Payments has changed dramatically over the past decade, but some of its biggest challenges have remained surprisingly consistent.
In this episode of Real Talk Payments, Kapil Mokhat is joined by Brian Wey, Senior Director of Commercial Growth at Oura Ring and Adam Hollenberg, Director, Payments Strategy and Operations at Discord, two payments leaders who have worked on both sides of the table, buying, building, managing, and optimizing payments at companies including Airbnb, PayPal, Adobe, Discord, Plaid, and others.
The conversation explores how payments has become more complex as merchants face more providers, more payment methods, more global requirements, and more decisions across the payments stack. They discuss why relying on a single processor may not be enough, what companies should consider when choosing payment partners, and how to think about the build-versus-buy decision as organizations scale.
The discussion also turns to the changing role of payments teams. Today’s leaders need more than payments expertise. They need curiosity, adaptability, strong business judgment, and the ability to connect payments strategy directly to broader company goals. Just as importantly, they need to build an internal narrative that helps executives understand payments not simply as an operational requirement, but as a lever for growth, customer experience, trust, and profitability.
The episode closes with a look at how teams should prioritize opportunities, measure payments performance, and separate what is truly changing in the industry from what may simply be hype.
If you’re responsible for payments strategy, operations, product, or growth, this episode offers a practical look at what it takes to build and manage a modern payments organization.