Read History at Queens’ College, Cambridge before working in insurance in the City of London. Taught briefly at Radley College before joining the Winchester College staff in 1976 where he taught History and English and directed many productions during the following 24 years. He was a Housemaster from 1988 until 2000. Headmaster of Sherborne School in Dorset from 2000 to 2010 and served as Chairman of HMC South West. Now a Senior Advisor for RSAcademics educational recruitment company, he is a Trustee of the Ernest Cook educational trust and acts as a Chairman of Stewards for the British Horseracing Authority. Simon has been a Governor of several schools in the UK and of the English College since 2010. He is a member of the Education Committee.