OpenAI’s “second-in-command” resigns, losing another major figure on the eve of its IPO

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The OpenAI executive team is once again undergoing changes. At a critical juncture as the company prepares for its IPO, Sam Altman's trusted assistant and widely considered "second-in-command," Fidji Simo, announced her departure, leaving the world’s most high-profile AI company facing a new management vacancy.

According to The Wall Street Journal, Simo sent an internal letter to employees on Thursday, announcing that due to a worsening neuro-immune disease and a recovery period that far exceeds expectations, she will not return to her full-time position, but will instead remain in contact with the company as a part-time advisor. Simo wrote in the letter: "This is one of the hardest decisions of my career, but my body has left me no choice."

This change comes at OpenAI’s most sensitive period—as the company actively prepares for a potential IPO as soon as this year, while fiercely competing with rival Anthropic for enterprise clients. Simo’s departure means Altman must find a new core candidate to helm product and business, further increasing uncertainty around the IPO prospects.

Core responsibilities split three ways; power restructuring takes immediate effect

According to Simo’s internal letter, her original product and business duties will be shared among three executives: President Greg Brockman, CFO Sarah Friar, and Chief Strategy Officer Jason Kwon. Chief Revenue Officer Denise Dresser’s reporting line will also be adjusted, now reporting to Brockman.

Simo joined OpenAI last August, handpicked by Altman to lead the company’s product and business departments, taking over many management functions from Altman including direct oversight of the CFO and CRO. She was widely expected to play a bigger role post-IPO, even being seen as a potential core operator of the company.

In April, Simo first announced a leave of absence due to the worsening of her neuro-immune condition, raising concerns among investors and employees about the company's future direction. This formal resignation brings those uncertainties into reality.

ChatGPT’s growth under pressure, widening gap with Anthropic

During Simo’s tenure, the commercialization of OpenAI was mixed. She spearheaded commercial initiatives for ChatGPT, including introducing ad models and health advice features, and worked to build a programming-based "super app"—which was officially launched on Thursday.

However, ChatGPT’s user growth stalled late last year, causing the company to miss internal revenue targets. Meanwhile, OpenAI lagged behind Anthropic in enterprise client markets, forcing a rapid strategic shift toward AI programming tools for businesses.

Changes in the competitive landscape are particularly noteworthy. Anthropic recently overtook OpenAI in valuation for the first time, becoming the platform of choice for enterprise AI tool procurement. Both companies are embroiled in a price war, which could further delay profitability for both and put pressure on their respective IPO plans.

Executive turmoil on the eve of IPO, investor confidence under strain

Simo’s departure is the latest in a series of recent executive changes at OpenAI. For a company sprinting toward IPO, the stability of the core management team is always a key concern for institutional investors.

According to The Wall Street Journal, quoting sources, at this week’s Allen & Co. annual summit in Sun Valley, Idaho, OpenAI executives discussed specific strategies for competing with Anthropic in the enterprise client market, showing the company is actively projecting strategic confidence to the market.

In a post on X on Thursday, Simo admitted that she had previously failed to make timely decisions to rest: "The truth is, I am only making this decision now because I failed many times before." This statement reflects to some extent the personal cost executives bear in high-pressure environments.

For OpenAI, the current challenge is to maintain the IPO process and steady its position against Anthropic amid management restructuring.

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