Anthropic's annual recurring revenue reached $30 billion in May 2026, exceeding OpenAI's $24 billion ARR for the first time, per industry reporting summarized in the State of AI: May 2026 update. The crossover comes roughly 18 months after OpenAI was running 5× Anthropic's revenue. Both numbers are run-rate annualizations of the most recent reporting period; neither company has formally disclosed audited annual results.
OpenAI's ARR has roughly doubled in 18 months, while Anthropic's has grown roughly 6× over the same period, accelerating into the lead through enterprise sales, particularly the financial-services agent rollout from earlier this week. Revenue mix separates the two. OpenAI is more weighted toward consumer ChatGPT subscriptions and general API; Anthropic is more weighted toward enterprise contracts with longer sales cycles and stickier deployment. That enterprise mix is structurally less volatile and carries lower upside on a unit-economics basis. Crossing on top-line is one milestone. Gross margins, retention, and customer concentration will decide the comparison when both companies eventually disclose audited financials.
Bottom Line
If you're allocating compute budget across model providers, treat the ARR shift as a leading indicator of platform momentum and keep quality judgments for your own benchmarks. Make the technical decision on those benchmarks; use the financial decision (commercial terms, contract flexibility) to pick whichever vendor's commercial team is hungrier this quarter.