Shady Side Academy is thrilled to announce the appointment of Andrew Prince as the next Head of Senior School, effective July 1, 2025. With a reputation as an inspiring and levelheaded leader, Andrew brings a wealth of experience and a track record of fostering trust, confidence, and academic achievement at some of the nation’s most distinguished independent schools.

Andrew shared his excitement about joining Shady Side, stating, “I am thrilled to join the Shady Side Academy community because I deeply believe in its mission. A student who thinks expansively, acts ethically, and leads responsibly is well prepared to thrive in today’s world. Moreover, the warmth and kindness of the Shady Side community are palpable, and I could not imagine a better place to work and live with my family. I sincerely cannot wait to get started!”

Currently serving as Head of Upper School at Collegiate School in New York City, Andrew oversees academic programming, student life, and faculty development at the prestigious K-12 boys’ independent school. Collegiate’s Head of School, Bodie Brizendine, expressed her admiration for Andrew’s leadership in a message to her community:

“Andrew holds an unstinting commitment to the students and their intellectual and moral growth; he knows every student by name and they know his door is always open to them. As difficult as it is to hold a room of 200+ students at attention, Andrew’s presence always carries the gravitas necessary to do so. No matter the situation, Andrew always exudes joy and pleasure and his presence at Collegiate will be greatly missed.”

Before joining Collegiate, Andrew held senior leadership roles at the Taft School, a coeducational boarding school for grades 9–12 in Watertown, Connecticut. In addition to serving as a History and Government teacher, dorm advisor, and football and head baseball coach, Andrew guided Taft’s baseball team to a 16-1 season and Founders League Championship title in 2019, earning recognition as the New England Journal Baseball Coach of the Year.

Andrew holds a B.A. in Government from Harvard University, where he was a member of the Crimson Division I baseball team. He also earned a master’s degree in Private School Leadership from Columbia University’s Klingenstein Center.

The selection of Andrew Prince follows a national search, conducted in partnership with Carney, Sandoe & Associates, which produced a highly competitive candidate pool. The process involved input from a search committee, parent advisory group, and members of the Shady Side community who engaged with finalists during their campus visits. The candidates were consistently impressed by the community’s kindness, the richness of its history, and the strategic vision guiding its future.

Andrew’s appointment reinforces Shady Side Academy’s commitment to excellence in leadership and education. His passion for independent schools and dedication to students’ intellectual and moral growth will undoubtedly enrich the Senior School experience.

As Andrew prepares to join the Shady Side community, we also welcome his wife, Courtney, and their young sons, Austin (3) and Archie (2), to Pittsburgh. With the Academy’s hallmark hospitality and support, they are sure to feel at home in no time.

The future at Shady Side Academy remains bright, and we look forward to embarking on this new chapter under Andrew’s leadership.