What would you do differently if you rebuilt your payment stack today? In this episode of Behind the Checkout, John Lunn sits down with Michael Habermann, Senior Director of Operations at Radial Commerce Solutions, to explore the hard lessons merchants have learned from years of payment technology decisions. From legacy infrastructure and PSP dependencies to orchestration, platform-driven commerce, and the rise of AI-powered purchasing, they discuss how payment architectures are evolving and what retailers should prioritize if they were designing their stack from scratch. The conversation covers payment operations, authorization rates, checkout control, marketplaces, digital wallets, merchant strategy, and the future of commerce infrastructure in an increasingly platform-led world.