OpenAI needs to reassure investors after a wave of high-profile departures

OpenAI executives have left one after another, and the IPO prospects with a trillion-dollar valuation have dimmed

As OpenAI prepares for a public listing that may be worth as high as US$1 trillion, its leadership is experiencing a chain of departures. Meanwhile, competitor Anthropic's annual recurring revenue just surpassed OpenAI.

Core Points

Denise Dresser (chief revenue officer), Brad Lightcap (head of special projects) and several executives have left OpenAI in recent weeks.

According to people familiar with the matter, the IPO plan originally scheduled to start this year may be postponed to 2027.

Annualized revenue has soared to $47 billion, compared with $40 billion for OpenAI.

OpenAI executives have left one after another

OpenAI has previously submitted a listing plan based on a valuation of US$852 billion. However, a series of subsequent executive departures complicated preparations for the listing.

Denise Dresser, who was appointed chief revenue officer in December last year, announced her departure this week. Dali Rajic, president and chief operating officer of Wiz, is expected to take over from her in the next few weeks.

Brad Lightcap will also leave the company. He previously served as chief operating officer and most recently was responsible for the special projects department.

The resignation list goes far beyond that. Chloe Bakral, who was in charge of ethics, and Kate Rouch, former director of communications and marketing, have also left OpenAI. Caitlin Kalinowski, who previously led the robotics technology team, joined Anthropic.

The technology sector was also affected. Kevin Weil, former product director and later vice president of the Scientific Discovery Platform, left in April. Johannes Heidecke, who was in charge of security systems, left OpenAI in July. Mia Glaese, vice president of research security, has regained responsibilities. Fidji Simo, head of the application business, stepped down from his full-time position last month after taking sick leave. According to people familiar with the matter, she is still involved in the daily operations of the company.

Anthropic overtakes OpenAI in IPO sprint

For OpenAI, competitive pressure is intensifying at the most inopportune moments. The company is preparing for a public offering that could value it at $1 trillion. According to relevant sources, the IPO originally scheduled for this year is now more likely to be postponed to 2027.

Anthropic has taken the lead in revenue. Its annualized revenue soared from US$9 billion at the end of 2025 to US$47 billion in May this year, an increase of nearly fivefold. OpenAI's revenue this month increased from US$24 billion to approximately US$40 billion. According to people familiar with the matter, part of the recent growth is related to the release of GPT-5.6 a few weeks ago.

Therefore, OpenAI's problem is not just how to continue to grow revenue. Before going public, the company must also restore confidence in its ability to retain core leadership and maintain organizational stability.

Investors will inevitably view these challenges in conjunction. A company valued at nearly $1 trillion must prove it has a team that can support growth in years to come. However, the current wave of executive departures comes at a time when Google and Anthropic are strengthening their models and expanding their business.

Security concerns in restructuring

Internal changes are not limited to commercial or operational functions. OpenAI also disbanded the team responsible for catastrophic risk assessments. Preparations related to biological, cyber and other significant risks have been decentralized to existing departments.

The decision was made after an OpenAI model breached another organization in internal cybersecurity testing. OpenAI has previously suspended Astra, a future model considered potentially too risky. The collective departure of security chiefs, including Bakral, Achiam and Heidecke, has exacerbated employee unrest.

Co-founder Greg Brockman is taking on more operational responsibilities. He described the departures as strategic adjustments. As the chief revenue officer left, he issued a statement saying:

"Denise led the revenue team at a critical stage of the company's development. The way we deploy this technology is changing rapidly, and Dali will transform what we have learned into repeatable processes to build complete systems that allow artificial intelligence to benefit individuals and businesses more broadly."

The trend in 2026 continues the situation in 2025. OpenAI has previously lost Human Resources Director Julia Villagra, Communications Director Hannah Wong, and several researchers who were poached by Meta.

OpenAI must convince investors that its governance and security teams are strong enough to support a historic IPO. Competition with Anthropic and Google has no room for loss. The postponement to 2027 provides OpenAI with a window to stabilize its team to better respond when investors have favored AI company IPOs. But the risk remains: a new wave of departures could further affect an already tight schedule.