OpenAI’s “No. 2 executive” resigns, with another major leader lost again ahead of the IPO

OpenAI executives have undergone another round of shake-ups. At a critical point as the company prepares for an IPO, Fidji Simo, a key aide to CEO Sam Altman and seen as the company’s “No. 2,” announced her departure, leaving the highly watched global AI company facing a new management gap.

According to The Wall Street Journal, Simo sent an internal email to employees on Thursday, saying that due to the ongoing deterioration of her neuroimmune disease and a recovery timeline far beyond expectations, she will no longer return to a full-time role. Instead, she will continue to stay connected with the company as a part-time advisor. In the letter, Simo wrote: “This is one of the hardest decisions of my career, but my body leaves me with no choice.”

The change comes at OpenAI’s most sensitive time window—while the company is actively preparing for an IPO that could be completed as soon as this year, and at the same time is locked in a fierce contest in the enterprise customer market with its competitor, Anthropic. Simo’s departure means Altman will have to find again the key person capable of coordinating both product and business, further increasing uncertainty around the IPO outlook.

Core responsibilities are split into three, and power reshuffles take effect immediately

According to Simo’s internal message, her existing product and business responsibilities will be divided among three executives: President Greg Brockman, Chief Financial Officer Sarah Friar, and Chief Strategy Officer Jason Kwon. Denise Dresser, Chief Revenue Officer, will also have her reporting line adjusted, switching to report directly to Brockman.

Simo joined OpenAI last August, personally selected by Altman, to lead the company’s product and business division and take over a large portion of management functions from Altman, including direct oversight of the CFO and the Chief Revenue Officer. She was widely expected to take on a more important role after the company went public, and even seen as a potential core figure for the company’s day-to-day operations.

In April this year, Simo first announced she would take leave due to the worsening of her neuroimmune disease, which had already raised doubts among both investors and employees about the company’s future direction. Her formal departure turns that uncertainty into a more concrete reality.

ChatGPT growth faces pressure, and the gap with Anthropic widens

During Simo’s tenure, OpenAI’s commercialization efforts were a mix of progress and setbacks. She led the push to commercialize ChatGPT, including introducing ad formats and new features such as health advice, and began building a coding-centric “super app”—a product that was officially released on Thursday.

However, ChatGPT user growth stalled toward the end of last year, preventing the company from meeting its internal revenue targets. Meanwhile, in the enterprise customer market, OpenAI fell behind Anthropic, forcing it to rapidly shift its strategic focus toward enterprise AI programming tools.

The changes in the competitive landscape are especially worth watching. Recently, Anthropic’s valuation first surpassed OpenAI, becoming the preferred platform for enterprises buying AI tools. Both companies are currently mired in a price war; this war of attrition could further delay the timeline for each side to achieve profitability, and create additional pressure on their respective IPO plans.

Executive shake-ups ahead of the IPO weigh on investor confidence

Simo’s departure is the latest example in a series of recent executive changes at OpenAI. For a company racing toward an IPO, the stability of top management is one of the dimensions that institutional investors have long focused on.

Citing people familiar with the matter, The Wall Street Journal reported that at the Allen & Co. annual summit held in Sun Valley, Idaho this week, OpenAI executives discussed with the outside world the specific strategies the company will use to compete in the enterprise customer market against Anthropic, indicating that the company is actively sending confidence in its strategy to the market.

In a post on the X platform published on Thursday, Simo admitted that she had previously failed multiple times to make the decision to rest and recover in a timely manner. “The truth is, I’m only making this decision now because I failed many times before,” she said. To some extent, her statement reflects the personal costs that executives bear under high-pressure conditions.

For OpenAI, the challenge now is to maintain the pace of the IPO while reorganizing management, and to hold its ground in competition with Anthropic.

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