The Opportunity In Legal Tech

Why you should consider making the jump to the frontier of a fast-growing space, and also why you should come to my happy hour in LA

Feb 17, 2022

Earlier this week, I came across an article from Insider titled: There Are Hundreds Of Open Jobs At Legal Tech Companies Like Ironclad, Disco, and Rocket Lawyer. We Talked To Their Execs About How To Stand Out In The Booming Industry and I just HAD to share it with you all. Not only because it was written by my favorite legal tech journalist (and Off The Record subscriber!) Yoonji Han. But also because the subject matter is so relevant to what I write about in this newsletter. If there’s anything you take away from this article, it’s this:

The legal tech industry is currently growing incredibly fast. Which means it’s going to be messy and uncertain if you try to build a career in it. But the chaos also means that it’s not too late to seize opportunities especially if you go directly to the frontier.

Let me explain what I mean.

To do that, I’m going to first highlight couple of key points from Yoonji’s article, especially for those who got blocked by the Insider paywall. First, she explains why hiring for technology companies that serve the legal industry can be so challenging. You need the right kind of people who can gain trust among a skeptical audience:

Lawyers and law firms can be difficult clients to win over, given the sheer number of competitors in the space and the risk-averse nature of the industry.

Sometimes that means hiring lawyers or ex-lawyers themselves. But not necessarily. Some of the greatest legal tech sales reps I’ve ever met never went to law school. They just know how to speak credibly, avoid overpromising, and quickly gain trust with the other person. Which doesn’t require a law degree.

OK, so that’s who legal tech startups are looking for. If that’s you, how do you break your way into the space? Well, you can always check the careers page of a legal tech company’s website. Or, as Yoonji shared, you can be a bit more clever and proactive:

Attending virtual conferences and events that legal-tech companies host can be another good way to get your foot in the door
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This is such an underrated way of getting your name to the top of the list. It wasn’t how I did it, but knowing what I know now, it’s what I’d do. Having been in the startup space for almost six years, I can’t tell you how many people break in just by having a familiar name or face to the hiring execs. Although this could be from pre-existing networks, it could also equally likely be from who the execs meet at events and conferences.

This is probably a good time for a quick plug: Next week, I’ll be hosting an in-person happy hour in downtown Los Angeles (which you can register for HERE). It’ll take place at DAMA on Friday, Feb. 25th, at 5:30PM. And guess what? All drinks are paid for! By Ironclad.

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If you’re in LA and you want to explore legal tech you absolutely need to be there. Based on the initial registrations, attendees will include other legal tech startups, lawyers from leading tech companies, and lawyers doing super interesting work at forward-thinking firms. We might even have the person behind a well-known Instagram law meme account attend—anonymously of course.

Wait a minute, you might be wondering. Ironclad’s paying for drinks? For this type of event? How? Why? Is this part of Alex’s job? How the F did he end up in such a cool, unicorn job, where he gets paid to hang out? And perhaps most importantly, is this a valid and viable career path for me?

Before I answer that question, I’m going to quickly summarize what exactly it is I do for work. My title at Ironclad is Head of Community Development. It’s not a common job title, nor is it an established role. What I essentially do is help drive engagement among all communities that Ironclad touches.

That includes our customers (we have an incredible online forum for users) but also the broader legal ecosystem, many of whom live on social media. It’s why part of my job involves sharing inspirational messages on LinkedIn. And funny videos on Instagram and Tik Tok. And dumb memes and shitposts on Twitter. I create content to get a reaction from people, and then micro-communities form and self-organize in the comments. All of which contribute to driving awareness to Ironclad itself.

I’ve had this job for less than a year though. So how did I get here?

A few years ago, I was a legal tech salesman who was given an impossible quota. I know, all sales reps complain about their quotas. But I knew mine was impossible because I actually did the analysis. Based on historical data, and on an increasingly competitive environment, there was absolutely no way I could ever hit my sales numbers on my own.

