Anthropic reached a $965 billion valuation in May 2026 following its Series H funding round. This figure exceeds the $380 billion valuation from its February 2026 Series G round. While Anthropic attracts investors, OpenAI faces a $14 billion loss projection for 2026. Anthropic’s annualized revenue climbed from $1 billion in January 2025 to $9 billion by the end of 2025, hit $14 billion in February 2026, and reached $65 billion by July 2026 as enterprise demand for AI models accelerated. OpenAI doubled its revenue to $40 billion from its $20 billion level at the end of 2025, but Anthropic’s growth rate remains higher. Google committed up to $40 billion to Anthropic in a strategic investment in April 2026. Anthropic is already larger than several pure-play software companies like Salesforce and Adobe based on its annual revenue run-rate.
The exodus of leadership from OpenAI complicates its competitive standing. Ilya Sutskever left to found Safe Superintelligence, and Mira Murati started Thinking Machines Lab. Co-founders John Schulman and Jan Leike moved to Anthropic. Bob McGrew and Barret Zoph also departed. By the end of 2025, only Sam Altman and Wojciech Zaremba remained as full-time co-founders. This talent shift aligns with the rapid growth of Anthropic. The seven original co-founders remain with the company, and they each hold approximately 1.8% of the shares.
The enterprise shift
Enterprise users favor Claude over ChatGPT for technical workloads. Anthropic holds 40% of the enterprise AI market share as of December 2025, while OpenAI holds 27%. In the coding sector, Claude commands 54% of the market compared to the 21% held by ChatGPT. Claude Code alone generated $2.5 billion in annualized revenue by February 2026. This product functions as a colleague rather than a simple tool because it writes code, creates files, runs tests, and submits changes without human intervention. Boris Cherny, the head of Claude Code, says his engineering team generates 70% to 90% of its code with the tool.
You should note that enterprise logic differs from consumer hype. Anthropic’s share of corporate AI expenditure grew from 10% in early 2025 to 65% by February 2026. Claude Code’s success reveals that businesses invest in tools that integrate into workflows and replace specific job functions. Anthropic also released Claude Cowork in January 2026, which allows the AI to manipulate files in user-selected folders on macOS. This feature works for all paid plans, including Pro, Max, Team, and Enterprise. While ChatGPT has 1.2 billion weekly active users as of October 2026, its revenue comes mostly from individuals. Anthropic generates 80% of its revenue from enterprise customers and API calls. Can Anthropic maintain this momentum once the coding niche stabilizes?
Comparing subscription models
Pricing structures define the competition between these two companies. OpenAI’s heavy reliance on consumer subscriptions makes it vulnerable to churn when new models arrive. Anthropic generates the majority of its money from businesses that sign long-term contracts. These contracts involve high switching costs and high renewal rates. Anthropic’s enterprise pricing differs from its consumer tiers because it uses a combination of seat fees and usage-based billing.
| Feature | Claude Enterprise | ChatGPT Business (Teams) |
|---|---|---|
| Minimum Seats | 20 (Self-serve) / 50 (Sales) | 2 |
| Pricing Model | Seat fee + API usage | Per-user subscription |
| Security | SCIM, Audit logs, US-only | SOC 2, SAML SSO, MFA |
| Data Privacy | No training on business data | No training on business data |
Anthropic’s Enterprise plan requires a minimum of 20 seats for self-serve customers or 50 seats for sales-assisted deployments. The seat fee is $20 per user per month when billed annually. Users pay for AI usage separately at standard API rates. ChatGPT Business offers Standard seats for $20 per user monthly when billed annually or $25 monthly. Premium seats cost $100 annually or $125 monthly.
Anthropic scales its pricing based on the complexity of the task. Users can utilize the Batch API for a 50% discount on asynchronous workloads. Prompt caching also reduces repeated input costs by up to 90%. In contrast, OpenAI’s Business edition offers a shared workspace for teams of 2 to 200 employees. OpenAI’s Enterprise edition uses custom pricing and adds features like 24/7 priority support and SLAs. Anthropic’s ability to monetize output through tokens allows it to capture more value from heavy users than seat-based models.
