Assistant/Associate Dean for Campus Life & Engagement

Reports to Dean of Students

12-month position, full-time exempt position

The Assistant or Associate Dean of Students for Campus Life and Engagement provides strategic leadership for a comprehensive Community Life Program that supports both the residential and day student experience at Cheshire Academy. This role is central to fostering a vibrant, inclusive, and engaged campus community aligned with the school’s mission, values, and commitment to belonging.

As a member of the Program Leadership Team, the Assistant/Associate Dean is a visible campus leader who collaborates closely with students, faculty, staff, and families. The position requires residence on campus and active participation in the daily life of the school.

The level of appointment (Assistant or Associate) will be determined based on experience and qualifications.

PRIMARY RESPONSIBILITIES:

Community Building and Student Experience

• Foster a strong sense of community and belonging across residential and day student populations.
• Serve as the Community Life Team lead for boarding/day integration initiatives.
• Supervise and support campus life leaders to ensure a safe, welcoming, and engaging environment.
• Collaborate with the Dean of Students and Associate Dean for Campus Culture and Belonging on student discipline, including support of the Citizenship Committee.
• Partner with the Student Leadership Advisory Team to implement student leadership development programs.
• Oversee the Student Life curriculum in collaboration with the Student Activities Coordinator.
• Design and implement new student and residential orientation programs.
• Lead the planning of major community events and a robust weekend activity program.
• Oversee club programming and student engagement initiatives.

Campus Life and Residential Management

• Partner with Admissions on enrollment strategy, including boarding/day and domestic/international balance.
• Implement transparent systems for the selection, support, and evaluation of Dorm Heads.
• Lead onboarding and mentoring for new residential faculty.
• Collaborate with Human Resources, Director of Facilities, and Head of School on residential faculty housing and move-in processes.
• Define, assign, and supervise evening and weekend duty teams, including oversight of the Administrator on Duty (AOD) program.
• Facilitate training, support, and evaluation processes for residential faculty.
• Facilitate meetings with boarding students and families to discuss school policies and procedures.
• Oversee student housing assignments, move-in, and move-out processes.
• Supervise the residential discipline system and prefect programs.
• Manage individual dorm budgets and the overall Residential Life budget.
• Oversee the use of Orah as it pertains to the creation and monitoring of passes and train all faculty on proper use of the Orah student management system.
• Collaborate with the International Student Affairs Coordinator to plan and execute the residential program for Thanksgiving and Spring Break.
• Oversee student and faculty campus move-outs as well as summer storage, fridge rental, and dorm clean-outs.

OTHER RESPONSIBILITIES:

• Maintain an active and visible presence across campus.
• Collaborate across departments to reinforce community culture and expectations.
• Participate in professional development and contribute to student experience initiatives.
• Serve on the Safety Committee and coordinate with Facilities regarding residential spaces.
• Serve as an advisor or co-advisor and may be assigned additional responsibilities by the Dean of Students or the Head of School.
• Contribute to policy development and annual updates to the Student & Family Handbook.
• Communicate clearly and consistently with students, families, faculty, and administrators.
• Track and analyze student engagement data to inform programming and support.
• Serve as Administrator on Duty on a rotating weekend team.
• Perform other duties as assigned by the Head of School.

Salary and benefits are competitive. Candidates must be able to pass a criminal background check.

Must be eligible to work in the U.S. to be considered.

EDUCATION AND EXPERIENCE

• Bachelor’s degree required; master’s degree preferred.
• Experience working in a boarding school environment as residential faculty required.
• Teaching experience and co-curricular leadership preferred.
• Demonstrated ability to manage people and complex interpersonal dynamics.
• Clear commitment to belonging, inclusion, and community building.

SKILLS AND ABILITIES

• High ethical standards, discretion, and professionalism.
• Strong interpersonal skills, approachability, and a sense of humor.
• Collaborative and innovative problem-solver.
• Ability to manage complex schedules and multiple priorities.
• Exceptional organizational skills and attention to detail.
• Excellent written, verbal, and conflict-resolution communication skills.
• Proven ability to build effective relationships with students, colleagues, and families.