He graduated with a degree in philosophy from the
University of Bolton in 1995. Having spent time working in the travel industry as managing director of
Travelocity Business, non-executive at
Skyscanner and commercial roles with
lastminute.com, Stockwood went on to become the international managing director of dating website
match.com. In 2010, Stockwood became CEO and then vice-chairman of
Simply Business. Simply Business was voted as the number one ‘Best Place to Work’ in the UK by The Sunday Times in both 2015 and 2016, with Stockwood winning the overall Best Leader award in the latter year. The company's awards led to it being accredited as a
certified B Corporation.
Simply Business raised capital through a number of private equity investors, most notably from New York-based Aquiline Private Equity. It was eventually sold to
The Travelers Companies in 2017 for $500m. He is an investor in early stage technology companies through 53 Degrees Capital. Notable investments include
Olio, Chiaro,
Be My Eyes and AI social services company, Beam. Since 2019 he has been the chair of the board raising the money to build the Horizon Youth Zone in Grimsby. In 2020 he was invited to become a Transformational Leadership Fellow at The Blavatnik School of Government,
The University of Oxford. Since 2021 he has written a number of articles for
The Guardian newspaper relating to football, politics and culture.{{cite news |first=Thom |last=Gibbs |title=Grimsby Town chairman on hopes to 'rebuild civic value in the town' He is a 2023 Fellow of Practice at the Government Outcomes Lab, at the
Blavatnik School of Government, Oxford University. ==Football ownership==