Retail Media Breakfast Club

The conventional wisdom says AI advertising is something for the future, but I’m not buying that. Today, I extrapolate on Debbie Ajo Williamson’s insights shared on a recent Retailgentic episode, and break down why AI ads are already here, moving fast, and reshaping how retail media works in real time. Debbie digs into what’s actually happening behind the scenes with ChatGPT’s ad rollout, and why this is far more than a simple experiment.
I also unpack what this means for retailers: from early adoption trends to the emerging tension between platforms and brands, and ultimately where this is all headed. Finally, I delve into the idea that ads may soon stop targeting humans altogether, and start influencing AI agents instead. If you’re in retail media, this is one of those “pay attention now or regret it later” moments.

This episode is sponsored by Mirakl Ads

Timeline
[00:15] - Why ChatGPT’s ad rollout is not a test: it’s the beginning of a major shift 
[01:15] - How early ad formats are intentionally simple (and why that matters) 
[03:00] - The “18 years vs. 18 months” comparison between Amazon and OpenAI 
[05:00] - Retailers jump in early and the rise of the “frenemy” dynamic 
[06:30] - The next wave of AI ad formats and evolving user interfaces 
[08:00] - The future of ads targeting AI agents instead of humans

Links & Resources
Listen to the full Retailgentic episode: The AI Ad Gold Rush: Inside ChatGPT’s Ad Test, Retail Media’s Next Battle, and the Rise of “AI Media” with Debra Aho Williamson
Subscribe to Retailgentic: Apple Podcasts and YouTube
Subscribe to Debra Aho Williamson's newsletter: The AI Ad Economy
Follow Debra Aho Williamson, founder @ Sonata Insights, on LinkedIn
Read my related articles:ChatGPT Ads Are Here. I'm Not Panicking.
What Is Your AI Agent Buying? [New Research]
Should Your Industry Advertise in AI Media in 2026?

I'm hosting a LIVE event with In-Store Marketplace and Catalyst Media Consulting on April 22 about In-Store Retail Media: are we measuring the wrong things? We'll discuss New Research on the state of in-store retail media measurement — and why the path forward may actually be simpler than the industry is making it. REGISTER HERE
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A few months ago, it felt like everyone in retail media was bracing for impact. Agentic commerce, zero-click search, and Gen AI were being treated as existential threats. But lately, I’ve noticed a shift. In this episode, I unpack what I’m hearing behind closed doors and on the ground at Shoptalk. The panic is cooling, and smarter, more strategic conversations are taking its place.
I dive into what this transition actually means for retailers right now. Are they behind? Are they ignoring the disruption? Or are they playing a longer, more deliberate game? From Costco’s methodical approach, to Target’s massive AI overhaul, I explore why the real challenge isn’t reacting quickly: it’s building the infrastructure to respond at all. If you want to understand where retail media is truly headed in an AI-driven world, this episode is for you.

This episode is sponsored by Mirakl Ads

Timeline
[00:00] – The 2025 survey that revealed retail media’s biggest fears around Gen AI and zero-click search 
[00:45] – Why the mood is shifting from panic to practical strategy among retail leaders
[01:30] – Costco’s “order of operations” mindset and why patience may be a competitive advantage 
[03:00] – Why modular tech stacks and data layers are becoming critical for future AI integration 
[04:45] – Target’s bold move: rewriting 60% of its app to become AI-ready 
[07:00] – The shift toward focusing on onsite experience instead of chasing external AI trends

Links & Resources
EMARKETER/Bain survey from 2025: Retail Media, Unfiltered: What RMNs Told Us About Scaling, Struggling, and Succeeding
Replay of my livestream with Mark Williamson (Costco) and Jon Flugstad (MetaRouter): Costco Retail Media & The Commerce Media Tech Stack 2.0
Read my related articles:The 3 Ways Agentic Commerce Could Destroy Retail Media
Dark Search, Broken Signals, and What Comes Next for Retail Media
The Secret Hopes & Dreams of RMN Leaders
While We Debate What's 'Really' Agentic, Retail Media's Foundation Is Already Shifting

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Today I’m revisiting my recent article for The Drum and digging into a piece of research that stopped me in my tracks. And honestly, it might change how you think about retail media measurement altogether. I walk through new findings showing that something as simple as methodological choices can dramatically swing incremental ROAS (iROAS), sometimes even flipping campaign results from positive to negative. If you’ve ever trusted a single performance number at face value, this conversation is going to challenge that assumption.
I also explore what’s really going on beneath the surface of iROAS, why transparency might matter more than standardization, and what both brands and retailers need to start doing differently. Plus, I share a perspective shift inspired by Brené Brown that reframes how we approach metrics, uncertainty, and decision-making in retail media. This one’s all about asking better questions: and getting closer to the truth behind the numbers.

