Go where you're a unicorn

How going off the beaten path led me to develop unique and differentiated skills in the legal tech world

Last week, I mentioned that having some kind of unique and differentiated expertise can protect you on the job market. Based on the results of my poll, it seems like a lot of you are curious to hear more about my personal experience with differentiated expertise.

Before I tell my story, let me be clear: I was never able to develop this kind of expertise as a lawyer. It all happened in the legal tech world. My hope is that my journey will demonstrate patterns that you can apply to your own work or practice—even if it’s in a completely different domain. 

Going nowhere fast

During law school I worked super hard to try to land a federal clerkship. I heard it was a fantastic credential. It promised to provide world class legal training, and was an established way to set yourself up to be an Assistant U.S. Attorney (AUSA)—one of the rare jobs that could help you become high powered trial lawyer. Through a combination of hard work and luck,¹ I ended up landing a clerkship with a fantastic judge, and I learned A TON about courtroom advocacy, motion practice, and legal research.

I thought *that* would be a way to differentiate myself. It wasn’t. When I returned to my Biglaw firm, I realized that former federal clerks were a dime a dozen and that demand for that type of “cool” litigation work was limited. So instead, the firm staffed me on this massive case a ton of discovery—the non-glamourous grunt work of litigation—with unlimited billable hours and unlimited documents.²

That’s not what I wanted to do. I knew it was grunt work. I knew if I wanted to be an AUSA, or any kind of trial lawyer, I needed to deposition experience or standing-up-in-court experience. That’s the kind of stuff I went to law school for. But instead, I was spending my days preparing document productions, making deposition binders, and other types of shitwork. I was going nowhere fast. 

The pivot

I eventually left Biglaw and went to an e-discovery startup.³ There were many reasons but part of it was that I realized that I didn’t want to be an AUSA. It took a few moves, but I ended up joining a legal tech startup as an entry level sales rep, and took a giant pay cut. I had no formal sales training whatsoever. But it felt … different than when I was working at a law firm. Because at a law firm, I simply wasn’t that valuable. Even though I had an impressive set of credentials on my resume, I was missing important core skills & experience, like depositions and courtroom experience.

On the flip side, I was massively valuable to the startup. When I interviewed, they had maybe 30 employees, but zero lawyers or ex-lawyers in their ranks. It was all tech bros and engineers. As someone with a law degree AND domain experience with e-discovery and doc review, who would be on the front lines of sales—I was viewed as a complete unicorn.⁴ 

Now being a unicorn didn’t translate into me making a lot of money. At least not at first. I had to negotiate my base salary, and even then they were only willing to pay me $55,000 a year. Had I stayed in Biglaw, I probably would have earned that just with my end-of-year bonus. But the important part was that being a unicorn meant that lots of super interesting work opportunities were funneled directly to me. All without having any special mentors or sponsors. 

Becoming a unicorn

I’m going to pause here for a second because I want to go back to talking about law firms for a second. To advance and get big career breaks, it’s SO important to have some type of mentor or sponsor who guides you along the way. I’ve written about this before, but it’s not easy to get one of these senior partners to look out for you, especially if you’re not a rich white man. Mentors like to help those who remind them of themselves, and if you’re on the outside, you won’t be one of The Chosen Ones.⁵

When I was at that discovery startup, I was one of The Chosen Ones. And *not* for the usual reasons. The execs didn’t really like me. In fact, there was on exec in particular who specifically held me back in my career growth because I was viewed as a direct competitor to one of his people. The reason why I ended up getting all these interesting opportunities was because I was a cheap FTE. So execs could throw me at these high risk high reward opportunities. I was smart enough to potentially solve hard problems, but if I failed—it wasn’t very expensive.

Exposure to these hard problems was the greatest thing to happen to me. Because it forced me to face the reality of the marketplace where there were no existing solutions. I had the freedom to apply general principles to unique situations. For example, one of my earliest projects was to expand usage of our cloud e-discovery tech at a major law firm. There was no playbook for me to follow because cloud tech was so new. 

