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Troy Holaday has extensive work experience in the education and academic advising field. Troy began their career at Ball State University in 2000 as an Assistant Director of Academic Systems, where they worked until 2007. In 2002, they also took on the role of Chair of Advising Transfer Students Commission at NACADA, a position they held until 2005. In 2007, they became the President of CollegeSource Inc. and continues to serve in that role.

Troy Holaday completed a Bachelor of Fine Arts degree in drawing from Ball State University in 1990. Troy then pursued a Doctorate in English Composition and Rhetoric at the same university, graduating in 2002.