Ken Pilot

Founder of Ken Pilot Ventures

Ken Pilot, a veteran retail executive and strategic advisor, has transformed legacy brands and startups in the evolving retail landscape. With over 30 years at Gap, J.Crew, Ralph Lauren, and American Eagle, Ken is renowned for scaling global operations while fostering culture and innovation. His leadership during Gap’s rise under Mickey Drexler solidified his status as a transformative merchant. In 2015, he founded Ken Pilot Ventures, investing in cutting-edge retail tech platforms like Ometria, Firework,Curated For You and Lily AI, focusing on enhancing customer experience and operational efficiency. Ken’s advisory expertise is highly sought after, notably advising Steve Madden on store transformation and omnichannel integration, and working with Knot Standard, an AI-powered custom menswear brand. In 2023, Ken launched The Retail Pilot: Leaders & Legends podcast, featuring influential voices in retail and consumer leadership, quickly becoming essential listening for founders, executives, and aspiring entrepreneurs.