Selling shares · Checkout.com

How to sell your Checkout.com shares

Hold vested shares or options in Checkout.com (payments, the United Kingdom)? Here's how a private secondary sale works, the rules that apply in the United Kingdom, who buys, and what to expect.

Checkout.com is a private payments company headquartered in the United Kingdom. If you hold vested shares or options in Checkout.com and want to turn part of that into cash before an IPO or acquisition, this is a plain-English guide to how a private secondary sale actually works — and what's specific to Checkout.com and to the United Kingdom.

Independent guide. PrivateTechShares is not affiliated with, endorsed by, or connected to Checkout.com. This is general educational information for people who already hold Checkout.com shares or options. Always check your own share/option agreements and take professional advice.

Can you sell Checkout.com shares before an exit?

Often, yes. Selling existing shares you own in a private company to a private buyer, before the company is sold or lists, is called a secondary sale. It's possible for Checkout.com shares if they're vested and transferable, and once you've cleared Checkout.com's transfer rules. There's no public market for a private company, so a sale is a private, negotiated transfer — not a click of a button.

What you probably hold

First, pin down what you actually have. In the United Kingdom, startup equity is usually held as EMI options (which you exercise into shares first) or ordinary shares. You can generally only sell shares, so if you hold options you typically exercise them (pay the strike price to convert them into shares) before you can sell. Check your grant documents for your vested amount, strike price and any deadlines.

The rules that apply in the United Kingdom

How a sale works, and how it's taxed, depends on the rules in the United Kingdom — transfer formalities, any right of first refusal, and the tax on a gain. We've written a dedicated plain-English guide: selling startup shares in the United Kingdom. Read it alongside this page.

Who buys Checkout.com shares

There are four realistic buyers, roughly in order: Checkout.com itself (if it runs a buyback or tender), existing investors or shareholders (often via a right of first refusal), the investor in Checkout.com's next funding round, and — when those don't apply — a private individual investor who wants exposure to Checkout.com. Recognisable names like Checkout.com tend to attract private-investor interest; the hard part is finding that buyer discreetly, which is the gap we fill.

What to expect on price

A private, minority, all-cash secondary usually happens at a discount to Checkout.com's last headline valuation — because the buyer takes an illiquid stake with no guaranteed exit, and because you likely hold common shares, which are worth less than investors' preferred shares. That's normal, not a trick. See what discount is fair for a realistic range.

Thinking about selling your Checkout.com shares?

You can list them privately — you stay anonymous until an investor signs an NDA, and you only pay a fee if a deal actually closes. We focus on exactly these small European secondaries (€10k–€750k).

List your shares →

Hold options and weighing whether to exercise first? The exercise & tax calculators (US) and the valuation estimator can help you put a number on it.

Questions people ask

Can I sell my Checkout.com shares before an exit?

Often yes. If you hold vested, transferable shares in Checkout.com you can sell them to a private buyer in a secondary before an IPO or acquisition, subject to Checkout.com's transfer rules — typically a right of first refusal and board or company approval. If you hold options rather than shares, you generally exercise them into shares first. Checkout.com is a private company, so there is no public market; a sale is a private, negotiated transfer.

How much are my Checkout.com shares worth?

There is no live price for a private company like Checkout.com. A rough estimate starts from the price per share at its most recent funding round, adjusted for your share class (common shares are usually worth less than the preferred shares investors hold) and a discount for selling a private, minority, illiquid stake. Use our free valuation estimator as a starting point, and remember it is only an estimate.

Who buys Checkout.com shares?

Four types of buyer: Checkout.com itself (via a buyback or tender, if it runs one), existing investors or shareholders (often via a right of first refusal), the investor in an upcoming funding round, or a private individual investor seeking exposure to Checkout.com. Well-known names often attract private-investor interest, which is where an introductions-only marketplace helps.