Career Center

Head of School

July 1, 2023

Westover School invites nominations and applications for a passionate, innovative, and thoughtful educational leader to serve as Head of School effective July 1, 2023. 

Westover is an independent college-preparatory day and boarding school for girls located in Middlebury, Connecticut. Serving students in grades 9-12, Westover prides itself on challenging smart, motivated girls to become confident, connected women. Twenty-two percent of the roughly 190 Westover students identify as students of color, and 63% live on campus. Westover students hail from 14 states and 17 countries.

Westover empowers young women to lead lives of consequence. It is a school where girls are comfortable taking risks and where they feel completely free to be themselves and let others do the same. Westover is committed to their core values of strength of character, women’s empowerment, passion for learning, and community.

Westover prides itself on providing every student with a robust liberal arts education, and a range of opportunities to explore her interests more deeply through a pioneering engineering or business program, an extensive arts curriculum, and a competitive athletics program. Innovative programs such as WISE (Women in Science and Engineering), IIG (Invest in Girls), and Independent Senior Projects allow students to pursue specific interests while preparing for college and beyond.

Westover is a place where girls have the desire and the opportunity to connect with each other, with the adults on campus, and with the broader world around them. The Campus Life program has been carefully designed to foster connection, allowing each girl to build a sense of self while she develops lifelong friendships and interests.

Westover seeks to unite their community in support of equity and justice, and make the School a model of inclusivity. They strive to cultivate curiosity in students about who they are and about their experiences both in the community and in the wider world. Westover ensures that no member of the community has to hide who they are. They encourage, appreciate, and celebrate different opinions, traditions, and experiences. They nurture a student’s courage to step outside of her comfort zone and help students find ways to support each other. Additionally, they recognize their responsibility to create a multicultural learning environment that reflects the larger community and the world.

An ideal candidate for the Head of School will demonstrate the following:

• Exceptional senior level management experience at an independent school
• Alignment with Westover’s mission and vision
• Excellent listening, verbal/ written communication, and public speaking skills
• Ability to build community with a focus on healthy and positive relationships
• A commitment to DEI, social justice, and belonging that is inclusive and responsive
• A proven ability to hire and retain strong and diverse faculty and staff
• Ability to lead, cultivate, and encourage the School’s senior administrative team, faculty, and staff 
• An appreciation for and understanding of a boarding school environment
• Dedication to collaboration, transparency, and accountability as a leader
• Foster robust engagement and partnerships with the wider Westover community, including current and prospective families and alumnae of the School
• Ability to collaborate and communicate positively and effectively with the Board of Trustees

Westover’s Head of School will report directly to the Board of Trustees and will work collaboratively with a passionate and dedicated community. Building upon a strong foundation rooted in a commitment to the development of young women, the new Head of School will work in partnership with a strong and dedicated leadership team, as well as an extraordinary, passionate, and committed faculty. The successful candidate will demonstrate a deep commitment to all-girls independent school education.

Westover School’s Search Committee is accepting applications now. For best consideration, please send all nominations and applications (a resumé and cover letter) via email to WestoverHOS@StorbeckSearch.com: 

For more information, please visit Westover School at www.westoverschool.org. 

Westover School is an Equal Opportunity employer that does not discriminate on the basis of actual or perceived race, creed, color, religion, alienage or national origin, ancestry, citizenship status, age, intellectual or physical disability, sex, marital status, veteran status, sexual orientation, transgender identity or status, genetic information, or any other characteristic protected by applicable federal, state or local laws. Administrators must be familiar with this policy with respect to recruitment, hiring, placement, promotion, transfer, training, compensation, benefits, employee activities and general treatment during employment.