E301 | Smarter Dunning: How Data and Intent Change Payment Recovery with Charles Rosenblatt of Butter Payments

Today on the show, we have Charles Rosenblatt, CEO of Butter Payments, providing ML AI-driven payment recovery for subscription merchants and recurring payments. Previously, Charles was CSO of Payoneer, CRO at Velo Payments, and ran treasury at D.E. Shaw during the late 90s—where managing a financial crisis taught him that outside factors can derail even the best strategies and smartest teams. 

In this episode, we uncover why the 14-day dunning period is an arbitrary standard that shouldn't exist—and how decoupling dunning strategy from product access unlocks smarter business decisions. Charles shares how Butter analyzes 128 variables across billions of transactions to predict payment recovery within 10 seconds, allowing companies to shut off high-cost AI users immediately when recovery is unlikely, while keeping loyal customers active when payments will clear. 

We explore why involuntary churn creates dangerous false signals: 30% of customers leaving might actually want to stay but have expired cards or temporary payment issues. This can lead product teams to catastrophic decisions—like Coca-Cola changing their formula when the real problem was payment infrastructure, not product-market fit. The lesson: understand what's within your control versus what's not before making strategic pivots. 

We also discuss how Capital One shifted their best people from acquisition to retention after realizing they were churning the equivalent of the 7th largest credit card company every year—because spending $20 to save a $500 NPV customer beats spending $300 to acquire a new one who might churn anyway. 

Finally, we dig into payment recovery ethics and strategy: why Butter refuses "forced payments" that drive customer accounts negative, how different card types (Amex vs. debit vs. prepaid) require completely different retry logic, and why competitors who inflate recovery promises by 100% damage trust across the industry.

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