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Retail Leadership with Steve Worthy
You’ve earned your position. Now let’s make sure you lead like it.
Retail leadership isn’t what it used to be.
And if you’ve been doing this long enough, neither are you.
The job gets bigger. The expectations get louder.
But the guidance? That usually disappears right when you need it most.
And most leaders are left figuring things out quietly while still being expected to have all the answers.
This podcast is for experienced retail leaders who’ve already proven themselves
and know there has to be a better way to lead than just carrying more.
I’m Steve Worthy. I’ve spent over 30 years working across retail — from boardrooms to regional and district markets, through restructures, reinventions, and the parts of leadership no one really prepares you for.
I’ve coached thousands of retail leaders and advised teams that support the retail industry, and this podcast exists for one reason:
To give you the perspective and clarity most leaders are expected to figure out on their own.
Now let’s make sure how you lead actually matches 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
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