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.¹ 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.