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Olessya was part of the Greenlight Re team from 2016 to 2017 and returned in 2021 as an underwriter in the Cayman office. She has over 10 years of industry experience, working for Chubb, Hannover Re, and Hub International in Toronto, Canada. Olessya holds a Master of Science degree in Risk Management and Insurance from Florida State University, as well as the Associate in Reinsurance, Certified Risk Manager, and Chartered Insurance Professional designations.