The End of Silos: How Enterprise Thinkers Will Shape the Future of Compliance — Beyond the Fine Print

AI is advancing faster than the rulebook, digital assets are going mainstream, and risk leaders are being asked to make big calls before the precedents exist. In that world, compliance becomes less about checking boxes and more about judgment.Host Remy Rosen sits down with Hillary Rosenberg — a risk and compliance executive who's gone from prosecuting financial crimes at the Manhattan DA's office to leading enterprise compliance at Standard Chartered, BNY Mellon, and Valley Bank. They get into why risk and compliance can no longer live in silos, how AI is reshaping what compliance careers reward, and why the best leaders rarely just say "no." Hillary also breaks down the shift in digital assets — from the "Wild West" to the GENIUS Act and beyond — and shares the mindset she uses to make decisions she can still stand behind five years from now.A candid, practical conversation for anyone navigating compliance when the map keeps changing.Chapters (approx.)00:00 Intro00:56 Meet Hillary Rosenberg02:21 The end of silos: risk & compliance converge05:47 AI, automation, and the rise of the generalist08:26 Figuring out "the gray"13:04 The five-year test for tough calls15:32 Rarely saying "no": risk, reward, and enabling the business18:31 Digital assets & crypto: what changed21:58 The GENIUS Act, the Clarity Act, and a new paradigm24:18 Regulatory pullback and managing risk responsiblyBeyond the Fine Print is brought to you by Sedric. Follow for new episodes.