In the thrilling world of enterprise AI spending, where the only thing more volatile than model benchmarks is market share, new data from Ramp suggests that OpenAI is staging a comeback against Anthropic. But let's not pop the champagne just yet - this is like a tennis match where the lead changes faster than a startup pivots.

Ramp, the corporate credit card and expense management company, has released data covering over 70,000 U.S. businesses that spend billions via its products. The data shows that Anthropic, which overtook OpenAI in May with 41% market share to OpenAI's 39%, has since extended its lead to nearly 44% versus OpenAI's nearly 40% as of July. But here's the twist: in Q3 to date, OpenAI is actually growing faster among Ramp's paying business users. With a month left in the quarter - which, in AI terms, is roughly 30 years - the trend could easily flip again.

Ramp economist Ara Kharazian attributes OpenAI's resurgence to the appeal of 'GPT-5.6 Sol,' which he claims is 'really good, increasingly the choice for developers.' Meanwhile, he notes that Anthropic's 'Fable 5' has 'disappointed both in adoption and real-world application given price + data retention requirements imposed by regulators.' Anthropic's Fable tier is indeed pricey, but it's also designed for more targeted use cases than your average chatbot. Still, the company did raise eyebrows when it warned users that it must retain their data for 30 days - a policy that surely didn't help its popularity.

Before you start declaring winners, remember: this data only covers Ramp customers, excluding large enterprises that use tools from providers like American Express. But it's enough to show that the enterprise AI market is anything but settled. Businesses are happily flitting between labs as new models drop, which should give investors in both companies a moment of existential dread about how 'sticky' enterprise AI spending really is.

Meanwhile, the overall pie is growing: the percentage of Ramp customers paying for AI has climbed steadily, topping 50% in March and reaching nearly 56% by July. So both companies can bicker over slices while the whole cake expands. For now, the race continues, and the only certainty is that nothing is certain - unless you're the AI itself, which probably already knows how this ends.