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. These investments reflect his passion for future-defining technologies that enhance customer experience and operational efficiency.

Ken’s advisory acumen remains in high demand. 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. His guest list includes bold names like:

• John Legend – Discussing the creation of Loved01 and the importance of inclusive, accessible entrepreneurship.

• Mickey Drexler – Ken’s longtime mentor and the visionary behind Gap and J.Crew.

• Steve Madden – Sharing stories of perseverance, creativity, and business grit.

• Mindy Grossman – Unpacking reinvention, brand purpose, and human-centered leadership.

Through candid, insightful conversations, Ken explores the personal journeys behind powerful retail empires—bringing out lessons in resilience, innovation, and values-driven growth.

Ken has also served several boards spanning fashion, home, and tech (including Lenox, Koio, and Dormify) and has been a champion of philanthropy through organizations like Delivering Good and FIDF. His ability to bridge operational excellence, capital strategy, and storytelling continues to make him a unique force in retail.

Whether advising household names, mentoring the next generation of founders, or celebrating legends on air, Ken Pilot remains one of retail’s most connected, thoughtful, and future-focused voices.