
Anthropic has more verified business customers than OpenAI for the first time, according to the Ramp AI Index released in May 2026. The fintech firm’s survey of more than 50,000 US companies shows 34.4% of businesses now pay for Anthropic services, compared with 32.3% for OpenAI. This marks the first time Anthropic has held the top position in the index, which tracks billions of dollars in monthly AI spending through corporate card and bill-paying activity. The shift represents a dramatic reversal from January 2026, when OpenAI held a commanding lead across software development, research, finance, and customer support segments.
TechCrunch reported on May 13, 2026, that Anthropic’s 26-percentage-point surge over 12 months signals a structural shift in enterprise AI preference. In May 2025, only 9% of businesses in the Ramp index paid for Anthropic products. That figure climbed to 34.4% by May 2026, while OpenAI’s share declined by 1% over the same period. The overall share of businesses using some kind of AI product increased by 9%, indicating that Anthropic’s gains came partly at OpenAI’s expense rather than solely from new market entrants. OpenRouter’s leaderboard, which samples a different portion of users, confirms the trend: OpenAI last ranked above Anthropic in December 2025.
Anthropic’s Technical-First Strategy vs. OpenAI’s Deployment Push
OpenAI responded to the competitive pressure on May 11, 2026, by launching the OpenAI Deployment Company, a new venture with more than $4 billion in initial investment designed to help organizations build and deploy AI systems. The venture, which is majority-owned and controlled by OpenAI, acquired applied AI consulting firm Tomoro to bring approximately 150 forward-deployed engineers into the unit from day one. The partnership includes 19 investment and consultancy firms, including Bain Capital, Goldman Sachs, Brookfield, Advent, and SoftBank, as founding partners. OpenAI Chief Revenue Officer Denise Dresser, formerly CEO of Slack and hired in December 2025, said enterprise AI adoption is “at a tipping point” and that the deployment company structure will allow OpenAI to help businesses implement complex workflows “at speed and scale.
Anthropic’s growth trajectory has been fueled primarily by the explosive adoption of Claude Code, its software development tool that launched in 2025 and gained significant momentum in late 2025 and early 2026. Ramp economist Ara Kharazian noted that Anthropic “has already been in the lead amongst the high adoption groups like finance, tech, professional services,” while OpenAI maintained leads in other segments that have been shrinking over the past couple of months. Anthropic has expanded beyond software development into legal operations, finance, and research workflows through its Cowork product, which targets less technical users. The company is also preparing for a wider release of its Mythos model, currently available only to a select group of partners through its Project Glasswing cybersecurity initiative.
Revenue Growth, Valuation, and the Path to IPO
Anthropic’s business adoption surge has been accompanied by extraordinary revenue growth. CEO Dario Amodei said at the company’s Code with Claude developer conference in San Francisco in May 2026 that the company saw 80-fold year-over-year growth in revenue and usage in the first quarter of 2026, far exceeding the 10-fold increase the company had planned for. Amodei described the growth as “too hard to handle” and said he hopes for “more normal” expansion going forward. According to the Financial Times, Anthropic’s annualized revenue is expected to cross $45 billion imminently, a fivefold increase from $9bn at the end of 2025. Bloomberg reported that Anthropic is in early talks with investors to raise at least $30 billion in fresh financing at a valuation of more than $900 billion, with the round expected to close as soon as the end of May 2026.
OpenAI, meanwhile, was valued at $852 billion post-money in March 2026 after closing a record $122 billion funding round. The company is spending $50 billion on computing resources in 2026, according to President Greg Brockman. Both companies are racing to secure computing capacity to meet surging demand. Anthropic has struck deals with SpaceX, Google, Broadcom, and AWS in recent months. OpenAI moved earlier to lock in data center capacity, inking deals in autumn 2025. Investors in both companies are positioning ahead of expected blockbuster initial public offerings, with Anthropic’s IPO anticipated as soon as the end of 2026.
