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

When in-store retail media is done right, it can deliver something digital ads simply can’t: a multisensory brand experience that drives immediate sales and long-term brand recall. In this episode, I’m sharing highlights from my recent LinkedIn Live with Jordan Witmer from the agency SALT, where we dug into what’s really possible with experiential in-store activations, and why so few brands are fully taking advantage of them.

Jordan brings a rare, well-rounded perspective, having spent years on the brand side before moving onto agency side leadership. We talk candidly about why in-store activations in the U.S. often fall flat, how brands are leaving value on the table, and the real reason these high-impact experiences struggle to get funded. If you’re a brand or retail media leader trying to balance short-term ROI with long-term brand building, this conversation is for you.

This episode is sponsored by Mirakl Ads

Timeline

[00:00] Why in-store experiential activations deliver value that sponsored products and display ads can’t

[01:00] The gap between what’s possible in-store and what’s actually happening in the U.S.

[02:30] How experiential activations drive both immediate POS lift and long-term brand recall

[03:15] Data that proves experiential marketing deepens brand connection and drives purchase

[04:00] Inside the Topo Chico Target activation that drove 3X same-store sales growth

[06:30] The real challenge: measuring ROAS and funding experiential retail media across siloed budgets

Links & Resources

• Listen to the full replay of my conversation with Jordan
• Learn more about SALT
• Follow Jordan Witmer on LinkedIn
• Read my related articles:
  • Sam's Club Cracked the Code on In-Store Retail Media—Here's How They Did It
  • Three Companies Monetizing Moments That Most Retailers Ignore
  • It’s Time To End Retail Media “Versus” Organic Search
• 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

A couple of weeks ago, OpenAI quietly made one of the most important announcements for the retail media industry, and I don’t think we’re fully reckoning with what it means yet. In this recap of my January 20 article for The Drum, I break down why OpenAI testing ads inside ChatGPT responses isn’t just an interesting experiment, but a signal that the foundations of retail media are already shifting.

Let me be clear: this isn’t a doomsday episode! Retail media isn’t dead, but it does need to evolve. I walk through why AI-enabled shopping is fundamentally different from past hype cycles, how consumer trust and behavior are changing faster than we expect, and where retail media networks are most exposed — and most defensible — as AI becomes an increasingly powerful commerce intermediary.

This episode is sponsored by Mirakl Ads

Timeline

[00:00] – OpenAI’s ad announcement and why a sponsored hot sauce recommendation matters more than it seems

[01:26] – Why AI-enabled shopping will succeed where the Metaverse and voice commerce failed

[02:00] – The real pain in today’s ecommerce experience and why consumers are primed for change

[03:24] – Trust, culture, and the rise of AI as a shopping companion (not just a tool)

[05:00] – How OpenAI ads threaten the 70-80% margins of onsite retail media

[09:45] – Why in-store retail media may be the most defensible channel in an AI-driven future

Links & Resources

• My full January 20 article on The Drum - Why OpenAI’s ad announcement should worry retail media networks
• Read my related articles:
  • Should Your Industry Advertise in AI Media in 2026?
  • ChatGPT Ads Are Here. I'm Not Panicking.
  • Three Companies Monetizing Moments That Most Retailers Ignore
• 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

New data from Sensor Tower confirms what many of us suspected but couldn’t yet prove: AI-assisted shopping on Amazon has quietly crossed the threshold from experiment to default behavior. During the 2025 holiday season, Amazon’s AI assistant Rufus didn’t just influence shopping — it captured a disproportionate share of actual purchases. In this recap of my recent article for The Drum, I break down what the data really tells us, why Amazon’s headline claims may have undersold the impact, and how AI-assisted journeys are reshaping conversion dynamics.

I also unpack what this means for retailers and brands as AI becomes a primary decision aid. From late-funnel “rescue” moments, to early decider confidence boosts, the evidence suggests we’re not dealing with a single funnel anymore. And if AI assistants replace search as the dominant interface, the future of retail media may depend less on placement, and more on inclusion.

