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Heather Fletcher has work experience at WaterStone Bank, where they hold the position of Community Bank President starting from March 2023. Prior to this, they have worked at Walgreens in various roles, including Store Manager from March 2020 to February 2023, Assistant Store Manager from June 2014 to March 2020, Shift Lead from November 2012 to June 2014, and Customer Service Representative from November 2002 to November 2012.

Heather Fletcher obtained their Associate's degree in Business, Management, Marketing, and Related Support Services from Milwaukee Area Technical College. Heather attended the school from 2005 to 2012.