How I Found My First Legal Tech Job

I'll also talk about the startups that rejected me, and why I left a $200k/year job on the table

If you recall from my previous posts, I had just spent the last year getting fired from my job and closing down my solo practice. I knew I needed a win to get back on track. Any win, really. So in 2016, I decided to go back on the job market. In this post, I’ll be sharing the ups and downs of that process. I ended up having to choose between two jobs, one of which paid more than double the other. Crazy, I know. But let me give you some background first.

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How I ended up here

Before I begin, I want emphasize that there were three things that were super important to me as I entered the job market in 2016. First, whatever job I ended up with had to involve working with people as a core responsibility. Which would make it different than all my previous jobs. In the past I’d always optimized for money, and all of my jobs involved trivial amounts of person-to-person interaction.

Which made me miserable, and reduced the odds that I’d thrive. I always felt like I had to pretend to be someone else at work. As I wrote in 2016:

Looking back at my own job history, for all my big talk on following your passion, I’ve usually chosen the job that pays the most . . . I think the main reason why people are unhappy with their jobs is that people are forced to recreate themselves into this “ideal” employee personality. (source)

Second, I wanted to make sure I stayed in the legal industry. Not because it would be a “waste” of my J.D. to do something unrelated to law necessarily. But because I thought staying in the same field would give me competitive advantages by leveraging my resume, contacts, and experience.¹ I did rule out practicing law though, because I just felt like it wasn’t right for me.²

Third, no job was too small for me. I knew I was making a pivot, so I’d have to take a step back in pay and title. Given that I’d spent the previous year on a solo practice that lost money, psychologically, it was easier than ever for me to accept making a low salary.

Ultimately, I knew I had to broaden my search. I’d have to look at roles and opportunities I’d never considered before. I didn’t want to squeeze myself into this next job—I wanted to find the job that fit most closely with who I was authentically:

I think we could all benefit from taking stock of our unique traits instead of trying to change ourselves to fit into some predetermined role set by our employer, peers, or society. It’s tempting to see changing yourself as “self improvement” and that when you improve your weakness, you’re becoming a better person. But really it’s just trying to turn yourself into someone you’re not. (source)

With that in mind, I began to send out resumes.

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My first job application

I fell immediately in love with the first job I found on LinkedIn. The company was called UpCounsel, and they had just raised a $10 million Series B from venture capitalists to build out a marketplace for lawyers and clients. Now in 2021, that’s not a huge amount of money, especially for a Series B, but trust me, back in 2016 that was an enormous number. So they were for sure a hyped startup. And they happened to be hiring.³

The job was called “Attorney Operations Analyst” which kind of confused me. Was it a law role? Was it operations? I dug deeper, and learned that they were looking for someone to help onboard new lawyers to their marketplace. There was no indication of how much the job would pay but given that the phrase “operations analyst” was in the title, I suspected it wasn’t going to be a whole lot.

I wrote up a custom cover letter and attached it to a highly customized resume. I spent hours, and I mean, really, hours on the application. Not just my materials, but on researching every single person in the company. Looked at every one of their LinkedIn profiles. I guess I knew, in the back of my mind, that doing that was a pointless exercise. Like, it wasn’t going to help my chances of getting that first interview. But I was just so excited. I wanted to know everything about them.

Too bad they never responded.⁴

I mean, that wasn’t completely unexpected—it’s just how the hiring game works, right? But it made me realize how much time and energy I spent researching when I should have been applying to more jobs. Which was a good reminder for me. Moving forward I’d prioritize action and activity. I told myself that I’d research opportunities only if I received an interview.

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Another setback

Around that time, I came across another legal tech startup⁵ called Judicata. I’d heard of them before, and was very excited when I learned that they were hiring. I first heard about them because it was co-founded by a guy named Blake Masters,⁶ who I’d heard of from a series of blog posts summarizing conversations with famed investor Peter Thiel—whose career path I studied obsessively because Thiel and I were both former clerks who became Sullivan & Cromwell associates.⁷

Judicata seemed like a perfect match for someone with my skills. The company’s mission was to map the legal genome—to turn all of the unstructured data in law cases into structured data. As a former clerk I thought this was A Very Cool Idea, plus working at the company would enable me to leverage my strong legal research background.

The job, which they called “Relationships Associate” seemed like it was perfectly designed for someone like me. They wanted someone to help introduce and onboard the many lawyers who had signed up for a beta version of the Judicata platform. To do that successfully, you’d have to be a good communicator, like to work with people, and understand judicial opinions.

I thought my odds were good, especially after they responded to my application quickly and after I sailed through the first two interviews. “You guys, I think this is it,” I told my friends. “I can’t believe how easy it was to find my dream job.”

