Giles began his career at Lloyd’s in 1981 working as a marine broker for Bain Dawes Plc. In 1988 he joined Wren Underwriting Agencies as a Members’ Executive, subsequently becoming deputy chairman. While there, he became a founding director of Cathedral Capital Plc, a group conversion scheme for Members set up in 1997. In 2001 he joined CBS, and in 2006 moved to Hampden following Hampden’s purchase of CBS. Giles stepped down from full time client work and his position on the board in Sept 2021, but remains a consultant and advisor to the company.