This episode is sponsored by Mirakl Ads

Timeline

[00:00] Why AI-assisted shopping is no longer a novelty and how Rufus captured 66% of purchases on Black Friday

[01:02] Andy Jassy’s $100B Rufus claim and why the industry struggled to validate it

[02:22] How Amazon positions Rufus against third-party AI shopping agents

[03:26] The strategic restraint that sets Rufus apart from other retailer AI experiments

[04:45] Sensor Tower’s “cart reconsideration” journey and a surprising 50% conversion rate

[08:21] What AI-assisted shopping means for the future of retail media monetization

Links & Resources

• My full article on The Drum - While everyone debates agentic shopping, Amazon’s Rufus is racking up sales
• Sensor Tower research results - Retail Embraces AI: How Did Rufus Impact Amazon's November Sales?
• Read my related articles:
  • The 3 Ways Agentic Commerce Could Destroy Retail Media
  • Amazon is playing agentic commerce chicken. Other retailers should not.
  • At NRF, Retailers Say "Bring On All The Bots"
• 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

Sometimes I feel like the town crier waving a bell about AI and retail media, proclaiming "the end is nigh!", but there's a reason I keep humming the same tune. AI-enabled shopping isn’t a future problem. It’s already reshaping how consumers discover, research, and decide what to buy, yet much of the retail media industry is still eerily quiet about it.

In this episode, I react to telling statements made by Sam Khoury, Chief Strategy Officer at Marketecture, who recently appeared on the ADSN podcast. What happens when shoppers move their intent upstream — away from retailer-owned surfaces and into LLMs like ChatGPT? If retail media was built on upper-funnel signals, what happens when those signals disappear? Sam shares insights that every retailer, brand, and retail media leader needs to be paying attention to right now.

This episode is sponsored by Mirakl Ads

Timeline

[00:00] Why AI is the “silent concern” no one in retail media wants to talk about

[01:09] Sam Khoury on why hiding from AI-driven consumer behavior won’t work

[02:30] The data point retailers can’t ignore: AI referrals and in-store LLM usage are surging

[03:20] How AI tools are replacing Google as the starting point for research and discovery

[04:33] The real retail media risk: losing upper-funnel signals, surfaces, and measurement

[07:36] Why this shift may be bigger than mobile, and what early recognition enables

Links & Resources

• Listen to the full ADSN interview with Sam Khoury - Sam Khoury on B2B Creator Businesses, Netflix+WB4EVA, the $1B Digital Twin, and Meta the Energy Company
• Subscribe to the ADSN podcast, hosted by James Borow and Daniel Druger
• Follow Sam Khoury on LinkedIn
• Subscribe to Marketecture
• Read my related articles:
  • The Secret Hopes & Dreams of RMN Leaders
  • Why RMNs Keep Their Tech Stacks Secret
  • Costco: The Retail Media Network That Refuses to Promote Itself
• 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

Today, I'm sharing a portion of a sharp and timely analysis from Deborah Aho Williamson, one of the most trusted voices in digital advertising and platform strategy, on why advertising inside AI-powered platforms is becoming unavoidable for certain industries. The piece is titled Should Your Industry Advertise in AI Media in 2026? from Deborah's wonderful newsletter The AI Ad Economy.

Deborah shines a light on ads inside LLMs becoming a front-burner priority, and why retailers are uniquely positioned to benefit from testing AI media now. From consumer AI usage data to search ad spend trends and lower-funnel alignment, what signals matter most, and where advertisers can realistically start experimenting today, this episode runs the run the gamut of important questions sweeping through retail media.

This episode is sponsored by Mirakl Ads

Timeline

[00:00] Why I’m sharing a guest post, and why this one matters so much
[01:07] Deborah Aho Williamson’s AI ad research and the industries that should act now
[02:47] The three factors that determine whether your industry is ready for AI media
[04:17] Why retail stands out: search ad spend, AI usage, and category readiness
[05:26] Key consumer behaviors: how shoppers use AI in retail purchase decisions
[07:15] The big takeaway, and why Microsoft Copilot is the easiest entry point for LLM ads

Links & Resources

• Read Deborah's article in full - Should Your Industry Advertise in AI Media in 2026?
• Subscribe to The AI Ads Economy on Substack or on LinkedIn
• Follow Debra Aho Williamson on LinkedIn
• Read my related articles:
  • Ads in AI Are Older Than You Think
  • ChatGPT Ads Are Here. I'm Not Panicking.
  • The 3 Ways Agentic Commerce Could Destroy Retail Media
• Join me and Jordan Witmer from Salt XC at 11am Thursday Feb 5 (that's today!) for a LinkedIn Live on The Store As Media: Retail Media That's Scalable, Memorable & Worth Buying. We'll be answering questions LIVE -- join us!
• Subscribe to Retail Media Breakfast Club's daily newsletter
• Follow Kiri Masters on LinkedIn