It was inevitable, wasn’t it? Of course, those helpful AI agents would end up hawking products while users were inside the chat? This week, TWIRM is asking: How will Target’s new in-chat advertising initiative with OpenAI shake up the retail media landscape?
TWIRM, as every retail media maven knows, is the This Week in Retail Media podcast, hosted by Kate Dickson, Head of Marketing and Communications, Retail Media, STRATACACHE, and Jonathan Rosen, STRATACACHE’s Global EVP of Retail Media Strategy. Each week, Kate and Jonathan swap hot takes across the Atlantic on three of the coolest new retail media stories.
The first story Kate and Jonathan get chatty about comes from Retail TouchPoints. Target and its retail media arm Roundel, it reports, is joining OpenAI in a pilot that places sponsored product links within ChatGPT, alongside the AI’s responses at the moment shoppers are actively researching purchases. OpenAI pledged (for now) that the targeted ads will stay contextual, rather than drawing on personal data.
Jonathan’s takeaway: The rise of advertising within conversational AI is coming fast, and it will weaken the impact of online ads. “It will disintermediate retailers’ websites and make chat the primary channel to advertise in,” he predicts — and that shift, paradoxically, will strengthen the value of in-store digital. When an AI layer sits between the shopper and the retailer’s homepage, the store floor becomes the one touchpoint no intermediary can own.
Next, Kate and Jonathan look at German discount retailer Netto’s move to make more than 7,000 in-store screens available programmatically. Finally, they check out Tesco’s surprising new study that finds that the vast majority of purchase decisions are made inside the store, in the moment, as shoppers’ mindsets shift.
Click here to listen to Kate and Jonathan discuss whether Target has hit the mark and what in-chat advertising means for the future of the store.


