Simon is CEO of LOVEFiLM, Europe's largest online DVD rental service that merged with Video Island in April 2006. Prior to the merger Simon was CEO of Video Island.  Before joining Video Island in July 2005, he held senior management positions at Riverdeep, Dell, Pepsi and Unilever.

Before that he was International VP of Sales Operations for PepsiCola, based in the US for three years and as General Manager and VP of PepsiCola UK where he launched Pepsi Max and Pepsi Blue.