Simon graduated from the University of Sheffield and subsequently became a Clinical Lecturer in Oral Surgery, being responsible for the training of undergraduate dental students. He was awarded Membership of the Faculty of Dental Surgeons from the Royal College of Surgeons of Edinburgh in 2010. He later studied at the School of Law, King's College London and gained a Master's degree in Medical Ethics and Law. Simon was appointed a Specialist Registrar in Dental and Maxillofacial Radiology at Guy's Hospital London in 2014. He has an interest in CBCT and dento-legal disputes, and regularly teaches undergraduates and postgraduates.