OpenAI's chief revenue officer, Denise Dresser, has been in the role for just six months, but she's already aggressively pushing the company's enterprise expansion. She's taken over the partnerships and ad negotiations previously handled by former COO Brad Lightcap. Meanwhile, rival Anthropic closed a new funding round on Thursday at a $900 billion valuation — for the first time surpassing OpenAI's current $730 billion valuation. The battle for enterprise AI customers is heating up.
To speed up its enterprise push, Dresser is assembling a formidable 'Salesforce and Slack squad' inside OpenAI. Former Slack chief customer officer Peter Doolan joined in April as global head of AI transformation, and ex-ServiceNow CMO (and former Salesforce SVP) Colin Fleming came on board this month as CMO for commercial business. The team also includes at least six other veteran sales and channel execs, including Colleen Kapase, a former Google channel VP. Under Dresser's leadership, OpenAI has smoothed out the chaotic co-selling process with Databricks and landed flagship clients like Hertz and KPMG this year.
The rivalry isn't just about valuation — it's a clash of business models and infrastructure. OpenAI aims to boost enterprise revenue from 40% to 50% of total by the end of 2026. Anthropic, by contrast, already gets over 80% of its revenue from enterprise customers, earning fierce loyalty by optimizing for database connections and long-context parsing. In an internal memo, Dresser went on the offensive, calling Anthropic's practice of limiting compute purchases a 'strategic mistake' that leads to frequent rate limits and reliability issues. She also accused Anthropic of building its marketing narrative 'on fear and restrictions.'