Six weeks was all it took. On 9 February, OpenAI switched on advertisements inside ChatGPT for free-tier users in the United States. By late March, the company disclosed that the pilot had crossed $100 million in annualised revenue, drawn more than 600 advertisers, and reached fewer than a fifth of eligible users. Now OpenAI is enlisting outside help to make those ads considerably more ambitious. According to Business Insider, the company is working with Smartly, the Helsinki-based advertising automation platform, to bring conversational, interactive ad units to ChatGPT, formats that do not simply sit beside a response but respond to the user in turn.

The partnership marks a quiet but significant escalation from the static, labelled placements that OpenAI introduced when it first confirmed its advertising plans in January. In those early tests, a sponsored card might appear beneath a product query, an air fryer ad after a question about countertop appliances, say, or a hotel promotion following a travel inquiry. The new conversational formats, according to Smartly’s own description of the collaboration, would allow a user to click an ad and enter a chatbot experience that offers tailored suggestions, effectively turning the advertisement into a secondary dialogue within ChatGPT’s interface.

Smartly, which reported roughly $101 million in revenue in 2025 and is valued at approximately $300 million, is best known for helping brands optimise campaigns across Meta, Google, TikTok, and Snapchat in real time. Its role in the ChatGPT partnership appears to centre on performance optimisation, adjusting creative and targeting on the fly based on how users interact with the new formats. OpenAI has separately brought on Criteo, the French commerce-media company, as its first formal ad-tech partner, connecting approximately 17,000 advertisers to ChatGPT’s inventory since 2 March. The company has also held early-stage discussions with The Trade Desk about scaling ad sales further, according to The Information, though no deal has been announced.

The commercial infrastructure is assembling rapidly. In late March, OpenAI hired David Dugan, a former vice-president at Meta who led the platform’s global clients and agencies division for more than a decade, to run its new global advertising solutions team. Dugan reports to chief operating officer Brad Lightcap and joins a leadership bench that already includes Fidji Simo, the former Facebook executive who serves as CEO of OpenAI’s applications division, and Denise Dresser, the former Slack chief executive who was appointed chief revenue officer in December 2025. The hires suggest a company that is no longer experimenting with advertising but building a permanent sales organisation around it.

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OpenAI has told investors it expects ChatGPT consumer revenue to exceed $17 billion in 2026, with advertising representing a meaningful share of income from its non-paying user base. The maths are suggestive: the company says it has more than 800 million weekly active users, but only about 5 per cent pay for subscriptions. Self-serve advertising tools, which would remove the current $200,000 minimum commitment and open the platform to small and mid-sized businesses, are scheduled to launch this month. Pilots in Canada, Australia, and New Zealand are expected to follow, with broader international expansion planned throughout the year.

The initial pricing has been aggressive. ChatGPT ads launched at roughly $60 per thousand impressions, a premium that OpenAI justifies with early performance data: Criteo reports that users referred by large language models convert at 1.5 times the rate of other channels. Nearly 80 per cent of small and medium-sized businesses have reportedly signalled interest in advertising on the platform, a figure that, if it translates to actual spend once self-serve access opens, would represent an extraordinarily rapid ramp.

The privacy architecture around these ads will determine whether the conversational formats succeed or provoke a backlash that damages ChatGPT’s core appeal. OpenAI says conversations remain private and are never shared with advertisers, who receive only aggregate performance data such as views and clicks. Ads are restricted from appearing near health, mental-health, and political topics. Users under 18 do not see them. But the safeguards have not silenced critics. Zoe Hitzig, a former OpenAI researcher, has publicly argued that the company is building an economic engine whose incentives will eventually override its own rules, noting that ChatGPT holds an unprecedented archive of deeply personal conversations. Purchase-tracking data can flow back to OpenAI when a user clicks an ad and completes a transaction, and the company’s updated privacy policy permits contact-syncing features that could process a user’s phone number even if that user has not personally opted in.

Competitors have been swift to exploit the opening. Anthropic, maker of the Claude chatbot, ran Super Bowl advertisements that implicitly contrasted its ad-free model with OpenAI’s decision. The framing was clear: one company treats its users as the product, the other does not. Whether that distinction matters to the hundreds of millions of people who use ChatGPT for free remains an open question, but the reputational risk is not trivial for a company that has positioned itself as the responsible steward of artificial general intelligence.

The conversational ad format that Smartly is helping to build represents something genuinely new in digital advertising — not a banner, not a sponsored link, but a dialogue that mimics the interface the user came to ChatGPT to have in the first place. If it works as intended, it could blur the line between commercial and organic content more effectively than anything Google or Meta has attempted. If it erodes the trust that made ChatGPT the fastest-growing consumer application in history, OpenAI will have traded its most valuable asset for a revenue stream it could have built more cautiously. The $100 million annualised run rate suggests the former outcome is more likely. The hiring of an entire Meta-era advertising team suggests OpenAI is not leaving anything to chance.