Online Head of Upper School

🏒 Dwight School · company page
πŸ“ United States
πŸ’° USD 115,000 / annual
πŸ“… Posted Oct 14, 2026 Β· via Himalayas
🏷 Head Of School, School Administration, Education Administrator, Academic Director, Principal, Online Education Leader +3 more
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Position: Head of Upper School (HOUS)

Reports to: Head of Academics and Student Affairs, and Head of School
Salary: $115,000
Direct Reports:
- Heads of Department (in coordination with the Director of Curriculum & Instruction)

Position Overview

The Head of Upper School (HOUS) is responsible for overseeing the Upper School program (Grades 9–12) at Dwight Global, with the ultimate goal of achieving Dwight Global’s mission of igniting the spark of genius in every child. The HOUS works and collaborates with a team, including the Upper School Deans, Curriculum & Instruction, Heads of Department, the Dean of Student Life, the IB DP Coordinator, and Upper School faculty members, as well as with administrators and faculty members within The Dwight School s worldwide network.

This position is remote; the Head of Upper School should anticipate travel to New York City a few times each year.
Responsibilities of the Position
Academic Department Support and Supervision

- Work with the Head of Academics and Student Affairs and the Director of Curriculum & Instruction, overseeing the recruiting, hiring, evaluation, and supervision of faculty (Grades 9–12).

- Collaborate with the Curriculum & Instruction team to oversee the creation, implementation, and ongoing development of the Upper School curriculum, ensuring rigor, innovation, and alignment with school-wide standards.

- Oversee and develop Division and Grade Level meetings that incorporate vertical, horizontal, pastoral, and departmental planning.

- Address and coordinate scheduling and staffing for unique student situations (new class sections, personalized classes, independent studies, etc.).

Pastoral Care, Student Discipline, and Deans

- Work with the Associate Head of Academics and Student Affairs to oversee the Upper Deans

- With the Deans, build a healthy school culture through assemblies, advisories, and other programs that promote belonging, integrity, and leadership.

- Oversee creation and continued improvement of the Upper School Orientation course and parent education programs

- Cultivate an Upper School school culture that values academic honesty, intellectual curiosity, and ethical decision-making. Develop and implement clear expectations and practices around academic integrity, ensuring that students understand the importance of original work, responsible scholarship, and accountability.

- Coordinate Honor Council to maintain fairness, transparency, and integrity across all academic and behavioral processes.

- Manage and implement online proctoring review and disciplinary process for academic honesty infractions

- Manage summer grade recovery process for Upper School students

College Counseling and Post-Secondary Planning

- Collaborate with the Associate Head of Academics and Student Affairs and Director of College Counseling to ensure that each student in Grades 9–12 receives personalized and developmentally appropriate guidance.

- Oversee integration of academic advising and college counseling through joint meetings, workshops, and parent sessions.

- Support the implementation of standardized testing, college readiness programming, and family information sessions.

Accommodations/Quest

- Work with the Head of Quest and Learning Support to oversee accommodations and ensure support for students with learning needs in Grades 9–12.

- Ensure that Quest plans are implemented consistently across academic departments and that faculty are equipped to support students with approved accommodations.

School Authorization and Accreditation

- Work in conjunction with the Head of Academics and Student Affairs on all school accreditation and authorization processes (Cognia, IB, etc.).

- Provide evidence, documentation, and data as required for accreditation and program evaluations related to Grades 9–12.

Other Responsibilities

- Work with the Scheduler to develop the Upper School Schedule.

- Update the Head of School, Head of Academics and Student Affairs regularly on all significant issues in each area of the school under their supervision.

- Participate in admissions programs as needed (e.g., open houses, student interviews, committee reviews).

- Participate in cross-campus projects and worldwide Dwight-Franklin collaborations.

Data Analysis

- With the Curriculum & Instruction team, review all Upper School assessment data (internal and external), including AP, IB, PSAT, and other performance indicators.

- Ensure that data informs curriculum development, personalized learning strategies, and student success planning.

- Work with Heads of Department to use data for reflection, goal-setting, and instructional improvement.

Originally posted on Himalayas

Flights + hotels

This role requires you to be in the United States. If that means relocating or flying in, it is worth checking fares before you commit to a start date.

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