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Rob Heubeck

Rob Heubeck


Rob has been part of independent schools for almost 30 years. He began his career at John Carroll School in Bel Air, Maryland, where he served as a classroom teacher, Dean of Student Affairs, Department Chair, and Head Soccer Coach. At John Carroll, Rob also helped organize and run outdoor education trips to the Everglades, Adirondack Mountains, and throughout the Chesapeake Bay. 


In 2004, Rob continued his independent school career at Gilman School. While at Gilman, Rob has served as a member of the History Department, Upper School Director of Educational Technology, class dean, and student advisor. In 2014, Rob was appointed Head of Upper School where, among other things, he has been instrumental in implementing a student-centered daily schedule, creating an academic support program, supporting a faculty/student wellness program, and helping to develop a restorative justice program in collaboration with the school’s Office of Community, Inclusion, and Equity.


As part of Gilman’s leadership team, Rob has helped to develop Gilman’s crisis management plans, including the challenges of COVID and hybrid learning. He has also been an integral part of implementing the school’s long-range plan and teacher evaluation process. In addition to his roles as division head, teacher, and advisor, Rob has coached varsity soccer and baseball, and has worked closely with Gilman’s Athletic Department to preserve and enhance the school’s teacher-coach model.


Rob is from the Baltimore area and attended John Carroll School, where he is a member of their Athletic Hall of Fame. He has two children, both graduates of Baltimore independent schools, and currently lives in Baltimore with his wife, Elizabeth.

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