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Rob Woodward worked at Aviva from 2000 to 2006 as a Claims Investigator. Rob then joined NFU Mutual in 2006, where they held the position of Regional Claims Inspector until 2011. From 2011 onwards, Rob worked as the Head of Claims Inspectors at NFU Mutual.

Rob Woodward completed their education at the University of Warwick - Warwick Business School from 1991 to 1994, earning a Bachelor of Science (BSc Hons) degree. Their field of study focused on Chemistry and Business Studies. Prior to attending university, Rob attended Bolton School, although specific details about their degree and field of study during this time period are not available.