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Dreama Gentry has a wealth of experience in various roles throughout their career. From 1992 to 1995, they worked as an Attorney in Bowling Green, KY. Dreama then transitioned to Berea College, where they held the positions of Director of External Programs from 1995 to 2011 and Executive Director of Partners for Education from 2011 to 2022. During their time at Berea College, they also volunteered as a Coordinator for Project Meet Me Halfway from 2010 to 2012. Currently, they are serving as the Chief Executive Officer and President of Partners for Rural Impact since May 2022.

Dreama Gentry's education history includes a Juris Doctor degree in Law from the University of Kentucky J. David Rosenberg College of Law, obtained from 1989 to 1992. Dreama also holds a Bachelor of Arts (BA) degree in Political Science from Berea College, earned between 1985 and 1989. In addition, they have a Bachelor's degree in Political Science and Philosophy from Berea College, although the specific dates are not provided. Dreama Gentry has obtained various certifications, including being a Certified Professional Co-Active Coach (CPCC) from the Co-Active Training Institute in 2021, an MBTI Administrator from The Myers-Briggs Company in 2020, and an EQi Emotional Intelligence Administrator from Collaborative Growth in 2020.