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Cassandra Grantham's work experience begins in 2000 as a Student Health On Campus Coordinator at Colby College. Cassandra then worked as an Intern/Consultant and later as a Project Assistant at Swardlick Marketing Group. In 2004, they started their Graduate Student program at Emerson College. In 2005, they interned at Fleishman Hillard International Communications and also worked as an Assistant to the Director at Tufts University's Drug and Alcohol Program. Cassandra continued their tenure at Tufts University as a Resident Director and simultaneously worked as a Graduate Student from 2005 to 2006. In 2006, Cassandra served as a Graduate Student Practicum at Blue Cross Blue Shield and as a Major Gifts Coordinator at the Senator George J. Mitchell Scholarship Research Institute. Their next role was at MaineHealth, where they held various positions from 2007 to 2022, including Program Coordinator, Program Manager for various programs, and Director of Child Health Programs. Currently, they serve as the Chief Operating Officer at Greater Portland Health since 2022.

Cassandra Grantham completed their B.A. degree in French and Religious Studies at Colby College from 2000 to 2004. Cassandra later pursued an MA in Health Communication at Emerson College from 2004 to 2006.