As early movers launch ads within OpenAI's ChatGPT, they're closely watching how consumers interact with their campaigns and where this emerging channel fits within broader strategies.

“Investment in technology and AI…goes hand-in-hand with great experience,” said Target CEO Michael Fiddelke, at the retailer’s 2026 Financial Community Meeting. “We know those tech investments pay off with stronger experience, whether that's digital or whether that's in-store.”

OpenAI announced in early February that they would begin testing ads in ChatGPT's Free and Go subscription tiers. Though many questions around discoverability, placement, and other considerations still exist, large retailers like Target and Williams-Sonoma are jumping on the chance to kick off their AI advertising experiment.

Back on Target

Target’s plan to reverse a multi-year sales slump includes how the retailer shows up on ChatGPT and other AI chatbots. In February, the company said it began testing ads on ChatGPT in a pilot program which builds on a 2025 partnership with OpenAI.

Target said they worked with OpenAI to test contextual ads that appear in ChatGPT conversations, and assured consumers that sponsored ads are clearly marked and served based on keywords in a user’s prompt.

In the pilot, a Target ad for a new product or deal appears embedded in the AI chatbot’s personalized response, but “does not influence the answer provided by ChatGPT,” according to a company release.

This presence in ChatGPT conversations makes the retailer an early mover in a space with growing relevance to shoppers.

• Traffic from ChatGPT to Target is growing 40% on average each month, per Target.
• AI chatbots are expected to assist 63.3 million US shoppers in 2026, EMARKETER forecasts.

Williams-Sonoma logs on

Williams-Sonoma also announced a ChatGPT ads pilot program in February.

The retailer said it will use the program to discover key moments when customers are making decisions and serve ads for relevant products contextually in a ChatGPT conversation.

“AI is rapidly enhancing product discovery and becoming an integral part of how consumers make informed purchasing decisions,” said Williams-Sonoma, Inc. president and CEO, Laura Alber, in a release. “By collaborating with OpenAI in this early test, we have the opportunity to help develop a new advertising approach, one designed to engage consumers thoughtfully, contextually, and in a manner that aligns with how users expect to interact with information on their platform.”

Williams-Sonoma said their participation in this pilot program extends their experimentation with new digital tools, including ecommerce technology and digital visualization tools.

Spinning up a flywheel

As more shoppers adopt AI assistants to discover and purchase products, a presence in these conversations ensures that retailers keep up with changing behaviors and demands.

“We're at the forefront of innovation with some of the big tech partners in this space, and that allows us to make sure that just like we did with social as it exploded, we're staying front and center for guests as the way they shop evolves in the months and years to come, in ways that probably none of us can fully predict,” said Fiddelke.

Additionally, Target's ChatGPT pilot aims to add another potential revenue stream with the retailer's retail media network, Roundel, being part of the strategy.

• Roundel is expected to grow 20.2% to $1.07 billion in 2026, according to EMARKETER.

Brand partners show up in embedded ads and can benefit from insights into customer behavior on this emerging channel.

Target hopes AI chatbots make for a natural ally as the retailer uses merchandising to power its turnaround.

• Target says it is currently undergoing the biggest refresh of its assortment in over a decade, including 3,000 new items and 60 new brands in beauty alone, according to Fiddelke.

“At its core, merchandising authority is about curation and playing to our strengths,” said Fiddelke. “For many guests, their experience starts with discovery on social and in search. This is where our scale allows us to lean in and invest at the top of the purchasing funnel, so that we reach consumers in all the ways they're shopping today.”

This was originally featured in the Retail Daily newsletter. For more retail insights, statistics, and trends, subscribe here.