John Ainsley

John serves as Grove’s Dean of Students and On-Call Director, bringing thoughtful leadership, steady presence, and nearly a decade of experience to his work with students and staff. Originally from Quincy, Massachusetts, John joined Grove in 2015 as a Teacher/Counselor and History Teacher. He lived in the dorms for almost three years before being promoted to Residential Administrator in 2017, giving him deep insight into both the academic and residential sides of student life.

John graduated from St. Lawrence University in 2014, where he studied Education and Government and played baseball. He earned his Master’s in Special Education from Southern Connecticut State University in 2018 and is currently pursuing a Master’s in School Administration at the University of Virginia, with an expected graduation in 2026.

Throughout his time at Grove, John has contributed to the school’s evolution in multiple ways—as a history teacher, athletics liaison, and contributor to the redevelopment of staff training and crisis intervention programming. In his current role, he is deeply committed to helping students understand who they are and recognize their potential, regardless of past experiences, while supporting staff growth through collaboration and the occasional well-timed sense of humor.

John met his wife at Grove; she is now a special education teacher at a local middle school. They have two children, Wyatt (4) and Brooke (1). Outside of work, John enjoys watching baseball, playing golf, skiing, and decompressing in his workshop after the demands of everyday life.