About

Team size: 80

Major legal advisers: Ashurst, Baker McKenzie, Macfarlanes, Travers Smith, Wilson Sonsini Goodrich & Rosati

A little-known London-based fintech company was thrust into the spotlight in 2019 after announcing it had raised $230m at a valuation of about $2bn – its first capital raise and touted as Europe’s largest fintech Series A round ever.

Checkout.com, a payment processing company that has deals with the likes of Visa, Mastercard, Apple Pay and PayPal, and boasts customers such as Deliveroo, TransferWise and Samsung, has been around for close to a decade. Joshua Kaplan joined the company as GC, and later chief operating officer, three years ago.

‘When I joined the company, it was fewer than 100 people based in London and a small office in Dubai,’ he comments. ‘But over the last three years we’ve been in hyper-growth mode: expanding to more than a dozen countries, adding about 450 people, upgrading to an e-money licence in the UK and adding licences in France and Singapore, with pending applications in Hong Kong, Brazil, the US and Canada. There’s been a real transformation of the business, all of which was validated by the fundraising last summer.’

Kaplan has an impressive CV as a banking lawyer, having started at the US Federal Reserve before working at Deutsche Bank, Crédit Agricole and Bank of America Merrill Lynch. He joined Checkout as the banks stalled post the global financial crisis and he was lured by the excitement and opportunity to help scale a fintech start-up. Furthermore, having completed an MBA he was looking to do more than purely technical legal work.

He assumed a second role as chief operating officer (COO) shortly into his tenure, and wore numerous hats while building out the division, including head of compliance and money laundering reporting officer, as well as de facto head of government and regulatory affairs, and company secretary. The company was entering its growth phase and Kaplan built up five areas under an overarching COO banner: legal, compliance, risk, operations and financial partnerships. About 80 people now report to him, while his legal team has eight lawyers and three paralegals.

‘Most of the team I built from the ground up. When I joined there was only one lawyer and compliance didn’t exist,’ he says. ‘But it was a challenge. I was getting pulled in a lot of different directions. I was very deliberate in selecting the teams that we combined under the COO division because I felt a lot of the problem-solving we did as a company required the collaboration of those teams.’

Having established the compliance and operating structure for the company, Kaplan intends to now build out different COO teams across the company’s jurisdictions. ‘We keep a lot in-house, that’s the DNA of the company to build everything internally, from technology to legal to finance work.’

Macfarlanes partner Alex Edmondson comments: ‘Josh has overseen a group-wide reorganisation across multiple jurisdictions involving multiple steps. He has an encyclopaedic knowledge of capital markets regulatory issues and runs many of Checkout’s regulatory approval applications himself with minimal – or no – assistance from external counsel.’