Next in Media: The Future of Retail Media with Kiri Masters

Host: Mike Shields
Guest: Kiri Masters
Date: January 27, 2026

Episode Overview

In this episode, Mike Shields sits down with Kiri Masters—retail media authority and host of the “Retail Media Breakfast Club” podcast—to dissect the rapidly evolving landscape of retail media. Centered on recent breakthroughs like ads in generative AI platforms (e.g., ChatGPT), the Walmart-Google partnership, and the ongoing “retail media land grab,” the duo explores the future of advertising, the challenges and opportunities behind new consumer interfaces, and what will shape the industry next. The conversation is peppered with both historical perspective and optimism for innovation, while maintaining a pragmatic eye on whether the hype will deliver real value for consumers, retailers, and brands.

Key Discussion Points & Insights

1. Ads in Generative AI and Conversational Commerce

Timestamps: 02:10 – 07:46

• Initial Reactions:

  • Mike introduces the topic of ads in conversational AI (notably ChatGPT), questioning whether this new advertising surface will be as large and effective as earlier digital shifts.
  • Quote: “We all knew that was going to happen at some point... but what is your initial take?” – Mike Shields [01:55]

• Potential & Skepticism:

  • Kiri emphasizes both excitement and caution over ads in AI systems, noting that it all depends on both ad unit design and consumer trust.
  • Quote: “If AI-enabled commerce becomes one of these surfaces... Brands are fairweather friends. They’ll just take whatever budget isn’t working somewhere else and move it over.” – Kiri Masters [03:11]

• Ad Experience & Relevance:

  • Discussion on the evolution of ad formats: The future could be multimodal (voice, video, virtual try-ons), potentially making ads more contextual and less intrusive.
  • The hosts agree AI ads have the opportunity to be more relevant and less annoying, provided platforms proceed with care—not replicating the mistakes of traditional “sponsored products.”
    • Quote: “I think that ads in LLMs have the potential to actually be really cool.” – Kiri Masters [06:43]

• Trust and Privacy:

  • Kiri notes that LLMs are uniquely trusted because users share deeply personal information, so the implementation of ads must respect this dynamic carefully.
  • There’s growing consumer awareness that “if something is free, you are the product.”
  • Quote: “There is an expectation or understanding for most people that if something is free, you are the product.” – Kiri Masters [07:47]

2. The Walmart-Google Partnership and the Future of Shopping Interfaces

Timestamps: 08:10 – 17:38

• Behavioral Change:

  • Kiri remains skeptical that a significant volume of shopping is currently happening through LLMs but expects gradual behavior shifts, similar to the evolution of trust in e-commerce.
  • Anecdote: She reminisces about her first online purchase (a “clunky, chunky iPod” via eBay on dial-up), drawing parallels to the slow build of trust in new shopping formats. [09:50–10:47]

• Merchant of Record:

  • Retailers are wary of ceding control and are adamant about remaining the merchant of record—even as agentic commerce (AI agents negotiating on behalf of users) looms.
  • Quote: “A line that they are not prepared to cross is giving up being the merchant of record.” – Kiri Masters [13:14]

• Keeping Consumer Needs Central:

  • The panel agrees consumers have varied motivations and preferences—retailers and platforms must balance objectivity, personalization, and not default every solution to a single retailer.
  • Quote: “We don’t all make decisions based on price. Right?” – Kiri Masters [15:42]

• Piggly Wiggly History Lesson:

  • Kiri recounts the rise of self-service grocery (Piggly Wiggly, 1916) to highlight how fundamental retail behavior changes only stick if the consumer benefits tangibly—usually financially.
  • Quote: “If you want consumers to get on board with something, you might need to cut them in on that with some rewards.” – Kiri Masters [17:01]

3. State of the Retail Media Industry

Timestamps: 17:38 – 24:31

• Market Concentration & Growth:

  • Despite hype, retail media is dominated by two major players, especially Amazon—setting industry standards now hard for others to match.
  • Quote: “Advertisers love it… Amazon was early to the game. They’ve trained brands on what to expect, and other retailers just… they can’t compete with what Amazon has done.” – Kiri Masters [18:15]

• Offsite and In-store Retail Media:

  • Offsite acceleration (using first-party data to buy ads elsewhere) and in-store retail media are “resilient to AI-enabled shopping” but still small parts of the market. [19:46]
  • Kiri notes consumer transaction data could shift from retailers to LLM platforms if conversational commerce grows—posing a risk for retailers’ high-margin offsite businesses.
  • Both agree that wherever the data flows, brands will follow what's effective and close to transactions.

