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 W...

Checks still power a shocking amount of insurance money movement, and that single fact creates slow claims, higher operating costs, and an open door for fraud. Greg Myers sits down with Ian Drysdale, CEO of One Inc, to talk about what it really takes to drag property and casualty insurance payments into a modern digital payments era without breaking the workflows carriers rely on. We unpack how One Inc handles both sides of the insurance payments stack: premium payments (inbound merchant acqu...

Mailing checks to pay off a credit card in 2026 sounds like a joke, but it is still a real debt consolidation workflow at scale. Greg Myers sits down with Jose Bethancourt, Co-Founder and CEO of Method, to unpack why liability payments are uniquely messy and what it takes to make them feel as seamless as modern fintech promises. Jose shares his path from growing up in South Texas near the Mexico border to building products at UT Austin, then turning a personal problem into a company. GradJoy...

Fraud doesn’t usually announce itself with a flashing warning sign. It shows up as a chargeback, a fake account that looks “normal,” or an account takeover that slips through the exact same checkout flow your best customers use. Greg Myers sits down with Tamas Kadar, Co-Founder and CEO of SEON, to unpack how modern fraud actually works and how digital businesses can protect revenue without burying users under friction. Tamas shares the origin story that started with a real loss: a crypto che...

A “successful” card payment can still leave merchants waiting days to actually access their money, paying layers of fees along the way, and carrying fraud risk that never truly goes away. That gap between authorization and settlement is where cash flow gets squeezed, reconciliation gets messy, and margins get quietly taxed, especially as more commerce shifts to e-commerce and other card-not-present channels. We sit down with Marshall Greenwald, Founder and CEO of IoniaPay, to talk about chan...

A $400,000 B2B card payment sounds simple until a processor flags it, the finance team cannot reconcile it, and the invoice sits open while DSO creeps up. That gap between delivering product and collecting cash is where B2B payments either become a growth engine or a constant operational headache. I sits down with Thomas Cecil, Co-Founder of PAYRA, to unpack how modern accounts receivable automation actually works when you have real scale like thousands of invoices per month and customers pa...

AI is moving from “helpful assistant” to autonomous actor, and payments leaders are about to feel the difference. I sit down with Russell Moore, Co-Founder and CEO of Amotivv, to get concrete about what breaks when generative AI and agentic AI leave the lab and touch regulated data, customer outcomes, and real money movement. We talk through why so many AI initiatives stall after a promising proof of concept: not because the model is useless, but because teams cannot control the context, pro...

Payments don’t fail because teams lack ambition, they fail because the infrastructure can’t keep up with what customers expect. We sit down with Mike Milotich, CEO of Marqeta, to unpack how modern issuer processing is changing card issuing from a rigid bank product into configurable, real-time payments infrastructure built for innovation. We trace Mike’s 20-year journey across American Express, PayPal, Visa, and now Marqeta, and use that ecosystem view to explain what actually makes a card p...

Payments are speeding up everywhere, but the real story is what that speed breaks and what it demands from the people running the rails. I’m joined by Jennifer Barker, Global Head of Payments and Trade and Depositary Receipts at BNY, for a clear-eyed conversation about what’s changing in the payments industry and what leaders should do next when complexity keeps piling up. From her journey through consulting and nearly two decades in payments to leading multiple global roles at BNY, Jennifer ...

Paper checks are the easiest payment method to hate and one of the hardest to remove. They are slow, expensive, fraud-prone, and deeply baked into legacy workflows. Greg Myers sits down with Steven Faust, CEO of Dash Solutions, to unpack what it really takes to modernize business payouts and why disbursements have become one of the biggest growth engines in the payments industry. We dig into how Dash builds configurable payments software that supports multiple use cases through a single plat...