Director of Enrollment Management

Middlebury, CT

Westover School

Middlebury, Connecticut

Director of Enrollment Management

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. With extensive academic offerings, including the Women in Science and Engineering program and robust visual and 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.


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%

Total financial aid: $4.6M 

Campus size: 146 Acres

Grades: 9-12 

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

Learn More 

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

School Website

School History

Belonging and Justice

Core Values

School Profile

PositionWestover is seeking a Director of Enrollment Management to partner with the Head of School to build enrollment solutions that advance the school’s mission in order to connect great students and families with Westover. The Director of Enrollment Management is responsible for the strategic and operational components of enrollment, including marketing and recruitment of new families, tuition and financial aid strategy, selection and onboarding of new students, and retention and reenrollment programming. This is a twelve-month position starting July 1, 2024 that reports directly to the Head of School and is a member of Westover’s senior team, overseeing a dynamic and engaged admissions team of five staff members. They work in close collaboration with the Director of Strategic Communications, Chief Finance and Operations Officer, Chief Development Officer, and members of the senior team to support strategic enrollment efforts in support of a diverse and inclusive school community.  

The Director of Enrollment Management is responsible for developing a comprehensive enrollment plan that: centers the school’s Vision for Belonging and Justice; identifies target day-student, domestic boarding-student, and international boarding-student audiences; elevates the school’s value proposition; engages research-based data driven decision making; creates strong marketing and communications channels; and measures and analyzes results. They are expected to create an enrollment management infrastructure that builds on the existing strengths of the admission office while further developing a school-wide enrollment management mindset. The Director of Enrollment Management is attentive to demographics, expanding the footprint of the Westover’s market and the school’s market presence in all its manifestations. 

As one of the school’s most visible spokesperson, the Director of Enrollment Management represents Westover School to all constituents.

About the Head of School

Polly Oppmann Fredlund is Westover’s eighth Head of School. She is an independent school leader with over twenty-five years of experience working in schools and, prior to Westover, served as the Assistant Head of School for Community Engagement at The Bush School in Seattle, Washington.

Over her time in schools, Polly has served as an Assistant Head of School, Director of Admissions and Financial Aid, Assistant Director of Upper School, English teacher, coach, outdoor leader, and advisor. 

Polly’s background in educational leadership includes extensive experience in girls’ schools, enrollment management, and community building. She values the critical partnership between the Head of School and Director of Enrollment Management and has served as a mentor and champion for admissions leaders in her schools and beyond around this mission critical work. A unique opportunity to partner with a Head of School with a deep-care and robust network who will support, value, and elevate the work of the admissions team.

Polly has also worked at her alma mater Hathaway Brown School (Shaker Heights, OH), National Cathedral School (Washington, DC), and Forest Ridge (Seattle, WA). She is a life-long learner and athlete who enjoys reading, getting outdoors, running, and traveling to destinations new and familiar. She lives on campus at Westover with her family, husband Camron, two daughters Sigrid and Louisa, and their pack of three energetic dogs.

Duties and Responsibilities

  • Provides leadership in enrollment management, which includes admission, marketing, and recruitment and directs the process of attracting, enrolling, and retaining students at Westover.

  • Sets annual enrollment and admission goals, in accordance with the school’s mission to promote economic, racial, and ethnic diversity in the student body, based on enrollment goals set by Head of School and the Board of Trustees.

  • Organizes and administers the school’s financial aid program and budget in conjunction with the chief financial officer.

  • Manages new student enrollment and assists with the reenrollment of current students in close connection with the division heads and business office.

  • Understands and informs the senior team, admission staff and community about research and demographics and admission and enrollment trends, ensuring that changes and challenges are anticipated, understood, and addressed.

  • Formulates an annual admission and enrollment action plan, with specific goals and objectives outlining tactics.

  • Attends Board of Trustee meetings when appropriate, is involved in strategic planning and keeping the Board fully apprised of the school’s enrollment management endeavors.

  • Maintains statistical and trend data related to admission and enrollment, and presents this information to the senior leadership team, board of trustees, and faculty.

  • Manages an admission and financial aid staff of five.

  • In conjunction with the communications office, develops and implements strategic marketing ideas, oversees the management of admission marketing materials. Also oversees the admission’s section of Westover’s web site and social media.

  • Works closely with advancement staff, coordinating an admission volunteer network.

  • Works closely with Associate Head of School and Dean of Student Life on issues relating to academic and student life.

  • Provides training and professional development opportunities for admission staff.

  • Participates as an active member of the senior team.

  • Oversees all on-campus visitation programs-including interviews and spring accepted student programs.

  • Directs the entire application review process, and assigns reading and committee assignments to associates in the office and faculty representatives.

  • Represents the admission office and school at public events, on and off campus.

  • Maintains and encourages relationships with feeder schools, counselors, and consultants.

  • Maintains and enhances the school’s good standing in relevant professional organizations.

  • Is an integral leader for the school community and participates fully in daily community life of the school. 

  • Extends beyond the responsibilities of a job description when the need arises. Assists the Head of School with all other duties as assigned.

Qualifications and Personal Attributes

  • Bachelor’s degree, master’s degree preferred;

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

  • Five years of admission and financial aid experience;

  • Strong commitment to grades 9-12, boarding and day school education;

  • Superior communication skills both written and spoken;

  • Superior interpersonal, organizational, and managerial skills;

  • High energy, flexibility, warmth, and sense of humor;

  • Champion of the School’s mission and core values;

  • Joy and passion in working with adolescents;

  • Demonstrated leadership, engagement in, and a commitment to diversity, equity, and inclusion;

  • Excellent writing, copyediting, organization, planning, and interpersonal skills; ability to work collaboratively with colleagues, and a strong work ethic;

  • Commitment to participation and engagement in the life of the School in order to support, know, and serve the student body;

  • Ability and inclination to collaborate effectively with faculty and staff, alumnae, parents/guardians, and all school constituents;

  • Inclination to respond in a timely fashion with energy and empathy to the needs of constituents.

To Apply

Westover School has retained The Baker Group and Carney, Sandoe & Associates, to assist in the recruitment of Director of Enrollment Management. 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 and thorough résumé of no more than three pages;

  • A writing sample, e.g., a parent communication, newsletter, open house speech, blog, or article;

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

Christine Baker

President, The Baker Group; Practice Leader, Admission & Enrollment Management Practice, Carney, Sandoe & Associates

Jennifer Wong Christensen

Senior Consultant, Carney, Sandoe & Associates

Click here to view the official position announcement PDF

Westover celebrates diversity of all kinds and is committed to creating an inclusive culture built on a foundation of respect for all individuals. The School seeks to hire, develop, and retain talented people from all backgrounds. Individuals from non-traditional backgrounds, historically marginalized or underrepresented groups are strongly encouraged to apply.