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Debra Cagwin has worked in a variety of roles since 1990. Debra began their career as the Director of Wyoming County Victim Services, followed by a role as Grants Administrator for Hunter's Hope Foundation in 1999. In 2001, they became the Executive Director of CORSA (Citizen's Committee on Rape & Sexual Assault). In 2004, they were hired as the Director of Communications & Governmental Affairs for the National Organization for Women - NYS. From 2005 to 2007, they worked as both the Business Manager and Communications Director for Lothlorien Therapeutic Riding Center, and as the Finance & Marketing Manager and Marketing Manager for Global Learning Partners, Inc. In 2012, they took on the role of Web Marketing Coordinator for GenTech Scientific. In 2015, they became an Independent Contractor, working as a Paralegal. Finally, in 2020, they began working as a Web Developer/Marketer for GenTech Scientific LLC.

Debra Cagwin attended the University at Buffalo from 1983 to 1987, where they earned a Bachelor of Arts in Political Science.