The technology boss who believes in business with a human face

Technology must become a tool and not a taskmaster, according to the businessman and author Jason Stockwood. He metDeputy Business Editor Greg Wright.

Jason Stockwood

WILL our obsession with mobile technology ever be regarded as being as damaging as an addiction to smoking?

Quite possibly, according to some analysts. They include Jason Stockwood, an experienced businessman who believes we must always hold the whip hand over technology.

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In his book – Reboot: A Blueprint for Happy, Human Business in the Digital Age – he makes a passionate plea for business to be conducted with a human face, in a corporate world where the shareholder is too frequently regarded as king.

Jason Stockwood

His CV suggests that he has always possessed a single-minded drive to get to the top. Over the last 20 years, Mr Stockwood has held leadership roles at,, Skyscanner and Travelocity.

He is currently vice chairman of Simply Business, which has twice been recognised by The Sunday Times as the UK’s best company to work for.

Simply Business, which is a business to business insurance broker, was acquired by the US insurance group Travelers in 2017 for $490m. Following the acquisition, Mr Stockwood sits on the management board of Travelers, an S&P500 company employing more than 30,000 people.

So it may come as a surprise to hear that Mr Stockwood describes himself as an accidental businessman. He comes from a single parent family in Grimsby and certainly did not follow a conventional route to the boardroom.

“It was a very happy and very normal childhood,” he said. “Looking back on it, it was liberating because there was very low expectations. I was able to do things that I was naturally interested in and curious about, rather than feeling family pressure or peer pressure to do a particular job or be really successful.

“I’ve gone through my career just doing stuff I am passionate about, rather than having an end state to be aiming for.”

Although he was a promising student, Mr Stockwood left school after his A levels and toured the world.

He recalled: “I went on a kibbutz in Israel then I went and worked at Disney World in Florida, I was a holiday rep in Greece. I did all this stuff just because it was fun and interesting.”

He was an avid reader and, over time, this led him towards academia.

“I started to educate myself properly,’’ he said. “I’ve got no idea why, but I found I had a love for classic literature and poetry. So I started to follow the root causes and sources of that.

“It always led to philosophy. So I found that I started to read philosophy and I struggled because it’s complex. It was 1992, the last year you could get a mature student grant, so I went and studied full-time at Bolton. This gave me the intellectual tools to think properly and deeply about the things I was curious about.”

The technological revolution of the late 1990s fired his imagination.

He said: “There was no plan. I happened to be living in London with some friends of mine in the late 1990s and I was curious about this technology. I started reading about the internet and I became immersed in it and when floated, I thought ‘that’s an interesting business’.”

The website, which was founded in 1998 by the digital entrepreneurs Martha Lane Fox and Brent Hoberman, aimed to be unstuffy and dynamic, at a time when many firms were struggling to cope with the rising power of the internet.

“It was a breath of fresh air,’’ said Mr Stockwood. “It’s what we see today in businesses, with open plan offices. Martha and Brent were sitting in the corner of the room. There was amazing energy.

“We were breaking new territory. It was completely tech led. It was an amazing seven or eight years I spent there. It massively informed the type of culture I wanted to be part of.”

He has earned rave reviews for Reboot, a book which reflects his belief that business must be driven by humane impulses

“Technology needs to be a force for good,” he said. “It needs to be a tool rather than a taskmaster. People are blindly accepting this AI (artificial intelligence) revolution which will do away with swathes of jobs and disrupt society. It’s in our gift to try and articulate what the new society should be as a result of that.”

He added: “Businesses need to focus on not just shareholders, but stakeholders. There are a number of stakeholders that are as valuable to the success of the business.

“As a technologist, people might be surprised to hear that our kids weren’t allowed technology until they were five.

“I think we’ll look back on our relationship with mobile phones in the same way we think about smoking now.

“In our business, even as a tech business, if you come to a meeting you can’t bring technology.”

Face to face interactions are placed at the heart of the company’s life, because Mr Stockwood does not believe mankind should be enslaved by technology.

He added: “I leave my mobile phone near the door at home, so it doesn’t follow me around the house.

“There’s a lost generation of kids who are obsessed about creating an appearance that has no tangible relation to reality.

“There’s also a lost generation who are losing their core social skills and the ability to relate to individuals.”

He fears that economic rewards have been handed out to those who are already wealthy. He believes it would be hard for a child from a modest background in Grimsby to follow in his footsteps today because society has become more unequal.

He believes further revolutionary change could be on its way.

He added: “From 1973 onwards, if you look at the data, for 90 per cent of the population particularly in the US, real wages haven’t increased. For the top 10 per cent of society returns have been disproportionate.

“It’s created a divisive society. Every part is broken now. We’re in for a correction; that will either be societal disruption or just a reboot of capitalism to be more inclusive.”

Name: Jason Stockwood

Date of birth: July 6 1970

Title: Vice Chairman of Simply Business, a business to business insurance broker. It is among the Tech Track 100 of the nation’s fastest-growing tech nology companies. It was acquired by the US insurance group Travelers in 2017 for $490m.

Education: Undergraduate degree in philosophy

First job: Waiter

Last book read: Poverty Safari by Darren McGarvey

Favourite song: Fish on a Hook - Wild Rivers

Favourite film: Cinema Paradiso

Favourite holiday destination: Mallorca

Car drive: Volvo

What is the thing you are most proud of? My children