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5 of 184

The Retail Media Civil War Is Ending: How “Fluid” Sponsored Products Are Reshaping Search
In today’s episode, I dig into one of the biggest internal conflicts inside retail organizations—the clash between merchant teams and retail media teams. One side is incentivized to fill every available ad slot, the other is responsible for driving product sales, and shoppers are the ones caught in the crossfire. As Charlie Munger said, “Show me the incentive and I’ll show you the outcome,” and retail media is no exception.I share highlights from a recent LinkedIn Live with Andreas Reiffen, CEO and co-founder of Pentaleap, whose 2025 Sponsored Products Benchmark Report exposes cracks in the old model of separating organic search from sponsored placements. We unpack why retailers are finally beginning to merge these two systems into a single, relevance-driven engine, and how this “fluid” approach could end the long-running merchant vs. media standoff once and for all.This episode is sponsored by Mirakl AdsTimeline02:15 — The incentive problem: why merchant and media teams often work against each other03:30 — Andreas explains why onsite search tech already solved relevance years ago05:12 — The consequences of running two ranking engines that don’t communicate05:56 — The Fifth Avenue analogy: how fixed ad slots waste precious digital real estate07:00 — How dynamic, margin-based ranking blends organic + sponsored into one algorithm09:13 — Macy’s and Home Depot shift from fixed to fluid sponsored product distribution10:45 — A key question brands should ask every retailer about their algorithm setupLinks & ResourcesWatch the full replay of my LinkedIn Live with Andreas ReiffenGet Pentaleap's H2 2025 Sponsored Products Benchmarks ReportFollow Andreas Reiffen on LinkedInRead my articles:3 New Developments In RTB (Real Time Bidding) For Retail MediaHave Retailers Lost Discovery to AI for Good?Subscribe to Retail Media Breakfast Club's daily newsletterFollow Kiri on LinkedIn
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11:43
AI vs. Retail Media: The Platform Shift No One Is Ready For
In this 'Snips' episode, I unpack some of the most thought-provoking ideas from tech analyst Benedict Evans’ recent interview on The Knowledge Project, specifically his comparison of AI to the invention of the iPhone. Not electricity. Not the Industrial Revolution. The iPhone. And the second-order effects of that comparison are much more relevant than you might think for retail media and the future of commerce.I explore what this platform shift means for retailers, retail media networks, and the shopping journey as we know it. From behavior resets to disappearing data moats, to the existential risk facing both onsite and offsite RMN revenue, I break down why AI-enabled shopping represents a genuine unbundling of the retail experience, and why the window to respond is rapidly closing.This episode is sponsored by Mirakl AdsTimeline[00:22] – Why Benedict Evans compares AI not to electricity, but to the iPhone (and why that matters).[01:37] – How early assumptions about mobile were completely wrong, and what that teaches us about today’s AI shift.[03:06] – What retailers are getting wrong by treating AI like a “feature” instead of a platform transition.[04:30] – Understanding the consumer behavior reset that threatens retail sites as the starting point for shopping.[06:11] – Why onsite retail media revenue is vulnerable when LLMs intercept the shopping journey.[10:20] – The shrinking window for retailers to build AI-native consumer habits before external agents capture them.Links & ResourcesWatch the full Benedict Evans appearance on The Knowledge Project Podcast - Why Everyone Is Wrong About AI (Including You) | Benedict EvansSubscribe to The Knowledge Project Podcast YouTube channelFollow Benedict Evans on LinkedInRead my related articles:Have Retailers Lost Discovery to AI for Good?Maybe Ads in AI Don't Have To Suck?I'll be diving into the findings of the Pentaleap H2 2025 Sponsored Products Benchmark report with Pentaleap co-founder and CEO Andreas Reiffen on Thursday December 4 at 11AM ET! Join us LIVE hereSubscribe to Retail Media Breakfast Club's daily newsletterFollow Kiri on LinkedIn
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12:03
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12:03
Inside Costco’s Secretive Retail Media Strategy: What Mark Williamson Revealed
Costco has always been the effortlessly cool kid of the retail media world: unbothered by hype, quietly confident, and doing things entirely on its own terms. In this episode, I unpack what makes Costco’s retail media approach so different from the 80+ U.S. retail media networks vying for attention, and why their “member-first, margin-second” philosophy is more than just a tagline.After digging through Mark Williamson (Retail Media AVP at Costco) interviews, I piece together a clearer picture of how Costco is building a retail media business that deeply aligns with its culture, elevates member value, and defies the standard playbook. I explore their unique team structure and ruthlessly disciplined data foundation, as well as the philosophical stance that guides every media decision they make.This episode is sponsored by Mirakl AdsTimeline[00:19] – Why Costco avoids the splashy retail media hype and plays the long game[02:53] – Mark Williamson explains why “monetization” isn’t even in Costco’s vocabulary[04:47] – The uncompromising member-first philosophy and how it blocks “free money”[07:15] – How Costco’s Growth Management Team bridges merchants and media[09:00] – Why retail media revenue is immediately reinvested into merchandising[10:10] – The power of 100% member-identified transactions and deterministic dataLinks & ResourcesThis episode expanded on my recent article for The Drum - Costco: the retail media network that refuses to promote itselfThe Commerce Collective full episode with Mark Williamson - Putting Members First: How Value Guides Costco’s Retail Media VisionThe CPG Guys full episode with Mark Williamson - Media that Drives Retail Sales with Costco’s Mark WilliamsonFollow Mark Williamson, Retail Media AVP at Costco, on LinkedInRead my articles:The ‘How Brands Grow’ Dogma Wants To Have A Word With Retail MediaHow Can RMNs Tap Upper-Funnel Brand BudgetsI'll be diving into the findings of the Pentaleap H2 2025 Sponsored Products Benchmark report with Pentaleap co-founder and CEO Andreas Reiffen on Thursday December 4 at 11AM ET! Join us LIVE here Are you based in Atlanta or plan to be in the ATL area on Weds Dec 3rd? Join me and a couple dozen of your new retail media industry besties for a festive happy hour! Register hereSubscribe to Retail Media Breakfast Club's daily newsletterFollow Kiri on LinkedIn
