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Ian Whitehead has extensive work experience in the prison industry, starting in 1989 with the Scottish Prison Service. Their roles within the Scottish Prison Service include Governor in Charge, Acting Director of Business Services, and National Head of Operations, where they led on policy and strategy for all security matters. Ian also served as the Divisional Head of Operations for the Scottish Prison Service starting in 2020. Additionally, Ian Whitehead worked as a Prison Director for Sodexo, leading a team of nearly 400 staff and associates in a high-security privately operated prison. Prior to their career in the prison industry, they worked at Clydesdale Bank as a Deputy Branch Manager and Bank Officer/Senior Officer.

Ian Whitehead attended The Chartered Banker Institute from 1982 to 1986, where they obtained a Diploma in accounts, finance, foreign business, taxation, and law relating to banking. Ian then pursued further education at The Open University from 1993 to 2000, earning a Master of Business Administration (MBA) with a focus on Business Administration and Management, General.