Simon joined Winchester in 2023, having worked for the last seven years at Harrow International School in Hong Kong, firstly as Housemaster and then as a member of their Senior Leadership Team. Prior to this, his first teaching post was at the London Oratory School in Fulham. At both schools he was heavily involved with the Duke of Edinburgh's Award Programme, the CCF and whichever sports he had the opportunity to turn his hand to. 

Before making the move into teaching, Simon served in the British Army and commissioned into 1st The Queen's Dragoon Guards after a year at the Royal Military Academy Sandhurst. As a result, pastoral care has always been something that has featured prominently in his career choices.

Simon lives at Winchester with his wife Hannah, who is a Clinical Psychologist, his two young children, Matilda and Rory, and their two dogs. In their spare time the family enjoys exploring the great outdoors, walking, cycling and visiting family and friends.