OpenAI replaced its chief revenue officer after less than a year, pulling a cybersecurity executive from Wiz as the second top leader to leave in days

OpenAI's chief revenue officer lasted eight months. The replacement comes from a cybersecurity company, not enterprise SaaS. And the departure is the second leadership exit this week.

Denise Dresser, who joined OpenAI as chief revenue officer in December after serving as CEO of Slack and spending more than a decade as a Salesforce executive, is leaving to pursue other opportunities 1. Her successor is Dali Rajic, president and chief operating officer of Alphabet-owned cybersecurity firm Wiz 2.

The leadership churn lands as OpenAI prepares for a public offering. The company confidentially filed its IPO prospectus with the SEC in June 1. Its last funding round, in March, valued the company at $852 billion 1. OpenAI's annualized revenue reached roughly $25 billion as of February 2026 3. That valuation implies roughly 34 times current annualized revenue, a multiple that puts enormous weight on the revenue function now losing its second leader in a week.

The revenue leadership chain breaks in sequence

OpenAI's revenue operation has lost its architects one after another:

• April 2026: Brad Lightcap, OpenAI's chief operating officer, moves to a special projects role. Dresser takes over most of his responsibilities 4. Three other executives, including the leaders of the Sora video team and OpenAI for Science, depart the same month 4.
• July 2026: Fidji Simo, OpenAI's product and business chief, steps down to focus on recovery from a chronic illness 1.
• August 11, 2026: Lightcap announces his full departure after eight years. He had built the go-to-market team from roughly 50 people to more than 700 over an 18-month stretch through mid-2025 4.
• August 13, 2026: Dresser's exit is announced. Rajic is hired as her replacement 1.

Four months separate the moment Dresser absorbed Lightcap's enterprise responsibilities from her own departure. The person who scaled the go-to-market team to more than 700 people and the person hired to lead it have both walked out in the same week.

What the Rajic hire signals about where the money is

Rajic's career has been built in cybersecurity, not traditional SaaS. Before joining Wiz in February 2024, he spent more than four years at Zscaler as chief operating officer and president 5. Alphabet acquired Wiz for $32 billion in its largest acquisition ever 6.

Enterprise customers accounted for roughly 40% of OpenAI's business as of January 2026, and CFO Sarah Friar said she expected that share to approach 50% by year-end 1. Enterprise security contracts tend to be large, multi-year, and resistant to churn. They require deep trust in data handling and compliance, exactly the buyer relationships Rajic spent years cultivating at Zscaler and Wiz.

Dresser brought a different playbook from Salesforce and Slack, where her expertise was conventional enterprise cloud selling 1. The swap from a SaaS veteran to a security-first executive suggests OpenAI is betting that enterprise growth will come from contracts where the buyer is a chief information security officer, not just a procurement department. As AI models commoditize and API pricing drops, the competitive edge shifts from whose model is smarter to whose infrastructure buyers can trust with sensitive data.

For investors watching the IPO pipeline, the question is concrete. Can a new chief revenue officer with no OpenAI tenure hold a revenue trajectory that reached roughly $25 billion in annualized revenue 3 when the two leaders most responsible for building and inheriting that growth have both departed?