Greenwich Country Day School is an independent, co-educational day school with a current enrollment of over 1400 students in grades N-12, and a faculty and staff of over 350. The original Old Church Road campus is home to grades N-8. The High School, established in 2019, is located less than two miles away on Stanwich Road. Founded in 1926, Greenwich Country Day School is a family school where innovative teaching is encouraged as teachers model and foster a love of learning, challenge and inspire children toward academic excellence, and cultivate students’ interests and talents outside of the classroom. We value purposeful and personal learning in a joyful environment, with emphasis on the development of character, creativity, and a sense of personal value, along with strong academic skills. GCDS is committed to graduating ethical, confident leaders who possess a strong sense of purpose.

Greenwich Country Day School seeks a Head of Upper School, Grades 9-12, to begin July 1, 2026. The Upper School currently enrolls approximately 460 students in Grades 9–12. The Head of Upper School is a member of the Senior Administrative Team and is responsible for the strategic leadership, daily operation, and overall programmatic direction of the Upper School.

Key Responsibilities

Academic Leadership & Program Coherence

• Oversee the design, articulation, and alignment of the Upper School academic program.
• Supervise and develop Program Leads to build strong instructional leadership across disciplines.
• Approve new courses and program initiatives; partner with Program Leads to pursue research-based innovation.
• Maintain a visible instructional presence through classroom engagement and the teaching of one course.
• Promote a culture where intellectual rigor and joyful engagement are mutually reinforcing in the classroom experience.
• Use student performance data and trends to inform program adjustments and resource allocation.

Faculty Growth & Professional Culture

• Recruit, supervise, onboard, and evaluate faculty using the GCDS growth goal process.
• Foster a collaborative and reflective professional culture grounded in trust, teamwork, and continuous improvement.
• Provide coaching and feedback to deepen instructional practice and support faculty leadership.
• Strengthen cross-disciplinary collaboration and nurture faculty leadership capacity

Student Experience, Belonging & Wellbeing

• Partner with the Dean of Student Life to ensure a culture of safety, accountability, connection, and care.
• Build strong relationships with students and remain a visible, accessible leader in daily school life.
• Collaborate with the Director of Wellness and Student Support, Learning Specialists, and Advisors to ensure responsive systems of student support.
• Reinforce Upper School structures and routines that promote character, agency, and community participation.

Partnership with College Counseling & Admissions

• Align academic pathways and advising structures to complement college counseling guidance.
• Work closely with the Admissions Office to articulate the vision of the Upper School and support mission-aligned enrollment.
• Represent the division at admissions, college counseling, and family engagement events.

Operational & Community Leadership

• Oversee day-to-day operations of the Upper School, including scheduling and faculty coordination, in partnership with the Assistant Head of Division.
• Communicate proactively with families to promote transparency, understanding, and a strong home–school partnership.
• Represent the Upper School internally and externally, reinforcing a “one school” identity.
• Contribute to strategic planning, accreditation work, and institutional stewardship as a member of the Senior Administrative Team.

Qualifications & Leadership Attributes

Professional Qualifications

• A Master’s degree or higher in education or a related field.
• A minimum of five years of senior leadership experience in an Upper School or equivalent institutional setting.
• Demonstrated success supervising and developing faculty, including instructional leaders/Program Leads.
• Experience approving or managing curricular design, implementation, and innovation at the high school level.
• Proven ability to cultivate and leverage external partnerships with higher education institutions and industry or community organizations to enhance student learning in a project-based environment..
• Strong capacity for data-informed decision-making and systems-level thinking.

Leadership Style & Disposition

• A strategic, student-centered leader who connects vision with practical execution.
• A relational educator who builds trust through clarity, follow-through, and presence.
• An adaptive thinker with high emotional intelligence and the ability to navigate complex situations with poise and integrity.
• A culture-builder who models optimism, professionalism, and deep respect for adolescent learning and development.
• A visible joy in the work of schools and belief in the limitless potential of young people.

Interested candidates are invited to use the link provided to submit a cover letter and resume to Raquel Salcedo, Director of Recruiting & Talent