Ep. 11 - Breaking Silos, Building Retail Wins | With Toby Willse

About this episode

The most expensive mistake in retail media isn’t bad targeting, it’s planning in silos. We sit down with media leader Toby Willse to map how the field evolved from banner buys to agentic commerce, why teams still talk past each other, and what it takes to turn retailer-specific wins into brand-level growth. From his design roots to ad tech tours through AOL and Millennial Media, Toby explains how creative strategy, data access, and relationship management shape outcomes more than any single tactic.

We unpack the headliners from CES and NRF, including Google’s momentum in AI shopping, retailer partnerships, and the coming wave of sponsored prompts. Expect smart provocation on the “collapsed funnel” narrative: CTV with QR codes lowers friction, but it doesn’t magically become a conversion channel. Instead, think of new side doors to the bottom of the funnel and measure accordingly. We lay out a realistic framework for attribution that pairs platform signals with retail POS and modeled incrementality, while admitting there’s no silver bullet and AMC is a powerful slice, not the whole pie.

This conversation also goes human. Retail media teams juggle overlapping retailers, expanding JBPs, and constant change. We share practical ways to fight burnout, from using AI agents for repetitive work to establishing daily learning habits and grounding decisions with store and site walks. And if we could fix one systemic issue? Tear down the walled gardens to enable privacy-safe, interoperable measurement and smarter creative orchestration across channels.

If you care about better KPIs, cleaner alignment between brand and sales, and making AI work for your team instead of against it, you’ll find plenty to steal here. Follow the show, share it with a teammate who’s buried in dashboards, and leave a quick review to tell us your number-one retail media headache.