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Gary Bernklow has a diverse work experience. Gary started their career as a Billing Manager at Massachusetts General Hospital in 1999 and worked there for eight years. In 2005, they became a Member of the Stow Finance Committee and remained in that position until 2010. In 2007, they joined MedAptus as the Director of Product Management. In 2010, they became the Chief Executive Officer of Troop One Stow Alumni, Incorporated. In 2011, they took on the role of Selectman for the Town of Stow and held the position until 2014.

Gary Bernklow attended Boston University from 1984 to 1988, where they pursued a Bachelor of Arts degree in Archaeology and Journalism. Gary later went on to study at Eastern Washington University from 1993 to 1995 and obtained a Master of Arts degree in US History.