OpenAI Must Reassure Investors After a Wave of High-Profile Exits

OpenAI is losing its leaders in cascade as it approaches a public offering that could value the company at $1 trillion. The hemorrhage occurs as its rival Anthropic has just surpassed OpenAI in annualized revenues.

Senior executives leave OpenAI in series

OpenAI had already filed a public offering project based on a valuation of $852 billion. Since then, several departures have complicated the preparation of the operation.

Denise Dresser, appointed revenue chief in December, announced her departure this week. Dali Rajic, president and chief operating officer of Wiz, is expected to succeed her in the coming weeks.

Brad Lightcap is also leaving the company. Former chief operating officer, he most recently held the position of head of special projects.

The list doesn’t stop there. Chloe Bakalar, in charge of ethics issues, and Kate Rouch, former director of communication and marketing, have also left OpenAI. Caitlin Kalinowski, who led work on robotics, has joined Anthropic.

The hemorrhage also affects the technical functions. Kevin Weil, former product director turned vice president of the scientific discovery platform, left in April. Johannes Heidecke, who led security systems, left OpenAI in July. Mia Glaese, vice president of research and security, has resumed her responsibilities. 

Fidji Simo, head of applications, stepped down from her full-time position last month after medical leave. According to someone close to the file, she is nevertheless still involved in the company’s daily activities.

Anthropic surpasses OpenAI in full sprint towards the IPO

Competitive pressure is increasing at the worst time for OpenAI. The company is preparing a public offering that could value it at $1 trillion, according to sources cited by Cryptopolitan. The IPO, initially planned for this year, is now more likely in 2027.

On the revenue front, Anthropic has taken the lead. Its annualized revenues have quintupled, rising from $9 billion at the end of 2025 to $47 billion in May. OpenAI, for its part, has seen its revenues increase from $24 billion to about $40 billion this month. 

Part of this recent increase is reportedly linked to the launch of GPT-5.6, unveiled a few weeks earlier, according to someone close to the file.

For OpenAI, the problem is therefore not only to continue growing its revenues. Before going public, the company will also have to reassure about its ability to retain its leaders and maintain a stable organization.

Investors will inevitably view these two issues together. A company valued around $1 trillion must be able to demonstrate that it has a team capable of sustaining its growth over several years. However, the current departures come precisely at a time when Google and Anthropic are strengthening their models and their presence with companies.

Security in the background during restructuring

Internal movements do not only concern commercial or operational functions.

OpenAI also dissolved its team dedicated to catastrophic risk assessment. Work related to preparation for biological, cybernetic, and other major risks has been distributed among existing departments.

This decision follows the revelation that one of OpenAI’s models had hacked another organization during internal cybersecurity tests. OpenAI had already halted Astra, a future model deemed potentially too dangerous. The collective departure of security managers, including Bakalar, Achiam, and Heidecke, worsens the sense of uncertainty among employees.

Greg Brockman, co-founder, is taking more operational control. He described these departures as a strategic realignment. In a post published on the occasion of the CRO’s departure, he said:

Denise led our revenue organization during a formative period for the company. The way we deploy this technology is rapidly changing, and Dali will turn what we have learned into repeatable execution as we build the full system to make AI broadly useful to people and businesses.

The 2026 pattern extends a 2025 trend. OpenAI had already lost its HR director Julia Villagra, its communication director Hannah Wong, and several researchers recruited by Meta.

OpenAI will have to convince investors that its governance and security teams are strong enough to support a historic IPO. Competition with Anthropic and Google leaves little room for error. The postponement to 2027 gives OpenAI a window to stabilize its workforce before facing investors already favoring AI IPOs. The risk remains that a new wave of departures will further weaken this already tight schedule.