Finding product-market fit for AI is rarely a straight line. In this panel, Ketan Babaria (Chief Digital and AI Officer, eHealth), Beverly Rich Ingersoll (VP of AI and Innovation, UnitedLex), and Nitin Shingate (CTO, GoodRx) trade war stories from the health insurance and legal industries — from using Voice AI to cut customer wait times, to building AI advisory services for clients who don't yet trust the technology. They dig into change management risk, regulatory hurdles, and how to win organizational buy-in, before opening it up for audience Q&A on success metrics and the build-versus-buy debate.