Director of the Westover Fund

Posted on 10/31/2022

Westover School

Middlebury, CT

Westover School is an all-girls’ boarding and day school, grades 9-12 where smart, motivated girls become confident, connected women. We are committed to providing a college preparatory education in a small community atmosphere that emphasizes student-adult interaction. Westover, through program and faculty, endeavors to develop in each student the confidence and strength to shape their own life.

We are EMPOWERING students to be themselves, to make their own choices, and to appreciate diversity, resulting in young adults who find lives of purpose and meaning, who understand they can make a difference and who understand the power of relationships.

  • Do you find joy and passion in fundraising from alumnae and parents?
  • Can you demonstrate success in inspiring someone to take action through philanthropy?
  • Do you believe that donors give to the magic of an idea and want to be a part of a solution?
  • Does your leadership demonstrate engagement in and a commitment to diversity, equity, and inclusion?
  • Do you want to work on a collaborative team?

Westover is seeking dynamic, collaborative, and inclusive applicants for the Director of the Westover Fund position. This is a full-time, 12-month position that reports to the Chief Development Officer and works in close collaboration with the full Alumnae and Development team. This position will ideally begin immediately.

The Director of the Westover Fund provides both strategic insight and daily management of the $1.8+ million Westover Fund. This position is responsible for creating the cadence and content of solicitations and inspiring philanthropy to a wide audience. This position additionally staffs one committee of the Alumnae Board of Governors (the Westover Fund Committee) and collaborates as needed with other committees. Collaboration, teamwork, and a desire to inspire are keys to our success.

Westover is seeking a positive, energetic personality who enjoys fundraising and has a track record of success to bolster this important part of School life. We celebrate diversity of all kinds and are committed to creating an inclusive culture built on a foundation of respect for all individuals. We seek 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.


  • Bachelor’s degree and 5 or more years of experience working within an annual fund or similar role, where solicitation and creating annual calendars are an integral part of the role.
  • Initiative and self-starting capacity, a relationship builder.
  • Demonstrated comfort utilizing technology including databases and data processing.
  • Willingness and ability to travel occasionally, comfortable with both in-person and virtual meetings.
  • Engaged campus community member who can embrace the objectives of the School fundraising priorities and integrate goals with those objectives.
  • Demonstrated commitment to supporting an intentionally equitable and inclusive community and building a philanthropic program that embraces diverse cultures and perspectives and wide-ranging constituencies – students, parents, faculty and staff, alumnae, etc.
  • Excellent written and verbal communication.
  • A pleasant nature and commitment to building camaraderie with colleagues.



Manage the overall fundraising initiative by setting and executing the vision/strategy for the Westover Fund to achieve dollar and donor goals from all constituencies including alumnae, parents, faculty/staff, friends. Envision new and inspiring ways to lead a successful annual fund and be nimble in executing so that it best meets the needs and staffing of the program.


Create and execute annual giving solicitations and other content through targeted mailings, e-communications, etc. Conduct appropriate stewardship activities to further enhance the relationship between donors and Westover. Initiate and maintain contact to promote positive donor relations.


Build relationships and qualify, cultivate, and personally solicit Westover constituents capable of making leadership annual fund gifts. Effectively communicate and track progress of cultivation efforts and results of visits. Travel occasionally to meet with donors, prospects, and volunteers.

Volunteers and Events

Engage key volunteers and effectively utilize events and other activities to move solicitations forward, execute Giving Days, staff events that help move the Alumnae and Development mission forward.

Westover Seeks Colleagues Who:

  • Champion the School’s mission and core values;
  • Find joy and passion in working with adolescents;
  • Demonstrate leadership, engagement in, and a commitment to diversity, equity and inclusion;
  • Excel in writing, organization, planning, and interpersonal skills; ability to work collaboratively with colleagues, and a strong work ethic;
  • Participate in the life of the School in order to support and serve the student body;
  • Collaborate effectively with faculty and staff; and
  • Respond in a timely fashion with energy and empathy to the needs of students and families.

Westover School is located in Middlebury, CT; 45 minutes from New Haven, 1 1/2 hours from New York City, and 2 hours from Boston.

Application Notes:

Interested candidates should address these aforementioned qualifications and skills in their cover letter in addition to providing a résumé.

Westover School is an Equal Opportunity Employer.

To apply for this job please visit