Alexandra Sepulveda: Curiosity is a Superpower | Evolving with Jessica Nguyen

Some legal careers follow a straight line. Alexandra Sepulveda's runs from patent litigation to trademarks, from General Mills to gaming, ed tech, and now consumer legal tech at Trust & Will, and curiosity is the thread that ties it all together. In this episode of Evolving, Jessica Nguyen sits down with Alexandra to talk about what she's learned leading legal at early-stage startups, growth-stage companies, and large enterprises. They get into why new in-house lawyers should resist the urge to prove themselves on day one, how to scale your management style to the person in front of you, and why being a person of your word, and keeping the receipts, pays off. They also dig into how in-house teams really choose outside counsel, what AI is changing about billable hours and law firm economics, who pays to train junior lawyers when AI does the first draft, and the business Alexandra would build if she never had to work again. Evolving with Jessica Nguyen is brought to you by Sandstone, the AI-native platform for in-house legal teams - learn more at sandstone.com. Chapters 00:00 Don't disturb the herd 00:38 Meet Alexandra Sepulveda 02:43 Curiosity as a career superpower 04:32 General Mills and cutting her in-house teeth 07:59 Starting over and building resilience 11:56 Scaling your management style 14:02 Lessons from law firm mentors 19:59 Being a person of your word in-house 22:01 Legal can't meet every need 27:15 Theoretical risk vs. real risk 28:13 How in-house counsel really choose outside counsel 31:17 Survey: what in-house lawyers wish outside counsel knew 35:23 AI, billable hours and law firm economics 41:15 What to keep in-house vs. send out 43:11 Outside counsel billing pet peeves 44:25 Big Law's AI investment and the knowledge moat 47:05 The next five years for in-house and outside counsel 49:21 AI and training junior lawyers 52:13 The business she'd build