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Simon Legg has over 25 years of work experience in the field of information technology and security. Simon most recently served as the Chief Information Security Officer (CISO) at Hastings Direct since September 2019. Prior to that, they held the position of Group Chief Information Security Officer (CISO) at JLT Group from October 2017 to June 2019. From 2012 to 2017, they worked at PRA Health Sciences in various roles, including Information Technology, Risk, Security & Compliance Executive and Information Technology Executive. Simon has also served as a Non Executive Director at CapitalSouth Education Business Partnership Ltd from 2008 to 2015 and as a Director at Independent Management Consulting from 2011 to 2012. Earlier in their career, they worked at Bank of America Merrill Lynch as SVP Senior IT Business Executive in 2009-2010 and at Bank of America as SVP IT Risk, Services & Operations from 1994 to 2010. Simon started their career at Lloyds Business Machines as a Sales & Service Consultant in 1993.

Simon Legg attended Caterham School for an unspecified period of time. Later, they pursued a Bachelor of Arts with Honors degree at the University of Sunderland. No further details about their education history are provided.