On leaving university Simon spent 7 years in farm business management before joining racing’s governing authority with responsibility for racecourse licensing, Clerk of the Course training and Point to Pointing.

He was Clerk of the Course at Cheltenham Racecourse for over twenty years and in 2012 was appointed Regional Head of Racing for The Jockey Club South West courses which also included Exeter, Warwick and Wincanton. He left the Jockey Club at the end of 2021.

Simon was Chairman of the Point to Point Owners’ and Riders’ Association for 5 years before serving as Chairman of the Point to Point Authority from 2009 to 2012.