What This Means for Enterprise Buyers and Investors
For enterprise buyers, the intensifying competition between Anthropic and OpenAI translates into greater vendor optionality and more aggressive go-to-market strategies from both labs. Anthropic’s technical-first approach, starting with software developers and expanding into legal, finance, and research workflows, has proven effective at winning business customers in high-adoption segments. OpenAI’s Deployment Company represents a direct counter-strategy, embedding forward-deployed engineers into organizations to accelerate AI adoption across complex enterprise workflows. The presence of major private equity and consulting firms as founding partners in OpenAI’s venture, including Bain Capital and Goldman Sachs, signals that the deployment model is designed to scale across hundreds of portfolio companies.
For investors, the Ramp data confirms that enterprise AI adoption is accelerating overall, with the share of businesses using some kind of AI product increasing by 9% over the past 12 months. However, Ramp economist Ara Kharazian cautioned that AI competition remains unusually volatile, with businesses rapidly switching models based on cost, performance, and reliability. Rising token costs, compute shortages, and growing interest in cheaper open-source alternatives could reshape the market again within months. Kharazian noted that “we have never seen a software industry as dynamic, where newcomers can disrupt market leaders in a matter of months, and where the pace of development overrides the typical forces of vendor stickiness.” The full competitive analysis and what this means for Model Release investments at newsletter.krolmarc.com.
Risks, Volatility, and the Competitive Outlook
The primary risk for Anthropic’s newly claimed lead is the volatility that Kharazian explicitly warned about. Businesses are switching AI models rapidly based on cost, performance, and reliability factors, and the pace of development in the AI lab market overrides traditional vendor lock-in dynamics. Anthropic’s 80-fold revenue growth in Q1 2026 has created its own challenges: the company acknowledged “difficulties with compute” and has had to ration capacity during peak hours, frustrating some customers. The SpaceX deal for 300 megawatts at Colossus 1 addresses near-term capacity constraints, but the company’s planned wider release of the Mythos model will further increase compute demand. OpenAI faces its own execution risks with the Deployment Company, which must integrate Tomoro’s 150 engineers and coordinate across 19 founding partner organizations while competing against Anthropic’s momentum in high-adoption segments.
Three Questions on Structure, Terms, and Competition
Why did Anthropic gain business customers so rapidly, and can the lead hold? Anthropic’s 26-percentage-point gain over 12 months was driven by Claude Code’s explosive adoption among software developers, followed by expansion into legal, finance, and research workflows through Cowork. The company’s strategy of starting with a technical customer base and broadening out proved effective. However, Ramp economist Ara Kharazian explicitly warned that AI competition is unusually volatile and that these results should not be construed as Anthropic being the definitive leader. Businesses are switching models rapidly, and open-source alternatives could reshape the market within months.
Does OpenAI’s Deployment Company make Anthropic’s lead less significant, or do they target different buyers? OpenAI’s Deployment Company targets organizations that need hands-on help implementing AI across complex workflows, embedding forward-deployed engineers directly into teams. Anthropic’s strength lies in product-led adoption through Claude Code and Cowork, where users adopt tools independently. The two approaches address different stages of the enterprise AI adoption curve: Anthropic wins with product-market fit among technical users, while OpenAI is investing in services-led deployment for organizations that need more support. Both strategies can coexist, but the Deployment Company signals OpenAI is not ceding the enterprise market without a direct counter-attack.
What does the Ramp data tell us about the enterprise AI market over the next 12-24 months? The overall share of businesses using some kind of AI product increased by 9% over the past 12 months, confirming that enterprise AI adoption is accelerating broadly. Anthropic’s rise from 9% to 34.4% and OpenAI’s slight decline from 33.3% to 32.3% suggest that the market is large enough for both to grow in absolute terms even as share shifts. The key variable is whether the pace of model improvement and cost reduction continues to accelerate, which would benefit the lab with the strongest product roadmap. Anthropic’s Mythos model and OpenAI’s GPT-5.5-Cyber, released in limited preview to vetted cybersecurity teams in May 2026, represent the next competitive front.
Given that Anthropic grew from 9% to 34.4% business adoption in just 12 months while OpenAI declined 1%, do you think Anthropic’s lead reflects a permanent shift in enterprise AI preference, or will OpenAI’s Deployment Company and services-led strategy close the gap by the end of 2026?







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