How do legal tech founders become who they are? Every journey is different, but always compelling. In this case we hear from Jackie Schafer, the founder and CEO of Clearbrief, who takes us on a journey that includes the collapse of Lehman Brothers on her first day at Paul Weiss, love in Alaska, and the arrival of genAI.
And in case you’ve not seen it before, Clearbrief helps litigators to find and share the evidence behind legal writing, from generating a timeline to deposition summaries with hyperlinked citations, and more. Read on.
– How did it all start?
My first day after graduating from law school and starting as a litigation associate at Paul Weiss was the day Lehman Brothers collapsed in 2008. I remember being in a room with all my fellow first years for our orientation day and we were just looking at each other, terrified, thinking…will we still have a job?
It turned out there was a ton of litigation to be fought in the aftermath and we were kept extremely busy. But I do suspect that shock may have influenced my thinking about how the ‘safe’ path in life can have completely unexpected trapdoors.
– How did Alaska play a part in your trajectory?
I fell in love with a musician (who is now my husband, and a software engineer!) who is from Alaska, and that gave me the courage to take my first big career risk – leaving a lucrative and challenging Big Law role in NYC to move to Anchorage. Everyone in NY thought this was completely insane, but I decided to listen to my gut – one of the many bold decisions that took me to my startup journey years later.
I initially took an in-house role at an Alaska Native corporation, which gave me the chance to travel to the Northernmost part of the US (Barrow, AK) and gain some fascinating life and legal experience. I wanted to get back to litigation, though, so I joined the appellate section of the Alaska Attorney General’s Office, where I had the chance to regularly brief and argue cases before the Alaska Supreme Court and work on lots of thorny legal issues that impacted public safety across the state.
I spent ridiculous amounts of my day, every day, thinking about the art of legal writing and citations, reading Bryan Garner (who later became one of my first angel investors in Clearbrief!) which obviously influenced the product that I wanted to build years later.
A number of other career risks and steps outside my comfort zone took me to Seattle a few years later, when I started learning about AI, and I eventually founded Clearbrief in 2020. I don’t know that I would have done it if I hadn’t taken that first big career risk of moving to Alaska and realizing that I don’t need everyone else’s approval to do what I think is compelling in life!
– Now that Clearbrief is doing well, what are some of the main challenges you faced before?
Probably the biggest challenge in the early days was getting serious litigators to risk their time, energy, and reputation on using a new AI product for actual work they needed to file with the court on a deadline. But I always knew that was the bar we needed to pursue – it’s an insight I still think about a lot.
For example, playing around with ChatGPT and similar tools is fun and might reflect a lot of ‘usage’ if you just look at the data on interactions with it. But most of the time, I never actually use the results I get from ChatGPT for anything I’d put my name to. In contrast, Clearbrief has always been focused on creating and perfecting a Word document that has to get filed with the court and that has hyperlinked citations after every sentence – and the resulting usage stats of key actions in our product (and the feedback we get daily from customers) reflects that they are actually using Clearbrief on real work.
That focus on being truly helpful in the steps leading up to filing with the court helped us overcome the challenge of proving ourselves to litigation users, who have incredibly high standards for everything they write.
– Where is the company heading now? What do you hope to achieve in the next few years?
We are staying laser focused on litigators and investigators who do their writing and thinking in Word, with the goal of adoption by every law firm and in-house team in the US (and Europe)! We are doing that by intertwining classic and generative AI in ways that maximize the value of each approach. And most importantly, we are investing in training the users and making it super practical – helping them feel confident in the workplace about the value they are bringing as insightful humans.
– Finally, what has been the most satisfying moment of your career so far?
I have to say that while I am super-honoured to win awards for my work with Clearbrief, probably the best moment that stands out is being there at a massive clinic on MLK day this year in January where Clearbrief was used to help over 100 families in one day. Several folks from the Clearbrief team were there, my kids actually were there too (they had childcare at this event) and I looked around and really felt the impact that tech can have in the real world.
I am so, so proud of the work we’re doing to encourage our Big Law and enterprise customers to increase the impact of pro bono work they do for veterans, families, and people who desperately need legal help. If AI isn’t being applied to help with those needs, it won’t have fulfilled its promise of transforming the legal industry. (Close second – it was very fun to belt out a musical theatre parody I wrote to open this year’s ABA Techshow Startup alley competition!)
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Thanks Jackie, that’s a great founder’s journey.
You can find more about Clearbrief here.
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Legal Innovators California Conference, San Francisco, June 11 + 12
And if you’re interested in the cutting edge of legal AI and innovation, then come along to Legal Innovators California, in San Francisco, June 11 and 12, where speakers from the leading law firms, inhouse teams, and tech companies will be sharing their insights and experiences as to what is really happening and where we are all heading.
We already have an incredible roster of companies to hear from. This includes: Legora, Harvey, StructureFlow, Ivo, Flatiron Law Group, PointOne, Filevine, Briefpoint, Centari, eBrevia, Legatics, Knowable, Draftwise, LegalOn, newcode.AI, Riskaway, LawDroid, Crimson, SimpleClosure and more.
See you all there!
More information and tickets here.
