Move over, Google.
Digital data research platform Similarweb found that 83% of the queries triggering ads inside OpenAI’s ChatGPT would never have activated a Google Shopping ad. That gap isn’t incidental, it’s structural. Artificial intelligence (AI) assistants are reaching buyers at stages in the purchase journey that keyword-based search was never designed to monetize.
The difference is how each system reads intent. Google Shopping matches ads to declared product queries. ChatGPT surfaces ads during problem-solving conversations, research sessions and multi-turn exchanges, where commercial intent develops gradually rather than arriving pre-labeled.
OpenAI Crossed $100 Million in Ad Revenue
Reuters reported in March that OpenAI’s advertising pilot crossed $100 million in annualized revenue within six weeks of launching, with fewer than 20% of eligible U.S. users being shown ads daily at that point.
In May, OpenAI launched a self-serve Ads Manager in beta, removing the minimum spend requirement that had previously gated the platform to large commitments and opening it to businesses of any size.
The AI startup also added cost-per-click bidding alongside, giving performance marketers a buying model tied to user action rather than impressions. Combined with a Conversions API and pixel-based measurement, the platform moves closer to the frameworks advertisers already use on Google and Meta, though benchmarks for click quality and conversion rates in a conversational environment are still early.
ChatGPT Ads Now Fire at Turn 15, After Buyers Have Already Compared Options
The sharper finding in Similarweb’s data is not the volume of advertisers but where in the conversation ads land. Three weeks before a separate June report was released, leading advertisers were seeing their ads fire at a median of turns 7 to 8. By June 8, that figure had shifted to turns 14 to 22 for the same brands. Vanta’s average ad-firing turn reached 15.8. Monday.com’s reached 13.6.
Ads at that depth reach users who have already compared options, asked follow-up questions and narrowed a shortlist before encountering a sponsored placement. Similarweb’s broader report found that 41% of ad moments inside ChatGPT are purely research-oriented and that 46% of users who begin a session with no commercial intent develop buying signals before the conversation ends.
The distinction from keyword search is structural. A user who types “project management software” into Google has declared intent. A user who asks ChatGPT how to fix a team workflow problem, then discusses software options across eight exchanges, arrives at the same commercial moment through a different path. The ad placement in the second scenario reaches a more informed buyer, but requires the system to infer relevance from context rather than match it against a keyword.
Monday.com Leads ChatGPT Ad Impressions as B2B Brands Claim Early Position
Impression share on ChatGPT remains concentrated. Monday.com holds 5.05% of global impressions. The top five advertisers collectively account for nearly 17%. Eight of the top 10 advertisers by impression share are B2B SaaS or productivity brands, reflecting both the platform’s early audience composition and the speed at which software companies have moved to establish presence before auction costs rise.
Similarweb noted that brands entering a newly launched market on the platform appear to have roughly 30 days of category-level advantage before competition intensifies and auction dynamics normalize.
