Rupert began his career at the Alexander Howden Group in 1980 before moving to Catlin Underwriting Agencies in 1984. After spending six years at Catlin, as Deputy Underwriter, he left to join Talbot (then Venton Underwriting Ltd), to start Syndicate 1183 as Active Underwriter. In November 2001, Rupert was made Director of Underwriting. Following the sale of Talbot to Validus in the summer of 2007 Rupert was appointed as Chief Executive Officer of Talbot.
Rupert has served on a variety of market bodies including chairing the Lloyd's Underwriters' Association and Joint War Risk Committee and being a member of the Lloyd's Insurance Services Board, Lloyd's Regulatory Board, Lloyd's Professional Standards Committee and Lloyd's Charities Trust Committee. Rupert was Chairman of the Lloyd's Market Association from 2012 to 2015, served on the Council of Lloyd's from 2007 to January 2016, and was Deputy Chairman of Lloyd's from 2014 to January 2016. The retirement of Rupert as Chief Executive Officer of Talbot commenced on the 29th February 2016, since when Rupert has assumed the role of Non-Executive Chairman of the Talbot Underwriting Agency.
Rupert was appointed as non-executive director of AHJ Limited in January 2018.
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