Barry is the current head of schools at Cirrus Academy Charter School in Macon, Georgia, where he leads strategic planning, financial management, and instructional improvement for a diverse kindergarten through eighth grade community. He has strengthened organizational systems, expanded community engagement, and implemented data-driven strategies to increase student achievement.

Prior to this role, Barry served as head of schools at Atlanta Unbound Academy, where he led operations, academics, and strategic growth initiatives that significantly increased English language arts and mathematics proficiency. He previously worked as director of special projects at Atlanta Unbound Academy, focusing on organizational alignment and network-wide initiatives. Earlier in his career, Barry held multiple leadership roles at KIPP DC Public Schools, including project director, director of high school operations, athletics, and enrichment, and senior manager of campus operations, where he oversaw large operational teams, multimillion-dollar budgets, and cross-campus initiatives. He also served as a client service manager and advisory board member at SunTrust Bank, leading operational improvements and compliance efforts.

Beyond his professional work, Barry served in ministry leadership roles at Victory Grace Center, including youth pastor and director of discipleship, where he mentored students and developed community programs. He is a recipient of the KIPP DC Board of Directors Behind the Scene Award, recognized for his leadership in managing emergency crisis situations and executing large-scale organizational projects, and is a member of Alpha Kappa Psi fraternity.

Barry earned a master’s degree in divinity from Howard University, a Bachelor of Arts in General Business from the University of Florida, and an Associate of Arts in General Education from Florida State College.