Simon started his commercial property career with commercial property consultants Wilson & Partners in 1986. He stayed with the company through its evolution into Connell Wilson, working in London Docklands between 1991 and 1993 and then later (as a Director) heading up the North Northamptonshire region for Lambert Smith Hampton. He joined Underwoods as a Partner in 1998, subsequently founding Prop-search in 2008.

Simon is a Director and Ambassador of Wellingborough & East Northamptonshire Chamber of Commerce (and a former 3 term President), has Chaired the Wellingborough Town Centre Partnership for a number of years (and was instrumental in establishing the Wellingborough Town Centre BID), is a serving member of the Board of Trustees for Nene Rivers Trust CIO and an Envoy for SEMLEP.

Simon specialises in advising on commercial property development, including specialist renewable energy solutions, investment and agency.