Upper School Dean of Students

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