when the entire contracts space got red hot. Today I’ll highlight a few of the reasons why I made the move, despite having minimal experience with contracts as an attorney.

The Background

By the time I decided to leave my e-discovery 2019, I knew a few things. Mostly about myself. As it turned out, my hunch that I’d be good at sales was right.

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I also realized that I was bad at corporate politics. Much of success didn’t depend on whether you were good or not—it depended on whether you knew how to do this really weird thing called “managing up.”

Apparently, many successful employees have mastered the art of manipulating perceptions. I mean, everyone does it, a little. Like back in the day, before COVID, when I’d hang around the office with nothing to do until my manager leaves so I wouldn’t look like a slacker. It makes sense to manage your own perception and make yourself look as good as possible to the bosses.

But I’m really bad at it. And I quickly realized that as my company did better, the professionals started to show up. You know, people who had worked at bigger companies and were somewhat mercenary in how they approached employment. Because of their experience or perhaps connections with executives or board members, they were able to take high positions within the company without knowing very much about our customers or our market.

It was similar to the challenge I faced when I was still working in Biglaw. When you work in a mature business with entrenched employees, it is really really hard to move up and have an impact. My company had gone from a small, seed stage startup to a “grown up” Series B startup. And the e-discovery space as a whole had matured, with lots of gray haired executives at companies that had been around for a while. It started to remind me of what I hated most about the law firm world.

Because when the industry matures, and startups become bigger, the number of years of experience and relationships became more important. As someone just 3 years into the sales game, in the tech world where I knew no one—I had neither.

So I knew that I might need to find another space where my talents could have a bigger impact.

Organization Type

I knew I wanted to stay in the legal tech space. In fact, right around the time I was considering making a move, I’d been recruited for an enterprise sales role at a Major Silicon Valley Unicorn.

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They offered me 80% more money. As hard as it was to turn down, that’s exactly what I did because I knew I wouldn’t have any lasting competitive advantages there. Because it wasn’t part of the legal ecosystem.

But more than that, it was a relatively mature organization. I wanted to work at a company where I didn’t have to worry about “getting visibility.” I just wanted to figure things out. So when I came up with a list of potential next jobs, I really only looked at Series A and earlier companies—unless there was something else really compelling about the role.

That’s how I ended up deciding to join a twelve person startup in the contracts space. They had just raised a seed round of funding, and were looking for sales reps. When I showed up, they recognized how unique of a skillset I had — law, sales, and management experience. I knew that the company was probably messy, operationally. I mean, it’s a startup! But that also meant that I would be able to solve problems and do work without having to “manage up.”

Subject Matter

I was very excited about entering the contracts world. I mean, yeah I didn’t have any legal experience with contracts. But I could figure it out, right? I knew enough to realize that we lawyers overvalue credentials, and undervalue our ability to improvise and figure things out.

But there was definitely something happening in the contracts space. During my job search, I’d networked with a bunch of different people and many of them told me the same thing. “Watch out for contracts.” There was even one alternative legal services provider executive who I’d spoken to about a job, who advised me: “Get up to speed on all things contracts. It’s becoming an incredibly important part of the business.”

Other than rumors and random tidbits that would come my way, I also knew that contracts occupied a strategic part of the broader legal ecosystem. They were used by in-house lawyers—the ultimate end user / buyer of legal services. They touched all aspects of a company, from employment contracts, to sales contracts, to vendor contracts, and even to the company’s own commercial lease. It was just so broad especially compared to litigation focused e-discovery.

And finally, I knew that contracts tech was perfectly aligned with the subscription model. I’d read that there having your buyers purchase your software through an annual or multi-year plan was far more valuable than a one-off purchase. E-discovery is purchased on a usage basis. But contracts tech would be bought via subscriptions. Which meant that the tech companies in the contracts space would have bigger valuations and more resources to pay for revenue.

As a salesman, that last part was important—because it meant more money for me.

Conclusion

I don’t really have one because I tried to write this all out quickly and honestly. Let me know what you think! Would love to hear your comments and questions.

1. In part because I felt like I quickly grasped some of the first principles of selling to legal. I shared my framework a few weeks ago here.

2. An earlier draft of this article had the company name. Everyone in tech idolizes this company. Interestingly, the person who recruited me was a former lawyer too. That, and the fact that I had recent outbound sales experience, was how my name made it to the top of the list.