Greg grew up in Stone Harbor, New Jersey, and attended the Peddie School, playing football and lacrosse. Greg graduated from Wheaton College in Norton, Massachusetts, with a BA in Political Science. He then earned his MA in European History from Western Connecticut State University and his Doctorate in Educational Leadership and Policy from Drexel University. Greg continues to research, write, and present on staffing models in American boarding schools. His work has been featured in the National Association of Independent Schools magazine. Greg is a regular presenter at the annual The Association of Boarding Schools Conference. Greg has also been a guest on the Enrollment Management Association's podcast several times and has contributed to The Trustees Letter on two occasions. Greg serves on the advisory board for the Independent School MA program at Mount Holyoke College. Greg currently serves as the Humanities Chair at Vermont Academy.