Dean of Students, Upper School

The Bolles School, a Northeast Florida independent college preparatory day and boarding school founded in 1933, has long been known as one of the top educational institutions in the country. This prominence is rooted in an enduring All Things Possible™ mindset that encourages students to discover their strengths and excel in them throughout their Bolles experience. The Bolles School motto is ‘pursuing excellence through integrity, courage and compassion.’  Bolles proudly employs over 400 full time, part time and seasonal faculty, staff, coaches, and administrators.  Serving over 1,700 students on our four campuses in Grades Pre-K through 12, Bolles has a rich history in tradition and achievement that extends to our hiring practices and the professionalism and respect garnered in the independent school community.

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<