In Graphic Detail: Why OpenAI’s ad business is still a work in progress

May 27, 2026 Presented by OpenAI is reportedly heading toward a public market debut as early as September — a listing that could value the company at around $1 trillion. Right now though, it’s still learning how to be an ads business. Just 15 weeks into its ChatGPT ad pilot and the platform is already dealing with many of the tensions that have defined every major digital ad platform before it: scale versus safety, automation versus control and advertiser expectations versus product reality. Advertisement TOP STORY Marketing on Platforms In Graphic Detail: Why OpenAI’s ad business is still a work in progress As OpenAI is reportedly gearing up to go public as early as September, Digiday has charted the promise, and early tensions behind its ad business. OTHER THINGS TO KNOW There’s more information than ever. We separate the signal from the noise, so you know what to act on. Get 35% off a full year of Digiday+. Offer ends May 29. The winning move for advertisers isn’t to chase every new rights deal; it’s to find platforms, formats and buying methods that can aggregate across them. Partner insights from DIRECTV Advertising. Even with the biggest FIFA men’s World Cup in history rapidly approaching and modern sports fans continually demonstrating their digital savviness, the success of so many brands’ campaigns still relies on outdated strategies and technology. Partner insights from Sportradar. A MESSAGE FROM TATARI How Tatari shows marketers the impact of their TV ads TV that performs like digital isn’t new. It’s what Tatari has always done: CAC, ROAS, site visits, Amazon purchases, halo lift on paid social and search, and incrementality. All in near real time, with the same accountability marketers expect from digital. Ready to hold TV to the same standard as every other channel? How Tatari measures TV MEDIA & PLATFORMS Member exclusive Future of TV Briefing: How AI agents will figure into this year’s upfront negotiations This week’s Future of TV Briefing looks at the conversations that upfront sellers including Disney, Paramount and Warner Bros. Discovery are looking to have with advertisers regarding incorporating AI agents in ad buys. PARTNER INSIGHTS FROM SEEDTAG Together, identity and contextual data offer a more complete view of inventory First-party data provides a valuable view of known audiences, while contextual signals provide a real-time understanding of what those audiences are doing and why. PARTNER INSIGHTS FROM ADJUST How mobile gaming companies are navigating measurement migrations Measurement platforms have always been foundational to app marketing and growth success. But as complexity has grown and signal loss persisted, the underlying infrastructure has taken on greater strategic importance. Advertisement MARKETING Strategizing for the Future After Publicis' LiveRamp deal, marketers are still working out what to worry about — and why Publicis’ LiveRamp deal forces marketers to confront who controls their data, reshaping the neutrality debate around ad tech infrastructure. PARTNER INSIGHTS FROM OPTABLE Why publishers can’t afford to wait on agentic AI The agentic era is here. But the nearly one-third of publishers who lack immediate investment plans risk falling behind. The Sports Marketing Playbook Premier League gambling ban gives brand sponsors an open goal, but CMOs must still prove value An exodus of betting brands from the Premier League means there’s a chance for marketers to bag cut-price soccer partnerships. But proving the worth of that investment is another concern. Brands in Culture The AI paradox: Marketers trust AI to buy media, not build brands Some executives are wary of AI-generated creative ideas while using automated tools to brainstorm campaigns. ICYMI The Creator Economy Twitch tweaks monetization tools to try and help smaller creators build a following Twitch’s new community-driven monetization tools seek to give creators more ways to get paid, but creators need to get discovered first 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