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Penny McCune has a diverse work experience in the insurance industry. Penny began their career at SGI CANADA Insurance Services Ltd in 2006 as an Assistant Vice President, Canadian Operations. Penny then joined Coachman Insurance Company in 2010 as the Chief Operating Officer. After two years, they returned to SGI CANADA Insurance Services Ltd as the Vice President Customer, Distribution & Marketing Strategy. In this role, they developed a strategy to transition the company to a customer-centric organization, focusing on understanding customer needs, improving marketing strategies, and utilizing data effectively. In 2014, they took on the role of Executive Vice President, Claims and Salvage at SGI before becoming the Chief Operating Officer of Auto Fund in 2016. Currently, they serve as the President & CEO of SGI, starting in 2022.

Penny McCune earned a Bachelor of Business Administration (B.B.A.) degree with a specialization in Accounting and Finance from the University of Regina in the years 1981-1985. Penny also holds a certification in Bachelor of Admin, Accounting Major, although no information is available regarding the institution or the date of obtaining the certification.