Posted: 14-Feb-26
Location: Hilton Head Island, South Carolina
Type: Full Time
Categories:
Mission Alignment
Hilton Head Preparatory School is a joyful, accepting, and ambitious community where students discover what is great about themselves and the world around them. Our Core Values Scholarship, Community, Integrity, Excellence, and Creativity guide every aspect of teaching and learning. We seek educators whose instruction, character, and leadership naturally reflect these values.
Hilton Head Preparatory School seeks an experienced, student-centered Upper School Dean of Students to join the Upper School leadership team. This individual will work in close partnership with the Head of Upper School to ensure an Upper School experience that is joyful, demanding, supportive, and grounded in Prep’s Mission and Core Values.
The ideal candidate loves high school students, understands their complexity, and is deeply committed to helping them grow into confident, responsible, and compassionate young adults. This is a highly relational role, built on trust, visibility, communication, and follow-through.
Position Overview
The Upper School Dean of Students oversees the day-to-day student experience, including student conduct and co-curricular life, while keeping the Head of Upper School informed and supported. This role allows the Head of Upper School to focus on strategic leadership, academic programming, and faculty development, with confidence that student matters are handled thoughtfully, consistently, and in alignment with Prep’s values.
Key Responsibilities
Student Life & Discipline
- Serve as the primary administrator for student conduct and day-to-day discipline, ensuring consistent application of the Upper School Handbook.
- Inspire students to uphold community expectations and follow through with appropriate consequences when expectations are not met.
- Maintain a visible, approachable presence with students throughout the school day.
- Identify patterns or concerns and communicate them clearly to the Head of Upper School.
Partnership & Communication
- Work as a close, trusted colleague to the Head of Upper School, managing daily student matters while providing regular updates.
- Communicate clearly, promptly, and professionally with students, parents, faculty, and administrators.
- Support faculty in addressing student concerns while reinforcing shared expectations and consistency.
Co-Curricular Integration
- Seamlessly weave co-curricular programs into the fabric of Upper School life.
- Collaborate with faculty, coaches, and activity advisors to support balanced student engagement.
- Promote student involvement, school spirit, and a sense of belonging.
Student Leadership & Governance
- Assist with and support Student Council and Honor Council, helping students understand leadership, integrity, and accountability.
- Guide students through meaningful leadership experiences aligned with Prep’s mission and values.
Culture & Community
- Foster an Upper School culture that balances high expectations with empathy and support.
- Support students through moments of stress, growth, and transition, while reinforcing responsibility and independence.
- Partner with the Upper School team to ensure students feel known, valued, and held to standards.
Qualifications & Personal Attributes
- Bachelor’s degree required; advanced degree preferred.
- Prior experience in student life, dean of students work, administration, or related Upper School leadership roles.
- Deep appreciation for and joy in working with high school-aged students.
- Exceptional interpersonal skills; calm, steady, and fair in moments of challenge.
- Strong organizational skills with the ability to manage multiple student matters.
- A collaborative mindset and commitment to open, transparent communication.
- Alignment with Hilton Head Prep’s Mission and Core Values.
The Upper School Dean of Students plays a vital role in shaping the daily experience of Prep students, helping them learn not only how to succeed, but how to live well in community. This is an opportunity for a talented educator and leader to make a meaningful impact alongside a committed Upper School team.
About Hilton Head Prep
Hilton Head Preparatory School is a leading independent school serving students from 15 months through 12th grade, with approximately 560 students overall and just over 200 in the Upper School. Located within the Sea Pines Resort on Hilton Head Island, Prep offers unparalleled access to natural beauty, a thriving coastal community, and a supportive school environment. The school is entering an exciting period of strategic growth supported by strong leadership and community engagement.
Benefits
- Competitive salary commensurate with experience
- Comprehensive benefits package (health insurance, retirement, PD funding)
- Supportive, collaborative professional culture
Application Process
Interested candidates are invited to submit a cover letter, resume, and contact information for three professional references to Tina Webb-Browning (TWBrowning@hhprep.org). Please include "Upper School Dean of Students" in the subject line.
Deadline for Applications: March 9, 2026
Hilton Head Prep is an equal opportunity employer and does not discriminate based on race, color, religion, gender, sexual orientation, national origin, age, or disability.
We look forward to welcoming a dedicated and enthusiastic Upper School Dean of Students to our team at Hilton Head Prep!