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Retail Leadership with Steve Worthy
Retail leadership isn’t what it used to be — and neither are you.
After 30+ years of navigating the realities of store floors, boardrooms, restructures, and reinventions, I’ve learned this: the gap between what retail leaders need to grow and what companies actually provide is wider than ever. Promotions don’t come with clarity. Expectations rise, but context disappears. And while the metrics may shift, the pressure never does.
This podcast is for the retail leader who's already proven themselves — and still wants more.
This podcast is for the experienced retail leader who wants more — not more work, but more direction, more insight, and more impact.
I'm Steve Worthy — retail executive coach and founder of Worthy Retail Global. I’ve coached and developed thousands of leaders over three decades, and I created this podcast to give you the straight, strategic guidance I wish I had earlier in my career.
You’ve earned your position. Now let’s make sure you lead like it.
Retail Leadership with Steve Worthy
From Sneakers to AI Retail Leadership with Jenna Posner!
AI is transforming retail at an unprecedented pace, and in this episode of Retail Leadership with Steve Worthy, we explore what leaders need to know now.
From sneaker culture to digital transformation, Jenna Flatman Posner shares how her background as an elite athlete shaped her approach to leadership, strategy, and innovation.
We break down AI’s real impact in retail—cutting through the hype to reveal practical applications, branding challenges, and the evolving balance between human expertise and automation. Discover how AI is reshaping customer experiences, store operations, and leadership strategies, and why executives who fail to adapt risk falling behind. Whether you’re navigating AI adoption or rethinking retail’s future, this episode delivers bold insights and actionable takeaways to help you lead with confidence.
CHAPTERS:
00:00 - Intro
01:18 - Jenna Flatman Posner, Chief Digital Officer
02:55 - Sneakerhead Culture
09:03 - Early Sports Career and Olympics Journey
10:57 - Personal Athletic Journey
17:34 - Transitioning from Athlete to Entrepreneur
20:25 - Importance of AI in Today's World
21:10 - AI Applications in Retail
24:07 - AI Branding Challenges
27:17 - Human vs. AI Work Dynamics
30:31 - Future of AI Technology
34:04 - Future of Retail Trends
39:18 - Steve's Vision for AI Future
39:45 - Retail Leadership Strategies
42:20 - Retail AI Council Initiatives
Sponsors:
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