Head of School

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THE OPPORTUNITY

The Woodstock Academy, an independent day and boarding, co-educational high school, seeks its next visionary Head of School to lead this thriving, inclusive institution rooted in more than 200 years of tradition and shaped by innovation. Dedicated to developing global citizens and lifelong learners, The Woodstock Academy boasts extensive programs in academics, arts, and athletics, supported by state-of-the-art facilities, enriching clubs, performing arts programs, athletic teams, and opportunities to learn outside the classroom through field trips and travel.

Building on the school’s evolution over the last decade under Head of School Christopher J. Sandford, The Woodstock Academy seeks a leader to partner with its professional Board of Trustees to continue the school’s journey of success and inspiration. This is a unique opportunity to lead a growing educational community that is comprised of students from local sending towns in lieu of a public high school as well as private boarding and day students.

The successful candidate will be an accomplished and strategic educational leader who is passionate about equipping the next generation for future success, and who has the flexibility and acumen to navigate the complexities of an independent town academy.

 

THE WOODSTOCK ACADEMY AT-A-GLANCE

ACADEMIC PROFILE

• 1,060 students in 2024-25
• 15% international boarding students
• 900 local students from 13 towns
• 30 countries and 6 states represented by the student body
• 21 languages spoken on campus
• 230+ course offerings
• 14:1 student-to-faculty ratio
• 92% of faculty hold advanced degrees

 

ACTIVITIES AND CAMPUS LIFE

• 40+ student clubs and honor societies
• 50+ athletic teams
• Nationally recognized Model United Nations program
• Multiple drama performances per year
• 9 music ensembles
• Several travel opportunities available to students every year

 

STUDENT ACHIEVEMENTS

• 99%-100% graduation rate every year
• 85% College matriculation rate
• 3% Military service after graduation
• 12% Trade/career path

 

A RICH HISTORY OF EDUCATIONAL EXCELLENCE

Founded in 1801, The Woodstock Academy is one of the oldest schools in the United States. The key to its long history has been strong community support and an ability to adapt and change with the times.

The Woodstock Academy’s origins trace back to the early 19th century when local leaders, inspired by a 1799 Connecticut legislative act encouraging advanced education, established the school in 1801. The Woodstock Academy was among Connecticut’s first six academies, marking a commitment to educational excellence that has endured for over two centuries.

The Academy’s growth continued through the 19th and 20th centuries, adapting to challenges and expanding facilities. Landmark achievements included the designation of The Woodstock Academy as the public high school for the Town of Woodstock in 1913. Major developments in the latter half of the 20th century, such as the 1965 construction of the Bowen Building and the 1992 comprehensive campus expansion, laid a foundation for academic and extracurricular programs that emphasized inclusivity, community engagement, and innovation. In recent years, the addition of the South Campus in 2017, the establishment of the STEAM Center in 2018, and the renovation of the Academy Building in 2024 have positioned The Woodstock Academy as a leading day and boarding school, committed to preparing students for the future through a rigorous academic curriculum and advanced learning spaces.

 

 

LEADERSHIP PROFILE

The Head of School at The Woodstock Academy, as Chief Executive Officer, will embody a balance of strategic vision and community-centered leadership, guiding the school through continued growth while preserving its mission. The next Head of School will be expected to bring visionary skills, financial acumen, enrollment management expertise, and a commitment to inclusivity with the skills to communicate with diverse constituencies.

 

THE WOODSTOCK ACADEMY HEAD OF SCHOOL WILL BE:

• The Chief Executive Officer of this complex nonprofit organization.
• An accomplished leader in education with a track record of professional mentorship, building strong teams and maintaining academic excellence.
• A visionary and forward-thinking strategist capable of guiding the school through its next phase of development, honoring its rich history while embracing a vision for the future.
• A skilled financial steward with analytical insight and acumen prepared to oversee budgets, fundraising, enrollment, union partnerships, and investments.
• A compelling communicator who fosters trust and collaboration among faculty, staff, students, and families.
• A culturally aware and empathetic leader dedicated to fostering a diverse, inclusive community, providing all students with meaningful and accessible educational opportunities.
• A warm, visible, and accessible presence -– on campus and in the community.

 

RESPONSIBILITY FOCUS:

OPPORTUNITIES AND CHALLENGES FOR THE NEXT HEAD OF SCHOOL

The next Head of School will be responsible for ensuring The Woodstock Academy’s excellence in education continues and endures while providing the financial management and direction to provide the resources to make that success possible.

• Strengthening relationships across various constituencies and addressing the complexities of independent town academy dynamics.
• Addressing deferred campus maintenance to ensure a safe, inspiring learning environment, quality residential domiciles and polishing areas in need of a fresh look.
• Expanding the residential life program to enhance the boarding experience and increase boarding enrollment.
• Enhancing financial stability through the strategic fundraising efforts of The Woodstock Academy Foundation.
• Supporting faculty onboarding, training, and professional development, ensuring academic excellence.
• Building the support staff as the school evolves to its next level.
• Strengthening and broadening enrollment management, including day students and domestic and international boarding opportunities.
• Leading the development of The Woodstock Academy’s next strategic plan.

 

SKILLS AND ATTRIBUTES OF A SUCCESSFUL CANDIDATE

THE IDEAL CANDIDATE WILL DEMONSTRATE:

• Visionary and strategic planning capabilities.
• A student-centered approach to leadership.
• A commitment to inclusivity and cultural sensitivity.
• A history of loyal service to institutions at which they have served.
• Proven ability to sustain relationships with key internal and external constituencies
• Effective communication and political acumen.
• A macro-management approach, empowering staff and faculty while providing strategic oversight and support.
• Skills as an outstanding mentor and a personal investment in the continued growth of faculty and staff.
• Approachability, directness, humor, as well as an on-campus and local community presence.

QUALIFICATIONS

• Significant leadership experience in education.
• Strong decision-making skills, financial acumen, and strategic planning experience.
• Global outlook with experience managing diverse employee groups.
• Experience working with a governing board.
• Proven fundraising and budget management abilities and fundraising experience; capital campaign experience preferred.
• Track record of successfully identifying, mentoring, and developing new leaders to ensure continuity and long-term institutional stability.
• Qualifications for Connecticut’s 093 Certification Path - read more here. 
• Commitment to local residency and loyal service to the school’s mission.