Simon joined American Express from school initially working as a temp and then full-time as a customer service advisor. He subsequently worked in the planning, finance, operations, sales and marketing functions. After ten years with the company he was appointed to the role of Sales and Marketing Director for the UK business.

In 1990 he joined Lloyds Bank Insurance Services, initially as Commercial Director and subsequently was promoted to the role of Deputy Managing Director.

In 1993 he joined SAGA as a main Board Director in his capacity as Managing Director of SAGA Services, running the non-travel related parts of the SAGA Group.

In 1997 Simon joined Centrica Plc, a FTSE 25 Company, as Group Sales and Marketing Director - a role he maintained throughout his seven years with the Company. For a period of three years he was also Managing Director of Centrica Financial Services (incorporating AA and Goldfish finance businesses) and for a subsequent two year period, Deputy Managing Director of British Gas. He was also on the board of Centrica’s North America Business.

In September 2005 Simon joined AWD Chase De Vere in the role of CEO for the UK and moved to be non-executive Chairman in March 2007.

In February 2009 Simon was appointed to the role of Chief Executive of the newly formed National Apprenticeship Service, reporting directly to the Secretary for Education and the Secretary of State for Business Innovation and Skills.

Simon is also a non-executive Chairman of CMC Markets Plc, Chairman of SPARKS children's charity and is a life fellow of both the Marketing Society and the Institute of Direct Marketing.