· 2 min read · Features

People-focused CEOs: Jason Stockwood


In a series of interviews we meet some of the most people-focused CEOs in the UK

Jason Stockwood, CEO of B2B insurer Simply Business, describes himself as an “accidental businessman”. Raised by a single parent on a council estate in the north of England, in his words he had “no boundaries, no expectations” and so was able to do whatever he found personally interesting.

That turned out to be technology – he spent seven years at lastminute.com and three at online dating site match.com.

He joined Simply Business out of a desire to make insurance products better and disrupt what he saw as a non-customer focused and not particularly tech-savvy industry. It appears to be working: Simply Business, which employs about 350 people, is now the UK’s biggest business insurance provider.

Stockwood’s philosophy is simple: “I want to build the sort of business I want to work in. I want to work with super smart people, solving a big problem with technology, and have fun with it.” Here Stockwood reveals some other lessons.

Share the rewards

Stockwood, who describes his attitude towards running a business as “socialist”, believes in sharing the benefits of a growing organisation with everyone who works there. “I don’t believe the most senior people are the smartest people, and the shareholders shouldn’t be the only ones who are remunerated,” he says. “Everyone has to do well out it. When we recapitalised six months ago every person got a cheque.”

Rewards are not just monetary. Stockwood is in favour of offering a broad range of benefits, such as flexible working and sabbaticals. He has also taken most of the workforce (276 of them) to Barcelona. “In the scheme of things it’s good value,” he says. “The social capital you build in teams through things like that is worth a lot.”

Give people freedom

Stockwood has “an optimistic view of humanity”. “People are generally good and committed. They want to create great outcomes for themselves and the people they work with. It’s about trying to make people successful in their roles.”

As Simply Business offers some innovative products, this means giving people the freedom to “test hypotheses and fail a lot”. “You need to set a goal and let people test,” Stockwood believes. “You can’t manage people in the traditional sense, you’ve got to give them the conditions and freedom so they can be successful, but also fail.”

Managers are given the freedom to manage their teams in a way that suits them, when it comes to KPI-setting for example. “If you need to give people five objectives per week that’s fine, but if you need to give them one piece of work for the next six months that’s fine too.”

For HR this means thinking backwards when it comes to processes: “How do we give people the maximum amount of freedom and choice? If we give them total freedom on what they want to do we can work backwards to [building] a framework people can relate to.”

Consider the individual

That level of freedom means respecting that different people want different things from work. Take remote working: “Three years ago I assumed everyone would want to work from home. But we did a survey and more than half said they don’t like it.” That means investing in a new workplace for those who prefer to come into an office.

“When you’re a smaller company your biases are more implicit in your hiring processes and you get people who share your values,” Stockwood says.

“As you get larger you want more diversity. We want to give a suite of options, and say it’s OK [to choose].”

“If you’re a 30-year-old who wants to be CEO and wants to work seven days a week, fine. If you’re a middle-aged guy who wants to spend time with his kids and work three days a week that’s fine too. You have to give people the option to find what success looks like for them.”

Others in this series:

David Done, RHP

Martin Bennett, Homeserve