Unfortunately, that’s how I jinxed myself. A few days later, I got an email from the hiring manager saying that they were taking things in a different direction. They said they weren’t rejecting me, exactly. It’s just that they weren’t sure about whether this role made sense for the company at that time. “We’ll get back to you if we do decide to move forward with this role,” they said.

But of course they never got back to me, and I learned firsthand how volatile startups can be.⁸

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The importance of being at the frontier

My interviews with the other companies didn’t go any better. Some of them—like the headhunter firms I spoke with—wanted to pay me commission-only, which was a no-go for me. Others—like legal staffing companies looking for recruiters—didn’t seem excited about me, although it could have been because they could tell that I wasn’t particularly excited about them.

Looking back, I think I just wasn’t that excited because those jobs weren’t “at the frontier.” They were in mature industries or sub-industries. Which means that to move up in that world, I’d probably have to wait years for “my turn” to get promoted. I’ve written about this on Substack before, but it’s usually better take the path less traveled because there’s less competition. It’s better to go to an evolving space. As I wrote to myself in 2016:

It’s always safer to join the edge of a growing industry . . . than the middle of a stagnant industry. More jobs are being created, and it’s easier to find a niche you can dominate. (source)

Deep down inside I knew that probably meant somewhere in technology. Not necessarily a startup. But something that incorporated technology.⁹ Honestly I was hoping I’d be able to find a company where I was already familiar with the product. Like Clio or MyCase. I’d looked at both when I was a solo practitioner, and came very close to buying a Clio license. But when I looked on their job openings page, neither of them were hiring in the SF Bay Area. I was out of luck.

So yeah, finding my first post-law job ended up being a little bit harder than expected. Even though I was willing to take a big step back in compensation, which I already felt like was a big sacrifice.¹⁰ Some of the jobs had variable comp, and others were on a pure base salary, but none were anywhere close to what I had made as a first year law firm associate. I felt lost and uncertain about what to do next.

And that’s when I found Logikcull.

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Finding an opportunity in e-discovery

Most of the job openings I found were through LinkedIn, Angel List, or career sites like Indeed. Sometimes I’d even look at Craigslist, because hey, you never know, right? But the job I ended up taking wasn’t found at any of those places. Instead, I stumbled across a post on Logikcull’s company blog. Which opened with this:

Have you ever thought to yourself, "One day I'd like to totally upend the legal profession with Legal Intelligence software"?

No. Of course not. Which is why the legal space is still ripe for disruption -- like, "You're Tower Records and we're Napster"-type disruption -- and why Logikcull is perfectly positioned to be that disruptive force.

The legal industry largely relies on old technology that's pretty boring, pretty clumsy, really insecure and extremely expensive. So, in this space, a sexy product that's easy to use, cost-effective, accessible, transparent and secure goes a heck of a long way. There's tons of opportunity to shake up the status quo, and to make a career out of it to boot.

Have we piqued your interest? Good. Because we're hiring. (source)

The post went on to describe exactly what they were looking for. Which were hungry, entry level sales reps to generate leads and find new opportunities. But the part that stood out to me most was this:

The skills and knowledge you'll gain in this position will create the foundation for a long, successful career in sales -- but it will also give you a well-rounded experience that will set you apart in whatever you decide to do next.

This was exactly what I was looking for! A role that would help me develop foundational skills, where I could do more than just make decent money for a year or two. I wanted to learn, build relationships, and honestly, be coached. I’d spent so long not learning anything because I mean, I was an entrepreneur. Flying by the seat of his pants. The way I saw it, this job sounded like a MBA with a special focus on sales. Except instead of me paying them tuition, they’d pay me a base salary!

I immediately submitted an application. I’d learned not to make the same mistake as before, as with UpCounsel, and research them to death before making a move. I mean I did do some Googling—and saw that Logikcull’s product had very good reviews.¹¹ Which was a great sign. But even better—the sales manager responded to me almost immediately. They were just as interested in me as I was in them. He just had just one question.

“This job is an entry level position,” he explained. He saw that I had been a lawyer. Was I aware of the comp range for entry level sales reps and was I ok with that?

I was. I’d done some Googling and knew what the pay range was. It wasn’t much. But I thought that if I could get promoted quickly, I could get to six figures pretty fast. And after that, there would be a path to earn as much as I did in Biglaw.¹²

I told the sales manager yes, I would be OK with that. Personally, I knew I would be going into the job with the deck stacked in my favor. First, I knew I could cold call. Really well. I had spent some time volunteering for political campaigns and had done a lot of cold calling and door knocking. I just knew I could do it. Second, Logikcull was in the e-discovery space, and sold to law firms. In my previous life, not only had I worked for a law firm as an associate—I had been in the room when e-discovery vendor selections had been made.

