Jackie Schafer is the Founder and CEO of Clearbrief, the leading litigation drafting platform built directly inside Microsoft Word.

Jackie was named 2025 Innovator of the Year at the Legalweek Awards, and the American Bar Association honored her as a 2025 Legal Rebel for developing AI tools that help litigators, arbitrators, and judges write with greater accuracy and trust. Jackie currently serves as a Lecturer at Columbia Law School, sits on both the Texas Bar’s AI Taskforce and the Washington Bar’s Legal Technology Committee, and is a board member of Probono.net.

In this episode, Jackie shares how an improbable AI founder built one of the fastest-growing legal tech companies by grounding everything in real litigation pain points. Host Emily Parkhurst talks with Jackie about the asylum case that planted the seed for Clearbrief, and how that moment revealed a gap in the justice system that technology could close.