Assistant Director of the Westover Fund

Posted on 08/05/2022

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 alumni 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 Assistant Director of the Westover Fund position. This is a full-time, 12-month position that reports to the Director of the Westover Fund. This position will ideally begin immediately.

The Assistant Director of the Westover Fund is an integral member of the annual fund program for Westover School, focusing on marketing the annual fund, personal solicitation, and volunteer management to achieve a $2+ million Westover Fund. As a relationship builder, the Assistant Director is a front-facing advocate for our alumnae, students, and parents to make a philanthropic difference for Westover.

The Assistant Director will solicit alumnae, students, and parents and execute the marketing activities for the Westover Fund, including planning and executing Giving Days. In addition, this role will specifically oversee the reunion fundraising plan for a group of classes.

Westover is seeking a positive, energetic personality who enjoys relationship building and technology and is committed to thinking creatively to enhance a program that will inspire alumnae and parents to engage philanthropically with the School. 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
  • Has up to 2 years of experience in an annual fund or sales setting, where making an ask is an integral part of the role
  • An interest and willingness to solicit philanthropic support
  • A relationship builder
  • Interest in and experience with designing content
  • Excellent written and verbal communication
  • Demonstrated excellent interpersonal skills required to relate to donors, volunteers, and colleagues, including tact, diplomacy and discretion
  • Initiative and self-starting capacity
  • Excellent negotiating, organizational, and analytical skills with an attention to detail
  • Willingness and ability to travel; comfortable with both in-person and virtual meetings
  • 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, alumnae, etc.
  • A pleasant nature and commitment to building camaraderie with colleagues
  • Able to work with confidential information with discretion and the highest ethical standards


  • With guidance from the Director of the Westover Fund, execute and collaborate on an annual calendar for Westover Fund solicitations to reach revenue and donor goals. Segment audiences to include leadership prospects, alumnae celebrating reunion, parents, etc;
  • In collaboration with the Director, execute and collaborate on content for solicitations for the Westover Fund. Execute the sending of solicitations;
  • Create and execute texting campaigns, social posts, eblasts, and other innovative tools on behalf of the Westover Fund;
  • With support from the Director of the Westover Fund, execute Giving Days or similar fundraising events;
  • Maintain fundraising responsibility for the 19 youngest classes;
  • Oversee the 5th, 10th, and 15th Reunion fundraising efforts. Work closely with lead volunteers to draft solicitations and create engagement strategies for their class;
  • Qualify, cultivate and solicit an assigned young alumnae prospect pool through regular communication and face-to-face/virtual visits. Prospects will be capable of making gifts of $100 or more or are otherwise engaged as potential/key volunteers or prospects; must be able to ask for gifts on personal visits
  • Travel occasionally to meet with donors, prospects, and volunteers;
  • Effectively communicate and track progress of cultivation efforts and results of visits;
  • Staff all peer fundraisers at the direction of the Director. Recruit, train, and provide proactive support to volunteers to ensure their success in peer-to-peer solicitation efforts;
  • Provide administrative support for the Alumnae Association Board of Governors Westover Fund Committee;
  • In concert with the Assistant Director of Constituent Engagement, co-chair the Student Ambassador program. Capitalize on the senior class gift program to improve young alumnae donor loyalty;
  • Monitor progress towards goals for programs and adjust tactics as needed to ensure goals are met. Report on results;
  • Assist with executing Alumnae & Development events;
  • Exercise good judgment in discussing constituents, issues and results. Maintain composure and calm demeanor in difficult situations; and
  • Various other duties as needed within the Alumnae and Development Office

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.  For more information, please visit our website at

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