According to a PYMNTS article from July 21, 2026, ChatGPT started advertising in February and within six weeks had crossed $100 million in annualized revenue. On May 5, OpenAI removed the $50,000 minimum spend threshold and launched a self-serve Ads Manager. Active advertisers rose from 2,585 to 3,770 in the seven days ending June 8, a 46% week-over-week increase. Despite this, impression share remained concentrated, 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, and eight of the top 10 were B2B SaaS, productivity or developer-focused companies; no major retailer cracked the top 10. Similarweb found that 83% of queries triggering ChatGPT ads would never activate a keyword-based ad. Retailer absence also reflects the failure of ChatGPT’s Instant Checkout feature, launched in September 2025 and unwound six months later. On March 24, 2026, OpenAI announced it would let retailers use their own checkout experiences. Walmart made about 200,000 products available through Instant Checkout starting in November 2025; 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