Position Summary

The Dean of Students plays a key role in supporting the academic, social, and personal growth of Upper School students. This position focuses on maintaining a positive school culture, guiding student behavior, and fostering strong relationships across campus. The Dean works closely with students, families, faculty, and staff to uphold community standards and ensure a safe, respectful, and inclusive learning environment. The Dean is a visible and active presence on campus and helps shape the overall student experience at Bolles.

Essential Functions

• Support and enforce student expectations as outlined in the Student/Parent Handbook
• Oversee behavior management and collaborate with faculty, advisors, and counselors to address student conduct and well-being
• Coordinate and follow through on disciplinary matters, including those reviewed by the Discipline Committee
• Lead or assist in responding to student-related crisis situations
• Work with the Honor Council and faculty sponsors to promote and uphold the Bolles Honor Code
• Communicate with students and families regarding behavioral expectations and outcomes
• Organize and oversee Saturday detentions and student workdays as needed
• Partner with counseling and support teams to provide interventions for students in need
• Help supervise unstructured times such as arrival, dismissal, breaks, and lunch
• Monitor and enforce student parking expectations and follow up on violations
• Support safety protocols, including emergency response procedures
• Coordinate with the Transportation Department on student behavior issues
• Attend school events, including athletic contests, as needed to support student engagement
• Work some Saturdays as required for student-related responsibilities

Qualifications

• Bachelor’s degree required; advanced degree or relevant experience preferred
• Strong communication and interpersonal skills
• Experience working with students in an educational setting
• Ability to collaborate with families, faculty, and staff
• Organized and able to manage multiple responsibilities
• Comfortable handling sensitive situations with discretion and good judgment
• Proficient in Microsoft Office and general technology platforms

General Expectations

• Support and reflect the mission and values of The Bolles School: Courage, Integrity, Compassion, and Excellence
• Build meaningful relationships across the school community
• Promote a culture of respect, inclusion, and accountability
• Model professionalism and ethical behavior
• 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 various settings
• Must be able to remain standing and walking for extended periods during the school day and at events
• Must be able to lift and carry up to 25 pounds occasionally
• Ability to work evenings and weekends as needed for student supervision or events
• Capable of responding quickly in emergency situations

About The Bolles School

The Bolles School is a nationally renowned, independent day and boarding School serving over 1,600 students in Pre-K through grade 12 on four campuses in Jacksonville and surrounding communities. A leader in academics, arts, and athletics, the School is firmly rooted in the principles that have characterized its community and traditions for nearly 85 years: pursuing excellence through courage, integrity, and compassion. The vast resources and expert instruction available to students as they explore and hone their individual interests and strengths are embodied in the School’s motto -- All Things Possible -- and students eagerly embrace the myriad of opportunities available to them both in and out of the classroom.

Connections working at The Bolles School