Anthropic dethrones OpenAI in the enterprise — for now
Ramp's May AI Index puts Claude ahead of ChatGPT among paid business users for the first time, just as Anthropic eyes a $950B valuation..
Once a month, the corporate-card company Ramp publishes an index that tracks which AI vendors its 50,000-plus business customers are actually paying for. For two years, OpenAI sat on top by a comfortable margin. In the May 2026 release, that changed: 34.4% of paying businesses are now buying Anthropic, against 32.3% paying OpenAI. A year ago, Anthropic’s share was 9%. The shift matters because Ramp sees real invoices, not survey answers. It also lands in the same week Anthropic is reportedly raising up to $50 billion at a $950 billion valuation — ahead of OpenAI’s $852 billion. For a DAX40 buyer with a multi-year Microsoft Copilot or ChatGPT Enterprise contract, the question is no longer which lab is ahead. It is whether the lead is durable enough to bet the next renewal on.
Two months ago, in a memo that leaked out of OpenAI’s San Francisco headquarters, Fidji Simo — the former Instacart CEO who runs OpenAI’s applications business — told staff the company was now operating in what Sam Altman and research chief Mark Chen had internally labelled a “code red.” The trigger, she wrote, was Anthropic. Claude Code was eating into OpenAI’s developer base, and enterprise buyers were starting to ask uncomfortable questions about which lab they should standardise on. OpenAI needed, in her phrase, to put extra weight on productivity in general, and on enterprise productivity in particular. Inside the building, the message landed as an admission: the company that defined the consumer AI category was losing the part of the market that actually pays. On 13 May 2026, Ramp published the data point that turned that internal anxiety into a public scoreboard. Its monthly AI Index, drawn from corporate-card and invoice flows across more than 50,000 American businesses, showed Anthropic at 34.4% of paid business users and OpenAI at 32.3%. In April alone, Anthropic added 3.8 points; OpenAI shed 2.9. A year earlier, the gap ran the other way — OpenAI dominant, Anthropic in single digits. “Anthropic has already been in the lead amongst the high adoption groups like finance, tech, professional services,” Ramp economist Ara Kharazian told TechCrunch. “It’s across the other firms where OpenAI still has a lead, but that has been shrinking over the past couple of months.” The context made the moment heavier. The same week, Bloomberg and the New York Times reported that Anthropic was in talks to raise between $30 billion and $50 billion at a valuation of up to $950 billion, on the back of an annualised revenue run rate that has surged from roughly $9 billion at the close of 2025 to more than $30 billion today. Claude Code, the CLI-based coding agent that Allianz quietly rolled out to its workforce in January, is the fastest-growing product in the company’s history. If the round closes at the top of the range, Anthropic will, for the first time, be worth more than OpenAI’s $852 billion last mark. For Anthropic CEO Dario Amodei, this is the payoff for a deliberate strategy. Rather than chase Sam Altman into consumer chat, advertising and a Jony Ive-designed device, Anthropic spent eighteen months courting developers, regulated industries and integrators — the unglamorous middle of the enterprise stack. “What Anthropic did worked really well,” Kharazian said. “Start with a very technical customer base, focus on their needs, really succeed in execution and then start broadening out through tools like Cowork.” The Allianz deal in January, followed by AstraZeneca, Sanofi and Genmab signing for Claude in life-sciences workflows, gave the strategy proof points the average CIO recognises. Not by accident, those proof points sit precisely where DAX40 buyers — Munich Re, BASF, Bayer, Siemens — do their own evaluations.
Strip away the narrative and the index reads like a competitive blowout. Anthropic’s share of paid business users quadrupled in twelve months, from 9% in May 2025 to 34.4% in April 2026 — a 26-point swing. OpenAI’s share moved 0.3 points in the same window. To put that in perspective, AWS took roughly six years between 2010 and 2016 to build a comparable lead over its nearest cloud rival in business adoption; Anthropic compressed an equivalent re-rating into four quarters. On OpenRouter’s leaderboard, which samples a different population of model traffic, OpenAI last ranked above Anthropic in December 2025. Two independent panels, one signal. The revenue gap has narrowed in lockstep. OpenAI is reportedly running near a $20 billion annualised rate; Anthropic, by its own disclosure, has crossed $30 billion, with Claude Code representing the largest single contributor to growth. A January Menlo Ventures survey already pegged Anthropic at roughly 40% of the enterprise LLM market and over half of AI coding spend; the May Ramp data confirms that the trend has continued, not reverted. The funding round telegraphs the same conclusion. Google has committed up to $40 billion of additional capital, Amazon up to $25 billion, and an IPO is being discussed for as early as October 2026. But the same Ramp report carries its own counter-thesis, and Kharazian wrote it himself. The first risk is structural: Anthropic earns more when customers spend more tokens. That is not a neutral incentive. Uber’s CTO disclosed earlier this spring that the company burned through its entire 2026 AI budget in four months, much of it on Claude Code and Cursor, with individual engineers running monthly API bills of $500 to $2,000. Ramp economist Rafael Hajjar separately found that Anthropic’s most recent model update tripled token costs for any prompt containing an image — a pricing change that, in his reading, sits awkwardly with the company’s stated compute constraints. The second risk is operational. Anthropic spent much of April rate-limiting paying developers and quietly removing Claude Code access from some accounts. The Pragmatic Engineer’s Gergely Orosz argued in early May that the moves looked dev-hostile and likely masked a capacity shortage that an emergency SpaceX-Colossus deal — 220,000 NVIDIA GPUs, 300 megawatts — was rushed in to fix. The catch: enterprise procurement teams have long memories. Outages and silent quota cuts during a sales cycle are exactly what kills a multi-year framework agreement. The third risk is the one most relevant to a Großkonzern’s CFO. Some of the fastest-growing AI vendors on Ramp in April were not frontier labs at all. They were inference platforms — the Together AIs, Fireworks and Groqs of the world — selling cheap access to open-source Llama and DeepSeek derivatives. For routine classification, summarisation and customer-service workflows, good-enough AI at a fraction of frontier pricing is increasingly the rational FinOps choice. If that thesis holds, the leaderboard at the top is a fight over a shrinking premium tier.
