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OpenAI lost its chief operating officer and its chief revenue officer within 48 hours this week, capping a month in which the company also removed the independent reporting line for its safety organization and saw its head ethicist, its head of safety systems and its chief futurist all walk out the door.

The company is preparing for what would be the largest technology listing in history. Investors assessing that offering now have a leadership continuity question that the prospectus will have to answer.

The August exits

Brad Lightcap announced his departure on August 11. He had joined OpenAI in 2018, served four years as CFO, became COO in 2022, and was moved to a special projects role earlier this year. He told staff he was leaving to start something new and would stay on a few weeks.

Two days later, on August 13, Chief Revenue Officer Denise Dresser announced she was leaving after roughly eight months. Dresser, formerly CEO of Slack and a longtime Salesforce executive, had joined in December 2025 to build the enterprise business. In April she absorbed much of Lightcap's remit when he moved to special projects, and she had become the company's public face for enterprise AI - presenting at its enterprise adoption event and interviewing Sam Altman on stage there.

OpenAI said Dresser is leaving to pursue other opportunities, and immediately named Dali Rajic, previously president and COO of cloud security firm Wiz, as her successor. Wiz was acq......................

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