Head of Upper School

Head of Upper School 

About Charleston Collegiate:

Charleston Collegiate School (CCS) is an independent, co-educational, non-sectarian day school serving students from PS through 12th grade. Situated on a picturesque 30-acre campus of playing fields, wooded trails, and an Outdoor Education Center, CCS is located on Johns Island, just 20 minutes from Charleston’s historic district and the beach resorts of Kiawah and Seabrook Islands.

Founded in 1970, CCS fosters a challenging and supportive learning community that recognizes, nurtures, and challenges its diverse student body. Organized into Lower School (PS-5), Middle School (6-8), and Upper School (9-12), the school’s mission is to empower students through a student-centered approach that emphasizes collaboration, innovation, and individuality. With approximately 410 students, CCS is Charleston’s only independent PS-12 school of its kind, providing a unique education grounded in the pillars of project-based learning, entrepreneurship, arts and creativity, and outdoor education. These foundational elements equip students to become lifelong learners and resilient leaders ready for 21st-century careers.

Job Summary:

Reporting to the Assistant Head of School, the Head of Upper School serves as the primary academic and community leader for Grades 9–12, ensuring an Upper School experience that is safe, learning-filled, and joyfully energized. Leading through collaboration, coaching, cheerleading, and clear communication, the Head of Upper School works closely with peer division heads, members of the school’s extended leadership team, and directly leads the efforts of an Upper School leadership team to advance the mission and vision of the school.

Essential Duties and Responsibilities:

Guarantees a Safe, Learning-Filled, and Joyful Experience
Ensures physical, emotional, and psychological safety; fosters a learning-filled academic program; and promotes a rigorous, real-world, relationship-based, and responsive experience in the Upper School.

Elevates & Enhances Upper School Brand
Through ongoing review of base-level, signature, and pilot offerings (i.e., course catalog, internship/winterim programming, and curricular innovations), the Head of Upper School ensures a competitively viable and differentiated product. (Resource: Upper School Strategic Growth Plan).

Leads People Well
Serves as a collaborator, coach, cheerleader, and communicator for students, colleagues, and families, modeling integrity, empathy, optimism, and professionalism.

Student Experience & Accountability
Oversees student life, wellness, conduct, and community standards, ensuring expectations aligned with core values and productive daily operations are clear, consistent, and developmentally appropriate.

Colleague Leadership & Professional Growth
Recruits, develops, evaluates, and supports Upper School colleagues through coaching, feedback, accountability, and meaningful professional learning.

Academic Vision & Instructional Leadership
In collaboration with the Head of Academics, leads curriculum, instruction, assessment, and academic policies, articulating a learning-filled vision of excellence that balances rigor, choice, and student support.

Leads Upper School Team
Leads and coordinates the Upper School Leadership Team, including the Director of College Counseling, Upper School Counselor, Advisory Program Coordinator, and Student Life Coordinator, ensuring alignment, collaboration, and shared ownership of student success.

Culture & Community Builder
Cultivates a collaborative, inclusive, and growth-oriented culture that strengthens trust, pride, and shared purpose across the Upper School community.

Clear, Proactive Communication
Communicates early, wide, and often, prioritizing transparency and compassion, navigating complexity with clarity, composure, and follow-through.

Performs other duties as assigned or approved by the Assistant Head or Head of School. 

Qualification Requirements

Bachelor’s degree in related field; master’s degree preferred

At least 3 years of independent school leadership experience

Successful track record connecting with, collaborating with, and coaching students, colleagues, and parents in an independent school context.  

An appreciation for the value of diversity in all forms

Outstanding interpersonal skills and a dedication to a high level of confidentiality

Exceptional written and oral communication

Excellent organizational skills

Detail-oriented and able to work collaboratively

Strong work ethic and high level of integrity

Technologically savvy, experienced, and willing

High-energy and enthusiastic about working in an academic atmosphere

For more information and to apply visit www.charlestoncollegiate.org or contact Head of School Andy Gyves at [email protected].