OpenAI’s advertising business is moving from cautious experiment to strategic expansion, with the company signing adtech firm Smartly as a key partner in what could become one of the most consequential shifts in the digital media industry.
The deal marks a deeper push into monetization for ChatGPT, as OpenAI looks to transform its vast free-user base into a scalable advertising business without undermining the trust that underpins its product. At the heart of the partnership is a simple but commercially significant objective to make ads inside ChatGPT feel less like interruptions and more like extensions of the conversation.
Smartly, the 13-year-old advertising technology company led by industry veteran Laura Desmond, will initially help brands optimize how sponsored placements appear to users in real time, adjusting messaging and performance as campaigns run.
That first phase, however, is only the beginning. The broader ambition is to build fully conversational ad formats that mirror the ChatGPT interface itself, allowing brands to engage users in a question-and-answer flow designed to guide discovery and conversion.
This is a material departure from traditional digital advertising. Instead of static display units or sponsored search links, the future model being tested points toward interactive brand conversations, where a retailer, travel company, or entertainment brand can respond dynamically to user intent.
In practical terms, a consumer searching for holiday destinations could be guided by a branded assistant toward flights and hotels, while a shopper researching skincare products could be led through personalized recommendations inside a dialogue window.
Laura Desmond described the commercial logic behind the shift.
“The opportunity with conversational advertising is you can do more follow-ups, and you can ask again,” she said.
“The experience for people will get way more relevant, way more personal, and hopefully be seen as a much better value exchange. All of the research indicates people want to be known. Don’t serve me shoes I bought three weeks ago. Don’t serve me ads that aren’t relevant.”
The company’s U.S. advertising pilot has already crossed $100 million in annualized revenue within just six weeks of launch, according to Reuters, underscoring the speed with which advertiser demand is building. More than 600 advertisers are now participating, with a self-serve platform due to launch this month.
That pace of early monetization suggests that ChatGPT is rapidly emerging as a new layer of commercial discovery, one that could challenge parts of the digital advertising ecosystems long dominated by Google and Meta Platforms.
For nearly two decades, digital advertising has revolved around search queries, social feeds, and e-commerce marketplaces. ChatGPT introduces a different form of intent, one based not on keywords or scrolling behavior but on active conversation.
That means advertisers are no longer simply buying impressions; they are buying context. A user asking for “the best running shoes for marathon training under $150” presents a far more commercially valuable signal than a conventional search phrase, because the request contains purpose, urgency, and constraints.
This is precisely why the Smartly partnership matters.
The company has built its reputation on helping major clients such as Spotify and Uber adjust campaigns in real time across platforms. Bringing that capability into ChatGPT gives OpenAI an early operational framework as it builds out its own advertising stack.
Industry sources suggest the company is also moving steadily toward greater control over that stack, including campaign tools, ad measurement, and inventory management.
However, unlike search engines, ChatGPT’s interface offers limited screen real estate, and the company has been careful not to embed ads directly into its organic responses.
That separation is central to preserving user confidence. OpenAI has repeatedly stressed that sponsored placements are clearly labelled, separate from answers, and do not influence outputs. User conversations are not shared with advertisers, and ads are restricted around sensitive topics such as politics and health.
This is where the competitive contrast becomes particularly interesting. Anthropic has explicitly rejected advertising in its Claude chatbot, arguing that it could compromise its mission and trust architecture.
OpenAI, by contrast, appears to be betting that trust and advertising can coexist, provided the user experience remains carefully managed. That balancing act may define the next stage of the AI business model.
Subscriptions and enterprise contracts remain major revenue streams, but advertising offers something larger: access to hundreds of millions of non-paying users. Recent estimates suggest ChatGPT now serves roughly 900 million users globally, the vast majority of whom are on free tiers.
For a company facing massive compute and infrastructure costs, monetizing that audience is seen as a viable revenue source.
However, the move is mired in concern about whether conversational advertising can scale without feeling invasive. Some believe that if OpenAI gets the experience right, it could create an entirely new category of intent-driven media. But if it gets it wrong, it risks alienating the very users that made ChatGPT a mass-market product.






