That change lowered the barrier to entry and advertisers responded immediately. Active advertisers on ChatGPT rose from 2,585 to 3,770 in the seven days ending June 8, a 46% week-over-week increase, Similarweb found.
Software Brands Sweep the Top 10 Advertiser List
Despite that influx, impression share remained concentrated among a small group of early movers, with Monday.com alone accounting for 5.05% of global impressions. The top five advertisers — Monday.com, Shopify, Jotform, Resume.io and Cursor — captured nearly 17% of global impressions combined, and eight of the top 10 advertisers were B2B SaaS, productivity or developer-focused companies, according to Similarweb. No major retailer cracked the top 10.
The category breakdown reflects the platform’s audience. ChatGPT’s largest user group is adults aged 25 to 34, skewing toward professionals and developers, according to Similarweb traffic data. B2B software brands already target that demographic on LinkedIn and Google. A project management platform like Monday.com or a developer tool like Cursor fits naturally into a conversation about workflow problems.
A consumer retailer selling apparel or electronics does not have the same entry point. Retailers also built their ad operations around keyword bidding, product listing feeds and catalog-based targeting. That infrastructure that does not map onto a conversational system that infers intent from an ongoing exchange. Similarweb found that 83% of queries triggering ChatGPT ads would never activate a keyword-based ad, PYMNTS reported.
ChatGPT Checkout Underdelivered and Retailers Didn’t Return for Ads
The retailer absence from ChatGPT advertising also reflects a harder lesson from the platform’s earlier commerce experiment. ChatGPT’s Instant Checkout feature, which let users complete purchases directly inside the chat without visiting a retailer’s website, launched in September 2025 and was unwound six months later. On March 24, 2026, OpenAI announced it would let retailers use their own checkout experiences and focus instead on product discovery, TechCrunch reported. OpenAI staff internally acknowledged that ChatGPT users were researching products but not completing purchases inside the platform, The Information reported.
Walmart provided the clearest evidence. Starting in November 2025, the retailer 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 click-through transactions to Walmart.com and called the in-chat experience “unsatisfying.” Consumers completing a purchase inside a chatbot encountered no familiar brand environment, no visible return policies and no standard security signals.
In fact, Walmart did not abandon ChatGPT entirely. After pulling Instant Checkout, the company embedded Sparky, its own shopping assistant, directly inside ChatGPT and Google Gemini, letting users log into Walmart accounts, sync carts and complete purchases within Walmart’s own system, MarTech reported. Early data suggests Sparky-in-ChatGPT reached approximately 70% of Walmart.com’s conversion rate, more than doubling Instant Checkout’s performance, according to analysis cited by AI Automation Global reported. ChatGPT works as a discovery surface. It does not work as a replacement for the retailer’s own checkout.
ChatGPT’s share of product research climbed from 2% to 30% in two years, PYMNTS Intelligence found. Instant Checkout’s failure does not mean ChatGPT lacks value for retailers. It means the platform may be more effective at influencing a purchase than completing one. Consumers are already using ChatGPT to research products, compare options and narrow decisions, while AI-referred traffic converts at higher rates and produces larger orders once shoppers reach a retailer’s own site. That creates a significant opening for retail advertising. Meanwhile, Open AI is banking on the success of its ads business and expects $2.5 billion in ad revenue by the end of 2026 and projects $100 billion by 2030, Axios reported.
