Simon plays a variety of different styles, from classical symphonic concerts and recording sessions, to operas, musical theatre, TV shows, and pop concerts. He is regularly involved in programmes for the broadcasting corporations RTÉ & BBC and has performed and recorded with such outstanding and diverse artists as John Dankworth & Cleo Laine, Lance Ellington, Rachel Weston, Bryn Terfel, The Priests, Andrea Bocelli, Julie Feeney, Josh Ritter, and Sinead O'Connor.

He held the position of 3rd & Co-Principal Trumpet with the Illinois Symphony Orchestra and 2nd & Co-Principal Trumpet with the Illinois Chamber Orchestra and has also performed regularly with many other orchestras and chamber ensembles in and around the city of Chicago. He is a founding member of the International Chamber Artists of Chicago.

Simon moved to Ireland in 2007 and is now working as a freelance musician with the Irish Chamber Orchestra and the Italian based orchestra Spira Mirabilis. He has played with Irish Film Orchestras and the Orchestra of St Cecilia, as well as an extra or substitute player with the (BBC) Ulster Orchestra, the RTE Concert Orchestra & Big Band, and the RTE National Symphony Orchestra of Ireland.

Apart from playing with the Laudate Ensemble, Simon is also a member of the Vox Merus Brass Quintet.