#46 Tech, Tariffs & Team Building – Ken Pilot on Modern Retail Strategy

Links: Google - Pocket Cast - Anchor - Spotify - Apple 

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Reinventing oneself isn’t optional. It’s leadership.

In this episode of The Retail Reality Show, we sit down with retail strategist and podcast host at The Retail Pilot Ken Pilot – known for his leadership roles at GAP and J.Crew – to talk about how modern retail leaders can (and must) evolve.

Ken takes us through his journey from product-first operator to tech investor, reflecting on what it takes to lead today:

– The humility to get out of the way when others know better
– Challenging outdated playbooks
– Emotional intelligence

We also discuss:

– Why physical retail still lacks tech investment
– Why the PDP is no longer just a detail page – it’s the new homepage
– How AI-driven in-store tools might reshape customer interaction in the next few years

The conversation also dives into macro shifts – including tariff tensions and supply chain strategy – and what smaller brands must prepare for in a volatile landscape.

Whether you’re a founder, operator, or CEO, Ken doesn’t just describe where retail is heading; he explains what it demands from those leading it.

🎧 Listen to the full episode on Spotify or Apple Podcasts.