For procurement leaders in Frankfurt, Munich and Walldorf, the May index is less a vendor recommendation than a portfolio signal. The Microsoft-OpenAI bundle that anchored most enterprise Copilot rollouts in 2024 and 2025 is no longer the unambiguous default. Allianz’s January Claude Code deployment to its global workforce, paired with the Anthropic-built compliance logging layer that records every model interaction for regulators, is the template German buyers are now studying. So is the Anthropic DACH leadership build-out under Roman Howe, who has been hiring out of Munich since the start of the year. Bayer Pharmaceuticals’ Claude deal in clinical-trial documentation, BASF’s Mistral-led production-chemistry copilot, and Munich Re’s newly seated Chief AI Officer point to the same conclusion: DAX40 vendor selection is becoming portfolio construction, not single-vendor commitment. The operational risks Kharazian flags translate directly into RfP language. Token-pricing volatility, image-prompt cost multipliers, capacity-driven rate limits and the absence of EU sovereign-cloud parity with Microsoft’s Azure footprint are all material at framework-contract scale. A Großkonzern signing a multi-year Anthropic deal in Q3 2026 should expect to negotiate hard on per-seat caps, committed throughput, regional data residency and — critically — a contractual exit ramp into open-source inference for non-frontier workloads. The strategic move is not to pick a winner. It is to build a routing layer, internally or via partners, that puts Claude on coding and high-value reasoning, ChatGPT on broad employee productivity, and a cheap inference platform on everything else. The Cohere–Aleph Alpha–STACKIT path supplies the sovereign branch of that routing tree. The May Ramp data is the cleanest evidence yet that single-vendor lock-in to either lab is now the riskier option, and procurement teams that internalise that lesson before the next renewal cycle will save material money.
For a CIO at a DAX40 firm, the headline is uncomfortable: the AI roadmap signed off in 2024 was almost certainly OpenAI-anchored via Microsoft Copilot, and the people now driving the largest spend lines — engineering, legal, regulatory — are increasingly running on Claude. Allianz, Munich Re’s neighbour, has already crossed that bridge with a Claude Code rollout to its global employee base and a built-in audit-log layer designed for BaFin and ECB inspection. Expect procurement teams to push back on single-vendor Microsoft framework agreements and demand multi-model routing, BYO-key support and clean exit clauses for non-frontier workloads. Token-cost transparency, not benchmark scores, will decide the next renewal cycle.
The compliance-by-design pitch Anthropic embedded in the Allianz deal — every Claude interaction logged, queryable and exportable for regulators — is the template that EU AI Act enforcement under Article 13 transparency and Article 26 deployer obligations will reward. German supervisory authorities, including BaFin for financial services and the BfDI for data protection, have signalled they want auditable AI decision trails by default. OpenAI’s enterprise tier offers comparable controls, but Anthropic has spent eighteen months making them the marketing message rather than the fine print. For regulated industries — insurance, banking, pharma, utilities — that framing is now a tangible procurement advantage in the DACH market, and one OpenAI’s code-red pivot will need to neutralise quickly.
A $950 billion valuation on $30 billion of annualised revenue prices Anthropic at roughly 32 times revenue — rich, but lower than OpenAI’s implied multiple at $852 billion on a smaller base. The signal to European AI startups is twofold. First, the enterprise-first strategy has been validated by both Ramp’s adoption data and the funding markets, which favours Mistral, Aleph Alpha and the Helsing-class model labs that picked vertical specialisation over consumer chat. Second, the fastest-growing Ramp categories are not frontier labs but inference platforms running open weights. That is a green light for a wave of European FinOps and routing startups, and a yellow light for any seed-stage company still pitching “we build on top of GPT-4” as a moat.
Sources 11 references
- [1]Anthropic beats OpenAI on business adoption — Ramp AI Index May 2026
- [2]Anthropic now has more business customers than OpenAI, according to Ramp data — TechCrunch
- [3]Anthropic finally beat OpenAI in business AI adoption — but 3 big threats could erase its lead — VentureBeat
- [4]Anthropic overtakes OpenAI in workplace AI adoption — Axios
- [5]Anthropic In Talks to Raise $30 Billion at $900 Billion Valuation — Bloomberg
- [6]Sources: Anthropic could raise a new $50B round at a valuation of $900B — TechCrunch
- [7]Code red: OpenAI rethinks its all-things-AI strategy — Calcalist
- [8]Anthropic adds Allianz to growing list of enterprise wins — TechCrunch
- [9]Allianz and Anthropic Forge Global Partnership to Advance Responsible AI in Insurance
- [10]The Pulse: Did capacity shortages turn Anthropic hostile to devs? — Pragmatic Engineer
- [11]Perspective: AI demand is inflated, and only Anthropic is being realistic — CNBC