Leadership Gift Officer

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 and growing team?

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

The Leadership Giving Officer is an integral member of the leadership annual fund program for Westover School, utilizing in-person and virtual visits, email and phone, and volunteers to achieve a $2+ million Westover Fund. As a relationship builder, the Leadership Giving Officer is a front-facing advocate for our alumnae and parents who have the capacity to make an impactful philanthropic difference for Westover.

The LGO will solicit alumnae and parents and maintain a pool of prospects for solicitation, cultivation and engagement. In addition, this role is charged with maximizing the financial gift support to the Westover Fund by seeking contributions from alumnae, parents, and friends.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 2-4 years of experience in an annual fund or sales setting, where making an ask is an integral part of the role;
  • Knowledge and experience making a case for support;
  • A relationship builder;
  • 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, develop and implement strategic plans aimed at maximizing individuals’ support of the school;
  • Build relationships and qualify, cultivate and solicit Westover constituents capable of making annual fund gifts of at least $1,000 within an assigned prospect pool of up to 100 prospects;
  • Solicit other Westover unassigned constituents capable of making leadership annual fund gifts of $1,000 or more through face-to-face, email, phone, and virtual meetings;
  • Travel extensively to meet with donors, prospects and volunteers;
  • Effectively communicate, track, and report on all prospect activity and results of visits;
  • Attend regular frontline fundraiser meetings;
  • In partnership with the Director and Assistant Director, craft appropriate messaging for Leadership level prospects to the Westover Fund;
  • Oversee Reunion fundraising efforts;
  • Recruit, train, and provide proactive support to volunteers to ensure their success in peer-to-peer solicitation efforts. Work closely with lead volunteers to draft solicitations and create engagement strategies for their class;
  • Steward assigned donors and unassigned leadership level donors;
  • Organize small donor events and assist with executing Alumnae & Development events, including some weekend and evening activities;
  • Assist Annual Fund team with projects as needed;
  • 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.

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 westover-school-inc.checkwritersrecruit.com.