Retail Media Breakfast Club

We've spent the last year watching retailers race to launch AI shopping assistants, but I think we're asking the wrong question. Instead of obsessing over who has the smartest chatbot, we should be asking: What job are shoppers actually hiring these AI assistants to do?

In this episode, I unpack insights from a fascinating recent conversation on Jason Del Rey's newsletter The Aisle with former Amazon and Walmart product leader Mukesh Jain, explore why "nobody wakes up wanting to chat with a retailer," and explain why the future of AI shopping may have far less to do with conversation than we think. Along the way, I revisit one of my own predictions about retailer AI, and explain why recent research has changed my perspective.
This episode is sponsored by GrowthLoop
Timeline
00:00 – Why Clayton Christensen's "Jobs to Be Done" framework is still the best way to think about AI shopping assistants.
02:15 – The three distinct shopping jobs AI needs to solve, and why chatbots aren't the answer for every one of them.
03:32 – The quote that changed how I think about retailer AI: "Nobody wakes up wanting to chat with a retailer."
06:00 – Will ChatGPT and Gemini win shopping discovery, or can retailers build assistants shoppers actually return to?
08:28 – Why I changed my mind about Amazon Rufus, and what Kantar's latest research revealed about what consumers really value.
10:00 – My biggest takeaway: today's retail AI chatbots are just the beginning, not the finished product.

Links & Resources
Check out Jason Del Rey's interview with Mukesh Jain on The Aisle. 
Follow Mukesh Jain, Co-founder, SignalAI, on LinkedIn
Subscribe to The Aisle
Read Wave 1 of Kantar's AI-Enabled Commerce Pulse
Subscribe to Watson Weekly on Apple Podcasts
Follow Rick Watson, Founder, RMW Commerce, on LinkedIn
Follow Holden Bale, Global Chief Strategy Officer at Merkle, on LinkedIn
Read my related articles:What it means for retail media when AI chat has only 2 ad slots
The agentic media buying race has a problem: nobody's asked the buyers
AI-Enabled Shopping Hits 74% Adoption

Check out Basket Case, a project I’m part of with The Drum and QSIC, an irreverent and lively podcast series talking shop: latest episode
I'm sharing comedy skits on Instagram about retail media! Follow along: @retailmediabreakfastclub
Subscribe to Retail Media Breakfast Club's daily newsletter
Follow Kiri Masters on LinkedIn

AI agents are suddenly everywhere in retail media. Platforms, agencies, and retailers are all promising to automate media planning, buying, optimization, and reporting. But how ready are the people actually running these campaigns to hand over the keys?
In this episode, a recap of my recent article for The Drum, I dig into new Skai research on “agentic readiness” among paid media practitioners, including why leadership and practitioners appear to have very different views of how ready their organizations really are. I also look at why retail media should theoretically be a perfect environment for agentic buying, the challenges facing mid-market advertisers, and what could happen if every network, agency, and platform launches essentially the same AI agent.

This episode is sponsored by GrowthLoop
Timeline
[01:32] - Breaking down Skai's survey of 332 paid media practitioners and its nine dimensions of agentic readiness
[01:47] - Why the average agentic readiness score was just 35.7 out of 100
[03:20] - The surprising gap between C-suite confidence and the reality experienced by media-buying practitioners
[05:35] - Why retail media should be particularly well suited to AI agents and closed-loop optimization
[06:37] - The relationship between advertiser sophistication and adoption of algorithmic media buying
[07:06] - How Chewy Ads is approaching the tension between automated buying and sophisticated advertisers
[07:51] - Why an “agentic arms race” could leave the industry with lots of announcements — and a very large token bill

Links & Resources
Read my full article on The Drum: Media buyers are nowhere near ready for the agentic revolution
Ad management platform Skai surveyed 332 paid media practitioners in April of this year, scoring them across nine dimensions of agentic readiness
Read my related articles:ChatGPT Ads Are Here. I'm Not Panicking.
AI-Enabled Shopping Hits 74% Adoption
Maybe Ads in AI Don't Have To Suck?
Why Chewy's RMN Leader Isn't Gatekeeping First-Party Data

Check out Basket Case, a project I’m part of with The Drum and QSIC, an irreverent and lively podcast series talking shop. The latest episode dropped last week
I'm sharing comedy skits on Instagram about retail media! Follow along: @retailmediabreakfastclub
Subscribe to Retail Media Breakfast Club's daily newsletter
Follow Kiri Masters on LinkedIn

When I launched my first podcast back in 2017, I worried I'd already missed the opportunity. Nine years later, I'm asking a different question altogether: does the format even matter anymore?
In this episode, I dig into what my latest LinkedIn audience poll revealed about how retail media professionals actually consume information. And why, despite the explosion of AI-generated content, newsletters and written analysis remain the preferred format. I also explore what "AI slop" means for creators, marketers, and corporate leaders, and why I believe the real competitive advantage isn't the medium you publish in — it's the quality of your judgment. If you're building your career, your content, or your company's influence in the age of AI, this episode is for you.

This episode is sponsored by GrowthLoop
Timeline
00:00 – Why I thought I was too late to start podcasting and why I was wrong.
01:24 – What changed (and didn't) in my LinkedIn poll on how retail media professionals consume industry news.
03:00 – The rise of AI-generated "slop" on LinkedIn and why platforms are starting to push back.
04:30 – Why newsletters continue to outperform other formats for busy B2B professionals.
06:14 – If AI can generate text, audio, and video, what actually creates lasting value?
07:30 – The internal communication strategy that's becoming obsolete: and what leaders should do instead.

