Anthropic has surpassed OpenAI among verified business customers for the first time, according to fintech firm Ramp’s monthly AI Index. Drawn from expense data across more than 50,000 companies, the index shows 34.4% of participating businesses now pay for Anthropic services, edging ahead of OpenAI’s 32.3%. The shift reflects a dramatic 12-month surge: in May 2025, just 9% of businesses were paying for Anthropic products. Ramp economist Ara Kharazianattributed the rise to a deliberate strategy of targeting technical customers in finance, technology, and professional services before broadening outward — a playbook he said had been validated by results.
That momentum has been shaped in part by Cat Wu, Anthropic’s head of product for Claude Code and Cowork, who joined the company in August 2024. Working alongside Boris Cherny, the creator of Claude Code, Wu has helped transform Claude from a conversational AI into an agentic coding and task-automation platform. She described the next frontier as proactivity — building systems that understand a user’s work patterns and configure automations on their behalf, without being asked.
Anthropic is now pushing deeper into the small business market with the launch of Claude for Small Business, a new feature suite accessible via a toggle within Claude Cowork. The bundle includes bookkeeping tools, business insights, ad campaign generators, and integrations with platforms including QuickBooks, Canva, DocuSign, HubSpot, and PayPal. The company plans a ten-city promotional tour beginning in Chicago, offering free AI training workshops to 100 small business leaders at each stop.
The announcements come as Anthropic is reported to be raising fresh funding at a valuation approaching $950 billion — a figure that would surpass OpenAI’s March valuation of $854 billion. The company has also moved to block a string of unauthorised secondary market platforms, including Forge Global, Hiive, and Sydecar, from offering access to its shares, stating that any unapproved transfers will not be recognised on its books.