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13:50
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13:50
AI Shopping Hype? My Black Friday to Cyber Monday Halftime Breakdown
In this halftime recap of Black Friday — Cyber Monday, I unpack the avalanche of headlines claiming that AI shopping has finally arrived. Everywhere you look, analysts are touting explosive growth — 805% spikes, billions in generative AI-influenced sales, and a surge in chatbot-assisted shopping sessions. But as I dig into the data, I’m asking a much more important question: Does any of this actually signal a shift in real shopper behavior? The picture is far more nuanced than the hype suggests.I walk through what the numbers truly reveal, why AI referrals may be inflated by simple math, and what early usage patterns can — and cannot— tell us about consumer adoption. We also look at the timing mismatch of newly released AI shopping tools, why retailers themselves are blocking the very future they claim to want, and where genuine behavior change did happen this weekend. If you’re trying to understand what’s real and what’s noise in this year’s holiday results, this episode will help you read between the lines.This episode is sponsored by Mirakl AdsTimeline[00:15] The big headline stats: AI-driven traffic surges and billions in generative-AI-influenced Black Friday sales.[01:45] Why the 805% AI referral growth may say more about user base expansion than shopper behavior.[03:00] The real reason Rufus conversions appear higher, and why it’s likely better search, not agentic shopping.[04:00] The rush-job rollout of AI shopping tools and why consumers had almost no time to learn them before the retail holidays.[05:30] How retailers are blocking AI tools to save server costs (and the hidden downside for product visibility).[07:00] What actually changed this weekend: mobile dominance, wallet adoption, margins holding, and AI-powered customer support surging.Links & ResourcesIan Simpson, SVP of Innovation & Strategy at Sensor Tower, shared an insightful post on LinkedInScot Wingo has been tracking agentic commerce announcements on his Retailgentic blogJames Taylor, founder of ad-tech firm Particular Audience, dropped a post that captures the contradiction at the heart of retail's AI strategy2025 Turkey 5 Salesforce DataMy latest piece for The Drum shares how Amazon keeps its ad coverage super high, and other retailers are moving in the same direction. Read here: You're not imagining it: Amazon really is a sea of ads (and it still works)If you want a primer on the new research which I shared in The Drum article, join me and Pentaleap CEO Andreas Reiffen for a deep-dive this week, Thursday Dec 4 at 11AM ET [register for the LinkedIn Live event here]Are you based in Atlanta or be in the ATL area on Weds Dec 3rd? Join me and a couple dozen of your new retail media industry besties for a festive happy hour! Register hereSubscribe to Retail Media Breakfast Club's daily newsletterFollow Kiri on LinkedIn
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7:54
Why Retail Media’s Metrics Are Failing — And What Actually Drives Brand Growth
This week, I’m digging into a fiery debate that lit up LinkedIn — one that questions whether retail media is measuring the right things at all. After reading a thought-provoking post from Steve Gray, I found myself going down a rabbit hole of insights, rebuttals, and philosophical clashes about how brands actually grow—and what retail media should be optimizing for. Spoiler: the answers aren’t as simple as ROAS and impressions.In this episode, I unpack the tension between Byron Sharp’s “How Brands Grow” principles and the reality of how budgets get allocated in retail media today. You’ll hear perspectives from industry leaders pushing back on performance-only thinking, calling for better context, better metrics, and a more nuanced understanding of the messy, chaotic shopper journey. If you’ve ever wondered why the theory sounds so elegant but the execution feels so broken, this one is for you.This episode is sponsored by Mirakl AdsTimeline[00:22] – The LinkedIn post from Steve Gray that kicked off this entire discussion[01:16] – A quick primer on How Brands Grow and why penetration matters more than loyalty [02:45] – Steve Gray’s call for new metrics and why retail media struggles to operationalize them [04:51] – Jordan Witmer's argument for why impression-based models misread retail media [06:13] – Yuni Baker-Saito's warning that marketers are over-relying on measurement at the expense of context [07:46] – Anne Hallock's “chaos pendulum” and why the shopper journey no longer follows a clean funnel [09:15] – Why brands still default to ROAS, and why retail media keeps selling it despite its limitsLinks & ResourcesThis episode expanded on my recent article for The Drum - The ‘How Brands Grow’ crowd need to have a word with retail mediaThe LinkedIn post from Steve Gray that kickstarted the debateRead my articles:Retail Media's Measurement Problem: It's Not Just the RetailersHow Can RMNs Tap Upper-Funnel Brand BudgetsAre you based in Atlanta or plan to be in the ATL area on Weds Dec 3rd? Join me and a couple dozen of your new retail media industry besties for a festive happy hour! Register hereSubscribe to Retail Media Breakfast Club's daily newsletterFollow Kiri on LinkedIn
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