Previously, since June 2011 he was joint Chief Operating Officer for Boots in the UK and Ireland, together with Ken Murphy. That role included leading the UK and Republic of Ireland store networks, pharmacy, operations and customer care teams. He also had joint leadership responsibility for the delivery of the annual budget and operating plans.

He joined Boots as Regional Director of the South Region in 2003. Additionally, Simon spent the first 15 years of his career at Marks and Spencer in a number of store, regional and divisional leadership roles across the UK.