OpenAI revenue chief Denise Dresser leaves, second high-profile executive exit this week

OpenAI is losing another top executive at a pivotal moment for the AI company.

Chief Revenue Officer Denise Dresser is leaving OpenAI less than a year after joining the ChatGPT maker, marking the second high-profile executive departure at the company in just days. Her exit comes as OpenAI scales its enterprise business, spends heavily on computing infrastructure, and prepares for what could become one of the largest technology IPOs ever.

OpenAI said Thursday that Dresser is leaving “to pursue other opportunities.” The company has named Dali Rajic, the former president and chief operating officer of cybersecurity company Wiz, as her replacement.

“Denise Dresser helped make that possible. During a formative period for both OpenAI and the enterprise AI market, she built the team, strengthened relationships with major customers, and established the commercial foundation that has brought our business to this point. Denise will leave OpenAI to pursue other opportunities following a transition period, during which she will work closely with the business team to support our customers. We’re deeply grateful for her leadership and everything she’s done for OpenAI,” the maker of ChatGPT said in a statement.

The timing puts fresh attention on OpenAI’s senior ranks. Longtime executive Brad Lightcap announced Tuesday on X that he was leaving the company to “start something new.”

Two major departures in the same week would draw attention at almost any company. At OpenAI, where investors are watching its growth, spending, corporate structure, and path to the public markets, the exits carry extra weight.

From Slack CEO to OpenAI revenue chief

Dresser joined OpenAI in December after more than a decade at Salesforce, bringing years of experience selling enterprise software to large organizations.

She became CEO of Slack in 2023, taking charge of the workplace messaging company several years after Salesforce acquired it for more than $27 billion. Her move to OpenAI came as the AI company was pushing deeper into corporate accounts and trying to turn enormous demand for ChatGPT into a durable enterprise business.

That made Dresser an important hire.

OpenAI has evolved far beyond its roots as an AI research lab. It now operates one of the industry’s largest consumer subscription businesses, sells AI services to companies and developers, and faces enormous infrastructure costs tied to training and running increasingly capable models.

Revenue leadership sits at the center of that equation. OpenAI needs to convert its huge user base and corporate interest into enough recurring revenue to support its spending ambitions and satisfy investors expecting continued growth.

Dresser’s departure less than a year into the role means Rajic will inherit that job at a particularly sensitive time.

Rajic brings his own enterprise credentials. Before joining OpenAI, he served as president and COO of Wiz, the cloud security company that became one of the most closely watched enterprise software startups of the past several years.

His appointment suggests OpenAI is looking for an operator familiar with scaling enterprise sales at high speed, rather than changing course on its push into corporate AI.

Two OpenAI executive departures in days

Dresser’s exit stands out more when viewed alongside Lightcap’s departure.

Lightcap had been one of OpenAI’s longest-serving senior executives and played a major role in the company’s commercial growth and international expansion. He announced his departure Tuesday in a post on X, saying he plans to “start something new.”

There is no indication that the two departures are connected. Yet losing two recognizable senior executives within days creates an unusual leadership moment for a company approaching what may be its biggest transition yet.

An IPO would expose OpenAI to a very different level of scrutiny. Public investors would have far greater visibility into revenue growth, operating expenses, infrastructure commitments, customer concentration, margins, and the economics behind serving hundreds of millions of AI users.

That makes stability across OpenAI’s leadership team increasingly significant.

The company is trying to balance several major priorities at once: maintaining its lead in consumer AI, winning enterprise customers, competing with deep-pocketed rivals, securing vast computing capacity, and building a financial model capable of supporting its ambitions.

Dresser’s replacement now becomes one of the executives responsible for making those numbers work.

Rajic arrives with experience scaling a high-growth enterprise technology company. Yet OpenAI presents a challenge on another scale. Few companies have ever had to commercialize a technology attracting this much demand while simultaneously funding the infrastructure required to serve it.

For OpenAI, Dresser’s departure may prove to be a straightforward leadership transition. Coming just two days after Lightcap announced his own exit, though, it is certain to get more attention than an ordinary changing of the guard.