That’s when I turned to social media. I spent a lot of time creating content on LinkedIn. Many of my posts were dumb, cringey, or just controversial for controversy’s sake. I tried to emulate what other successful influencers were doing. At first, none of it really worked. But slowly, over time, I started to find my voice. My content started getting some engagement. And eventually it led to people DMing me, asking for sales conversations.

Note - If you’d like to learn more, read my post about how being an entry level salesperson gave me a strong foundation for social selling

I truly believed that I’d stumbled across something incredibly valuable. But not everyone saw it. I remember all the discouragement I received in the past. One manager pulled me aside and warned me that my content would reflect poorly on the company. Another suggested that I stop posting so much, even as I was generating leads for myself and the other sales reps (and apparently didn’t understand why I was always at the top of the leaderboard for outbound sales demos). One likened what I was doing to a “sorority girl on social media.”

Today, things couldn’t be more different.

I’m at a company that truly values the work that I’m doing, which I never imagined could be possible. I’ve seen friends take on roles similar to mine at other tech companies. The market is starting to catch up. For example, I’m advising another startup that’s trying to build its brand through social media.

None of this would have been possible, if I hadn’t joined an uncertain, chaotic, and fast-growing industry like legal tech.

I’m sharing my story because I believe many of you, who might be interested in joining the legal tech space, are afraid because there is no linear path. The job is undefined! The company might go under! How will I explain this to my future employers! My point is—if there was an established path, do you think there would be any real opportunity?

I’m bullish on tech because it’s growing so fast. It’s so different than a mature industry, where you need to wait in line for your turn to do something cool. Because tech is growing so quickly, there are so many jobs that need to be done, that haven’t even been fully defined yet. I can’t even tell you because it’s literally happening as we speak. At a startup you run into problems and you find a way to solve them.

That’s what I did. In 2016, when I first got into legal tech, the ecosystem was very different. It was nowhere nearly as competitive as it is today. Social media was viewed as a hobby, as a toy. And community? No one had ever heard of it. But over the years, I was lucky enough to develop unique skillset just by operating at the frontier. The little things I figured out then is what helped me be valuable today.

None of that would have happened in a mature, stagnant industry.

To bring it all the way back—does that mean you, too, can be a Head of Community Development years down the road? It’s certainly possible. But probably not. Because in the end it’ll come down to what your unique skills and personality are, and how the industry shifts in the coming years. It’s the intersection of the authentic YOU and the dynamic changes in the market. Which might be some combination of social media, humor, and community, like me. Or something else entirely.

In the end, if you have a hunch that you’d thrive in tech, especially legal tech, I highly encourage you to put yourself out there. The world is going to look very different in a few years. Now is the time to position yourself, before the frontier becomes the new normal.

So go ahead and strike. While the iron’s hot.

Thanks for reading my friends! As mentioned if you’re in LA, and can make it, please join me for happy hour next week! If you can’t, no worries at all—there are plenty of online events and conferences in the legal tech space in the coming weeks and months.

For those of you interested in joining Ironclad, this quote was from our Chief People Officer.

Having said that, even today there are a good number of doubters out there. But that’s because they don’t see the bigger picture. Paid ads are becoming more expensive and less effective. Apple’s recent privacy changes led to Facebook being worse at targeting ads. Just this week Android said it would be following Apple’s lead. When you combine that with the flood of money to venture capital / growth equity, and an increasing focus on the legal tech sector, you get a hyper competitive market where it’s a knifefight to get in front of potential customers. What used to be a toy (social media) is now a legitimate, effective way to drive conversions.

I share more about the rewards of going off the beaten path in this article.

I’m not gonna pretend that I’m some sort of visionary. I stumbled into legal tech in part because I was coming off a failed business and getting fired from my job. But I knew tech was growing and I could leverage my legal experience. Which ended up playing out even better than I expected.

I could be overstating my case here. For example, I do think if you choose an emerging practice area, it’s just like going into a new and growing industry. Like Joe Flom and Marty Lipton when takeovers were a new thing.