Upper School Director

We are seeking a dynamic educational leader to inspire and guide Windham Woods Upper School, home to approximately 75 exceptional students with mild to moderate learning challenges. We boast a state-of-the-art facility and 250 acres of fields, woods, and trails, providing a unique environment for hands-on, project-based learning. Our students engage in a curriculum that emphasizes real-world application and experiential learning. We are particularly interested in a collaborative and solutions-oriented individual to join our talented administrative team in shaping the upper school program. This position is available to begin immediately. With six years of operational history at WWS, administrators play a crucial role in implementing new policies and procedures. The ideal candidate should possess extensive experience working with upper school students, teachers and administrators, and demonstrate strong organizational, interpersonal, and communication skills. 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 Develop quarterly reports to present to Board of Trustees Faculty & Staff Support faculty and staff as needed, scheduling regular meetings Collaborate with Elementary and Middle School Directors and Assistant Head of School for training, staff development, and formal evaluations Communicate relevant student and programmatic information Meet with MCAS/SAS staff advisors around scheduling, training, and staffing Lead the hiring process for Upper School faculty and staff Coordinate completion and proofreading of trimester progress reports Students 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 readiness In 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 School Cultivate 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 respect Collaborate with public school liaison and school districts who fund students to WWS as needed Consult on the coordination of all-school social events Collaborate with after school coordinator to ensure success of after school program Programs & Curriculum Collaboration 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 differentiated Work with directors and staff to determine scheduling priorities and process Orchestrate upper school scheduling process Parents & Community Maintain frequent, positive, and constructive communication with parents and members of the community Organize and schedule parent conferences Conduct formal and informal parent meetings to provide progress updates Financial Contribute to the development of annual budgets based on program needs Coordinate with the Assistant Head of School and Head of School to ensure all Upper School expenditures are within budget, aligned with school mission and curriculum In Collaboration with WWS Directors, Asst Head of School, Head of School Address human resource-related queries and concerns with Upper School faculty Establish emergency response procedures Ensure 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 vision Collaborate 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 staff Positive, solutions-based attitude Compassion for students with diverse learning needs Understanding of various student learning profiles Strong organizational skills and ability to manage multiple initiatives Ability to jump in, take on responsibilities, follow through with tasks, initiatives, and communication throughout Excellent oral and written communication skills Creative and engaging outlook for students and staff Collaborative approach in management meetings