Retail Legend Ken Pilot Breaks Down Tariff Math, Retail Tech & Brand Survival

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.

About Us

Steve Dennis is a strategic advisor and keynote speaker focused on growth and innovation, who has also been named one of the world's top retail influencers. He is the bestselling authro of two books: Leaders Leap: Transforming Your Company at the Speed of Disruption and Remarkable Retail: How To Win & Keep Customers in the Age of Disruption. Steve regularly shares his insights in his role as a Forbes senior retail contributor and on social media.

Michael LeBlanc is the president and founder of M.E. LeBlanc & Company Inc, a senior retail advisor, keynote speaker and now, media entrepreneur.  He has been on the front lines of retail industry change for his entire career. 

Michael has delivered keynotes, hosted fire-side discussions and participated worldwide in thought leadership panels, most recently on the main stage in Toronto at Retail Council of Canada’s Retail Marketing conference with leaders from Walmart & Google.  He brings 25+ years of brand/retail/marketing & eCommerce leadership experience with Levi's, Black & Decker, Hudson's Bay, CanWest Media, Pandora Jewellery, The Shopping Channel and Retail Council of Canada to his advisory, speaking and media practice.

Michael produces and hosts a network of leading retail trade podcasts, including the award-winning No.1 independent re