OpenAI Expands Employee Share Sale to $10.3 Billion Allowing Staff to Cash Out at $500 Billion Valuation – Will Employees Cash In Before an IPO?

OpenAI Expands Employee Share Sale to Over $10 Billion Amid Strong Demand

OpenAI is giving current and former employees a significantly larger opportunity to sell their shares, raising the planned secondary stock sale from $6 billion to roughly $10.3 billion.

The offering comes at a company valuation of $500 billion, aligning with expectations and reflecting continued investor confidence in the AI leader.

Why Employees Are Getting a Bigger Window to Sell

Employees who have held OpenAI stock for more than two years have until the end of September to decide whether to participate in the sale.

The transaction is scheduled to close in October.

By allowing staff to liquidate a portion of their holdings, OpenAI offers a way for employees to realise profits without the pressure of an imminent public listing.

A person familiar with the matter, who requested anonymity due to the private nature of the details, shared,

“Staffers who have held shares for more than two years have until the end of September to decide whether to participate.”

High-Profile Investors Step In

The shares being sold will be transferred to a mix of prominent investors including Japan’s SoftBank, U.S.-based Thrive Capital, Dragoneer Investment Group, Abu Dhabi’s MGX, and T. Rowe Price.

This participation reflects strong market interest in OpenAI despite the company remaining privately held.

Secondary Sales as a Strategy Among Top Tech Firms

OpenAI is not alone in offering these structured secondary sales.

Companies such as SpaceX, Stripe, and Databricks have used similar approaches to help employees monetise equity while attracting additional investment.

In November 2024, OpenAI allowed employees to sell around $1.5 billion in a tender offer with SoftBank, demonstrating an ongoing strategy to balance employee liquidity with investor demand.

A $500 Billion Valuation Highlights Market Appetite

The scale of this secondary sale, up over $4 billion from the initial target, reflects both the financial strength of OpenAI and a sustained interest from global investors.

This round allows employees to convert long-held stock into cash while supporting a steady influx of capital from institutional backers.

The company’s approach combines employee incentives with strategic funding, offering liquidity options without the immediate need for an IPO.

As a result, OpenAI continues to attract high-profile investors while keeping its private structure intact.