OpenAI is losing its second executive this week

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Denise Dresser, who joined OpenAI as chief revenue officer in December 2025 after serving as Slack CEO, is departing in the coming weeks. Her replacement is Dali Rajic, current president and COO of Wiz — the cloud security company Microsoft attempted to acquire for $23B. Dresser had also taken on some of Brad Lightcap's responsibilities when he moved from COO to a special projects role, making the CRO seat operationally heavier than typical. The executive turnover is accelerating: Lightcap announced his own departure two days earlier, and former AGI division chief Fidji Simo and former CMO Kate Rouch also recently stepped down. That makes four C-suite exits in a short window. The timing is notable: OpenAI submitted a confidential S-1 to the SEC in June for a planned IPO. Executive instability at this stage typically raises concerns for institutional investors, though OpenAI's revenue momentum may offset those concerns. Bringing in Rajic from Wiz signals a deliberate push to strengthen enterprise security credentials alongside revenue operations — particularly relevant given OpenAI's ongoing fallout from the Hugging Face agent breach.