This week, Dave speaks with Steve Dennis, President & Founder of Sageberry Consulting.

Steve brings decades of experience across retail strategy, operations, and transformation — and shares a candid look at why so many companies struggle to adapt, even when they know what needs to change.

In this episode, he breaks down the challenges of breaking down silos, the leadership mindset required to drive transformation, and why incremental thinking is one of the biggest risks in today’s rapidly evolving retail landscape.

He also shares his perspective on AI, retail media, and what separates companies that successfully evolve from those that fall behind.

Topics covered:

Why retail transformation is so difficult to execute
The impact of organizational silos on customer experience
The “knowing vs. doing” gap in leadership
Why incremental thinking holds companies back
How AI is reshaping the retail landscape

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Theme music: "Happy" by Mixaud - https://mixaund.bandcamp.com

Producer: Jake Musiker

The Leadership Gap in Retail Transformation - with Steve Dennis