Having worked for property agents Chesterton in both their Exeter and Bristol offices for six years dealing with commercial property throughout the South West and South Wales, Simon moved to Crest Nicholson with responsibility for retail and mixed use development in 1995. In 2001 he joined the Exeter office of Rok Development to undertake commercial development throughout the South West region.

In 2003 Simon was made an Area Director and set up the Bristol office of Rok Development with Paul.

Simon set up Eagle Land with Jon and Paul in 2007.