Chief Academic Officer
Start Date: July 1, 2022
Girls, Day & Boarding School Grades 9-12
190 Students
1237 Whittemore Rd. Middlebury, CT

Westover School, a 9-12 day and boarding school for girls in western Connecticut, seeks applicants for the Chief Academic Officer (CAO). This is a full-time, exempt position with a July 2022 start date.

The CAO is a member of the senior administrative team and, as such, works interdependently with all team members toward achieving the strategic priorities of the school. Specific responsibilities fall into four primary areas:

  1. Oversees management, day-to-day operations and budget of the Academic Office;

  2. Leads the pedagogical direction and support in alignment with the Schools mission and vision while championing Westover’s Vision for Belonging and Justice in its integration into academic life;

  3. Provides vision, strategy and planning for the growth and development of the faculty;

  4. Chairs the Curriculum Committee and supervises all Academic Department Heads.

Middlebury, Connecticut

Westover is located in the scenic small town of Middlebury, CT, just west of the city of Waterbury. With a population of approximately 7,800, it is a friendly and warm town with a rural feel while easily accessible to Waterbury (10 minutes away) and New Haven (40 minutes away). New York City is two-hours away by car, though a train is accessible in many towns along the CT shoreline.

Middlebury is on the edge of what is known as the Litchfield Hills of Connecticut, a beautiful and bucolic area popular as a weekend get-away for many New Yorkers.  Upscale shops and restaurants abound, as well as other day and boarding schools such as Taft, The Frederick Gunn School, Rumsey Hall, Fraser Woods Montessori and Washington Montessori. According to Niche.com Middlebury is #40 of 252 CT towns to live in. Despite its small size, Middlebury is home to many wooded hiking paths and the Middlebury Greenway, a 4.5 mile rail-trail. The town also boasts the well-known Quassy Amusement and Water Park, which is located along Lake Quassapaug.

Duties & Responsibilities

  • Support the academic program: curriculum development, course placement, selection and scheduling, supporting students in academic difficulty, and attendance.

  • Serve as a member of the Student Assistant Team, Admissions Committee, Retention Oversight Group, and International Exchange Committee.

  • Manage, conduct and execute the faculty review process

  • Meet regularly with Department Heads and observe every classroom teacher at least once per term.

  • Coordinate in-services and monthly faculty meetings with the Director of Teaching & Learning, Assistant Head of School for Student Life and Chief Strategic Inclusion Officer.

  • Support the Director of Teaching & Learning in allocating Professional Development funding.

  • Advise and assist the Academic Office and advisors in managing parent communication.

  • Manage student violation of the Academic Honesty Policy with the Assistant Head of School for Student Life.

  • Work with the Assistant Head of School for Student Life and Health Center to manage support for students who are off campus for extended periods of time (quarantine, concussions, medical leaves, etc.).

  • Interview Admissions candidates as needed and read files for the Admissions Committee.

  • Partner with the Assistant Head for Student Life in managing the Learning Center which includes oversight of an advisory program that reflects both the social emotional and learning skill development in our students


  • Knowledge of current best practices in pedagogy and curriculum development

  • Appreciation for working with and understanding the developmental stages of girls/young women

  • A commitment to DEIB, acknowledging the need for constant work in creating equity and justice in schools

  • A lifelong learner with an insatiable curiosity about ways to improve upon what’s possible in schools

  • A creative mind that is open to others’ ideas when developing vision and solving problems

  • Investment in the growth and development of others

  • A strong work ethic

  • Excellent oral and written communication skills

  • Collaborative team member and leader, but who can be decisive and directive when the situation calls for it

  • Has at least five years’ experience as an academic leader at the secondary level

  • Has earned a Master’s Degree, or higher, in a related field

How to Apply:

Educators Collaborative (EC) is assisting in this search. To learn more about this opportunity and receive a copy of the EC Candidate Summary and Disclosure Forms, which are needed to complete an application, please contact:

Sally Mixsell at smixsell@educatorscollaborative.com

To submit a completed application, the candidate will provide in a single PDF file:

  • A completed EC Candidate Summary Sheet (see above)

  • A cover letter to the Westover Search Committee

  • A résumé

  • A statement of Educational Philosophy

  • 3-5 references, including phone and email contacts and brief explanation of connection to the candidate

  • A completed EC Disclosure Form (see above)

Listing Date: January 31, 2022