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Simon Swain has over 15 years of experience in the legal field. Simon is currently the Head of Legal at Advanced Medical Solutions since March 2020. Prior to that, they worked as the Head of Legal at Certas Energy for four years. Simon also held the position of Senior Corporate Counsel at Speedy Hire PLC for four years. Simon served as the Group Legal Counsel at Klarius Group Limited for three years, where they drafted commercial contracts and developed a group Bribery Act policy. Simon began their career as a Solicitor at DLA Piper, where they worked on various transactions including the acquisition of a care home charity. Simon also gained experience in corporate and insurance law at Slaughter and May, where they worked on demutualisation and flotation projects.

Simon Swain attended Horsforth School from 1993 to 2000 where they completed their GCSEs and A Levels. Following this, they enrolled at the University of Oxford from 2000 to 2004 and obtained a degree in Law, specializing in Jurisprudence.