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Who is Jason Stockwood? From Kazbah and kibbutz to Blundell Park boardroom


Jason Stockwood today became chairman of Grimsby Town. Here is our Humber business editor David Laister’s interview with him after he agreed another momentous deal in late 2017.

AN online insurance company led by a Grimsby-born technology entrepreneur is to be bought out in a deal worth more than £400 million.

Former Waltham Toll Bar school pupil Jason Stockwood is chief executive of Simply Business, which is to be acquired by New York Stock Exchange-listed The Travelers Companies Inc from Aquiline Capital Partners.

Launched 11 years ago, and now employing nearly 400 people across offices in London and Northampton, Mr Stockwood joined in 2010 after more than a decade building a career with world wide web giants that have become household names.

Delighted with the “strong validation of the business model” the acquisition has brought, the 46-year-old said: “We are really proud. The deal we put together works for everyone, we are thrilled about it. Most of all, as everyone in the business is a shareholder, everyone has done well, but there is more ahead of us than behind us.”

He is to remain at the helm of the business as it is gears up to take success in the UK wider.

“I just do stuff I love, and I love what we are doing here,” he said. “We have launched internationally, and we are rolling out globally, building a great business. What else would I do?

“I have never been financially motivated, I do stuff because I am learning and having fun with people I enjoy. It has never been about making money, it is stretching myself and helping people.

“I am very values-driven, and coming from Grimsby is a great place to come from and a place where many people in the town have a disproportional sense of confidence in relation to ability! It is not cockiness, but confidence, and a sense of humour, and not being afraid of hard work.”

Jason Stockwood, pictured when chief executive of Simply Business.
(Image: Simply Business)

Hard work is something he certainly knows all about, from his first memories.

“I came from a single parent family, very working class. My mum was a real grafter, even though she was a single parent, she had three jobs and a real work ethic.

“She is my inspiration, I never knew my Dad growing up, which is not an unusual story in a town like ours.

“I never had expectations, I just followed my passion. There was never a plan, I worked hard, got fortunate, and had some great teachers.”

One he particularly credits is Alan Boxall, from those Toll Bar days.

“He had a massive impact on me. People underestimate teachers, but he was a massive influence, he took an interest in me and was really instrumental as a kid.”

The PE teacher, a former professional footballer with Scunthorpe United, got a young Jason playing football for the district and county, and then with adults at Grimsby Borough.

“A lot of success comes from playing sport, it is an amazing confidence builder,” Mr Stockwood said, who said form teacher Mrs Peaty also “always looked out for me”.

Jason Stockwood and Andrew Pettit taking a look around Grimsby Town's Blundell Park as part of the due diligence process.
Jason Stockwood and Andrew Pettit taking a look around Grimsby Town’s Blundell Park as part of the due diligence process.
(Image: Sam Strandt/GTFC)

Circumstances at home and school led to him being awarded a scholarship to the US after his A-levels “went badly”, having been “left to my own devices when my mum was working”.

The transatlantic experience gave him a taste for travelling, and led to a stay on a kibbutz in Israel. He also discovered a passion for literature and philosophy, going on to study the latter at Bolton University, “the only place I could get in with rubbish A-levels”.

His taste for adventure led to a job with travel giant Trailfinders which “looked interesting” and in the late Nineties he got involved with Lastminute.com.

“No-one knew exactly what the internet was going to be, I just grafted at it,” he said.

“It doesn’t matter where you are from, hard work marks you out.”

Mr Stockwood reached a senior level – global head of flights and group procurement – before becoming international managing director at Travelocity Business.

Swapping fare aggregation for internet dating, in 2007 he became international managing director for Match.com.

“That was a success, and was sold on, and I was then looking at the next new interesting thing.

“Technology and data run through every business I have been involved with, and I have wanted to build businesses where it meets a need.”

Modest about a CV of international excellence, he recalls his first forays into gainful employment in places where so many local memories have been made.“

At 15 I worked as a waiter at the Winter Gardens, and I worked down the docks for a few months, and that was ‘real’ work. Doing what I do now, it is not ‘real’ work, it is a privilege to be doing stuff with technology.”

Simply Business is a leading distributor of small business insurance policies, offering third party products online. It has more than 425,000 customers and the past three years have seen insurance premiums placed grow by 17.5 per cent to £93 million.

Since Mr Stockwood joined the business it has featured in The Sunday Times Tech Track 100 companies and was included on the Deloitte Technology Fast 500 Europe, Middle East and Africa list. It was also named Best Company to Work For by The Sunday Times in 2015 and 2016.

Last year a personal accolade arrived, with Mr Stockwood named Best Leader of mid-sized companies, completing a hat-trick with The Sunday Times for the keen Grimsby Town fan. And while he has a strong emotional commitment, he doesn’t see himself becoming financially involved at Blundell Park.

“I’d never say never, but it is not the plan to do that,” he said, having appreciated how Wembley has almost become a second home in recent times while he has been in London. “I think John Fenty does a great job. What he has done in the last couple of years is nothing short of a miracle,” he enthused.

Had he not been finalising the deal alongside Aquiline and Travelers, something that has occupied virtually every hour of the past two months, he’d have been enjoying the delights of the 3-0 win at Leyton Orient, with his brothers, one of whom is in Grimsby and the other is in Bristol.With a Manchester-born wife he has also successfully staved off City blue, ensuring his children, aged eight and five, are clad in black and white.

They’ve also taken in their first games.

Of the deal, Mr Stockwood said: “This is a tremendous opportunity for our company and employees, as well as a strong validation of our business model.” It is now scheduled to complete this autumn.

Looking ahead, he added: “I am excited about Simply Business benefiting from Travelers’ extensive knowledge of the US market as we develop our approach there, as well as the resources it has to support potential expansion into additional markets. Our shared values and commitment to innovation make this transaction a perfect fit.”

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