In this episode of the LendAPI Partner Podcast, host Timothy Li, Founder & CEO of LendAPI, sits down with Ryan Hildebrand, EVP & Chief Innovation Officer at Bankwell, to discuss what it truly takes to transform a community bank into a fintech-grade institution. Ryan brings a rare perspective as a serial founder, former CPA, and fintech builder who helped launch Simple (the first consumer fintech bank) and Seed (the first business fintech bank), and led landmark fintech partnerships at Cross River Bank with companies like Coinbase, Stripe, and Plaid.
What You’ll Learn:
Why technology is the great equalizer for community banks — and how nimble decision-making lets smaller institutions outmaneuver billion-dollar competitors without matching their budgets
How Ryan is using AI and modern fintech platforms to modernize SBA and small business lending at Bankwell — reducing friction for borrowers and improving outcomes for the bank
The inside story of building Simple and Seed — two fintech firsts — and what those exits taught Ryan about what real banking innovation requires
Why Ryan would give back a $100M innovation budget — and how lean, focused teams with the right AI tools consistently outperform large, well-funded innovation departments
The hidden systemic risk of legacy core banking infrastructure — why banks feel trapped, why VC funding dries up for alternatives, and what needs to change
How AI adoption in banking is a cultural transformation, not a technology project — and why front-line employee buy-in determines whether AI investments succeed or fail
What the coming wave of community bank consolidation means for institutions that are innovating versus those that are waiting — and how to end up on the right side of it
About Bankwell
Bankwell is a $3B+ commercial bank headquartered in New Canaan, Connecticut, built on a foundation of strong relationships with businesses across the region. Under the leadership of Chief Innovation Officer Ryan Hildebrand, Bankwell is executing a deliberate strategy to deliver fintech-grade technology and service to small and mid-sized businesses — starting with SBA lending and expanding outward. Bankwell was the first bank customer and investor in Casca, a Y Combinator-backed AI-native loan origination platform, underscoring its commitment to partnering with the most innovative builders in the industry. Bankwell's approach to innovation — resourceful, accountable, and customer-focused — reflects the belief that the best community banks can compete with anyone.
📢 Explore more on the LendAPI Marketplace
Listen now on YouTube, Spotify, or Apple Podcasts.