Developing expertise

I did a lot of weird shit during that time. For that “expansion” project, I tried a million things. Most of them didn’t work. In fact, the vast majority of the I tried during my 5 years in legal tech sales never ended up working. But some things did. And when they worked—I figured out how to turn them into repeatable playbooks that gave me an enormous competitive advantage in the job market. I had specialized expertise that no one else had.

For example, one of the earliest things I learned how to do was to leverage social media for sales. Cold calling law firm lawyers was super ineffective, but all the execs told us to do it because it was part of an existing playbook. I did the cold calls and emails like I was told to— just to keep the higher ups happy. But in my free time I would start posting on LinkedIn, and it eventually helped drive inbound leads.⁶

My learnings weren’t just limited to just social media. I learned how to build a webinar program from scratch. During the early part of the pandemic, I learned how to host online events on Zoom, interviewing guests while engaging with attendees in the Zoom chat. I was able to do all this because I could use my LinkedIn to drive attendance. I did all of these “experiments” in my free time, but also layered on more traditional skills, from my day job. Like forecasting revenue, reviewing sales pipeline, and managing a team of sales reps. 

All of my skills were combined in a way that gave me deep knowledge about sales and marketing technology to lawyers. And my status as a unicorn in this space gave me all of these training and development opportunities I would never have had if I worked in an environment where I was just another face in the crowd.

Lessons learned

I’m a bit hesitant to generalize from my story, which might have limited relevance to those who are practicing law. If you’re at an established firm, it’s best to take the tried and true path of finding a sponsor or mentor to guide you to professional success.

However, if you struggle to get that kind of support from the higher ups, you absolutely must take matters into your own hands.

To do that, you have to leave your comfort zone and go where you’re a unicorn. You’ll likely have to go off the beaten path to find a place like that. It’ll likely be a niche industry or unpopular practice area. Ideally, you want to look for a growing space where the rules are still being written. You want to go where it’s still in the “Wild West” stage.

When you make the move, it’ll feel unimpressive, and you might be embarrassed whenever you try to explain to family and friends what you’re doing with your career. But if you can get yourself into that position, it won’t be long before you start getting lots of opportunities to solve hard problems no one knows how to fix. Do that, and layer on some more “traditional” skills, and—well—the results might surprise you.

Good luck my friends. 

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Latest news

• My friend Nathan Cemesnka made some predictions on the second order effects of AI making its way through the law in a ALM/Corporate Counsel article called AI Could Reduce Billable Hours, But Is That Really A Bad Thing? Spoiler alert: If you’re at a firm and you don’t like sales, I’ve got bad news for you.

• Super interesting post on Reddit about how to advance in a professional services firm. It’s specifically about management consulting, but the lessons strike me as applicable to anyone who wants to succeed in a law firm as well. It’s not enough to just “put your head down and do good work.”

• At least 110 lawyers reportedly quit Biglaw firm Lewis Brisbois en masse to spin off a completely new firm. The lawyer leading the departure (who chaired LB’ s employment practice) said the group was looking for “more flexibility.” I’m not sure what that means exactly, but I bet it’s because the lawyers found a market opportunity based on the limitations of what a typical Biglaw platform could offer. Would love to hear from anyone who has more insights.

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1. I ended up getting rejected by all the judges I applied to. But then someone I met during an APALSA event ended up getting nominated to become a federal judge.

2. It was a huge, high profile case, and when it eventually settled, the WSJ wrote an article about the 10-figure settlement.

3. It actually took me two years between leaving Biglaw and joining the startup. I wrote about my journey in How I Found My First Legal Tech Job

4. In the legal tech space, most lawyers avoid sales roles and instead take on the more analytical, thoughtful roles, like in product or customer success. A lawyer who chooses to do sales is relatively rare.

5. From my article Climbing The Corporate Ladder: “Becoming one of The Chosen Ones means you’ve been selected by a sponsor—a powerful mentor who puts their credibility at risk to support you. Sponsors do things like place you on strategic matters that help you develop valuable expertise that the firm needs. They protect you. You’ll get opportunities to get in front of clients, and receive intel about the market. You’ll get visibility, so people will know your name.”

6. I’ve started to document some of the lessons learned on how to use LinkedIn for sales and business development. For example: The Right Way To Do LinkedIn and Optimizing Your LinkedIn Profile Page For Marketing