Software advertisers dominate early ChatGPT ad spending

OpenAI’s ChatGPT advertising business has expanded quickly since its February launch, with annualized revenue passing $100 million within six weeks, CNBC reported. The market broadened further after OpenAI removed a $50,000 minimum spend requirement and introduced a self-serve Ads Manager on May 5, according to Digiday.

Advertiser participation rose sharply after the change. Similarweb found that active advertisers on ChatGPT increased to 3,770 in the seven days ending June 8 from 2,585 a week earlier, a 46% rise.

The early spending pattern is concentrated in software and productivity categories rather than retail. Similarweb said Monday.com accounted for 5.05% of global ChatGPT ad impressions, while Monday.com, Shopify, Jotform, Resume.io and Cursor together represented almost 17% of impressions. Eight of the 10 largest advertisers were B2B software, productivity or developer-oriented companies, according to Similarweb, and no major retailer appeared in the top 10.

Software brands find a clearer fit

The category mix reflects the audience using ChatGPT, according to Similarweb traffic data. The platform’s largest user segment is adults aged 25 to 34, with usage tilted toward professionals and developers. That makes the service a closer match for companies that already spend to reach business users on platforms such as LinkedIn and Google.

Conversational ads also differ from conventional search advertising. In a search system, marketers often bid against keywords or connect ads to product feeds. In ChatGPT, ad placement depends on the context and intent inferred from an exchange between the user and the chatbot. PYMNTS, citing Similarweb, reported that 83% of ChatGPT ad-triggering queries would not have activated a keyword-based ad.

That structure gives software providers a more direct route into user intent. A project management platform can appear in discussions about workflow, while a developer tool can surface in conversations about coding or productivity. Retailers selling consumer goods face a less direct path because their ad systems have been built around catalog data, product listings and transaction-focused targeting.

Retailers remain cautious after checkout test

Retailer caution also follows OpenAI’s earlier attempt to make ChatGPT a transaction channel. The company launched Instant Checkout in September 2025, allowing users to buy products inside the chat. TechCrunch reported that OpenAI changed course on March 24, 2026, saying retailers could use their own checkout systems while ChatGPT focused more on product discovery. The Information reported that OpenAI employees had acknowledged users were researching products in ChatGPT but were not completing purchases there.

Walmart’s experience illustrated the gap between discovery and checkout. Beginning in November 2025, Walmart made about 200,000 products available through Instant Checkout. Daniel Danker, Walmart’s executive vice president of product and design, told Wired that purchases completed inside ChatGPT converted at one-third the rate of transactions in which shoppers clicked through to Walmart.com. He described the in-chat buying experience as “unsatisfying.”

Walmart later shifted to a model that kept more of the transaction inside its own systems. MarTech reported that the retailer embedded Sparky, its shopping assistant, inside ChatGPT and Google Gemini, allowing users to log into Walmart accounts, sync carts and complete purchases through Walmart’s infrastructure. AI Automation Global cited analysis indicating Sparky-in-ChatGPT reached about 70% of Walmart.com’s conversion rate, more than twice the performance of Instant Checkout.

ChatGPT still has a growing role in shopping research. PYMNTS Intelligence found that its share of product research rose to 30% from 2% over two years. Axios reported that OpenAI expects $2.5 billion in advertising revenue by the end of 2026 and projects $100 billion by 2030.

This story draws on original reporting from PYMNTS.