In this milestone 500th episode of the Leaders in Payments Podcast, I bring together seven respected leaders from across the payments ecosystem for a special look at the state of the industry.
Rather than a traditional one-on-one interview, this episode features perspectives from Jim Oberman, CEO of Payroc; Kathleen Pierce-Gilmore, President of SoFi Tech Solutions at SoFi; Greg Cohen, CEO of Fortis; Alex Shtilman, CEO and Co-Founder of Rapyd; Steve Pinado, CEO of NMI; Jess Houlgrave, CEO of WalletConnect; and Derek Dean, CEO of Flute.
Each guest shares their view on three important questions: what shift they are seeing in payments right now, what is still harder than it should be, and what the industry should be preparing for over the next three to five years.
The conversation covers the continued rise of embedded payments, the role of software in reshaping distribution, the growing importance of stablecoins and real-time money movement, the impact of AI and agentic commerce, and the ongoing need to simplify the merchant experience. Guests also discuss the friction that still exists behind the scenes, from onboarding and reconciliation to fraud, false declines, global commerce, regulation, and legacy infrastructure.
Episode 500 is both a celebration of the first 500 conversations on the podcast and a forward-looking discussion about where payments is headed. It reflects how much the industry has changed, how much complexity still needs to be solved, and how much opportunity remains ahead for payments leaders, fintech innovators, software platforms, banks, and the broader commerce ecosystem.
A special “thank you” to all who have listened, watched and participated over the last 5+ years. And now on to the next 500!
