Suffield Academy Announces Next Head Of School After Nationwide Search

SUFFIELD, CT — Suffield Academy has named its next Head of School following a nationwide search, the school announced.

The school unanimously approved Casey Hagerman Bobo as Suffield Academy’s next Head of School. She will begin the role on July 1, 2027, following a planned transition year.

Bobo currently serves as Assistant Head of School at Dexter Southfield School in Brookline, Massachusetts. Her career includes leadership roles at Belmont Hill, Brooks School, The New School, and The Hockaday School, as well as experience as a teacher, coach, advisor, college counselor, and admissions professional.

According to the school, the search attracted 11 finalists from across the country. Trustees said Bobo stood out for her authenticity, communication skills, and passion for independent schools.

Bobo grew up on the Deerfield Academy campus, where her parents were faculty members, and later attended The Hotchkiss School and Dartmouth College, where she was a scholar-athlete. She is the mother of three adult sons. Her husband of 28 years, Mike Bobo, passed away in 2024.

As part of the transition, Bobo will spend the 2026–27 academic year working alongside the current Head of School, Charlie Cahn. School leaders said the yearlong overlap is intended to ensure continuity for students, families, faculty, and staff.

“I am very honored, humbled, and excited about joining the Suffield Academy family,” Bobo said in a statement. “I am excited to learn from Charlie next year and then help lead Suffield forward.”