Ken Pilot

Ken Pilot is a veteran retail executive, strategic advisor, and podcast host who’s redefined how legacy brands, startups, and tech platforms grow in today’s fast-shifting retail landscape. Over a 30+ year career spanning influential roles at Gap, J.Crew, Ralph Lauren, and American Eagle, Ken became known for his ability to scale global retail operations while nurturing culture, creativity, and innovation.

His operational leadership, particularly during Gap’s historic rise under Mickey Drexler, cemented his reputation as a transformative merchant and mentor. Later, he led various DTC and multichannel initiatives across fashion and lifestyle brands, building teams that balanced brand storytelling with sharp business execution.

In 2015, Ken launched Ken Pilot Ventures, blending his retail expertise with a growing portfolio of early-stage investments and strategic advisory work. His firm backs cutting-edge retail tech platforms—including Ometria, Firework, Cimulate, Radar, Raspberry.ai, Toolio, Lily AI, and Curated For You—focused on everything from livestream shopping and AI-powered analytics to next-gen RFID and inventory solutions. Among his most recent and notable engagements, he advised Steve Madden, the global footwear powerhouse, on store transformation efforts, live shopping, and omnichannel integration. He also played a hands-on role with Knot Standard, the AI-powered custom menswear brand, where he  As both an investor and advisor, Ken champions personalization and tech-backed experience in modern menswear.

In 2023, Ken launched The Retail Pilot: Leaders & Legends, a podcast spotlighting the most influential voices in retail and consumer leadership. It’s quickly become a go-to listen for founders, executives, and aspiring entrepreneurs.