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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 an Assistant Head of Upper Elementary School, Grades 3-5, to start July 1, 2026. With a current enrollment of 267 students, the Upper Elementary School is housed on the Old Church Road campus.

Position Summary

The Assistant Head of Upper Elementary School (UES) is a key academic and community leader who ensures a developmentally aligned and mission-centered experience for students in Grades 3–5. In close partnership with the Head of Division, this leader advances a culture in which students are known, supported, and challenged, and in which faculty are equipped to grow in their practice and thrive in community.

The Assistant Head serves as a connective bridge between day-to-day divisional life and schoolwide priorities, reinforcing coherence in instructional practice, student experience, and community expectations in alignment with the Portrait of a Learner.

Key Responsibilities Strengthen Coherence and Alignment

+ Support vertical and horizontal alignment across classrooms and grade levels to foster continuity of experience for students.

+ Collaborate on student grouping and placement processes to ensure developmentally appropriate and mission-aligned learning environments.

+ Use academic and SEL data (MAP, reading benchmarks, summative assessments) to inform intervention, enrichment, and instructional reflection.

+ Partner with Lower Elementary, Middle School, and the Assistant Head of School to strengthen curricular alignment across divisions.

+ Partner with Lower Elementary, Middle School, and the Assistant Head of School to  align academic calendar, class lists, cross divisional teacher and course assignments

Support Faculty Growth & Professional Culture

+ Serve as a coaching partner to faculty through observation, reflection, and feedback grounded in shared expectations for practice.

+ Reinforce Responsive Classroom and restorative approaches in classroom community and school culture.

+ Support the supervision, development, and evaluation of co-teachers, including onboarding and mentoring.

+ Help cultivate professional collaboration within and across grade-level teams to build instructional alignment and collegial culture.

Partner in Student Success, Belonging & Wellbeing

+ Lead Student Focus Meetings and collaborate with the Student Support Team to coordinate proactive and responsive interventions.

+ Meet with students and families to address more complex academic, social, or behavioral concerns in partnership with teachers and UES counselor.

+ Maintain a visible presence during the school day and in community programming to support belonging, safety, and joyful engagement.

+ Support divisional programming such as Tiger Time, Tiger Cup, Community Times, 5th grade Student Leadership, and signature UES traditions (Field Day, Birthday Celebrations, Morning announcements, etc).

Operational Stewardship & Division Leadership

+ Serve as acting division lead in the Head of Division’s absence to ensure consistent operation and communication.

+ Provide leadership and guidance for Grade Level Facilitators as they work with their teams.

+ Partner on scheduling, staffing, safety procedures, and readiness planning.

+ Coordinate assessment logistics (including MAP) alongside teachers and the Student Support Team.

+ Coordinate logistics for grade-level newsletter creation and quarterly distribution to families

+ Serve as an accessible and responsive liaison for families, helping to maintain clarity, consistency, and alignment across home and school.

Professional Qualifications

+ Advanced degree in education or a related field, and a demonstrated commitment to ongoing professional learning.

+ Successful classroom teaching experience at the elementary level with a strong understanding of child development and age-appropriate pedagogy.

+ Familiarity with Responsive Classroom, restorative practices, and frameworks that support whole-child development.

+ Experience supporting teacher growth through coaching, mentorship, supervision, or structured feedback processes.

+ Demonstrated ability to use student data to guide instructional decisions and monitor student progress.

+ Experience partnering with families in a school setting, with the ability to foster trust and shared purpose.

+ Strong technology and organizational skills with disciplined follow-through, with the capacity to manage multiple priorities while centering student experience.

Leadership Style & Disposition

+ A relationship-centered leadership style grounded in care, clarity, and high standards.

+ High emotional intelligence with the ability to navigate student, faculty, and family needs with empathy and professionalism.

+ A collaborative, reflective problem-solver who invites perspective and builds shared ownership of solutions.

+ Visible joy in the life of the school and enthusiasm for working with elementary-aged children and the adults who serve them.

+ A growth mindset and a steady, optimistic presence.

+ Excellent written and spoken communication skills, with the ability to maintain confidentiality and generate trust.

+ A commitment to fostering a learning environment where every student is known, included, challenged, and connected to the Portrait of a Learner.

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

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