Simon was first elected on to the County Council in June 2009. He is deputy leader and Cabinet Member for Highways, Transport and Infrastructure.

He was educated at Queen Elizabeth Grammar School in Ashbourne. Simon is a former firefighter serving from 1978 to 1997 and also serves as a company director for Spencer's of Ashbourne

Simon Played rugby for Ashbourne Rugby Club and is a member of Ashbourne Golf Club. Additionally he is a trustee of Old Trust Ashbourne and Assistant Governor of Queen Elizabeth Grammar School and Alms House Trust.