Tom I’m sharing highlights from a conversation I had on the Retailgentic podcast with Scot Wingo, one of the sharpest thinkers tracking agentic commerce and how AI is reshaping the shopping journey. I’ve spent plenty of time talking about the threats AI-enabled shopping poses to retail media — compressed journeys, fewer page views, shrinking onsite inventory — but in this conversation, we go deeper. What happens next?

We unpack what Retail Media 3.0 could actually look like. From collaborative bidding between brands and retailers, to new AI-driven ad surfaces inside tools like Gemini and Rufus, to the promise (and risks) of contextual targeting inside LLMs: this could be the moment retail media stops feeling like margin extraction and starts becoming a true win-win. If brands and retailers are willing to rethink the model, this may just be the best era of retail media yet.

This episode is sponsored by Mirakl Ads

Timeline

[00:00] – Why agentic commerce is reshaping everything we thought we knew about the shopping journey.

[01:08] – Are AI shopping agents just customer support tools, or are they about to fundamentally change product discovery and accelerate shoppers straight to PDPs?

[02:15] – The uncomfortable truth: some retail media budgets feel like margin extraction. What has to change to create real brand–retailer alignment?

[04:49] – Collaborative bidding explained: how brands like Maytag and retailers like Lowe’s can jointly fund ads, and why this model could become even more important in AI environments.

[06:08] – The ad tech enabling collaborative retail media (including Symbiosys and Ampd) and what’s happening behind the scenes operationally.

[08:15] – Contextual targeting vs. “creepy” behavioral targeting: why I’m hoping AI models learn to target the query (rather than the shopper) and what that means for Retail Media 3.0.

Links & Resources

Retail Media 3.0: Why AI & Agentic Commerce Could Spark the Golden Era of Advertising

Retail Media Breakfast Club