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Simon Strickson has a rich work experience in the finance and accounting sector. Simon began in 2000 as a Group Chief Accountant at Motorline Ltd, where they worked until 2008. From 2007 to 2014, they served as a Financial Controller at Watford Jaguar. In 2020, Strickson became the Finance Director at Prestige Cars Kent until 2023. Simon then moved on to Ancaster Group as their Financial Director, where they are presently employed. Additionally, in an unspecified period, they held the position of Group Chief Accountant at Motorline Group.

Simon Strickson attended St Richard Reynolds Catholic College, but no information is given regarding the degree or field of study.