Failing My Way To Success 

“This is the most important initiative at the company right now, and we need you to really focus on this,” they said. It was 2017, and I was a salesman who sold e-discovery technology to small law firms. The company I was working at was a hot venture-backed startup that was looking to move “upmarket” and to start selling their tech to some of the largest firms in the world.

On paper it seemed pretty straightforward. Large firms are just like small firms, except they have a lot more money and cases, right? It seemed like I was the right person for the job. I used to work in Biglaw, as a litigation associate, and had firsthand knowledge of what kind of sales pitches would be compelling to large firms.

But deep down inside, I had my doubts. Small litigation firms needed our tech to work more efficiently to keep price points low, as they competed for clients against larger firms. Biglaw, on the other hand, had very little use for our technology. Efficiency would cut down on billable hours, which would reduce overall firm revenue. The incentives just weren’t aligned.

There were other headwinds too. Biglaw firms have a decentralized org structure (kind of like an archipelago) which means it’s incredibly hard to convince them to buy software for the whole firm. This was especially true in the e-discovery space where Biglaw firms typically use lots of different providers, depending on the case or client. Which meant the whole initiative was probably less lucrative than it seemed.

I went to great lengths to try to make it work out, though. I hosted happy hours and dinners, asked people out for coffee, and just cold called virtually everyone at the firm. But they all ignored me. Biglaw just had too many other priorities, and just wasn’t interested in hearing what I had to say.

In the end I had absolutely zero revenue to show for it. Eventually, my company scrapped the initiative and reassigned me to my previous role. I stopped thinking about Biglaw completely.

That is, until about a year later, at a conference out in Chicago.

The Epiphany

For technology vendors, conferences all kind of feel the same. You show up in your booth and try to hand out swag and attempt to persuade attendees to stop by and talk to you, who by the way, want absolutely nothing to do with you.

But at this conference things were different. At least for me. Because early on, someone influential introduced me to a bunch of his friends, all of whom were in-house lawyers at corporate legal departments.

Now as an e-discovery salesman, I’d never really paid too much attention to legal departments. They didn’t typically buy e-discovery tech. But at this conference I didn’t know anyone else. What else was I going to do? So I just hung out with these in-house lawyers. Which turned out to be the best thing because we all got along great and had a fantastic time. We got drinks, stayed out late, and just had a lot of fun.

And that’s when I noticed Biglaw firms starting to treat me differently.

You see, before they saw me hanging out with these in-house lawyers, the firms had zero interest in talking to me. They did the whole “avert your eyes” thing to avoid having to speak with me. But. Once they saw me rubbing elbows with their potential clients, everything changed. They started to approach me for conversations, presumably to get a warm transition or introduction to my new friends.

I felt like the nerd who accidentally became part of the cool crowd.

The change in how I was treated made me think. It dawned upon me that the corporate legal department is central to the legal ecosystem in a very unique way. These assistant GCs and deputy GCs might not earn as much money as their law firm counterparts. But they had sway. They had clout.

And yet, in the legal tech startup world, entrepreneurs often focused their attention on Biglaw firms instead.

Could you blame them? From the outside, Biglaw seems to be the most important customer segment. They do the most interesting and cutting legal work, and are at the top of the economic food chain. They are absurdly profitable (the economic “slowdown” of 2022 has so far resulted in a mere 3.6% drop in profits) which seems to imply that they also have the largest technology budgets. Which isn’t always the case.

When it comes to innovation, though, the hierarchy is very different. Corporate clients are far more influential when it comes to driving tech adoption. They love efficiency. The incentives are aligned. And who knows? If you won them over, they might force their outside counsel to adopt your technology, because it could make *the firms* more efficient — which could minimize legal fees.

That was the first moment I wondered if I needed to make a change. Maybe I was doing it all wrong. Maybe I needed to work for a legal tech company that serves corporate legal departments instead of law firms.

The Transition

That insight is what eventually led me to abruptly leave the e-discovery space to join the contracts technology space in 2019. There were a few different factors that played into my decision. It wasn’t easy though. I’d be leaving a lot of money on the table. There was an arms race for talent in the e-discovery space, and not only would I earn less by moving to contracts instead — I’d also be giving up a lot of the skills and connections I’d built up.

Plus, I mean, I had no experience with contracts. I’d done exactly zero transactions while I was in Biglaw. I’d never worked as an in-house lawyer, and knew just about nothing about commercial contracts. There was nothing on my resume, or in my background, that would suggest that I’d be successful in the emerging contracts space.

No matter. Once my eyes were opened, I couldn’t look away. I started to notice other trends. There was, for example, the explosive growth of legal operations and CLOC. The existence of an established legal ops community meant that you could efficiently sell technology to lots of different corporate legal departments. Which at the time was unprecedented.

Buyers in this world also preferred to pay for subscriptions, which was aligned with the “enterprise SaaS” revenue model. And the potential market for contracts tech was huge. Because every single company has contracts.

There was a lot to like in this new world. Even if I felt uncomfortable in it.

Three Years Later 

Looking back, making the switch to the contracts space in 2019 was absolutely the right decision for me. I found a new segment of the legal industry that was far more receptive to new technology. Because it was such a new niche, I was exposed to lots of different opportunities to grow. Which never would’ve happened in an established category like e-discovery, where I’d be overlooked for promotions or have to wait in line behind countless execs with decades of experience.

The best and most unexpected part was that my next job — running sales for a contracts tech startup — helped me stumble into a hyperniche involving legal tech, marketing, and content creation. I was somehow able to figure out how to use social media to capture attention from corporate legal departments at scale. Which ended up being valuable enough to help me land the perfect role designed specifically for me at the leading company in the contracts tech space.

I’m not sure what the most important lesson from all this is. Maybe it’s that legal tech startups should focus on corporate legal departments instead of Biglaw. Or maybe it’s that sometimes the right decision is to walk away from what you’re comfortable with, to something completely unfamiliar. Hell, maybe it’s that going to conferences is still valuable.

Whatever it is, I’m glad that I was sent on that mission to sell e-discovery tech to Biglaw years ago. Because even though it didn’t work out, it put me on the path I’m on today. And I’m so thankful for it.

Alex Su is currently the Head of Community Development at Ironclad, a leading legal technology company that helps accelerate the contracting process. Earlier in his career, he was an associate at Sullivan & Cromwell and clerked for a federal district judge. Alex graduated from Northwestern Pritzker School of Law, where he was an editor of the law review and the student commencement speaker. In his free time, he writes about his career journey and legal tech in his newsletter Off The Record. You can find Alex on Twitter, Instagram, LinkedIn, and yes, even Tik Tok.