Here’s a riddle for you: what’s ugly, chaotic, color-coded, constantly changing but absolutely essential? If you guessed the family calendar, you’re correct. But I’m also talking about how brands are managing retail media in 2026.

Today I unpack why the best-performing brands have stopped waiting for retailers to hand them a clean, unified dashboard, and are instead building their own operating systems on top of retail media networks. Drawing on fresh data from the fifth annual Stratably × Skai State of Retail Media report, I break down the widening gap between brands that are designing systems versus those still juggling platforms. I discuss measurement, incrementality, closed-loop attribution, retail media DSPs, and why only 12% of brands have truly integrated media and commerce data.

If you’re still logging into eight dashboards and hoping your spreadsheet holds, this one’s for you!

This episode is sponsored by Mirakl Ads

Timeline

[00:00] – The 'family calendar' riddle and why it perfectly describes retail media management today

[01:15] – Inside the State of Retail Media report: 166 marketers, 40 interviews, and a growing systems gap

[02:12] – The big numbers: 77% want better cross-network measurement, 68% want operational efficiency, and 52% are shifting budgets to retail media DSPs

[03:16] – The 12% stat that should make you uncomfortable: integrating media spend with commerce data

[04:00] – Why retail media measurement standards exist (but infrastructure fragmentation is still the real blocker)

[06:30] – Retailers’ scaling problem, long-tail advertisers, and why brands are building self-serve control layers

[08:00] – My spicy take: stop asking “Which retail media network should I add next?” and start asking “What system am I building?”

Links & Resources

• Download the fifth annual Stratably × Skai State of Retail Media report from Skai’s website here.
• Read my related articles:
  • The Case for the ‘Long Tail’ of Retail Media Networks
  • Retail Media's Measurement Problem: It's Not Just the Retailers
  • How Can RMNs Tap Upper-Funnel Brand Budgets
• Join me and Jordan Witmer from Salt XC at 10am ET Thursday Feb 19, for our next LinkedIn Live on When RMNs Come Calling for Your Brand Marketing Budget. We'll be answering questions LIVE -- join us!
• Atlanta-based retail media professionals: Wednesday, February 25 is the next In-Person Atlanta Happy Hour! RSVP here.
• Subscribe to Retail Media Breakfast Club's daily newsletter
• Follow Kiri Masters on LinkedIn

I really, really hoped that ads in AI wouldn’t suck. And now… we’re starting to find out.

In this episode, I break down what we’ve learned about how ads are actually showing up inside ChatGPT, following a recent interview with OpenAI’s advertising lead Asad Awan. I share instances where my earlier (admittedly optimistic) predictions were right, what genuinely surprised me, and my concerns, especially if you care about retail media, first-party data, and the future of shopper marketing.

Listen to learn about the architectural separation between ads and the model, contextual targeting vs. surveillance tracking, the “one good ad is enough” philosophy, and what happens when ad surfaces move upstream of the retailer. Most importantly: will AI ads avoid the retail media doom loop, or are we watching it form in real time?

This episode is sponsored by Mirakl Ads

Timeline

[00:00] – Why my City Hall wedding perfectly explains how ads creep into trusted environments.
[01:01] – The OpenAI interview that reveals how ads work inside ChatGPT and why it matters.
[02:30] – The hard wall between the model and the ad layer (and why it's better than I expected).
[05:00] – “One good ad is enough” vs. the saturation playbook of traditional retail media.
[06:00] – The rise of algorithmic, agentic advertising, and why my Spidey sense is tingling.
[08:35] – The real threat to retail media: AI as a high-intent ad surface upstream of the retailer.
[10:30] – AI agents facilitating purchases behind the scenes, and what that means for first-party data.
[11:45] – The year-three test: will revenue pressure break the wall between ads and the model?

Links & Resources

• Watch the full interview with Asad Awan on The OpenAI Podcast
• Subscribe to Debra Aho Williamson's The AI Ads Economy newsletter on Substack or on LinkedIn
• Read my related articles:
  • Maybe Ads in AI Don't Have To Suck?
  • ChatGPT Ads Are Here. I'm Not Panicking.
  • Should Your Industry Advertise in AI Media in 2026?
  • Why OpenAI's Ad Network Should Concern RMNs
• Join me and Jordan Witmer from Salt XC at 10am ET Thursday Feb 19, for our next LinkedIn Live on When RMNs Come Calling for Your Brand Marketing Budget. We'll be answering questions LIVE -- join us!
• Atlanta-based retail media professionals: Wednesday, February 25 is the next In-Person Atlanta Happy Hour! RSVP here.
• Subscribe to Retail Media Breakfast Club's daily newsletter
• Follow Kiri Masters on LinkedIn