Jackson received his early education at the London Nautical School before transferring to Chatham House Grammar School in Kent. An academically strong student, he had an interest in football but did not participate extensively in extracurricular activities. He later attended Royal Holloway, University of London, graduating in 1988 with a BA (Hons) in Economics and Public Administration.

Student Leadership and Further Education

During his university years, Jackson became known for his direct and assertive style. He was elected President of the University of London Union for the 1988–1989 term. However, his presidency came to an early end following a vote of no confidence.

He continued his studies at the University of West London, earning a Master’s Degree in Human Resource Management. He also became a graduate member of the Chartered Institute of Personnel and Development (CIPD).

Early Career in Business and Community Involvement

Before entering politics full-time, Jackson worked in the financial services sector. He was employed by Lloyds Bank, where he served as a branch manager for nine years. He later held the role of Business Services Manager at Business Link in London. In addition to his corporate responsibilities, Jackson served as a board member and trustee of the London City YMCA for five years, contributing to community development initiatives.

Local Government and Political Emergence

Jackson's political career began in local government. He was a Conservative Party spokesperson on Ealing Borough Council, serving from 1990 to 1998. He also held the position of Vice President of the Local Government Association and was a board member of the New Local Government Network, actively participating between 2010 and 2013.

Although he unsuccessfully sought a position within the Parliamentary Executive on two occasions, these experiences cemented his commitment to public service and the Conservative Party.

Parliamentary Career and Elections

Jackson first stood as a Parliamentary candidate in 2001 and was elected as the Conservative Member of Parliament for Peterborough, winning the seat from the Labour Party. He served on the Regulatory Reform Select Committee in the House of Commons and developed a reputation as an articulate contributor to parliamentary debates.

He was selected by the Peterborough Conservative Association Executive Council in 2007 to run again and retained his seat in the 2010 General Election with an increased majority. That same year, he was appointed Parliamentary Private Secretary to the Secretary of State for Northern Ireland, though he stepped down from the role in 2011.