Target Tests Roundel Ads Within ChatGPT Conversations
Target has expanded its presence in conversational AI by testing contextual advertising within ChatGPT, which introduces retail media placements directly into users’ shopping-related conversations.
The pilot places Roundel, Target’s retailer media network, inside an early-stage discovery environment that increasingly sits upstream from traditional search and e-commerce browsing. As consumers turn to generative AI tools for product research, inspiration and comparison, retailers are exploring how — and where — advertising fits within those interactions.
Beginning in February, sponsored ads from Target and select Roundel brand partners are appearing alongside relevant ChatGPT responses. The ads are clearly labeled and triggered by keywords within a user’s prompt, according to a Feb. 9 fact sheet published to Target’s corporate website.
For example, a user asking ChatGPT for recommendations on “countertop cooking appliances that make everyday meals more convenient” may see a sponsored placement for an air fryer embedded separately within the response. The ad does not influence the answer generated by ChatGPT, Target said, but appears as a distinct promotional unit tied to the context of the conversation.
With traffic from ChatGPT to Target growing 40% on average each month, according to the retailer, the test reflects a broader effort to meet shoppers earlier in their decision-making journeys. It also extends Target’s ongoing partnership with OpenAI.
In November, Target and OpenAI launched a conversational shopping experience within ChatGPT that allows users to receive curated product recommendations, build baskets and complete purchases across fulfillment options including drive up, order pickup and shipping. That move followed a similar announcement from Walmart and signaled retailers’ growing interest in embedding commerce capabilities directly into AI platforms.
OpenAI’s advertising pilot with Target adds a monetization layer to the conversational commerce experience launched in November. For Roundel brand partners, the test opens a new contextual environment outside traditional sponsored search and on-site display. It also will provide insight into how users respond to advertising embedded within AI-driven dialogue rather than search results pages or product grids.
OpenAI’s Ads and Monetization lead Asad Awan added in the fact sheet that the pilot is designed to test new ad experiences while maintaining user trust and ensuring ads are clearly differentiated from responses.
The move underscores a larger shift underway in retail media: shopper engagement is no longer confined to retailer websites and marketplaces. As generative AI becomes part of everyday shopping behavior, retailers and brands are evaluating how to extend media strategies into conversational platforms, without disrupting user experience.
For Target, the ChatGPT advertising test also aligns with its broader AI strategy. In addition to launching a dedicated Target app within ChatGPT, the retailer is embedding AI across enterprise operations.
The retailer is also partnering with Google to co-develop the Universal Commerce Protocol, which in January resulted in a new capability allowing shoppers to browse product listings and buy directly from Target in AI Mode in Google Search and the Gemini app, Google’s AI assistant.
