Discovery is entering a new phase. As consumers increasingly turn to conversational AI to ask questions, explore ideas, and make purchase decisions, the opportunity to engage with customers is becoming more dynamic. For retail media, this shift presents both an opportunity for advertisers and a responsibility to understand how brands can add value in these environments.
Roundel is taking an early step forward by participating in the OpenAI Ad Pilot Program testing ads within ChatGPT’s free US experience. The pilot is intentionally designed as a high-signal learning opportunity, focused on understanding how advertising can work in conversational environments where relevance, timing, and usefulness matter most.
Matt Drzewicki, senior vice president and general manager at Roundel, explains that the effort is centered on exploring a different approach to advertising. “We’re testing how ads can align to conversational intent and appear only when they are contextually appropriate,” Drzewicki said. “The goal is to better understand what effective, user-first advertising looks like in AI-driven conversations—and how it can support discovery.”
Through the pilot, Roundel is testing how Target-owned ads perform in ChatGPT with select brand partners. Clearly labeled ads are matched to conversational context and dynamically connected to Target, allowing guests to move seamlessly from inspiration to exploration within a trusted retail ecosystem. The experience is designed to feel natural and helpful—reinforcing discovery while preserving the integrity of the conversation.
Off-platform advertising is already a core part of Roundel’s media strategy. Today, Roundel advertisers already over-index on offsite media compared to the broader retail media industry, reflecting strong demand for discovery beyond owned and operated environments. This pilot builds on that foundation, extending off-platform reach into emerging, intent-rich conversational spaces.
The pilot allows Roundel and OpenAI to observe engagement patterns, understand how users interact with ads in conversational settings, and identify where advertising meaningfully contributes to the experience. More broadly, the learnings from this effort are expected to help inform how advertising evolves within conversational AI across the industry. Insights around relevance, placement, creative approach, and user response will help shape future models.
As retail media continues to expand beyond owned and operated platforms, this pilot represents an important step in understanding how off-platform discovery can evolve. By learning early and collaborating closely with platform partners, Roundel is helping shape what the future of user-first, AI-enabled advertising can look like—not just for today, but for what comes next.