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John O'Leary has extensive experience in education, community service, and insurance management. Since 2009, John has served as a substitute teacher for the Portsmouth School Department. Additionally, John was a trustee for the Portsmouth Public Library in New Hampshire until September 2014 and held the position of Insurance Services Manager at the New Hampshire Bankers Association from June 2010 to February 2014, where responsibilities included managing the Health Insurance Trust. John's civic involvement includes membership on the City of Portsmouth Charter Committee and serving as a city councilor from January 1986 to January 1994. Prior to these roles, John worked for Anthem Blue Cross and Blue Shield for over two decades, retiring as a Senior Account Manager and Labor Relations Consultant in December 2008. Educational achievements include an MBA in Administration from Golden Gate University, a BS in Administration from the University of New Hampshire, and a marketing and sales certificate from Purdue University.