Upper School Dean of Students

Cannon School seeks a collaborative, student-centered educator to serve as our next Upper School Dean of Students. Beginning in the 2026–27 school year, this 11-month role oversees the student experience for one Upper School grade level and plays a key part in shaping community, culture, and leadership within the division. Reporting to the Head of Upper School, the Dean supports daily operations;

leads advisory and student life programming; partners with faculty, families, and student leaders; and helps foster a safe, inclusive, and connected school environment. The Dean may also teach 1–2 classes per year.

Ideal candidates bring strong communication skills, proven leadership experience, and the ability to navigate a dynamic school environment with care, clarity, and professionalism. A bachelor’s degree is required; a master’s degree and a minimum of two years of relevant experience are preferred.