I was excited. Because I’d be going into this job with a lot of unfair advantages.

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Saying no to more money

Before joining Logikcull, there was still one more hurdle. A startup I had applied to months ago finally responded and brought me onsite for a conversation with the CEO. The company was called Laterally, and it was looking to disrupt the legal recruiting industry by replacing headhunters. I’m not sure how interested in the job I really was. But then the CEO told me how much I’d get paid.

“You’ll make at least $200k during your first year at Laterally” he said.

That really made me think. Logikcull offered base pay that was a fraction of that. And even if I crushed my sales numbers that first year, I’d still earn less than half of what was being offered. Was I truly ready to leave that money on the table?

The Laterally job itself seemed like something I could be great at too. They were looking for someone to speak with all of the law firm associates in their database who were in the process of switching firms. So it would involve working with people—a bit of sales, and a bit of client management—and let me remain in the legal industry.

It appeared to check off the boxes. But I still wasn’t sure. Because even though they paid less, there were two things that Logikcull offered that Laterally couldn’t.

First, Logikcull had a built out sales team. They had marketers, sales managers, and several account executives. They had a process. I could learn from them. Which meant I might be able to find a mentor, or a coach who could guide me, not just for that job, but for the jobs that came afterwards. I didn’t just want to be a rich sales rep. I wanted to learn everything about sales.

Laterally, on the other hand, had a smaller and less experienced team. It seemed like their success was driven by their highly charismatic CEO. I wasn’t sure if there would be anyone to help guide me through my sales career.¹³

Second, Logikcull was in a high potential industry that was poised for growth. At the time, legal tech was a niche space, but I could see from other startups in the software space that cloud technology was experiencing massive growth. Business-to-business software subscription (B2B SaaS) companies were really poised to break out. Legal was an untapped vertical within that market.

Being in a fast-growing market meant there was less pressure to produce at that specific job. Which was important because even though I suspected I could do well at sales, I didn’t really know. If I underperformed at Laterally, I’d get fired and have to start over from square one. But at Logikcull, I could probably quickly find another job in the space and continue my sales education. I couldn’t really lose.

In the end there were just so many different ways to win at Logikcull. Which, as I mentioned in my previous post, was exactly what I was looking for at that moment. So I told the Laterally CEO thanks, but no thanks, and signed my Logikcull offer. My official title would be Sales Development Representative, and I’d be paid a base salary of $55,000/year.

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What happened next

Going to Logikcull changed everything. It served as the foundation for everything good that has happened to me career-wise since. I ended up learning a ton about sales. All of that helped me do well at the job itself. Which led to promotions. Which led to more money and equity.¹⁴

More than that, it put me squarely at the center of a niche that experienced immediate explosive growth. I joined Logikcull during the summer of 2016. Over the next five years venture capital flooded the space and law firms & legal departments started purchasing software subscriptions at a record pace. My analysis about the space Logikcull occupied¹⁵ ended up being spot-on and helped me position myself in front of the approaching tailwinds.

I ended up spending three great years at Logikcull. I learned the blocking and tackling involved in selling software. I also discovered how to leverage social media to generate revenue, which is what I consider my unique superpower today. I also had the privilege of working with some incredibly wonderful people and will always be thankful for my time there.

Thanks for reading! My journey from getting fired to landing a job in legal tech lasted for just a year. But as I mentioned, that first sales role made everything else possible. I’ll be sharing more about what it was like to be an entry level sales rep (Spoiler alert: I got disrespected a lot); what I learned about the legal tech startup space; and what led me to make the jump from e-discovery to contracts in 2019.

1. I had a feeling that my personal network was going to get incredibly valuable in the next 5-10 years. My law school friends, who I drank with and played pickup basketball with, were going to become partners and GCs. Having a robust network of lawyers was an appreciating asset on my personal balance sheet. Staying near the legal profession meant my network would continue to be a big advantage in my career.

2. There were several reasons why I ruled out practicing law. But at the end of the day, I felt that the job didn’t align with my personality. Yes there are many ways to be a successful lawyer that don’t involve being super detail oriented, meticulous, and careful. But why swim against the current if I could find something else entirely? Maybe it was also because I’d failed the bar exam years ago, and deep down inside I felt I would never be a great lawyer. It’s a lot to unpack and I might write more about it someday. But the takeaway was, I knew I didn’t want to practice law.

3. It wasn’t easy finding interesting companies that were also hiring. For example, I was fascinated by InCloudCounsel, which was founded by a bunch of ex-Biglaw lawyers. I came across them when I was a solo and met some of their team because I was considering using them. (They were a platform for freelance attorneys to do work for clients.) I thought they might be a great place to work but when I looked on their website, they weren’t looking to hire anyone. Over the years, they’ve posted job openings stating their interest in looking for someone with my profile - ex-Biglaw, interest in tech, functionally a salesperson. As with most things in life, the timing was just off.

