Anthropic now has more verified business customers than OpenAI — 34.4% to 32.3% — according to Ramp’s May 2026 AI Index. It’s the first time anyone has knocked OpenAI off the enterprise top spot since ChatGPT launched. And Anthropic got there in just 12 months, climbing from 9%.
🔍 THE BOTTOM LINE
The enterprise AI market has a new #1 — and Anthropic’s “win technical users first, broaden later” strategy just delivered results faster than anyone predicted.
How We Got Here
Ramp’s AI Index tracks AI spending across more than 50,000 companies on its expense management platform. It’s not a perfect proxy for the entire market — Ramp’s client base skews toward startups and mid-market companies — but the sample is large enough that the trend is hard to dismiss.
The numbers tell a clear story:
| Metric | May 2025 | May 2026 | Change |
|---|---|---|---|
| Anthropic adoption | 9% | 34.4% | +25.4pp |
| OpenAI adoption | ~33.3% | 32.3% | -1pp |
| Any AI adoption | baseline | +9pp | +9pp |
Anthropic didn’t just grow — it grew 26 percentage points while the overall AI market expanded only 9 points. That means Anthropic pulled share directly from competitors, primarily OpenAI.
What is the Ramp AI Index? The Ramp AI Index is a monthly benchmark that tracks which AI services businesses are actually paying for, based on expense data from more than 50,000 companies using Ramp’s corporate cards and spend management platform. It measures verified commercial adoption, not just hype or signups.
The Strategy That Worked
Ramp economist Ara Kharazian laid it out plainly: “What Anthropic did worked really well — start with a very technical customer base, focus on their needs, really succeed in execution, and then start broadening out through tools like Cowork.”
This is worth unpacking:
- Technical users first — Claude earned credibility with developers, researchers, and engineers who evaluate models on benchmarks and capability, not marketing
- Execution focus — Anthropic shipped reliable, high-quality model upgrades without the chaos that’s plagued OpenAI’s product launches
- Broadening with Cowork — Anthropic’s workplace AI tool brought Claude to non-technical users who previously only knew ChatGPT
Meanwhile, OpenAI has been fighting on multiple fronts: enterprise sales, consumer products, the GPT Store, and an increasingly public governance crisis. Each distraction was an opening Anthropic exploited.
The OpenRouter Confirmation
Ramp’s data isn’t the only signal. On OpenRouter’s leaderboard — which tracks API usage across a different customer base — Anthropic has ranked above OpenAI since December 2025. Five consecutive months of leading on a platform that measures actual model usage, not just expense reports.
Two independent datasets, same conclusion: Anthropic is winning the enterprise ground game.
But Will It Last?
Kharazian is skeptical about Anthropic’s staying power, and he has reasons:
- OpenAI’s brand advantage — ChatGPT is still the default AI product for consumers and many businesses. Brand recognition doesn’t evaporate overnight
- Distribution reach — OpenAI’s Microsoft partnership gives it enterprise channels that Anthropic can’t match through Amazon alone
- Anthropic is still burning cash — climbing from 9% to 34% required enormous investment in inference, model development, and enterprise sales
The counterargument: technical quality compounds. Every business that switches to Claude and gets better results is a business that’s hard to win back.
What This Means for NZ Businesses
For New Zealand organisations evaluating AI tools, this shift matters:
- It’s no longer a one-horse race — The “just use ChatGPT” default is no longer the safe enterprise choice. Anthropic is a credible alternative with growing market validation
- Negotiating leverage — More competition between providers means better pricing and terms for NZ businesses, especially mid-market companies
- Evaluating on substance — Anthropic’s rise was built on technical quality over hype. NZ organisations should apply the same standard: benchmark models against actual use cases, not brand recognition
The AI tooling landscape is shifting fast. The provider you chose six months ago may not be the best fit today.
❓ Frequently Asked Questions
Q: Does this mean ChatGPT is dying? No. OpenAI still has enormous consumer reach and a massive user base. This data measures business spending, not total users. ChatGPT remains the most recognised AI product globally. What’s changed is that businesses now have a viable #1 alternative.
Q: How did Anthropic grow so fast? Three factors: Claude’s technical quality earned credibility with hard-to-please technical users; consistent execution built trust (no chaotic product launches); and Cowork extended Claude’s reach beyond developers to general business users. The 9% to 34.4% climb in 12 months is one of the fastest enterprise adoption curves in tech history.
Q: Should NZ businesses switch from OpenAI to Anthropic? Not automatically — but it’s worth evaluating. Run side-by-side benchmarks on your actual use cases. Anthropic’s strength in coding, analysis, and long-context tasks may suit your needs better than ChatGPT’s general-purpose approach. The market shift means you have real choice now.
🔍 THE BOTTOM LINE
Anthropic didn’t just catch OpenAI in the enterprise — it passed it. A 26-point climb in 12 months through technical credibility and execution focus. The question isn’t whether Anthropic can compete; it’s whether OpenAI can respond fast enough to stop the bleeding.
