Upper School Director
We are seeking a dynamic educational leader at Windham Woods to inspire and guide the Upper School division, home to approximately 80 exceptional students with mild to moderate learning challenges. This position begins July 1, 2025. WWS boasts a state-of-the-art facility, a vibrant group of experienced faculty members, and a 250 acre campus ideal for hands-on, project-based learning. Our students engage in a curriculum that emphasizes skill development in all subject areas and learning by doing.
We are interested in candidates who are collaborative, solutions-oriented individuals looking to join our talented administrative team in leading the upper school program. The ideal candidate should possess extensive experience working with upper school students, teachers and administrators, and demonstrate strong organizational, interpersonal, and communication skills.
Please email Matt Taffel for more information or to apply : mtaffel@windhamwoods.org
Key Responsibilities :
Managing & Directing
- Oversee the growth and success of 25-30 faculty members on the upper school team
- Address all questions and concerns from relevant parties in a timely and effective manner
- Manage all Upper School Department of Education requirements
Faculty & Staff
Support faculty and staff as needed, scheduling regular meetingsCollaborate with Elementary and Middle School Directors and Assistant Head of School for training, staff development, and formal evaluationsCommunicate relevant student and programmatic informationMeet with MCAS / SAS staff advisors around scheduling, training, and staffingLead the hiring process for Upper School faculty and staffCoordinate completion and proofreading of trimester progress reportsStudents
Work with the Director of Admission to understand individual student learning profiles and assist with placement of students in classes based on learning style, academic skill level, and overall school readinessIn collaboration with the Dean of Students, ensure that all aspects of the Upper School student experience (academic and emotional) are aligned and consistent with the mission of Windham Woods SchoolCultivate and maintain an environment that validates every member of the WWS community (students, staff, families) and promotes an atmosphere of academic success, compassion, acceptance, mutual respectCollaborate with public school liaison and school districts who fund students to WWS as neededConsult on the coordination of all-school social eventsCollaborate with after school coordinator to ensure success of after school programPrograms & Curriculum
Collaborate with other WWS Directors, Assistant Head, and potential Curriculum Coordinator / Department Heads, to ensure that the development and implementation of all aspects of the Upper School programs and curricula are engaging and appropriately differentiatedWork with directors and staff to determine scheduling priorities and processOrchestrate the upper school scheduling processParents & Community
Maintain frequent, positive, and constructive communication with parents and members of the communityOrganize and schedule parent conferencesConduct formal and informal parent meetings to provide progress updatesFinancial
Contribute to the development of annual budgets based on program needsCoordinate with the Assistant Head of School and Head of School to ensure all Upper School expenditures are within budget, aligned with school mission and curriculumIn Collaboration with WWS Directors, Asst Head of School, & Head of School
Address human resource-related queries and concerns with Upper School facultyHelp establish emergency response proceduresEnsure compliance with state and federal laws and regulations.Continuously review and refine the vision of WWS and ensure that all actions taken by employees and greater WWS community are designed to achieve that visionCollaborate with the Elementary and Middle School Directors on whole school matters and initiatives (e.g., Development of School Calendar, Daily Schedule, August Training Week, Transition from Middle to Upper School, Ensuring Curriculum Continuity from Middle-Upper, Emergency Response Procedures, etc.)Preferred Candidate Qualities :
Professional approach when interacting with students, families, and staffPositive, solutions-based attitudeCompassion for students with diverse learning needsUnderstanding of various student learning profilesStrong organizational skills and ability to manage multiple initiativesAbility to jump in, take on responsibilities, follow through with tasks, initiatives, and communication throughoutExcellent oral and written communication skillsCreative and engaging outlook for students and staffCollaborative approach in management meetings
