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Head of Upper School, Grades 9-12
Head of Upper School, Grades 9-12Greenwich Country Day School • Greenwich, CT, United States
Head of Upper School, Grades 9-12

Head of Upper School, Grades 9-12

Greenwich Country Day School • Greenwich, CT, United States
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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
  • 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

    The following questions are entirely optional. To comply with government Equal Employment Opportunity and / or Affirmative Action reporting regulations, we are requesting (but NOT requiring) that you enter this personal data. This information will not be used in connection with any employment decisions, and will be used solely as permitted by state and federal law. Your voluntary cooperation would be appreciated. Learn more .

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    Head Of School • Greenwich, CT, United States

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