Kristo Käärmann, Wise CEO and fintech pioneer for payments

But despite topping all the major leaderboards in the industry, this savvy businessman did not get a golden foothold in the industry as a result of his background.

Rather, he describes himself as a typical ‘Soviet boy’, who grew up under the shadow of the former Soviet Union’s draconian and laid-back business environment.

He has described that experience and told interviewers; “For the first ten years I grew up like all the Soviet children did at that time. It wasn’t until 1991 when the country became independent again that it went on to a pretty incredible growth story from nothing to then becoming part of the EU, joining NATO, and now, generally speaking, it’s doing pretty well.”

But despite the lack of technology that affected his early years, Käärmann quickly caught up, and in the early 90s he got his first taste of personal computing. His first computer was a ZX Spectrum, which then graduated to a Commodore 2001 – a 1970s model on which Kaarman wrote his first piece of code.

Once bitten by the technology bug, there was no going back, and by the time Käärmann was 19, he had started his first business. It was an online investment tracking portal called Investor.ee.

Although Investor.ee was never profitable, it was still a popular product, and a few years later Käärmann sold it for an undisclosed sum.

Now technology and mathematics interested him the most, and in 2002 he obtained a BSc, followed by an MSc in mathematics and computer science from Tartu University.

He then applied for a number of jobs – and was accepted by a PwC, where his role was to assist banks in Estonia as well as telcos to get a better handle on their data. It was an eye-opening experience because Estonia’s new trade community was still in its infancy because only 15 years had passed since democracy and Western trade were born in the region.

Käärmann saw that legacy systems were not a problem to deal with, because Estonian companies simply weren’t old enough to have them. He said of the experience, “If you look at what consultants usually do in the old world, in Europe or in the US, they usually go to really old companies and help them deal with legacy and help them with change, either new processes or new better ways to run the company. At that time in Estonia, all companies were very young.” This experience led him to concentrate on innovation and organization of data, rather than upgrades, and deepened his interest in space.

A move to Europe

Not long afterwards, Käärmann joined PricewaterhouseCoopers in a consulting role. He found himself responsible for the analysis and design of management information systems for private clients – a field that sparked his interest in fintech and the transaction field.

In 2007, Käärmann had joined Deloitte as a manager. It was here that he honed his skills in systems implementation and delivery, actuarial modelling, tools and data environments for client finance, actuarial departments and risk. He also oversaw Deloitte’s technology strategy to support clients with management information and systems architecture challenges in response to Solvency II regulatory requirements.

It was this experience that put Käärmann in the way of insurance companies and Western banks. He realized their systems were archaic and provided poor value to customers. The revelation saw him form a business partnership with Taavet Hinrikus, who at the time was Skype’s director of strategy. The couple decided to create a new system aimed at cross-border money transfers.

TransferWise was launched in London in 2010 and quickly established offices in Tallinn, New York and Singapore. Business took off – with much demand generated from migrant Estonians working in the UK and sending money back to their families abroad.

By 2017, business had skyrocketed – and TransferWise launched a new service called the Borderless Account, which opened up their services to freelancers and businesses, essentially giving customers a borderless account that could operate in multiple currencies – and still save customers significantly fees compared to offers from traditional banks.

In 2021, TransferWise rebranded and became known as Wise. To date, the fintech has seen 12 rounds of investment and has raised $1.3 billion in capital to develop and scale the business. The company’s latest valuation saw it reach $11 billion.

Käärmann continues to be an avid technologist in his spare time and recently saw his 1,000 employees hold an open technology school in Estonian for homeschooled children.