Webb Stevens, Chief Operating Officer of Swap Commerce joins the podcast to unpack how brands can sell globally without the compliance headaches that have historically killed international expansion. He explains Swap's "control, cash, customer" model, why agentic storefronts are replacing chatbots and even websites, and shares early data showing 2x conversion lifts and 3x time-on-site. Plus: why change — not certainty — is now the only constant in global trade policy.
Global e-commerce expansion has long intimidated even sophisticated retailers and brans — but according to this episode's guest, Webb Stevens, Chief Operating Officer of Swap Commerce, that fear is now solvable with technology, not tolerance. Stevens, whose career spans high-growth operating roles at Avalara and Qualtrics plus time as an investor and board advisor, joins the podcast to explain why brands leave international revenue on the table and how Swap is removing the operational barriers that keep them from going global.
Stevens walks through Swap's "three Cs" framework — control, cash, and customer ownership — arguing that legacy cross-border models force merchants to resell through intermediaries, losing the direct customer relationship, data, and margin along the way. With Swap, he says, brands retain merchant-of-record status while offloading the complexity of duty reclaim, tariffs, and compliance, some of it retroactively.
A major thread of the conversation centers on agentic commerce — a term Stevens argues is more than a buzzword. He distinguishes chatbots (which answer questions) from true commerce agents (which complete transactions), and makes the case that brands should consider replacing their websites entirely with conversational, agentic storefronts rather than bolting AI onto an existing site. Early results from Swap's launch partners, including brands onboarded through its Air Mail brand-in-residence program in London and New York, show a 2x lift in conversion, 3x more time on site, and double-digit reductions in returns.
The episode also covers how AI-driven discovery is reshaping the top of the purchase funnel, with Stevens noting that more than half of shoppers now use AI or LLM tools during product discovery — while conversion still tends to happen in merchant-controlled environments. He and co-host Jim Okamura discuss why U.S. merchants have historically been slower than UK counterparts to prioritize international expansion, tying it back to operational fear rather than lack of demand.
On regulation, Stevens addresses the shifting landscape head-on — from new EU fees to the removal of de minimis thresholds — arguing that brands working with the right infrastructure partner shouldn't need to track these changes themselves. His advice for "dabbler" brands already selling internationally in a limited way: eliminate pricing and delivery surprises, since inconsistent cross-border experiences erode long-term customer trust and Net Promoter Score.
Special thanks to Webb and the Swap team for being one of our Presenting Sponsors of our NYC Global Experts Workshop July 15, 2026! Still a few invites available for cross-border retailers or brands!