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Rupert Crayston's work experience includes their current role as Group Head of Risk at The Goodwood Group, which they started in July 2023. Prior to this, they were the Group Head of Health and Safety at The Goodwood Group from June 2021 to July 2023. Before joining The Goodwood Group, Rupert worked at Canary Wharf Group plc, where they held various positions. Rupert was the Acting Head of Fire, Safety, Environment, Quality and Compliance from August 2020 to June 2021, the Deputy Head of Fire, Safety, Environment, Quality & Compliance Manager from July 2019 to August 2020, and the Compliance Officer from October 2018 to July 2019. Rupert's earlier work experience includes roles at Assurity Consulting, where they served as the Consultancy Services Manager (Maternity Cover) from July 2017 to September 2018, the Consultancy Services Deputy Manager from July 2014 to September 2018, and a Consultant from September 2008 to July 2014.

Rupert Crayston attended the University of Brighton from 2005 to 2008, where they pursued a degree in Environmental Science. Rupert successfully completed their Bachelor of Science (Honours) program during this time.