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Rebecca Side has extensive work experience in the insurance industry. Rebecca was most recently the Director of Business Development at ClaimDeck since 2020. Prior to that, they held the same position at Hermes Law since 2016, where they also worked as the London Market Liaison until 2020. Earlier in their career, they worked at Crawford & Company as a London Liaison / Account Executive from 2011 to 2016. Rebecca began their career at Woodbrook as a Personal Lines Underwriter from 2007 to 2011 and then worked at Personal Lines Underwriting Management as an Assistant Underwriter from 2005 to 2007.

Rebecca Side's education history includes a Diploma in Insurance from The Chartered Institute of Insurance, obtained from 2009 to 2012. Rebecca also pursued Acupuncture and Naturopathy at the College of Natural Medicine from 2014 to 2019, earning a License in Acupuncture and Diploma in Naturopathy, along with membership at MBAcC. Additionally, they attended Townley Grammar School for Girls, although the specific details and degrees obtained during that time are not provided.