Director of Leadership and Planned Giving

Posted on 06/09/2021

The Westover School

Middlebury, CT

School Information: 

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?
  • Are you passionate about the power of women’s philanthropy?
  • Westover School is seeking applicants for the full-time, twelve-month position of Director of Leadership and Planned Giving beginning after July 1, 2021.

Qualifications and Key Responsibilities:

The Director provides both strategic insight and daily management of leadership and planned giving initiatives and cultivating, soliciting and stewarding a portfolio of potential donors. Under new leadership, the Alumnae and Development office is expanding and preparing for a major fundraising initiative on the horizon. 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.

Key Responsibilities:

  • Qualify, cultivate and solicit Westover constituents capable of making leadership annual, capital, endowed and planned gifts to the School at the $10,000+ level.
  • Re-establish Westover’s Planned Giving program.
  • Additionally, lead the post 50th class fundraising initiatives.
  • Devise and implement cultivation and solicitation strategies.
  • Create and lead the Westover Leadership Council for donors at the $10,000+ level.
  • Participate in the execution of events and programs in support of development activities. Engage key volunteers and effectively utilize events and other activities to move solicitations forward.
  • Conduct appropriate stewardship activities to further enhance the relationship between donors and Westover. Initiate and maintain contact to promote positive donor relations.
  • Effectively communicate and track progress of cultivation efforts and results of visits.
  • Exercise good judgment in discussing alumni, issues and results. Maintain composure and calm demeanor in difficult situations.
  • Travel (possibly extensively, and possibly some internationally) to meet with donors, prospects and volunteers.


  • Bachelor’s Degree and a minimum of five years of frontline solicitation and relationship building or translatable experience.
  • At minimum, a basic understanding of Planned Giving vehicles with an expressed interest in growing a program.
  • Demonstrated comfort utilizing technology including databases and data processing.
  • Demonstrated excellent interpersonal skills required to relate to donors, volunteers and colleagues, including tact, diplomacy, discretion, and the ability to maintain confidentiality inside and outside the Alumni and Development Office.
  • Initiative and self-starting capacity. Excellent negotiating, organizational and analytical skills with an attention to detail.
  • Engaged campus community member who can embrace the objectives of the School fundraising priorities, and to integrate goals with those objectives.
  • 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.
  • Excellent communication skills and ability to connect with diverse and wide-ranging constituencies – students, parents, faculty, alumni, etc.
  • A pleasant nature and commitment to building camaraderie with colleagues.

Application Notes: 

The ideal candidate will have a background in frontline fundraising and planned giving with demonstrated success in asking for and closing major gifts. Interested candidates should address these aforementioned qualifications and skills in their cover letter in addition to providing a résumé and philosophy that addresses a candidate’s demonstrated experience in diversity, equity, and inclusion work. Westover School is an Equal Opportunity Employer.

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

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