Links & Resources
Check out my first podcast Ecommerce Braintrust on Apple Podcasts.
Read my related articles:AI in retail: selecting solution providers that deliver real value, not just hype
AI in real life: how retailers and brands are leveraging AI (real numbers)
AI in Retail Media: Practical Applications to Get Started Now

Check out Basket Case, a project I’m part of with The Drum and QSIC, an irreverent and lively podcast series where we talk shop.
I'm sharing comedy skits on Instagram about retail media! Follow along: @retailmediabreakfastclub
Subscribe to Retail Media Breakfast Club's daily newsletter
Follow Kiri Masters on LinkedIn

Today I'm sharing highlights from a lively panel discussion I joined at Cannes, hosted by The CPG Guys and sponsored by Sensor Tower. Alongside fellow retail media analysts Andrew Lipsman, Sarah Marzano and Debbie Aho Williamson, we unpacked some of the industry's biggest debates: from what's really holding retail media networks back to where the next wave of growth is likely to come from.
We didn't agree on everything — and that's exactly what made the conversation so valuable! We explored the future of marketplaces, the opportunities for retailers beyond Amazon and Walmart, and whether AI is already driving more commerce than current analytics can actually measure. If you're trying to separate the hype from reality in retail media, this episode is packed with ideas that will challenge your thinking.

This episode is sponsored by GrowthLoop
Timeline
[00:00] Why I wanted to share this Cannes panel discussion — and why healthy disagreements make the retail media industry stronger.
[01:42] My perspective on the "internal demons" of retail media networks and why organizational structure determines what an RMN can become.
[03:00] Sarah Marzano explains why long-tail retail media networks need a different playbook (and why physical stores may become their biggest media advantage).
[04:08] Andrew Lipsman makes the case for marketplaces as one of the biggest drivers of retail media growth.
[05:15] Debbie Aho Williamson shares surprising data on retailer advertising inside ChatGPT and why Best Buy stood out.
[08:09] We debate whether AI-driven shopping traffic is being dramatically undercounted, and why measuring AI referrals may be much harder than it appears.

Links & Resources
Watch the full CPG Guys episode of this Cannes 2026 panel event
Subscribe to The CPG Guys on Apple Podcasts and YouTube
Check out Sensor Tower's retail media insghts offering here
Follow Sarah Marzano, Retail & Commerce Media at EMARKETER, on LinkedIn
Follow Andrew Lipsman, Analyst at Media, Ads + Commerce, on LinkedIn
Follow Debra Aho Williamson, Analyst at Sonata Insights, on LinkedIn
Follow Ian Simpson, SVP, Innovation & Strategy at Sensor Tower, on LinkedIn
Read my related articles:The Demons Inside Retail Media, Part 3: SHORTCUTS
‘Dark Search’ Is Making AI-Facilitated Commerce Look Smaller Than It Really Is
11% of Shoppers Using AI Think They Bought Something Inside an AI App. They Probably Didn't.

I'm sharing comedy skits on Instagram about retail media! Follow along: @retailmediabreakfastclub
Subscribe to Retail Media Breakfast Club's daily newsletter
Follow Kiri Masters on LinkedIn

This week, I'm sharing snippets of a conversation from The Watson Weekly, one of my favorite podcasts, where host Rick Watson sat down with Holden Bale, Global Chief Strategy Officer at Merkle. One statistic mentioned completely stopped me in my tracks: 11% of consumers believe they've already purchased products directly through AI assistants like ChatGPT and Gemini. Even though, in most cases, that simply isn't possible.
What fascinated me wasn't that consumers are wrong: it's why they're wrong. We explore what this tells us about the future of AI-powered shopping, why perception may matter more than transaction data, and how today's "halo effect" could shape tomorrow's commerce landscape. We also dig into one of the biggest challenges facing AI assistants: building enough personal context to become truly useful shopping companions.

This episode is sponsored by GrowthLoop
Timeline
00:00 – Why one surprising AI shopping statistic immediately caught my attention
01:26 – The "misunderheard" consumer: why 11% believe they've already shopped through AI
02:18 – What social commerce teaches us about consumer perception versus actual transactions
04:49 – Why consumers believing they shopped with AI may be more important than whether they actually did
06:45 – The missing ingredient for AI commerce: personalization, memory, and shopping context
09:30 – Why marketplaces and order history could determine who wins the AI shopping race
10:46 – A preview of my own experiment using Amazon purchase history inside an LLM

Links & Resources
Listen to the full Watson Weekly episode: 88% Have Deployed AI. 6% Can Prove It Worked
Subscribe to Watson Weekly on Apple Podcasts
Follow Rick Watson, Founder, RMW Commerce, on LinkedIn
Follow Holden Bale, Global Chief Strategy Officer at Merkle, on LinkedIn
Read my related articles:ChatGPT Ads Are Here. I'm Not Panicking.
AI-Enabled Shopping Hits 74% Adoption
Maybe Ads in AI Don't Have To Suck?

Check out Basket Case, a project I’m part of with The Drum and QSIC, an irreverent and lively podcast series talking shop. The latest episode dropped last week
I'm sharing comedy skits on Instagram about retail media! Follow along: @retailmediabreakfastclub
Subscribe to Retail Media Breakfast Club's daily newsletter
Follow Kiri Masters on LinkedIn