OpenAI has held discussions with Citigroup and JPMorgan Chase about joining Goldman Sachs and Morgan Stanley on its IPO underwriting team, a signal that one of the most anticipated public offerings in tech history is now a live operation with serious infrastructure behind it.
A week after filing a confidential S-1 with the SEC, OpenAI is now reportedly in conversations to expand its bank syndicate. Bloomberg reported on May 29 that Citigroup and JPMorgan Chase have been in discussions about co-underwriting the offering alongside the two banks already engaged. The talks are ongoing and may not result in either institution formally joining the lineup, but the conversations alone tell you something: this deal has moved out of the planning phase and into execution mode.
Bringing four bulge-bracket banks into an IPO syndicate is not a decorative choice. It is a logistical one. Goldman Sachs and Morgan Stanley bring the prestige and the institutional relationships that anchor any major offering. Citigroup and JPMorgan bring distribution muscle, particularly among the large asset managers, sovereign wealth funds, and retail brokerage channels that a trillion-dollar deal would need to absorb. The wider the syndicate, the broader the order book can theoretically be built, and at the valuation OpenAI is targeting, that breadth matters enormously.
OpenAI filed its confidential S-1 with the Securities and Exchange Commission on May 22, setting the stage for a September 2026 public listing. Confidential filing is standard for high-profile offerings: it lets the company work through SEC comments and disclosure requirements without the full weight of public scrutiny until it chooses to go live. At this point, the September window is the working target, though IPO timelines have a habit of slipping when market conditions shift.
The valuation context has shifted considerably since early reporting on the IPO. OpenAI's March 2026 funding round closed at an $852 billion post-money valuation, with $122 billion committed, including major tranches from SoftBank, Amazon, and NVIDIA. That round alone reset the frame for what the public offering could look like. Analysts and investors are now pricing the IPO with a $1 trillion market cap as the base expectation, which would make it the largest tech IPO in history by a significant margin.
The revenue trajectory supports that ambition, at least directionally. Annualized revenue hit $25 billion in March 2026, up from $20 billion at year-end 2025. Sam Altman has stated publicly that the company is targeting $100 billion in revenue by 2027. Whether that number arrives on schedule is an open question, particularly given OpenAI's cost structure: in 2025, nearly half of annual revenue was directed toward employee stock-based compensation alone, averaging $1.5 million per person across a roughly 4,000-person workforce.
Who actually owns what
The IPO will clarify, for the first time publicly, the mechanics of a corporate structure that has been unusually complex for a private company. Following OpenAI's conversion to a public benefit corporation in late 2025, the ownership breaks down as follows: the OpenAI Foundation holds approximately 26%, Microsoft holds 27%, and the remaining 47% is spread across employees and outside investors. Those employee stakes are significant in dollar terms: roughly 165 current and former employees collectively hold equity valued at around $164.9 billion, averaging close to $1 billion per person on paper.
Those employees have already had some opportunity to convert paper wealth into actual cash. In October 2025, OpenAI ran a tender offer that allowed current and former employees to sell up to $30 million each in shares, with more than 600 participants collectively cashing out $6.6 billion. But for the vast majority of equity holders, the IPO represents the real liquidity event. Lock-up provisions will govern how quickly they can sell, and the public pricing will determine whether their paper gains hold up against the private market marks they have been sitting on.
For early investors, the calculus is similar. Microsoft's 27% stake, if maintained through the offering, would be worth roughly $270 billion at a $1 trillion valuation. The company's largest private backers will be watching the roadshow closely to gauge whether public market investors price the deal at, above, or below its last private mark.
What to watch next
The September listing target is real, but it is also aggressive given that the confidential filing only landed in late May. That leaves roughly 90 days for SEC review, comment resolution, roadshow planning, and pricing, all while managing a sprawling syndicate, a complex corporate structure, and a level of public attention that few companies have ever faced going into a debut. Any delay past September would likely push the deal into the fourth quarter, when market windows narrow and investor attention gets pulled toward year-end positioning.
The addition of Citigroup and JPMorgan to the conversation is the clearest public signal yet that OpenAI and its bankers are building for scale. A deal of this size demands more than two banks to place it cleanly. The question now is not whether OpenAI goes public, but whether the market on the other side of that roadshow will meet the valuation that nine months of private fundraising has already set as the floor.
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