Retail Media Breakfast Club

Today I’m taking you behind the scenes of something I don’t talk about enough: what it really feels like to start over, even after years of experience. From launching a brand-new Instagram account @retailmediabreakfastclub with barely any followers, to reflecting on my early days writing “into the void,” I share the uncomfortable truth about building content, credibility, and confidence in public.
I also dig into the process that’s helped me generate ideas consistently, navigate mistakes, and find my voice in a fast-moving industry like retail media. If you’ve ever struggled with imposter syndrome, wondered how to build your content muscle, or questioned whether your perspective is “enough,” this one’s for you.

This episode is sponsored by Mirakl Ads

Timeline
[00:00] - Starting from zero (again!): launching Instagram after building a LinkedIn audience 
[01:00] - Writing in obscurity: the early days of publishing with no audience 
[01:30] - My breakthrough moment: landing a paid contributor role at Forbes 
[03:00] - Why quantity drives creativity (and how I generate endless content ideas) 
[04:20] - The power of being wrong: how mistakes lead to better, richer content 
[06:45] - “The middle of the room”: finding your voice between expertise and curiosity 
[09:45] - Getting comfortable being bad at something new (and why it matters)

Links & Resources
My new Instagram account: @retailmediabreakfastclub
Read my related articles:My Media Diet
Get On The Damn Stage
Apply For The Damn Award

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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Follow Kiri Masters on LinkedIn

Not all shopping is created equal. And honestly, not all of it is fun.
Today I'm unpacking the tension between the idea of AI-powered shopping and the reality of how we actually shop today. While we love the experience of discovering products and making intentional choices, a huge portion of shopping — especially groceries — is repetitive, operational and tedious.
I explore where consumers are already signaling openness to AI assistance (hint: it’s not where you might think), and why the current tools still fall short of solving the real problem. From meal planning to managing the “messy middle” of grocery lists, I break down what’s missing, what’s coming, and why the future of agentic commerce may arrive faster than expected, once the technology finally catches up to demand.

This episode is sponsored by Mirakl Ads

Timeline
[00:00] – My daily cooking ritual and why grocery shopping is the least enjoyable part
[01:15] – The difference between “fun” shopping and repetitive shopping missions
[01:37] – What consumer behavior data reveals about how we actually shop
[02:15] – Where consumers are already comfortable letting AI step in
[03:00] – A real-world example of DIY grocery automation
[04:30] – Why current retail tools fail to solve the “messy middle” of shopping
[06:00] – The trust gap in grocery delivery (yes, even bananas matter!)
[08:30] – The real barrier to AI shopping adoption: technology, not psychology
[10:00] – Consumer attitudes toward AI agents completing purchases
[11:00] – What needs to happen before agentic commerce goes mainstream

Links & Resources
Andrea K. Leigh's LinkedIn post about the grocery ordering browser extension she built
Follow Andrea K. Leigh, Founder @ Allume Group, on LinkedIn
Read my related articles:Agentic Commerce Is a Sequencing Problem, Not an Existential One
Don’t Dance On The Grave Of Agentic Shopping Just Yet
How To Be Right About AI, And Still Lose

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
Subscribe to Retail Media Breakfast Club's daily newsletter
Follow Kiri Masters on LinkedIn

Today I'm unpacking a fascinating shift happening right under our noses in retail media — what has been coined “dark search.” I explore how AI-driven discovery is quietly reshaping the way consumers find and buy products. The big question: is this trend actually helping retail media grow, or is it eroding the very signals it depends on?
I dive into two new pieces of research that seem to tell completely different stories: one suggesting AI is expanding the e-commerce pie, and the other arguing we’re flying blind when it comes to measuring its true impact. If you’re in retail, e-commerce, or media, this episode will challenge how you think about attribution, conversion, and the future of shopper behavior.
This episode is sponsored by Mirakl Ads

Timeline
[00:00] – Why I’m cautious about extrapolating from my own shopping habits and how the Hawthorne Effect plays into consumer behavior
[00:45] – The “dark search” moment: how AI influenced my purchase before I ever hit a retailer’s site
[02:01] – Criteo’s report: AI-driven traffic converts 1.5x higher and lands directly on product pages
[03:45] – RefiBuy’s findings: up to 70% of AI-influenced traffic is invisible to analytics tools
[05:00] – The shocking conversion rates of “dark” AI traffic and what that means for retailers
[06:30] – Reconciling two opposing views: AI growth vs. measurement blind spots
[08:00] – Why this shift could be a structural threat to retail media economics
Links & Resources
Read Criteo's 2026 Commerce & AI Trend Report
Read ReFiBuy's DACT piece by Scot Wingo on LinkedIn: Dark Agentic Commerce Traffic (DACT): Answer Engines Are Sending High-Intent Shoppers to your PDPs, But Your Analytics Miss >70%
Read my related articles:‘Dark Search’ Is Making AI-Facilitated Commerce Look Smaller Than It Really Is
Dark Search, Broken Signals, and What Comes Next for Retail Media
Agentic Commerce Is a Sequencing Problem, Not an Existential One

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
Subscribe to Retail Media Breakfast Club's daily newsletter
Follow Kiri Masters on LinkedIn

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
Subscribe to Retail Media Breakfast Club's daily newsletter
Follow Kiri Masters on LinkedIn

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

Subscribe to Retail Media Breakfast Club's daily newsletter
Follow Kiri Masters on LinkedIn