From 1979 to 1982 Simon worked in the commercial claims department of Norwich Union, Leeds before embarking on his adjusting career which began with Graham Miller Sibila & Co., York in 1983.

For the period 1987 to 1990, he was engaged by Pycraft & Arnold at Leeds and Southampton offices, before transferring to Manchester as Branch Manager.

In January 1991 Simon was recruited by Brocklehurst Italia and engaged as Branch Manager of Milan office later becoming Managing Director for the Italian territory.

From January 1994 to June 1997 he was engaged by Quantum International Group to open and develop a new office in Milan, six months later opening an office in Rome and shortly thereafter in Genoa. Later he became responsible for the running of the Italian/continental European operation of Quantum International Group subsequently developing and opening new offices in Barcelona.

In June 1997, Simon left Quantum International Group to form his own company trading as The ACME Loss Adjusting & Risk Survey Co. S.r.l., based in Milan, Italy. Such concern currently has a workforce of ten full time staff in Milan.

During 2003 Simon co-founded the separate activity of C&N Insurance Services, specialising in the undertaking of coverholder audit assignments and provision of specialist services to Underwriters.

In 2014 and after working for thirty years as a Loss Adjuster, Simon established the specialist fine art insurance practice of Untitled (1960).

Simon is a Chartered Insurance Practitioner and a member of the Institute of Art and Law and holds the Diploma in Art Profession Law and Ethics (DipAple).