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Maria Chesky started their work experience in 2002 as a Client Care Coordinator at Gentiva Health Services. Maria then worked as a Resident Service Coordinator at The Barnstable Housing Authority from 2004 to 2011. In 2011, they joined Caregiver Homes of MA as a Care Manager/Intake Coordinator. From 2012 to 2013, Maria worked at Webster Light, LLC GAFC as an Outreach Coordinator/Care Manager.

Maria Chesky attended Cape Cod Community College in Barnstable, MA from 1976 to 1979 and obtained an Associate Degree in Liberal Arts. Later, from 2000 to 2003, they studied at Suffolk University in Boston, MA, and earned a Bachelor of Science degree in Communications/Journalism.