'Tenders are just a release valve for liquidity'
HR leaders who rely on equity to retain scarce technical talent have a fresh benchmark to weigh.
Early employees and investors at OpenAI and Anthropic have cashed out an estimated US$14 billion in private share sales over the past five years – a tactic that has eased the retention pressure firms normally feel when staff cannot sell vested stock.
The estimate was reported on June 14 by The Information, drawing on its own reporting and PitchBook data. Both AI developers have repeatedly arranged company-sponsored sales that let current and former staff turn otherwise illiquid holdings into cash — defusing a risk well known to compensation teams: employees locked into paper wealth they cannot touch.
One in four workers globally would trust artificial intelligence (AI) over their own HR department to audit and assess pay equity, according to a global study.
Eight sales, a US$14-billion windfall
OpenAI has been the more active of the two. The Information reported that the roughly 11-year-old lab has completed at least eight share sales in five years, delivering more than US$9 billion to its employees. Last week, as it filed draft IPO paperwork, the company began planning a fresh tender offer pegged to its March valuation of US$730 billion before new money.
Anthropic – maker of the Claude assistant – has moved less often, which the report attributes partly to its being younger, founded about five years ago. It ran its first buyback in May 2025 after investors valued it at US$58 billion, arranged another sale early this year following a US$350 billion round, and most recently raised US$65 billion at a US$900 billion valuation. The report said its annualised revenue has surged past US$30 billion.
The two firms sit within a wider shift. Citing Carta data, The Information reported that staff at private companies sold roughly US$1.7 billion in shares in 2025 – more than US$200 million above their combined 2024 and 2023 totals – as Stripe, Databricks and SpaceX delayed going public.
Recently, SpaceX began trading publicly on the Nasdaq under the ticker SPCX, priced at $135 a share and valued at $1.77 trillion, marking one of the most anticipated corporate milestones in recent memory.
The retention signal for HR
The core HR concern is that long stretches as a private company can turn generous equity into frustration. As organisations stay private for years, the report noted, employees may owe tax on stock compensation before they can sell any of it and realise the cash to pay the bill.
That squeeze is what company-sponsored sales relieve, Javier Avalos, chief executive of private markets data platform Caplight, told The Information.
"Employees will have been fully vested and holding on for a while for OpenAI," said Avalos. "At that point, you start to feel a lot of pressure to provide liquidity to employees." The lesson for total-rewards teams: vesting schedules and headline valuations are only part of retention; the ability to monetise equity is what staff increasingly weigh.
Liquidity alone has not removed the pull toward an IPO, which both firms need to fund vast computing costs.
"Tenders are just a release valve for liquidity," Ken Smythe – founder and chief executive of secondaries firm Next Round Capital – said in the report, adding that staff sales do not remove the incentive to list.
For HR, the balance is the takeaway — offering enough liquidity to keep equity-rich employees engaged without eroding the long-term upside that made the package attractive.
