The enterprise front reveals OpenAI’s clearest vulnerability. Anthropic’s positioning is unambiguous: “We’re an enterprise AI company.”
The Market Share Reversal
This clarity translates into:
- Contract structures: Committed capacity discounting that enterprises prefer
- Product strategy: Claude Code and Cowork designed for production workflows
- Sales focus: Dedicated enterprise motion without consumer distraction
Meanwhile, OpenAI’s enterprise approach has been confused by consumer-first feature cadence.
The Numbers Comparison
| Metric | OpenAI | Anthropic |
|---|---|---|
| 2025 Cash Burn | ~$8.5B | ~$2.5B |
| 2028 Operating Loss | $74B | Break-even |
| Revenue Per User | ~$25/weekly | ~$211/monthly (8x) |
| Break-Even Timeline | 2029-30 | 2028 |
The underlying mechanic: Enterprise buyers care about reliability, compliance, and vendor focus. Every consumer feature OpenAI ships signals to enterprise procurement that this is a consumer company selling to businesses on the side.
This is part of a comprehensive analysis. Read the full analysis on The Business Engineer.