4. In an interesting turn of events, I became an investor in UpCounsel five years later. The company struggled and was eventually acquired by a private equity group at the eleventh hour before shutting down. As I understand it, they rebooted the company and brought on experienced managers, including a former boss of mine who later became the VP of Sales at the famed legal startup Atrium. He helped stabilize and grow UpCounsel, which then launched a crowdfunding campaign to raise capital in 2021. That’s how I became an investor.

5. By the way, I wasn’t only looking at startups. I also applied to staffing agencies, headhunting firms, and other law-adjacent companies. It just so happened that many of the job openings I found were tech startups, maybe because I was only looking in the San Francisco Bay Area.

6. I didn’t know it at the time, but by the time I was considering joining Judicata, Blake Masters had already left the company. I recently looked him up and it looks like he’s running for the U.S. Senate out in Colorado. Guess you never know where your career will take you.

7. I know many have mixed feelings about Peter Thiel, especially since he’s weighed in publicly on a lot of issues outside of business & technology. Setting that aside, he’s had a pretty interesting career journey, leaving Biglaw after several months to be a trader and then a speechwriter. Thiel eventually found his place on the West Coast, helping co-found the company we now know as PayPal and made his mark in tech as an investor.

8. After five years operating in stealth mode, Judicata finally launched their product in 2017. The result was somewhat underwhelming according to some experts, especially given what had been promised (“mapping the legal genome”). Which was unfortunate. Three years after that, Judicata was acquired by legal research company Fastcase.

9. One example of this was Atrium, the tech enabled firm I mentioned in an earlier footnote. In 2017, while I was still cutting my teeth as a junior sales rep, a well-connected friend who was one of their early investors introduced me to one of their co-founders. On its surface it seemed like a wonderful opportunity to get in early on a promising startup. But I declined to pursue it further. A few weeks later, Atrium publicly announced that they’d raised $10 million in venture funding. Why didn’t I want to join? Well, there were a few things about their plan that struck me as not so well thought out, and I felt it would be better to stick around at Logikcull for a few more years. Learning and development were my priorities. Turns out it was the right move because the company closed its doors just three years later. Justin Kan, one of its co-founders, has publicly recounted the reasons afterwards in a fantastic Twitter thread. I highly recommend reading through it.

10. Every single role I looked at offered between $50,000 and $70,000 in base salary per year.

11. Interestingly, during my research, I’d learned that one of Logikcull’s competitors in the e-discovery space—a startup named Everlaw—was co-founded by my former boss. Yes, the very same boss who fired me. It now made sense why we always used Everlaw for all of our e-discovery. Anyways. There are times when I wonder if I decided to ultimately work at Logikcull as a way to “get back” at him. Life has a funny way of working out though. Today, Everlaw is one of Ironclad’s most important customers, and I have so many friends who work there. So the negative feelings I used to have about them has been replaced by warm fuzzy feelings.

12. I wasn’t optimizing for money, but I did pay attention to the potential upside.

13. When I told a close friend from law school about my decision, he said “What would you learn about sales, anyways? It’s not rocket science.” Which couldn’t be further from the truth. Unfortunately this is a common view among lawyers.

14. During my second full calendar year in sales, I earned more money than I ever did as a Biglaw associate. To be clear, it wasn’t an objectively large number—after all, I was an associate many years ago. But I was surprised at how quickly my income bounced back.

15. It’s kind of fun looking back at some of my writing from 2016. This is what I said in an email to a few friends talking about how uniquely positioned Logikcull was:

The company sits squarely in two different growing markets. The first is the SaaS industry. Software is increasingly moving from the old model, where you would pay up front, install the application, have to contact (or hire) IT personnel for tech support, and then a few years later, pay again for upgrades. SaaS changes things. It operates on a cloud-based subscription model where you pay $X per month, gain access by logging in through your browser, and have all your upgrades done automatically. It's like how instead of paying $1,000 up front for Adobe Photoshop, now you can pay $10 a month for a subscription. The economics of the SaaS model are compelling to both the business and the customer. 

The second is the market for legal technology. Most software products used by lawyers are archaic, complicated, and expensive. Unlike other industries that embrace innovation, the legal industry has resisted technological change. That means there are big opportunities in this space. Of course it won't be easy--resistance to innovation will be a huge obstacle because lawyers don't like change. That's where I come in. My job as a salesperson is to make sure I can convince lawyers to overcome their objections and adopt new technology that will benefit both them and their clients.