Why Target’s Roundel is one of the first to test ChatGPT ads

February 17, 2026 Weeks after unveiling ad plans, OpenAI is working to control the message. Part of that is working with brands to test and learn what’s working — and Target is at the front of the line. We checked in with their execs to see how that’s going. TOP STORY Marketing on Platforms 'An influential seat at the table': Why Target's retail media business Roundel is one of the first to test ChatGPT ads Roundel’s svp Matt Drzewicki talked about what they expect from the pilot. Advertisement OTHER THINGS TO KNOW The discussion around brand safety and suitability has matured. The industry is now entering a new phase, where brands expect more control, more extensibility into walled gardens and closer accountability to outcomes. Partner insights from Channel Factory. Fragmentation is no longer an edge case in TV — it’s the operating environment. And marketing strategies have to be built with that reality in mind. Here’s how that might play out during the World Cup. Partner insights from Nexxen. Weather impacts what people try, buy and how they feel. This powers targeting to predict the moments when weather shifts a consumer's mindset toward purchase, driving sales and long-term growth. Learn more in this video. Partner insights from The Weather Company. MEDIA & PLATFORMS Marketing on Platforms 'Being very careful': Weeks after unveiling ad plans, OpenAI works to control the message A month into its ad strategy, OpenAI tries to balance growth and trust. Generative AI AdCP vs. IAB Tech Lab: Inside programmatic advertising's agentic AI standards showdown Ad Context Protocol and IAB Tech Lab’s Agentic Roadmap offer two competing approaches for updating ad tech for AI agents. Can they coexist? PARTNER INSIGHTS FROM PADSQUAD How marketers are recentering ad quality and relevance Now that campaigns can accommodate mid-flight changes — adjusting visual sequences, calls to action or tone based on audience engagement — advertisers can treat creative as a dynamic asset, not a fixed deliverable. Member exclusive Ad Tech Briefing: A mid-term report card Despite earnings increases, stock prices are down demonstrating how the public markets are a cruel place. PARTNER INSIGHTS FROM EXPERIAN How marketers are interpreting context in real time Context takes many forms, often operating beneath the surface of consumer activity. Marketers are increasingly using technology to interpret these micro-signals, enhancing predictive accuracy and creative alignment. Advertisement MARKETING Subscriptions In Graphic Detail: Subscriptions are rising at big news publishers – even as traffic shrinks Publishers are raising prices, pushing bundles and prioritizing retention to make subscriptions a steady business amid volatile traffic. PARTNER INSIGHTS FROM KEEN DECISION SYSTEMS Steps for marketers to leave behind inconsistent pacing and wasted ad spend Timing structure should be a strategic lever in marketers’ planning processes. Key steps include auditing their current execution calendar, prioritizing shoulder periods, avoiding overload on peak weeks and accounting for media booking realities. AI Revenue Generation ChatGPT enters the ad game. Now what? OpenAI has begun testing ads in ChatGPT through premium brand partnerships, signaling a new phase in its monetization strategy. DIGIDAY+ Member exclusive Digiday+ Research: Brand marketing will be the priority in 2026, after revenues fell short of expectations Revenues fell short of marketers’ expectations in 2025. But they’ll be working with bigger budgets in 2026, and focusing on brand marketing. Written by Jim Cooper and Sara Jerde Were you forwarded this email? Sign up to get it daily. Advertise | Digiday+ | Events | Awards Update your email | Unsubscribe | Privacy policy