In this episode of This Legal Life, Ben Chiriboga sits down with Jenn McCarron, founder of Contracts.ai, to explore a career path that defies convention.

From touring musician to legal ops leader at Cisco, Spotify, and Netflix, Jenn shares how blending creativity with technical rigor shaped her approach to transforming legal work. They unpack the evolution of contracts—from static documents to dynamic data—and why the next frontier isn’t CLM, but revenue intelligence.

Along the way, Jenn reflects on risk, reinvention, and the power of trusting both sides of your brain in building something truly new