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Jamaica Charters has a diverse work experience in the field of safety and security. They most recently served as the Associate Director of Safety and Security at Fayette County Public Schools (KY). Prior to that, they held the role of Manager-Information Analysis at Orange County Public Schools and Justice Program Specialist at the Kentucky Department of Juvenile Justice. They also worked as a Court Designated Worker at the Kentucky Administrative Office of the Courts and a Corrections Officer at LFUCG Division of Community Corrections. In their role as a Corrections Officer, they had responsibilities such as maintaining security and inmate accountability, monitoring activities, enforcing rules and regulations, and reporting security breaches and disturbances.

Jamaica Charters obtained a Bachelor's Degree in Criminal Justice from Eastern Kentucky University in the years 2004 to 2008. Jamaica later pursued a Master's Degree in Criminal Justice at the University of Cincinnati from 2009 to 2010.