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Donald McDermaid has over 20 years of experience in the insurance industry. Donald started their career at Stanhope Simpson Insurance Ltd in 2001 as a Commercial Account Manager, where they worked until 2007. In 2008, they joined Scotiabank as a Credit Analyst, and then returned to Stanhope Simpson Insurance Ltd in 2011 as an Account Executive. Donald steadily progressed within the company, serving as a Partner in 2015, Vice President, Commercial Insurance Broker, and Director of Personal Lines in 2016, and finally Executive VP in 2018. Donald manages various complex commercial insurance accounts across industries such as seafood, hospitality, realty, and construction. Donald holds a Bachelor of Commerce degree from Saint Mary's University and has earned the Chartered Insurance Professional (CIP) designation, as well as completing the Fellowship CIP program in 2015.

Donald McDermaid completed their Bachelor of Commerce (B.Com.) degree from Saint Mary's University between 1997 and 2001. Donald furthered their education at the Insurance Institute of Canada, where they obtained a Chartered Insurance Professional degree from 2001 to 2005. Later, from 2011 to 2015, Donald pursued a Fellowship Chartered Insurance Professional degree from the same institute. The specific field of study for each of these education programs was not provided.