Molly Finn: Embracing a Nonlinear Career | Evolving with Jessica Nguyen

How do legal teams build trust in AI, and who keeps watch once AI agents are running? Molly Finn, former eBay Deputy GC, joins Jessica Nguyen to talk nonlinear legal careers, AI drift, and the rise of the agent officer. In this episode of Evolving, Jessica Nguyen sits down with Molly Finn of Finn Law, Advisor at Sandstone and former VP, Deputy General Counsel and Chief Compliance Officer at eBay. Molly shares how a startup job turned her into an employment law specialist, what being embedded in Cisco's HR team taught her about client service, and why the linear path into law is disappearing as AI reshapes early-career legal work. They also dig into hands-on lessons from building custom AI skills and catching where models drift, why legal-specific AI still outperforms general models, data walls and leakage risk inside the enterprise, and why every legal tech stack should be easy, and even fun, to use. Chapters 00:00 Meet Molly Finn: 18 years at eBay 02:02 What a nonlinear legal career looks like 03:46 From startup generalist to employment law specialist 04:32 Embedded in Cisco's HR team, then on to eBay 06:19 What business leaders want from their legal team 09:15 Why the linear path into law is disappearing 10:08 Advice for law students in the AI era 12:09 Building a custom AI skill and catching drift 15:10 Why corporate AI tools fall short for legal 19:49 Can a general LLM solve everything for legal? 22:00 Trust, privilege, and legal-specific AI 23:06 Legal's "four walls" and data leakage risk 25:03 Agent governance and the rogue agent story 26:49 The rise of the agent officer 30:10 What excites Molly in legal tech right now 32:31 Do legal teams still need a CLM? 34:42 Why legal tech should be easy and fun 39:03 Rethinking the legal tech stack 43:52 What's next for Molly and the future of AI in law Evolving with Jessica Nguyen is brought to you by Sandstone, the AI-native platform for in-house legal teams - learn more at sandstone.com. #InHouseCounsel #LegalAI #GeneralCounsel