Simon is Chairman of the Alacrity Graduate Entrepreneurship Foundation and Chief Executive of Wesley Clover Corporation. Before joining Wesley Clover, he was co-founder, President and CEO of Ubiquity Software Corporation. 

Simon is a Director of Wesley Clover, Talkative, Hut Six, The Celtic Manor Resort and Innovation Point. He is a Regent of Harris Manchester College at the University of Oxford, a Professor at the Swansea University School of Management and the Chair of Cardiff University’s Innovation Programme Oversight Board. He is an Honorary Fellow of Cardiff University and the University of South Wales. Simon was the Chair of the Wales MIT REAP Panel. He is a Trustee Director of the British Deer Society.

Simon was made an Officer of the Order of the British Empire (OBE) for his services to industry and to the community in South Wales in the 1999 Queen's Birthday Honours list. In the 2018 New Year’s Honours list he became a Commander of the Order of the British Empire (CBE) for services to the economy of Wales.