In the first of our 8-part series our guest Is retail veteran and tech investor Ken Pilot, recorded live at the CommerceNext Growth Show in New York City. Ken reflects on his expansive career at Gap, J.Crew, Ralph Lauren, and beyond, and shares timely insights on tariffs, generative AI, and the future of retail tech. With humor, candor, and even a pretty solid POTUS impression, Ken's perspective offers a masterclass in leadership and retail reinvention.
In the first of our 8-part summer series produced in partnership with CommerceNext, our guest is Ken Pilot—retail executive, tech investor, and host of The Retail Pilot: Leaders & Legends podcast.
Ken's legendary career spans decades and includes pivotal roles such as President of Gap Global, Factory Stores at Ralph Lauren, and leadership positions at J.Crew, American Eagle, and ABC Carpet & Home. He takes us behind the scenes of launching Gap Outlet, transforming a single underperforming store into over 100 high-margin locations in just 36 months, ultimately making it the most profitable division at Gap.
The conversation then shifts to current macro challenges, particularly tariffs and global sourcing. Ken unpacks the "tariff math" few are talking about, warning that even modest increases could wipe out 10 points of margin, especially for smaller brands without pricing power or manufacturing flexibility. He anticipates a hit to Southeast Asia, outlines strategic moves by companies like Gap to diversify sourcing, and speculates on the economic implications for North American retail.
Next, Ken delves into the retail tech landscape, providing a forward-looking perspective on Generative Engine Optimization (GEO), the emergence of natural language search, and how retailers must adapt both on-site and externally to remain visible and competitive. He highlights the companies he's advising and investing in, including "Curated For You" (an AI-driven occasion-based merchandising platform) and "Raspberry AI" (tools that help designers iterate visuals from sketches to campaign-ready assets). He also discusses the creative tension AI can introduce and how forward-thinking teams are adapting.
Finally, we examine the potential of Retail Media Networks (RMNs) as an underutilized profit stream, particularly in a high-cost, low-margin environment. Ken balances caution with optimism, emphasizing the need for retailers to experiment, remain agile, and stay laser-focused on the customer and core product offering.