Anthropic pulls ahead
Anthropic has emerged as a top pick for enterprise AI buyers and that momentum has prompted an internal strategic response from OpenAI. Reports say enterprise leaders are gravitating to Anthropic while OpenAI circulated a leaked memo outlining a plan to counter that shift, with industry pieces documenting rapid enterprise uptake and internal positioning moves. (emarketer.com, theverge.com)
Anthropic is becoming the enterprise artificial intelligence vendor more buyers ask about first, and OpenAI is now answering that shift internally. (emarketer.com, theverge.com) At the HumanX conference in San Francisco, eMarketer reported that buyers were moving spending from chatbot pilots toward “agentic” systems that can take actions across software tools, and that Anthropic’s Claude drew more discussion from decision-makers than ChatGPT. (emarketer.com) OpenAI’s chief revenue officer, Denise Dresser, sent employees a four-page memo that The Verge said stressed user lock-in, enterprise growth, and a wider moat around OpenAI’s products as model switching gets easier. (theverge.com) The memo said “the market is as competitive as I have ever seen it,” and singled out Anthropic as the rival OpenAI most needed to answer in sales and product positioning. (theverge.com) This contest is now centered on enterprise buyers, not consumer chatbot traffic. OpenAI said in November 2025 that more than 1 million business customers were paying for its tools, while Anthropic said in September 2025 that it served more than 300,000 business customers. (openai.com, anthropic.com) Anthropic’s pitch has been gaining weight with larger accounts. The company said last week that its run-rate revenue had passed $30 billion and that more than 1,000 business customers were each spending over $1 million on an annualized basis, up from more than 500 in February. (anthropic.com) OpenAI is pushing back on those numbers. CNBC and The Verge reported that OpenAI circulated arguments that Anthropic’s revenue run rate looked overstated and that OpenAI held a stronger long-term compute position, with a plan for 30 gigawatts by 2030 versus OpenAI’s estimate that Anthropic could reach 7 to 8 gigawatts by the end of 2027. (cnbc.com, theverge.com) The market is not moving to a single winner. eMarketer reported in February, citing an Andreessen Horowitz survey of 100 chief information officers from Forbes Global 2000 companies, that OpenAI still captured 56% of enterprise model spending while Anthropic was gaining quickly in a multi-model market. (emarketer.com) Anthropic has spent the past year building specifically for corporate use, including Claude Enterprise in September 2024 and a broader push into coding, document analysis, and internal knowledge work. OpenAI launched ChatGPT Enterprise in August 2023 and has since framed its business around security, privacy, and deployment at scale. (emarketer.com, openai.com) What changed this spring is that the rivalry stopped looking one-sided. Anthropic’s customer growth is now strong enough that OpenAI is writing internal strategy memos about how to keep enterprise buyers from drifting. (emarketer.com, theverge.com)
