By Krystal Scanlon • February 17, 2026 •
Ivy Liu
If ChatGPT’s move into advertising is to become a durable feature of its business rather than a short-term experiment, much will hinge on whether those ads can prove they drive real outcomes, not just impressions.
Target wants to be among the first to find out.
The retailer is one of the first wave of brands to start testing ads across ChatGPT’s free and Go tiers — a pilot which began on Feb. 9, having been delayed three days by OpenAI. It is promoting both its own business and select partners from its Roundel retail media network. The placements will align with specific keywords in user prompts, an attempt to mirror the intent-driven logic of search while adapting it to a conversational interface. Target did not share how much these placements cost, but Digiday previously reported that approached advertisers confirmed they had been told that the ads would be priced at $60 per 1,000 views.
In one theoretical example outlined by the retailer, a user asking ChatGPT for recommendations on convenient countertop cookie appliances could be shown an ad for an air fryer brand that advertises through Roundel. The idea is straightforward: match expressed intent in the moment with a relevant commercial message, without interrupting the flow of the conversation. Whether that alignment feels helpful or intrusive will ultimately shape how far — and how fast — this format scales.
Roundel confirmed OpenAI’s stance: ads will be clearly labelled, separated from core responses and will not influence the answers the system generates. Beyond the optics, though, the real test is commercial. The results will inform whether ChatGPT becomes another meaningful performance channel for Target — or simply an intriguing new line item in the experimentation budget.
Target did not say how long the ads will be running, or which specific customer categories they’re targeting.
“We don’t have a specific timeline to share,” Matt Drzewicki, svp of Roundel, wrote in an email. “The goal of the pilot is to take time to thoughtfully test and learn, while introducing new experiences in a measured way that prioritizes consumer relevance and trust.”
For now, those learnings will be measured in what Drzewicki called “aggregated performance metrics” — impressions, clicks and whatever early signals can indicate whether conversational intent translates into actual sales.
“Once the test period concludes, we’ll review the results closely with OpenAI, assessing campaign delivery, engagement trends and how effectively the ads supported product discovery during shopping moments,” wrote Drzewicki. “From there, we’ll evaluate what worked, where there’s room to improve and what future engagement might look like.”
Underneath that measured language sits a more pragmatic question: How competitive will this channel look next to the retail media ecosystems already delivering closed-loop measurement, first-party audience targeting and flexible buying models. If ChatGPT is to command meaningful budget, it will need to evolve into something that resembles those standards.
“Over time, we’d look for expanded capabilities that bring this offering closer to how Target and retail media networks operate today, including first-party data integration, closed-loop measurement and more flexible buying models,” added Drzewicki. “Greater flexibility in formats — particularly dynamic executions that can integrate product feeds — will also be important. Those capabilities allow brands to show up in more relevant, real-time ways during moments of active discovery. Ultimately, success for us means accelerating how guests find what they need in ways that feel seamless, personalized and helpful.”
The incentive is clear: Target has previously said traffic to its site from ChatGPT is growing roughly 40% month over month, making advertising a logical extension, though the retailer has not provided specific figures. The retailer launched a dedicated Target experience inside ChatGPT last November as part of its broader push into AI and agentic commerce, and earlier this year partnered with Google’s Gemini on similar shopping integrations.
“As shopping becomes more conversational and AI-driven, we want to meet guests where they are and make it easier for them to discover the on-trend products and curated assortment that define Target,” wrote Drzewicki.
That framing reveals how retailers like Target are viewing ChatGPT. It’s not simply another ad placement. It is a potential discovery avenue — one that could sit alongside search, retail media and app-based commerce. Getting in early is less about novelty and more about shaping that trajectory early, before the rules — and the integrations — are set.
“This work reflects our broader strategy of accelerating technology in ways that elevate the guest experience and lead with merchandising authority,” continued Drzewicki.
Whether ChatGPT can live up to that ambition remains an open question. The pilot is testing a familiar ad mechanic inside an unfamiliar interface. For some marketers, that mix of promise and ambiguity has been enough to pause. For others, like Target, it is precisely why securing an early seat at the table matters.
“Some of our clients who declined have said they were a little uncomfortable because they [OpenAI] couldn’t promise us when we’re going to show up, or where exactly we’re going to show up,” Adthena’s CEO Philip Thune said.
