OpenAI claws back business market share from Anthropic as both vie for enterprise loyalty

With neither OpenAI nor Anthropic yet public enough to share audited financials, observers have turned to alternative signals to gauge their commercial progress. Fresh insights from Ramp, a spend-management platform serving over 70,000 American businesses, reveal that the competitive terrain is shifting—OpenAI is mounting a comeback among enterprise buyers after ceding the top spot to its rival.

The shifting lead#

For much of this year, Anthropic held the upper hand in the Ramp dataset. The company claimed roughly 41% of AI spending share in May, compared to OpenAI's 39%, marking a notable reversal from the ChatGPT maker's earlier dominance. By July, that gap had widened further: Anthropic reached nearly 44% while OpenAI settled at close to 40%.

Yet the trajectory is now turning. According to Ramp's analysis, OpenAI is expanding faster than Anthropic among this cohort in the third quarter—though with a month of trading still to come, the picture remains fluid.

A volatile and expanding market#

The data paints a portrait of a market where corporate buyers hop between vendors based on recent model releases rather than showing deep loyalty to any single provider. This fluidity—driven by labs continuously shipping new capabilities—raises questions about the durability of enterprise AI contracts. Both companies stand to gain, however, since the total addressable market continues to grow: the share of Ramp's customers paying for AI services climbed past 50% in March and had reached nearly 56% by July.

A note on scope and recent friction#

Ramp's sample skews toward Silicon Valley and the tech sector, so it does not represent the entire enterprise landscape; major corporations with their own spend-management infrastructure are absent from the tally. Nonetheless, it offers a revealing window into how mid-market and tech-forward firms allocate their AI budgets.

Recent product moves by Anthropic—particularly its Fable tier's 30-day data retention requirement—have drawn criticism and may have dampened adoption. OpenAI's latest models, by contrast, have captured developer interest and fueled its renewed growth.