This episode is sponsored by Mirakl Ads

Timeline
[00:12] – Why methodological choices can drastically impact iROAS results 
[01:17] – The shocking finding: same campaign, wildly different iROAS outcomes 
[02:23] – What “iROAS Demystified” reveals about hidden variability in measurement 
[03:00] – The four key variables that influence how iROAS is calculated 
[04:00] – Why better match quality can actually lead to lower iROAS estimates 
[05:15] – Should iROAS still be a headline KPI? Industry perspectives 
[08:19] – How mid-market brands can ask smarter questions about their reports

Links & Resources
My original article on The Drum: 83% of retail media campaigns can be gamed on iROAS. Here’s how
White paper from Albertsons, Ovative Group, and Northwestern University’s Kellogg School of Management: iROAS Demystified: Understanding Your Brands Incremental ROAS
Follow Liz Roche, VP @ Albertsons, on LinkedIn
Follow Derek Nelson, Senior Director of Retail Media Consulting @ Ovative Group, on LinkedIn
Read my related articles:Why ROAS Refuses To Die
Brands demand retail media standards. Retailers say it's too hard. Do they kind of have a point?
Brian Monahan's 'Bloody Obvious' Bets Are Shaking Up Albertsons Media Collective

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Recently an essay stopped me in my tracks. My friend Drew Cashmore (Chief Strategy Officer at Vantage) wrote a brilliant piece for his Retail Media Leapfrog Series newsletter that draws a surprising parallel between the famous Fermi Paradox and the current state of retail media. And with Drew's permission I'm sharing sections of his essay in today's podcast.
The piece delves into a big, uncomfortable question: if retail media is such a massive opportunity, why are so few retailers actually winning? I walk through Drew’s concept of the “Retail Media Fermi Paradox” and unpack the structural challenges (what Drew calls “the great filters”) that are preventing most retailers from scaling. If you’ve ever wondered why the gap between Amazon/Walmart and everyone else keeps widening, this episode will get you thinking.

This episode is sponsored by Mirakl Ads

Timeline
[00:00] – Why I’m featuring Drew Cashmore’s essay and why it’s a must-read 
[00:39] – The original Fermi Paradox explained and why it matters here 
[02:15] – Introducing the “Retail Media Fermi Paradox” 
[03:00] – The shocking concentration: Amazon & Walmart dominate ~90% of spend 
[04:10] – Great Filter #1: The “tactic trap” and copying Amazon’s playbook 
[05:32] – Great Filter #2: The retail media “doom loop” and underinvestment 
[08:19] – Great Filters #3 & #4: Commoditization and fragmented tech stacks 
[09:30] – Quick preview: how retailers can break through these barriers

Links & Resources
Read Drew Cashmore's essay: Retail Media Leapfrog Series: The Fermi Paradox
Subscribe to Drew's newsletter: Retail Media Leapfrog Series
Follow Drew Cashmore, Chief Strategy Officer at Vantage, on LinkedIn
Read my related articles:The Retail Media Doom Loop
Retail Media's Next Challenge: Proving Real Results
7 Ways to Break the Retail Media Doom Loop

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Today I'm unpacking a fascinating conversation from a recent episode of the Unlocking Retail Media podcast with Andrew Covato and host James Avery that reframed how I think about measurement in retail media networks. If you’ve ever wondered why brands keep getting frustrated — or why retail media struggles to prove its value — this conversation gets right to the heart of it.
I use snippets from the podcast to break down three major gaps that are holding retail media back, from misaligned measurement strategies to outdated data approaches. I also explore why the biggest ad platforms succeed where retail media often fails, what sophisticated advertisers are really asking for today, and how measurement needs to evolve to stay credible. If you're in retail media, brand marketing, or ad tech, this is an important primer on how to tackle measurement head on.

This episode is sponsored by Mirakl Ads

Timeline
[00:00] - The recurring disconnect: why brands ask for data but get dashboards instead
[01:09] - Lesson #1: Why big ad platforms win by staying measurement agnostic
[04:00] - Lesson #2: Retail media is solving for the wrong measurement questions
[05:15] - The shift from user-level attribution to aggregated modeling & experimentation
[07:03] - Lesson #3: Why first-party lift is “grading your own homework”
[09:00] - The measurement maturity curve: from attribution to incrementality to MMM
[10:00] - The hidden problem: why most brands can’t actually evaluate the data they’re given

Links & Resources
Listen to the full Unlocking Retail Media episode: Measurement Science and the Future of Performance with Andrew Covato
Subscribe to Unlocking Retail Media on Apple Podcasts
Follow Andrew Covato, Founder & CEO @ Growth By Science, on LinkedIn
Follow James Avery, Founder & CEO @ Kevel , on LinkedIn
Read my related articles:83% of retail media campaigns can be gamed on iROAS. Here’s how (The Drum)
Brands demand retail media standards. Retailers say it's too hard. Do they kind of have a point?
Retail Media's Measurement Problem: It's Not Just the Retailers

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