Jason Stockwood: A Visionary Entrepreneur Committed to Social Impact

Introduction

Jason Stockwood is an English entrepreneur and philanthropist known for his business ventures, community involvement, and efforts to bring sustainable change to post-industrial regions. With roots in Grimsby, Lincolnshire, Stockwood has built a career focused on human-centered leadership, social impact investing, and local economic revitalization. His work spans across multiple sectors, including technology, football, and social entrepreneurship.

This article delves into the life and career of Jason Stockwood, highlighting his achievements, business ventures, community initiatives, and political involvement. By understanding his journey, we can gain insight into the power of combining business success with social responsibility.

Early Life and Education

A Humble Beginning in Grimsby

Jason Stockwood was born in Grimsby, Lincolnshire, a coastal town with a strong working-class identity. His early life was shaped by the values of hard work and perseverance. Raised by his mother, who worked multiple jobs to support the family, Stockwood learned the importance of determination and resilience.

Education: Laying the Foundation for Future Success

Stockwood attended Tollbar Academy, a secondary school in Grimsby, where he developed a strong academic foundation. He later pursued higher education at the University of Bolton, where he studied Philosophy, and went on to complete a Transformational Leadership Fellowship at the University of Oxford’s Blavatnik School of Government. These educational experiences equipped Stockwood with critical thinking skills and a deep understanding of human-centered leadership, both of which would later define his career.

Business Ventures and Career Highlights

Leadership at Simply Business

Jason Stockwood’s entrepreneurial journey began when he took on leadership roles at several high-profile technology and insurance companies. His most notable achievement came during his time as Group CEO and Vice Chairman of Simply Business, a UK-based business insurance provider. Under his leadership, Simply Business grew rapidly and became one of the top insurance firms in the UK. The company was ultimately acquired by Travelers Insurance for $500 million in 2017, marking a significant milestone in Stockwood’s career.

Other Notable Business Ventures

Stockwood’s career has not been limited to Simply Business. He has held leadership roles in several other well-known companies:

• Travelocity: As Managing Director, Stockwood helped grow this online travel platform, making it a key player in the industry.

• Match.com: Stockwood was the International Managing Director at Match.com, overseeing its global operations.

• Skyscanner: Stockwood served as a Non-Executive Director, contributing to the company’s expansion and success.

• Lastminute.com: He worked in commercial roles at Lastminute.com, gaining valuable experience in the travel industry.

• 53 Degrees Capital: As a co-founder and partner, Stockwood played a pivotal role in investing in early-stage tech companies, focusing on those with a social impact mission.

His leadership at these companies helped shape the digital landscape, and his focus on socially responsible business practices earned him recognition in the tech and entrepreneurial communities.

Grimsby Town Football Club: A Passion for Community

Ownership of Grimsby Town F.C.

Beyond the business world, Stockwood has a deep connection to his hometown of Grimsby. In 2021, he co-led a consortium that took over the ownership of Grimsby Town Football Club through 1878 Partners Ltd. The acquisition was driven by Stockwood’s desire to revitalize the local community and bring about positive change through sport. As a lifelong supporter of the club, Stockwood understood the potential of football as a tool for social cohesion and local development.

Achievements with Grimsby Town

Under Stockwood’s leadership, Grimsby Town F.C. achieved significant milestones, including promotion back to the English Football League (EFL) in 2022 and a historic run to the FA Cup quarter-finals in 2023. His work with the club demonstrated his ability to apply business strategies to the football world, all while focusing on community engagement and development.

Football Club Ownership and Community Investment

Stockwood’s approach to football club ownership goes beyond financial success. He sees football as a vehicle for community engagement and local economic development. The club’s achievements have revitalized the town, bringing new opportunities for local businesses and boosting the town’s pride.

Political Involvement: Advocating for Change

Greater Lincolnshire Mayoral Election

In 2025, Jason Stockwood took his commitment to community development further by running for the Greater Lincolnshire mayoral election as the Labour and Co-operative Party’s candidate. His platform focused on improving public services, investing in infrastructure, and enhancing community safety. Stockwood’s candidacy was rooted in his belief that local leadership should prioritize the needs of working-class communities and focus on sustainable development.

Although he ultimately lost the election to a candidate from the Reform Party, Stockwood’s involvement in politics demonstrated his dedication to improving the lives of people in his region. His candidacy also reflected his growing influence as a leader in both business and public life.

Social Impact and Community Engagement

The “Our Future” Initiative

Stockwood is also deeply involved in social entrepreneurship. He co-founded “Our Future,” an initiative aimed at empowering citizens in post-industrial communities. This project focuses on providing tools, resources, and support to help these communities build a sustainable future through innovation and collective action.

Other Community Projects

In addition to “Our Future,” Stockwood is the Chair of Horizon Youth Zone, a youth center in Grimsby that provides young people with opportunities to grow, learn, and thrive. His work with Horizon Youth Zone reflects his commitment to investing in the next generation and helping them achieve their potential.

Social Entrepreneurship and Social Impact Investing

Stockwood’s philosophy on business is rooted in social entrepreneurship and social impact investing. He believes that businesses should prioritize people over profits and work toward creating a positive, long-lasting impact on communities. His investments and leadership roles in companies like B Lab UK, which certifies B Corporations, are further examples of his dedication to socially responsible business practices.

Publications and Thought Leadership

“Reboot: A Blueprint for Happy, Human Business in the Digital Age”

In 2018, Stockwood authored Reboot: A Blueprint for Happy, Human Business in the Digital Age, a book that advocates for a more human-centered approach to business. In it, Stockwood explores the challenges businesses face in the digital age and offers solutions for creating more sustainable, ethical, and people-focused organizations.

Contribution to The Guardian

Stockwood regularly contributes to The Guardian, where he writes about topics related to business, football, and social issues. His articles often explore the intersection of technology, leadership, and social responsibility, making him a thought leader in the fields of entrepreneurship and digital transformation.

Conclusion

Jason Stockwood’s career exemplifies the power of combining business success with social responsibility. His work in the technology sector, football ownership, and social entrepreneurship has had a lasting impact on both local and global communities. Whether through his leadership at Simply Business, his ownership of Grimsby Town F.C., or his political advocacy, Stockwood continues to push for positive change in the world.

As we look to the future, Stockwood’s work serves as an example of how business leaders can drive both financial success and social good. His story is a testament to the impact that one individual can have on their community and the world at large.

FAQ

What is Jason Stockwood known for?

Jason Stockwood is known for his leadership in the technology industry, particularly as the Group CEO of Simply Business, and his involvement in social entrepreneurship and football club ownership, particularly Grimsby Town F.C.

What is the “Our Future” initiative?

“Our Future” is an initiative co-founded by Jason Stockwood that empowers post-industrial communities to build a sustainable future through innovation and community action.

What was Jason Stockwood’s role at Simply Business?

Jason Stockwood served as the Group CEO and Vice Chairman of Simply Business, leading the company to significant growth and eventual acquisition by Travelers Insurance for $500 million.

What is Stockwood’s vision for business?

Stockwood advocates for a human-centered approach to business, focusing on social impact, sustainable development, and prioritizing people over profits.

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