• LLM Monetization Dilemma:

  • Discussion surfaces about whether LLMs will someday sell data or expand into offsite media (despite current promises not to).
  • Quote: “There’s a lot of ‘nevers’ in this business that don’t...” – Mike Shields [22:48]

4. Industry Consolidation and Shoppable TV

Timestamps: 23:02 – 25:51

• Retail Media Network Consolidation:

  • Kiri predicts more consolidation in 2026, with brands expressing clear fatigue over the sheer number of retail media networks; most want to work with just a handful (5-7).
  • Quote: “There’s over 250 [retail media networks] globally. Right, right? Something’s not adding up here.” – Kiri Masters [23:38]

• Coopetition Emerges:

  • The Macy’s/Amazon tie-up cited as a bellwether for collaborative arrangements—“cooperating with competitors where you can both win.” [24:02]

• Shoppable CTV (Connected TV):

  • Both hosts express skepticism and impatience for CTV shopping, suggesting that unless it fits the context, it’s unlikely to become mainstream soon.
  • Quote: “Jamming shopping into my entertainment time is… it’s hard to in the middle of a football game want to think about shopping.” – Mike Shields [25:04]

5. Forward-looking Perspectives and Closing Thoughts

Timestamps: 25:51 – 27:30

• Rethinking Retailer-Brand Collaboration:

  • Kiri suggests a return to joint “category growth” strategies between retailers and brands, focusing less on performance metrics and more on creating new demand.
  • Quote: “Let’s get back to that question… how can we together grow the category?” – Kiri Masters [25:51]
  • She acknowledges this is a tough shift, since retail media’s current promise of close-to-consumer, high-ROAS advertising is “a drug that’s easy to get hooked on.”

• Summary & Takeaway:

  • The episode closes with both experts agreeing the field is in flux, with innovations and risks ahead especially as AI, trust, and new interfaces reshape commerce.

Notable Quotes & Memorable Moments

• On the future of AI in commerce:
  • “The proof is going to be in the pudding. It all depends what these ads actually look like.” – Kiri Masters [04:36]
• Trust in new tech:
  • “After that first experience, I thought, you know what? I think I can trust eBay.” – Kiri Masters [10:47]
• On retail media network bloat:
  • “Brands… only want to work with 5, 6, 7 RMNs. There’s over 250 globally. Something’s not adding up here.” – Kiri Masters [23:38]
• The consumer is central:
  • “If you want consumers to get on board with something, you might need to cut them in on that with some rewards.” – Kiri Masters [17:01]

Timestamps for Key Segments

• Ads in AI and consumer trust: 02:10 – 07:46
• Walmart-Google & interface changes: 08:10 – 17:38
• Amazon’s dominance & retail media state: 17:38 – 19:46
• Risks from LLM commerce: 19:46 – 22:28
• Consolidation predictions: 23:02 – 24:31
• CTV & forward-looking themes: 24:31 – 27:30

Tone & Style

The conversation is direct, pragmatic, occasionally humorous, and optimistic without hype. Kiri’s style is grounded with historical perspective and personal anecdotes, while Mike brings a healthy skepticism and curiosity about how quickly consumer behavior will adapt. Both remain focused on the practical implications for brands, retailers, and shoppers.

For Listeners Who Missed the Episode

This episode offers a candid, nuanced look into the forces reshaping retail media. Listeners will hear why the shift to AI-driven consumer experiences may be both less imminent and more impactful than headlines suggest, how retail media’s big players have set the rules, and what it will take for new technology and ad formats to win consumer trust. With takeaways for marketers, techies, and retail leaders alike, it’s essential listening for anyone tracking the business of commerce in the age of AI.