Jon started his career at Sheffield Wednesday, where he scored twice in eighteen appearances. He was released at the end of the 2003/04 season, and joined Burton Albion, where he spent 3 years.

Jon scored 28 goals in all competitions during his time with Burton, but was signed by Halifax Town for undisclosed fee in August 2007. It was his great form at The Shay, scoring 20 goals in the Conference, that influenced Keith Hill to sign the striker in the summer of 2008 for another undisclosed fee.

Jon made his Dale debut in the Carling Cup penalties loss to Oldham Athletic. He scored his first goal in Dale colours in a 3-1 defeat of Barnet in August 2008, scoring the third goal with a well struck half volley. Unfortunately, Jon had to contend with injuries, and it was these that influenced his loan out to Crawley, where he scored 5 goals in 12 starts. He was brought back for the last game of the season at home to Gillingham, which he started, and he also featured as a substitute in the Play-Off semi-final 2nd leg defeat at Gillingham.