Associate Head of School

Middlebury, CT

Westover School

Middlebury, Connecticut

Associate Head of School

Start Date: July 2024


Westover School is a girls-centered boarding and day school where smart, motivated students become confident, connected adults. The School is committed to providing a college preparatory education in a small community atmosphere emphasizing student-adult interaction. Through program and faculty, Westover endeavors to develop in each student the confidence and strength to shape their own life. Westover is a school where students are free to take risks, learn from their mistakes, be themselves, and let others do the same. 

Founded by Mary Robbins Hillard in 1909 and designed by one of America’s first women architects, Theodate Pope Riddle, Westover empowers young women to lead lives of consequence and is committed to its four core values: fostering strength of character, women’s empowerment, passion for learning, and community. As suggested by the school motto, To Think To Do To Be, these values are not limited to the classroom, they extend to all aspects of a student’s time on campus. Westover’s Vision for Belonging and Justice is the school’s north star, fostering a culture where every member is engaged, valued, and respected.

The Westover community is grounded in the recognition of the importance of relationships and a solid sense of support in the growth and development of young people. There is a tangible sense of home that surrounds the Westover experience: a multilevel “square” with classrooms and academic learning on the ground floor, residential and the heart of the emotional connections on the upper floors, and sunlight, safety and sanctuary found within its courtyard in the center. The majority of faculty live on campus or in close proximity to the school, providing students’ access to their mentors, teachers, coaches, and confidants. The levels of trust and connection built through the different elements of the school is palpable.

Programmatically, with extensive academic offerings, including the performing arts offerings, complemented by afternoon athletics and activities, student-run clubs, and intentional affinity spaces, Westover cultivates innate curiosity into an enduring love of learning that serves students long after they graduate. Through Westover’s signature programs of Women in Science and Engineering (WISE), Rasin Center for Global Justice, and Invest In Girls, Westover students have the opportunities to explore the important landscape of science, technology, finance and social justice in and out of the classroom Students leave with a strong sense of agency and curiosity about the world. 

Following the strains of the intersecting challenges of COVID, racial reckoning, global tensions, and adult transitions in the school, there has been a sense of drift that the current adult community is eager to address. The bones of the academic program are strong, and the faculty are excited to be able to take a fresh look at what traditional aspects of the program need to be built upon, and what opportunities are ahead to refuse and design to excellence. 

The Associate Head of School (AHOS) will enter under a dynamic, engaging, creative Head of School, Polly Fredlund. The AHOS will be charged with the mission critical work of community building and helping the School to refocus and articulate the critical elements of its academic identity, building connections with the broader residential and student life program. They will work closely with other academic and school leaders across the educational program to coordinate the curricular, co-curricular, and operational goals, encouraging departments to consider new ways of understanding their interconnectedness by providing the frame to support and grow the program.

The AHOS will also work closely on larger school structure and system questions around strategic initiatives, providing thought leadership and support to the Head of School on long-term planning, impacting all aspects of the schools’ restoration and growth.  This is an exciting opportunity for an ambitious, creative educator to innovate educational programming and organizational change by marrying community building with the best of traditional pedagogy and current educational design.  The AHOS will champion the school’s pursuit to further define a robust educational identity by combining long-standing and proven tradition with new ideas in order to create the new iteration of a strong school.


Westover School empowers young women to lead lives of consequence.

At a Glance

Established: 1909

Enrollment: 150 

Total Full and Part-time Faculty: 38 full-time, 17 part-time faculty

Students of color: 66% 

Day Students: 33%

International Boarding: 33%

Domestic Boarding: 33%

Student/teacher ratio: 4:1

Financial aid awarded: $4.6M 

Campus size: 146 Acres

Grades: 9-12 

Total financial aid: $4.5M

Endowment Value: $62M

Motto: Cogitare Agere Esse (To Think To Do To Be)

Academic Consortiums: NAIS, CAIS, CSEE, One Schoolhouse, NCGS, TABS, NEASC, Small Boarding School Association, Business Association of Housatonic Schools, The Leader Network

Opportunities and Challenges

The Associate Head of School will play a central role in school leadership and administration of the educational program, bridging curricular, co-curricular, and operational goals at Westover. The Associate Head of School will be a strategic thought partner with the Head of School as well as a highly visible presence in the school, helping to shape the day-to-day implementation of the school’s philosophy, long-term planning, curricular design, and strategic initiatives. The Associate Head will bring a record as an educator and a community builder who has previously served in roles of considerable responsibility.

The Associate Head of School will:

Coordinate the integration of the faculty, staff and student experience across the academic office, student life, and DEIB;

Leverage the strength of the faculty’s knowledge and creativity to reimagine and articulate a shared educational vision for Westover, including the Vision for Belonging and Justice; 

Create cohesion across curricular and co-curricular departments to strengthen program alignment, community, and holistic integrity;

Draw together and further develop the signature programs (WISE, Rasin Center, IIG) to amplify the strength of the academic program;

Partner with external offices to highlight the unique opportunities at Westover in external marketing;

Facilitate the re-accreditation process within the Association of Independent Schools in New England and School's future strategic planning process. Coordinate selection of leadership positions on the internal side of the School;

Lead numerous committees and task forces, including Challenge Success initiative and school partner program task force with the goal of building future-focused, integrated educational program, schedule, and student life experience;

Develop strategies to boost faculty and staff agency and connections;

Work with the academic office, dean of faculty, and human resources in all aspects of managing faculty retention, recruitment, performance review, and professional growth;

Cultivate continued meaningful collaborations between faculty and staff;

Strengthen systems and policies that facilitate effective work;

Design and communicate systems that support employee engagement, expectations, and accountability.

Qualifications and Personal Attributes

A sense of joy and satisfaction in being a member of a community of adults and children; 

Appreciation for girls’ centered education and strong commitment to diversity, equity, and inclusion;

A strategic thinker and adroit implementer, with a systems-based approach to change;

A master teacher with a deep understanding of constructivist pedagogy;

Capacity to build strong relationships with faculty and staff while being comfortable holding them accountable to high standards;

Sophisticated emotional intelligence and multicultural competency;

High levels of self-awareness and a calm demeanor to navigate the complexities and ambiguities of managing change;

Experience in a senior academic leadership position with a proven record of engaging community building along with current educational design to implement organizational change; 

Experience supervising, managing and supporting staff;

A superb communicator, both in writing and as a public speaker;

Advanced degree in educational administration or a related field preferred.

Learn More 

Click on the links below to learn more about Westover School.

School Website

School History

Vision for Belonging and Justice

Core Values

School Profile

About Middlebury, Connecticut

To Apply

Interested and qualified candidates are invited to contact the consultants in confidence. Candidates will ultimately need to submit the following materials as separate PDF documents:

A cover letter expressing their interest in this particular position;

A current résumé;

A list of five professional references with name, relationship, phone number, and email address of each (references will not be contacted without the candidate’s permission) to:

Heather Flewelling

Consultant, Chief Talent Officer

Rice Bryan


Click here to view the official position announcement PDF.