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Ken Pilot

Ken Pilot Ventures: CEO, Board Member, Investor, Retail Advisor

Ken Pilot is a seasoned retail executive with over 30 years of C-level operating experience at renowned brands like Gap, J.Crew, Ralph Lauren, American Eagle, and ABC Carpet & Home.

As the founder of Ken Pilot Ventures, Ken actively invests in technology solutions that bolster retail and brand growth, especially focusing on early-stage innovations addressing online, stores, and operations.

Ken is deeply involved as an operating partner in his investments, providing valuable support and guidance to the founder/team of each venture.

With a background in retail operations and a keen understanding of technology, Ken excels in offering strategic direction at the board level and advising companies effectively.

Currently, Ken is engaged with various platforms including PredictSpring, Firework, Fabric, DeepNorth, Lily AI, ReUPP, Matterport, BackbonePLM, Radar, Inturn, CrosStar Network Solutions, and Crosswalk Ventures, bringing his expertise to enhance their services and offerings.

In his advisory role, Ken is working closely with Teak + Table, a prominent DTC outdoor furniture brand, while also having advised companies like Harbour Outdoor, Lenox, Calvin Klein, Kassatex, Burrow, and Alternative Apparel.

Ken serves as an investor/advisor to Burrow and Koio, besides holding a real estate associates license with KSR.

Ken's educational background includes a Bachelor of Arts (B.A.) in Art History and History from Colgate University.

Highlights

May 1 · linkedin

Banana Split...rebuilding Gap Inc.one brand at a time. Banana appeared to gain fashion momentum a year ago but was unable to maintain the momentum. What about design? Just read Jeffrey Kalinsky is available.

Jul 14 · linkedin

If Mickey Drexler were responding to the article below it might read as follows “Helllooooo…It’s the product stupid!” Yes, Mickey was laser focused on newness, point of view, presentation and marketing. He believed that customers didn’t know what the wanted next and the brands were tasked with finding the next “bingo” (double snap;). Gap “invented” the Hoodie,Puffer jacket and Crazy stripe sweater(and they didn’t come via focus groups). Mickey would have opted for a proctologist exam over listening to a group of consultants report their findings regarding “his” company. Technology meetings and big data would not have grabbed his attention either. AM (After Mickey)the pendulum swung the other way…the succession of CEOs to follow were laser focused on operations, data, consumer feedback and experience, technology, surveys and the like. Strong leaders with less passion for product and a greater appreciation for process. Product still key but relegated to the Presidents of each brand within the organization. As the company became more complex and complicated to run, the focus/obsession, from my perspective, shifted away from what makes brands great, the product.

The next Gap CEO will need to be a great balance of merchant and operator (well…maybe more merchant:). #gap #gapinc

Ken Pilot
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Location

New York City Metropolitan Area