Anthropic is taking a hard line with enterprise customers: once a client exhausts the token quota purchased under their contract, discounts are immediately revoked. This strategy has opened the door for OpenAI, which is adopting a more flexible pricing approach.

Managers at three software companies that simultaneously purchase products from both AI service providers said that while Anthropic and its main rival OpenAI both offer discounts to large clients committing to million-dollar annual spending, Anthropic takes a distinctive approach: once customers hit their contracted usage cap, the discount simply terminates. These people said that customers who reach the cap must renegotiate a new contract or face higher standard pricing.

"The moment you hit your usage limit, Anthropic's sales team immediately calls and emails saying: 'We noticed you've used up your quota. If you finalize a new agreement today, you can avoid overage charges,'" one person said. "Otherwise, the excess portion is billed at full price."

Jeff Muscarella, Chief Innovation Officer at NPI Financial, which helps Fortune 500 companies negotiate software agreements, explained that Amazon, Microsoft, and Google typically allow customers to continue enjoying discounted pricing on usage beyond committed spending levels during the contract term. Software licensing consultants familiar with both service providers' clients said that on enterprise customer policies, OpenAI's approach is more lenient than Anthropic's.

A person close to OpenAI said that if a customer exhausts their committed spending under a discount agreement, OpenAI gives them a window covering the remainder of the current month plus an additional month for negotiating a new contract; only after the window closes does list pricing resume. An Anthropic spokesperson declined to comment.

The three procurement managers mentioned above revealed that Anthropic's model discount is approximately 15% off list price. In the 12 months ending June, more than 100 enterprises spent over $10 million annually with Anthropic, and over 1,000 enterprises spent more than $1 million annually. For these companies, the discount is quite significant. Anthropic's top customers include Meta, Cursor, and others, using its models to power internal operations or product services. Numerous other enterprises purchase Claude Code and Claude Cowork, and after Anthropic adjusted its pricing, both products saw price increases. (Anthropic disclosed to at least one business partner that the gross margin on existing model sales is approximately 75%.)

In recent months, OpenAI has been pulling out all the stops to catch up with Anthropic; this year, Anthropic's revenue growth has significantly outpaced OpenAI's. OpenAI has publicly announced that customers accessing new models through intermediaries like OpenRouter and Vercel can enjoy a 50% price reduction. When OpenAI released its latest model on Tuesday, CEO Sam Altman posted on social media: the new model halves the price per token, lowering the cost of completing individual tasks.

"Right now OpenAI is focusing on enterprise business and is being more aggressive than Anthropic on discounts," said Fredrik Filipsson, co-founder of software agreement negotiation service provider Redress Compliance. Improvements in OpenAI's model quality have also enhanced its appeal to large AI buyers 鈥?code review service provider CodeRabbit is one example. CodeRabbit CEO Harjot Gill said that six months ago, CodeRabbit's service models were primarily supplied by Anthropic; now, OpenAI, with its more aggressive pricing strategy, has become its primary supplier. He declined to disclose specific discount figures but said the three-year-old company spends tens of millions of dollars annually on AI.

OpenAI's sales team is in a sensitive period of adjustment: the executive responsible for enterprise business development suddenly departed in August, and the enterprise business division is undergoing large-scale restructuring. An employee revealed that OpenAI is merging pre-sale and post-sale contract roles 鈥?positions that were previously separate are being combined: personnel who conduct product demonstrations for clients will also serve as customer success managers after deals are signed. Gill, as well as a manager at another software vendor negotiating contracts with AI labs, mentioned that as competition intensifies, both OpenAI and Anthropic have begun adding clauses to discount agreements requiring major customers to direct most of their AI budgets to their respective platforms 鈥?known in the industry as "share of wallet" clauses.