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This episode explores what it takes to build great products inside large financial institutions where product teams must balance modernization, legacy systems, scale, and regulation. Through conversations with leaders from Vanguard, Chase, and Affirm, Melissa Perri highlights how strong product organizations connect strategy, operating models, and customer outcomes. Marco De Freitas and Amber Brestowski from Vanguard share lessons from digital transformation, including why transformation is ultimately about people, culture, and clarity of outcomes rather than technology alone. They explain how Vanguard ties modernization to its mission by improving client experience in ways that help investors make better long-term decisions. Jameson Troutman, Head of Product for Small Business at Chase, discusses how large organizations can move from funding projects to funding product capacity so teams can continuously prioritize and deliver outcomes. The episode closes with Vishal Kapoor, Senior VP of Product Management at Affirm, who explains how fintech teams can work with legal and compliance as embedded partners instead of blockers. Across all three conversations, the episode offers a practical view of how product leaders can build judgment, align teams to strategy, and create systems that support responsible innovation in regulated environments. You’ll hear us talk about: Digital transformation lessons Vanguard’s perspective makes it clear that successful transformation is not mainly about replacing technology. It depends on culture, talent, operating model changes, and a clear set of goals that teams can return to over time. The conversation also stresses the importance of communicating progress and showing wins throughout long-running transformation efforts. Client experience as strategy The episode explores how client experience can become a direct expression of company mission. At Vanguard, modernization is framed not just as a design or usability effort, but as a way to help investors make smarter decisions through better defaults, guidance, and insight-rich experiences. Funding products instead of projects Jameson Troutman explains why large organizations need to shift from budgeting individual initiatives to funding product capacity across domains. That change gives teams more ownership and stability while still allowing leadership to manage the portfolio and rebalance where needed. The discussion also connects this funding model to stronger judgment, better prioritization, and faster delivery. Compliance as a product partner Vishal Kapoor describes how Affirm integrates legal and compliance directly into product development so teams can address constraints early and build responsibly at scale. The conversation also covers the role of weekly product reviews, strong metrics, and close cross-functional decision making in fintech environments where risk and trust matter. Episode Resources: Try Granola today: http://granola.ai/productinstitute Episode 213: How Vanguard is Modernizing Finance Through Digital Innovation with Marco De Freitas and Amber Brestowski: https://www.produxlabs.com/product-th... Episode 232: The Art and Science of Product Decisions with Jameson Troutman: https://www.produxlabs.com/product-th... Episode 196: The Affirm Card: Transforming Payment Flexibility with Vishal Kapoor: https://www.produxlabs.com/product-th... Marco De Freitas on LinkedIn: / marco-de-freitas-80416714 Amber Brestowski on LinkedIn: / amber-brestowski-019b56ab Jameson Troutman on LinkedIn: / jameson-troutman Vishal Kapoor on LinkedIn: / vkapoor Check our courses: https://productinstitute.com/