An agentic future of commerce is coming faster than merchants think—and PayPal wants to make sure small businesses don’t get left behind. In this live Money20/20 2025 episode of This Week in Fintech, hosts Nik Milanović and Jillian Williams sit down with PayPal’s Michelle Gill, EVP and General Manager of Small Business Financial Services, for a deep dive into how AI agents will transform shopping, loyalty, and merchant discovery.
They talk about the next phase shift in commerce: a world where over 40% of shopping journeys may start in chat surfaces, and agents—not humans—do the heavy lifting on search, comparison, and even checkout. Michelle explains why this upends traditional ideas about websites, SEO, and brand, and why “discoverability” and rich product descriptions become the new battleground for merchants of all sizes.
The trio dig into big questions shaping this new landscape:
- How will small businesses compete when shopping begins in agent interfaces instead of on their storefronts?
- What new infrastructure and open protocols are needed so merchants can “integrate once and propagate everywhere” across AI surfaces?
- Where does loyalty live when consumers no longer visit your website—but still expect rewards, points, and personalized offers to “just work” in their wallet?
- How far are consumers willing to let agents spend on their behalf, and what new trust markers will replace today’s checkout experiences?
Michelle also offers a small-business lens on AI: where it can save time first (customer service, email, hiring), where it could power new B2B flows like inventory and reordering, and why AI might both compress margins and lower barriers to becoming a proprietor. She argues that the real opportunity is in turning wasted browsing time into higher-value, more delightful discovery and post-purchase experiences.
Stay to the end for a rapid-fire round on Michelle’s recent favorite book, her current AI toolkit, and what she thinks the payments and e-commerce landscape could look like a decade from now. If you care about the future of agentic commerce, small business resilience, or how PayPal is positioning itself for the next era of the internet, this is an episode you won’t want to miss.
