Anthropic has overtaken OpenAI in paid business adoption for the first time, with 34.4% of companies in Ramp's May 2026 AI Index paying for Anthropic services versus 32.3% for OpenAI. The fintech's index draws on expense data from more than 50,000 client companies, making it one of the larger commercial signals available on which AI lab is actually closing enterprise deals.
The shift is sharper than the headline gap suggests. In May 2025, just 9% of businesses in the Ramp sample were paying Anthropic. That share has climbed 26 points over the following 12 months. OpenAI's share fell 1% across the same window, while the overall share of businesses paying for any AI product grew 9%.
Ramp economist Ara Kharazian told TechCrunch that Anthropic's lead is concentrated where it built its early reputation. "Anthropic has already been in the lead amongst the high adoption groups like finance, tech, professional services," Kharazian said. "It's across the other firms where OpenAI still has a lead, but that has been shrinking over the past couple of months."
Key facts
- 0134.4% of businesses in Ramp's sample pay for Anthropic services, vs 32.3% for OpenAI — the first time Anthropic has held the top spot.
- 02Ramp's AI Index draws on expense data from more than 50,000 companies.
- 03Anthropic's share rose 26 points over the past 12 months, from 9% in May 2025.
- 04OpenAI's share fell 1% over the same period, even as overall business AI adoption grew 9%.
- 05OpenRouter's separate leaderboard last placed OpenAI above Anthropic in December 2025.
The Ramp number is not the whole market — it captures only companies that use Ramp for expense management, which skews toward US-based, mid-market, and venture-backed firms. But the directional trend lines up with other data points. OpenRouter's leaderboard, which measures developer API consumption rather than corporate card spend, last showed OpenAI ahead of Anthropic in December 2025.
“Just 9% of businesses paid for Anthropic products in May 2025. Twelve months later that figure has climbed 26 points, while OpenAI's share has slipped 1%.”— Jaeden Schafer
Anthropic's enterprise traction has tracked closely with the rise of Claude as a developer favorite, particularly for coding. The company has leaned into that base with tools like Cowork, an agentic workflow product that targets professional services teams. Kharazian credits the sequencing: technical customers first, then expansion outward.
"What Anthropic did worked really well," Kharazian said, "which was — start with a very technical customer base, focus on their needs, really succeed in execution and then start broadening out through tools like Cowork."
For OpenAI, the Ramp data complicates the narrative that ChatGPT's consumer dominance translates automatically into enterprise lock-in. OpenAI still leads in raw user count by a wide margin and in many non-technical verticals tracked by Ramp. But the company's enterprise share has stopped growing in this sample even as the overall pie expanded, which means OpenAI is losing relative position in real time.
The two labs have taken visibly different go-to-market paths. OpenAI moved consumer-first with ChatGPT, then layered enterprise products on top. Anthropic largely skipped a consumer flagship and built directly into developer tooling, code editors, and back-office workflows. The Ramp data suggests the second route is converting to paid corporate seats faster, at least in the segments Ramp serves.
Kharazian is not convinced the lead will hold. In a blog post accompanying the index, he flagged reasons the gap could compress quickly, including OpenAI's deep installed base outside Ramp's high-adoption verticals and the speed at which model preferences shift inside large buyers. A 2-point spread on a single-source sample is not a structural moat.
Anthropic's commercial position is now meaningfully ahead of where the consensus had it a year ago. The company has converted a technical-first wedge into a measurable lead on paid enterprise share in one of the better commercial datasets available, and it has done so while the broader market for paid AI grew 9%. For OpenAI, the read-through is that the enterprise race is no longer theirs to lose — it's a contest, and on this particular scoreboard, they are now second.
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