Beginning with the 2026–2027 school year, Cannon School is seeking a dynamic and mission-aligned leader to serve as our next Head of Upper School. As a key member of the School’s Leadership Team, the Head of Upper School partners with the Head of School and fellow leaders to strengthen and uphold Cannon’s culture while guiding the strategic direction of Grades 9–12.

The Head of Upper School leads all Upper School educators in designing a growth-oriented, student-centered program that fosters belonging, supports wellness, and helps students and faculty realize their fullest potential. This leader will shape a compelling vision for the division; develop Upper School academic and community goals; cultivate faculty and staff through coaching, evaluation, and professional development; and partner closely with families, students, and colleagues to support student well-being and success.

Key responsibilities include curriculum leadership; supervision of key divisional leaders; partnership with Counseling and Learning Support; divisional operations management; and collaboration with Admission, Human Resources, Marketing & Communications, Athletics, and families to support a vibrant, inclusive, and mission-aligned Upper School experience.

The ideal candidate is a relationship-driven educational leader with strong communication skills, deep understanding of student development, demonstrated experience leading faculty and program growth, and a commitment to fostering an inclusive and thriving Upper School community.

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.

Cannon School seeks a dedicated and enthusiastic educator to serve as a long-term substitute teacher for Upper School Anatomy and Marine Science classes. This temporary position begins in April 2026 and is ideal for someone passionate about the biological sciences and eager to work with high school seniors.

The successful candidate will inspire curiosity and critical thinking through engaging, rigorous instruction and collaborate with colleagues to support students during this meaningful final chapter of their Cannon journey.

A bachelor’s degree in biology, marine science, or a related field is preferred, as is prior teaching experience.

We are seeking an energetic, creative teacher for Spanish for grades 5-8. This is a long-term substitute position for the third trimester of the 2025 - 2026 shool year. Successful candidates will have personal skills to work flexibly and adaptably with students within this age range.  The Spanish teacher is a member of the Middle School World Languages team and reports to the Head of Middle School. The curriculum for these classes offers both structure and freedom for the teacher. Cannon School welcomes candidates of diverse backgrounds.

We are currently seeking candidates for our Transportation Department. The ideal candidate will have a: valid CDL license with a P&S endorsement, prior driving experience, will be flexible, a team player and enjoy working with children. This candidate will also possess the qualities inherent in our core values of courage, teamwork, respect, integrity, passion and kindness.

Cannon School is looking for a committed, energetic, and knowledgeable middle school baseball head coach that can develop all players from beginners, to experienced players at each position. This position requires the coach to be an integral part of our culture, to provide a high level of energy and engagement with our players and coaches, to be a skilled communicator, as well as have the ability to develop the skills of all players. As part of the responsibilities, it is important you are able to communicate with parents, providing them with updates to schedules, etc. as well as sending out a weekly email.

The position of Middle School Assistant Baseball Coach is also currently available.

This is a seasonal stipend position. Practice times typically occur after school between the hours of 2:45pm-4:15pm with games typically starting at 4:30pm and ending around 6:00pm