Position Summary

The Dean of Students plays an important role in supporting the academic, social, and personal growth of Upper School students. This position helps foster a positive school culture grounded in respect, accountability, and strong relationships.

The Dean works closely with students, families, faculty, counselors, and staff to support student well-being, uphold community standards, and maintain a safe and inclusive learning environment. The Dean is a visible and active presence on campus and helps shape the overall student experience at Bolles. This position will commence with the 2026-2027 school year.

Essential Functions

• Support and enforce student expectations as outlined in the Student/Parent Handbook
• Oversee student behavior management and partner with faculty, advisors, counselors, and families to support students
• Coordinate disciplinary responses, including matters involving the Discipline Committee
• Serve as a key member of the response team in student-related crisis situations
• Work with the Honor Council and faculty sponsors to uphold and promote the Bolles Honor Code
• Communicate clearly and professionally with students and families regarding behavioral expectations and outcomes
• Partner with counseling and student support teams to provide interventions and support for students in need
• Help promote student leadership, engagement, and a positive campus culture
• Maintain a visible presence throughout campus and at student events
• Help supervise unstructured times including arrival, dismissal, breaks, lunch, and other student gatherings
• Organize and oversee Saturday detentions and student workdays as needed
• Monitor and enforce student parking expectations and follow up on violations
• Support campus safety procedures and emergency response protocols
• Coordinate with the Transportation Department regarding student behavior concerns
• Attend after-school events, activities, and occasional weekend responsibilities as needed
• Partner with academic leadership regarding attendance, student support, and concerns impacting student success

Qualifications

• Bachelor’s degree required; Master’s degree in Education, Counseling, Leadership, or a related field preferred
• Minimum of 5 years of experience working in a high school environment, preferably in student leadership or student support
• Strong interpersonal, communication, and relationship-building skills
• High degree of emotional intelligence, discretion, professionalism, and sound judgment
• Demonstrated understanding of adolescent development, student accountability, conflict resolution, and restorative practices
• Candidates with experience as an athletic coach or with oversight of extracurricular programs are preferred qualifications for the position

General Expectations

• Support and reflect the mission and values of the School
• Build meaningful relationships across the school community
• Promote a culture of respect, inclusion, accountability, and belonging
• Model professionalism, integrity, and ethical behavior
• Maintain appropriate confidentiality regarding student, family, and personnel matters
• Take on additional responsibilities as assigned by the Head of Upper School

Physical Requirements

• Ability to move safely around a large campus and supervise students in a variety of settings
• Ability to stand and walk for extended periods during the school day and at school events
• Ability to lift and carry up to 25 pounds occasionally
• Ability to work evenings and weekends as needed for student supervision and school events
• Capable of responding quickly in emergency situations

About The Bolles School

Bolles proudly employs over 500 full-time, part-time, and seasonal faculty, staff, coaches, and administrators. Serving more than 1,800 students across four campuses in Grades Pre-K through 12, Bolles has a rich history of tradition and achievement that extends to our hiring practices and the professionalism and respect earned within the independent school community.

Connections working at The Bolles School