Jon joined Octagon CSI (then CSI Ltd) in 1997 and quickly rose through the company to become one of its leading executives. He oversaw the creation of the CSI archive department and the commercialisation of its assets over a period of eight years. During this time he managed a number of key archives including: The FA Premier League, The Football Association, The Scottish Premier League, SANZAR and The ICC.

In August 2004 Jon launched Pitch International along with partners Paul McGrath and Hans Duikersloot.