How to Break Into Legal Tech and AI as a Lawyer with Ben Chiriboga episode artwork

EPISODE · Apr 20, 2026 · 45 MIN

How to Break Into Legal Tech and AI as a Lawyer with Ben Chiriboga

from The Former Lawyer Podcast · host Sarah Cottrell

Legal tech comes up constantly when lawyers are thinking about leaving practice. It's legal adjacent, the field is growing, and there seem to be a lot of jobs. But when lawyers actually try to make a move, they usually don't know where to start. The roles aren't standardized, the titles don't mean the same thing across companies, and it's hard to know where a legal background even fits in.Ben Chiriboga figured this out the hard way. He spent two years after leaving practice chasing legal tech roles without any real direction, burned through his savings, and eventually found his path, going on to become a founding team member of a legal tech startup. Now he runs Reframe Lawyer, a platform built specifically to help lawyers move into legal tech and AI careers.In this episode of The Former Lawyer Podcast, Sarah Cottrell talks with Ben about the three main career tracks available to lawyers in legal tech and AI, why a JD is a bigger competitive advantage than most lawyers think, and why figuring out who you are and what you want has to happen before anything else.0:52 - Ben Chiriboga on founding Reframe Lawyer and his path from practice to legal tech2:27 - Why legal tech keeps coming up for lawyers who want to leave practice4:07 - No agreed terms, no standardized titles, and what that means for your job search4:45 - You're not alone in being confused about where to start in legal tech9:17 - The three main career paths in legal tech and AI for lawyers leaving practice11:41 - Product roles and why lawyers are better positioned for them than they think13:00 - Go-to-market roles and why a JD is a competitive advantage in sales conversations13:48 - Why operations roles are booming inside legal tech companies right now15:13 - JD required vs. JD preferred and what your legal background signals to employers17:55 - Why lawyers automatically rank in the top 1% of candidates for legal tech jobs24:52 - Why lawyers try to execute before they know their objective30:25 - Why applying for every legal tech role is a recipe for madness35:37 - How to speak to a role you've never held and start building proof of interest39:38 - Why updating your resume is the last thing you should do42:24 - Ben's closing take on legal tech as a viable career path for lawyers ready to make a moveMentioned In How to Break Into Legal Tech and AI as a Lawyer with Ben ChiribogaReframe Lawyer | Ben Chiriboga on LinkedInEscaping Lawyer Burnout for Legal Tech with Ben ChiribogaHow To Revise Your Resumé For A Non-Legal JobFrom Biglaw to Legal Tech with Alex SuThe Claude-Native Law Firm by Zack ShapiroFirst Steps to Leaving the LawThe Former Lawyer Collaborative

Legal tech comes up constantly when lawyers are thinking about leaving practice. It's legal adjacent, the field is growing, and there seem to be a lot of jobs. But when lawyers actually try to make a move, they usually don't know where to start. The roles aren't standardized, the titles don't mean the same thing across companies, and it's hard to know where a legal background even fits in. Ben Chiriboga figured this out the hard way. He spent two years after leaving practice chasing legal tec...

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How to Break Into Legal Tech and AI as a Lawyer with Ben Chiriboga

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This episode was published on April 20, 2026.

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Legal tech comes up constantly when lawyers are thinking about leaving practice. It's legal adjacent, the field is growing, and there seem to be a lot of jobs. But when lawyers actually try to make a move, they usually don't know where to start. The...

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