I started this newsletter mostly to force myself to keep up with all the new AI marketing news. Things are moving fast! I figured other people might want to learn about it too, so here we are. If there are topics or companies you’d like me to cover, please send them over. I’m a team of one person, so I’ll do what I can. If you want to connect, you can find me running the fractional CMO arm of Foxtown Marketing on most days.

Welcome to today's edition of AI Marketing Geek, your daily dose of the latest AI developments, tools, trends, and actionable insights shaping marketing in 2026. As AI shifts from experimental hype to pragmatic, ROI-driven reality, we're seeing agentic AI take center stage. Autonomous agents are handling media buying, personalization, and commerce, which is wild to watch.

OpenAI announced a fundamental restructuring of how shopping works in ChatGPT today, and it came alongside one of the more significant retail partnerships to drop this week. The news landed at Shoptalk 2026 in Las Vegas and deserves more attention than a single headline gives it.

The headline is that Instant Checkout, OpenAI's experiment with completing purchases inside the chat window, is being wound down. But the replacement model is actually more durable. OpenAI said the new experience will make it easier for users to find and compare products. Shoppers will be able to find products by uploading images or describing items with criteria like budget and preferences. ChatGPT will offer more visual results for comparing different product offerings. Retailers like Target, Sephora, Nordstrom, The Home Depot, Best Buy, and Wayfair are already integrated. For now, checkout will continue on merchants' own websites and apps, with ChatGPT's primary goal being to serve as an entry point for high-intent shoppers.

The OpenAI Instant Checkout pullback happened for three reasons. Users liked researching but not buying inside chat. The operational complexity of managing real-time inventory, tax calculations, and return policies inside a conversational interface created more friction than it removed. And brands that had spent millions building optimized checkout experiences did not want to hand that over to OpenAI's generic flow.

The Sephora partnership announced alongside this is the clearest example yet of what the new model looks like. Sephora launched its app in ChatGPT today, piloting in the United States to help customers discover and shop using curated advice and recommendations. ChatGPT users can prompt beauty questions and receive answers personalized to their Sephora Beauty Insider account profile if they link their account. Customers will be able to use their Sephora loyalty rewards and member benefits including free shipping and samples. Future updates will enable in-app checkout with payment handled by Sephora, not OpenAI.

As Sephora's Global Chief Digital Officer Anca Marola put it on stage: the challenge has been replicating expert human beauty advice online. AI changes that. For the first time, Sephora can unify its search, chatbot, and customer service into a single conversational layer that behaves more like a personal beauty advisor than a traditional ecommerce interface.

The pattern being established is important to name clearly. AI handles discovery and recommendation. The retailer handles transaction and fulfillment. That split is not a temporary workaround. It is the architecture that actually works, because it lets each party do what they are trusted to do.

An Adexchanger column published yesterday gave a name to something that has been building for months, and the framing is worth understanding because it changes how you think about where AI sits in the media mix.

OpenAI's ChatGPT, Microsoft Copilot, Google's AI Overviews, and Amazon's Rufus are quickly becoming a new form of media. This new category is "AI media": ad-supported experiences inside AI assistants, AI-enhanced search, and AI-native interfaces where people ask questions, research, and make decisions. OpenAI's hiring of Meta advertising veteran David Dugan signals just how seriously these platforms are competing for marketing budgets.

What makes AI media structurally different from search or social is the stage of the customer journey where it operates. Consumers are turning to AI during the consideration and evaluation stages of the funnel to compare products, validate choices, and narrow options. AI platforms do not just capture intent, they help shape and accelerate it. As research and decision-making compress into one interface, high-intent moments manifest earlier than in search.

The organic and paid dynamics are also more intertwined in this environment than in traditional media. Organic visibility in AI media establishes credibility and shapes the narrative around a brand, while paid media amplifies and reinforces that narrative. When the two are aligned, they can improve performance. When they are not, the inconsistency is immediately visible, and the platform's answer will carry more weight than the ad.

The practical read for most marketers is that AI media is not yet a reliable performance channel in the paid sense, but it is already a brand discovery channel whether you have chosen to engage with it or not. In any emerging media environment, there is a tendency to wait for better formats, stronger measurement, or broader adoption. But the framing of AI media as something that can be watched from a distance misses that it is an emerging system already influencing how consumers discover, evaluate, and choose brands.

The implication for smaller businesses is different from the implication for enterprise brands. Enterprise brands like Sephora can invest in custom ChatGPT apps. For everyone else, showing up in AI media starts with making sure the organic signals AI systems use to form recommendations are accurate, current, and clearly structured. That is the GEO work covered in earlier editions of this newsletter, and it now has a formal category name to attach it to.

OpenAI updated its shopping infrastructure today for all ChatGPT free, Go, Plus, and Pro users. Here is how to make sure your products can show up in it.

The first step is the Agentic Commerce Protocol feed. OpenAI expanded its Agentic Commerce Protocol to bring more relevant, up-to-date product information directly into ChatGPT. Merchants can participate by sharing their product data through ACP, with deeper integrations available via ChatGPT apps that enable account and loyalty linking. If you are on Shopify, your products are already eligible through Agentic Storefronts. If you are not, go to openai.com/advertisers and check current merchant onboarding options.

The second step is your product data quality. The retailers getting recommended in ChatGPT right now are showing up because their product data is clean, structured, and rich with the kind of detail that helps an AI system form a recommendation. Product titles that read like plain language descriptions, accurate pricing, high-quality images, and specific product attributes all matter. If your product listings read like warehouse SKUs, they are less likely to surface in a conversational recommendation.

The third step, for brands that sell prestige or considered-purchase products, is thinking about how your brand shows up in the comparison and evaluation layer. ChatGPT is now presenting side-by-side product comparisons with reviews, specs, and price. If your reviews are thin, your pricing is unclear, or your product differentiation is not explicit in your catalog data, a competitor with better structured data wins that recommendation regardless of how much better your product might actually be.Looking Ahead

2026 is the year AI moves from "cool demos" to real and measurable business use cases. Expect more agentic tools, voice-powered targeting, and a focus on privacy-first data.

Stay ahead of the game by treating your AI reputation like your website. It would behoove you to make your brand easy for agents to understand and cite.

What AI experiment are you running this week? Reply and let me know. I'll feature top stories in future editions! (Everybody loves a good story)

Stay sharp,
Jon
@mistersterling
Chief AI Marketing Geek