EDUCATION

B.A. Political Science - Speech Communication, Wake Forest University

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Greg Angilly brings more than 25 years of experience in independent schools, athletics, leadership development, and community building to his role as Head of School at The Mountain School of Winhall.

Greg’s career in education began in San Francisco, where he discovered the power of athletics as a vehicle for mentorship, character development, teamwork, and belonging. As the Head Lacrosse Coach at St. Ignatius College Preparatory, Greg and his coaching staff helped transform the program from one of regional excellence into a nationally recognized program consistently ranked among the nation’s top 25 high school lacrosse programs. His work as a coach was recognized by US Lacrosse and the Northern California Chapter of US Lacrosse for his commitment to student-athletes, coaching excellence, and the growth of the sport.

From coaching, Greg’s path expanded into school leadership roles, including Director of Athletics and Director of Student Life at independent schools in California and Virginia. Throughout his career, he has focused on creating environments where students are known, challenged, supported, and encouraged to discover their passions. His work has centered on experiential learning, character development, belonging, and helping students build confidence through meaningful experiences.

Before joining The Mountain School, Greg served as Head of School at Virginia Beach Friends School, where he led significant enrollment growth, strengthened community partnerships, expanded experiential learning opportunities, and advanced initiatives that connected students more deeply to the world around them.

Greg’s background also includes entrepreneurship, real estate, and community engagement, experiences that have shaped his belief that learning happens everywhere — through exploration, collaboration, creativity, stewardship, and hands-on problem solving. He believes some of the most powerful lessons come when students are given opportunities to lead, take risks, and contribute to something larger than themselves.

At The Mountain School, Greg is excited to build on the school’s strong foundation while honoring its traditions and fostering the next chapter of a close-knit community. He is especially drawn to the opportunity to embrace Vermont as an extension of the classroom and to create experiences where students learn by doing, leading, and contributing.

Greg holds a bachelor’s degree in Political Science and Speech Communication from Wake Forest University. Outside of school, Greg enjoys the outdoors, athletics, music, and spending time with his family. He especially enjoys cheering on his daughter Leah at Vanderbilt University as she pursues her theatrical passions and spending time in the left field bleachers at Rhodes College supporting his son Cooper and the Lynx baseball team.