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Robert Doolittle has a diverse work experience spanning over several companies. Robert started their career at Coopers & Lybrand in 1986, working in the role of Business Assurance until 1998. Robert then joined Swiss Re as a Financial Business Analyst for four years. In 2003, they joined Allianz Global Assistance Australia as a Commercial Manager Insurance, where they managed financial performance, budgets, and led a finance team. In 2007, they moved to Allianz Global Assistance's head office in Paris, where they took on the role of Group Finance, leading a team of controllers for 30 entities worldwide. From 2010 to 2010, they were seconded to the Dutch holding company of 5 European branches, serving as Group Controller and Risk Officer. In 2011, they briefly worked as Group MI and Planning Manager at Resolution Operations LLP before joining Towergate Partnership Ltd as FP&A Manager until 2013. Since then, they have been working at the Pension Protection Fund, first as Head of Finance until 2017, and then as Director of Finance.

Robert Doolittle attended Durham University from 1983 to 1986, where they studied Physics. No further information is available about their education after this period.