Simon played professional tennis, playing at Wimbledon qualifying. In 1990 Simon was appointed an LTA National Coach and was successful in leading GB 14 boys to the European and World titles.
In 1995 Simon worked at the University of Bath establishing the first LTA Academy and as Team Bath Director of Coaching. During this period Simon was also part of the Great Britain Davis Cup Team support staff. In 2006 Simon moved to the National Tennis Centre as Head of Performance Support leading a department of multi-disciplinary support staff who were part of the successful GB Davis Cup winning Team in 2015. Simon was also part of the LTA Executive Team and was a regular attendee at the LTA Main Board. In 2019 Simon left the LTA to take up consultancy roles as the Head of Coach Development at Chelsea FC and Coaching advisor to the Premier League. He is now Head of Performance at Chelsea FC (Academy).