Former Toll Bar pupil at centre of £400m deal for insurance giant Simply Business

By Grimsby Telegraph | Posted: 16 Mar 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 pupil Jason Stockwood is chief executive of Simply Business, which is being 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 at offices in London and Northampton, Mr Stockwood joined in 2010 after more than a decade working his way up with web giants that have become household names, including Trailfinders, and

Simply Business is a leading distributor of small business insurance policies, offering third party products online, with more than 425,000 customers.

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Delighted with the "strong validation of the business model" the acquisition has brought, he 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."

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

"We are rolling out globally, building a great business," he said.

In the past three years insurance premiums placed have grown by 17.5 per cent to £93 million, while awards have flowed for the company, and personally, as he was named Best Leader for mid-size businesses by The Sunday Times last year.

He believes his home town has helped him succeed.

"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."

The deal with Travelers, which turns over £23 billion, is scheduled to complete this autumn.

It comes a fortnight after Grimsby payment processing specialist Paul Bentham sold his business, RMS. TCV, a major US investor in global technology companies, swooped for his second venture in the sector, following the creation of Cardsave, as reported.

NEXT WEEK: Read about Mr Stockwood's incredible journey and the inspirations who helped shape him in Grimsby. Full interview in next week's March Business Telegraph edition, and online at

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