Checkout.com: what a 409A reset actually looks like

The situation

Checkout.com raised a $1 billion round in January 2022 at a $40 billion valuation, one of the largest private fintech valuations in Europe at the time. Fintech multiples then compressed sharply through 2022 as public comparables fell and growth-stage capital repriced across the sector.

How the deal worked

Rather than wait for a down-round primary raise to reset the number, Checkout.com's board lowered the company's internal 409A-style valuation directly — first to around $11 billion in late 2022, then again to $9.35 billion in 2023, a roughly 77% cut from the January 2022 peak. That reset wasn't primarily about outside investors: it reduced the strike price on new employee option grants, making them meaningfully cheaper to exercise than options struck near the $40 billion high.

In September 2025, with the business stabilized, Checkout.com ran an employee share buyback that valued the company at $12 billion — still far below the 2022 peak, but a real, company-funded liquidity event rather than another paper markdown, and evidence the board saw enough of a recovery to put cash behind it.

The outcome

Employees who joined or received grants after the reset benefited from a much lower strike price; those holding older, high-strike options faced years of being underwater before the buyback offered any real liquidity at all. The company itself has said it has no near-term plans to go public, treating periodic internal resets and buybacks as its liquidity mechanism instead.

What it teaches

A company's internal valuation isn't fixed — it can be cut sharply without any external funding round at all, purely through a board-approved 409A-style reset. See409A valuation for how that number diverges from what a secondary buyer actually pays, and why a markdown this large changes the economics for anyone holding options through it.