Leadership and Legacy Gift Officer

Staff / Full-Time

Waynflete School, Portland, ME

Waynflete School, a non-profit, independent day school in Portland, Maine,  has been home to families seeking an extraordinary education for their children since 1898. Our mission is to engage the imagination and intellect of our students, to guide them toward self-governance and self-knowledge, and to encourage their responsible and caring participation in the world. Our aim is to provide a program that combines security with challenge, playful exploration with rigorous expectation, and range of experience with depth of inquiry.

The Waynflete development team secures philanthropic resources that propel the work of our faculty, establish access, equity, and belonging for our students, and empower Waynflete to realize its fullest potential, securing the school into the future.


Waynflete School seeks an Officer of Leadership & Legacy Giving to qualify, further cultivate, and manage existing entry-level donors to support the ambitious and strategic fundraising growth of the school. The ultimate focus of this position will be to create and manage long-term leadership and legacy giving programs for Waynflete to best maximize the generosity and potential philanthropic donor impact over the course of the next 3+ years, especially as Waynflete gears up for the second phase of a multi-phase comprehensive campaign effort starting in the fall of 2023. This individual will be responsible for building a program to qualify, identify, cultivate, and ultimately solicit and steward donors and prospects.

Reporting directly to the Director of Development, this position will work closely with Director of Alumni Giving and the Director of Parent Giving, with a long-term goal of preparing the Head of School and the Campaign Director, key volunteers, and other key stakeholders to expand and grow the fundraising efforts of Waynflete in Phase 2 of the aforementioned comprehensive campaign. Given the fact that Waynflete is in a very important moment in its growth and is the leading independent educational institution in Maine, this is an exciting opportunity to truly build out the next stage of Waynflete’s Leadership & Legacy Giving pipeline. Your impact will help the school to realize its fullest potential as an intellectually challenging, forward-thinking, and culture-driven environment.

Leadership Gift Portfolio Management

  • Qualify, cultivate, and grow a portfolio of 100-125 leadership gift prospects capable of making five-to-six figure philanthropic commitments.
  • Identify and qualify new leadership gift prospects and create a comprehensive strategy for donor cultivation, solicitation, and retention.
  • Partner with development staff and/or volunteers on prospect qualification by providing background research, strategic guidance, and assistance with potential or cultivation-stage donor communications.
  • Ensure that key prospects are actively managed by meeting and corresponding regularly with them; communicate fundraising goals and move prospects through the qualification pipeline.
  • Enhance the operational efficiency of Waynflete’s leadership giving program by adhering to and building upon existing systems and processes—from tracking prospect activity to qualification techniques to reporting—to ensure that they are accurate and align with the needs and requirements of the Development, Marketing and Communications, and Finance Offices.
  • Work strategically, as assigned, to communicate fundraising priorities.

Prospect Cultivation and Donor Stewardship

  • Liaise with the Marketing and Communications team to develop, plan, and participate in donor engagement events.
  • Lead the development and implementation of qualification, cultivation, and stewardship for your portfolio of potential major and leadership donors.
  • Personally acknowledge all gifts from assigned prospects where appropriate.

Legacy Giving Program

  • Establish a plan, including specific goals and timetable, to cultivate and, where appropriate, solicit prospective planned gifts and maintain up-to-date planned giving knowledge.
  • Work closely with endowment and finance personnel to maximize the potential of the legacy giving program at the organization.
  • Work closely with department staff and key volunteers including Board members to qualify, cultivate, solicit, and steward new prospects for legacy gifts.
  • Deepen relationships with estate administrators, financial advisors, and legal professionals whose work has the most potential to impact the legacy giving efforts of the organization.
  • Connect legacy giving to annual giving, by maximizing legacy giving programs to cultivate and confirm additional major gifts for annual, capital, special projects, and campaign funding.
  • Adhere to best practices for moves management, maintaining accurate and up-to-date records of donor contacts and ongoing legacy giving conversations with current and historic donors.

Responsibilities and General Operations

  • Ensure relationships are developed with alumni and families through engagement tactics that complement fundraising activities.
  • Partner with the Director of Development to ensure the growth and development of all fundraising efforts at Waynflete as it applies to the qualification process.
  • Qualify 125-150 new prospects per year over the course of three years (for a total number of 375-450 qualified prospects over a three-year period), with a goal of 100-125 new leadership gift prospects being added to the donor network for solicitation in 2026-2028.
  • Engage with the Waynflete community beyond development initiatives to represent the school authentically. Be an active member of the broader Waynflete community.

Experience, Knowledge, and Skills

  • A belief in independent school education, keen understanding of Waynflete’s mission and goals, and the ability to articulate its uniqueness and relevance.
  • Minimum of 3 years or equivalent experience in leadership gifts fundraising in a mission-driven nonprofit institution. Bachelor’s degree required.
  • Excellent communication skills and a strong ability to inspire and engage a wide range of donors and build long-term relationships in order to close major and leadership gifts.
  • The ability to provide thoughtful insights and high-level strategic input in all areas of fundraising and prospect management.
  • A working knowledge of constituent management systems and Microsoft Windows suite.
  • A solution-oriented mindset, a demonstrated sensitivity in handling confidential information, strong skills in diplomacy, communication, collaboration, and a sense of humor.
  • Some weekend and after-hours work required.

Position details: 

This is a year-round, full time position; salary will be commensurate with experience.

Benefits include:

  • Medical Insurance
  • Dental insurance
  • Life, AD&D, and long-term disability insurance
  • 403(b) retirement plan with generous school matching contribution
  • Medical and dependent care flexible spending accounts
  • Tuition benefit and financial aid
  • Discounted summer camp and after-care programs
  • Employee education/professional development grants
  • Use of school library and fitness room
  • Paid leave

With an institutional commitment to the principles of diversity, equity, and inclusion, Waynflete seeks candidates who are committed to developing inclusive methods in their teaching, teamwork, and leadership. We believe that all students benefit from more inclusive environments. Taking inspiration from our mission, we seek qualified faculty and staff with the knowledge, skills, and abilities to enhance the student experience and strengthen our community.

To apply, please click here and upload a resume and cover letter. If available, letters of recommendation and unofficial transcripts are also appreciated. Applications will be reviewed immediately and the position will remain open until filled. No phone calls, please.

Waynflete School

Portland, ME
Early Childhood, Elementary, Middle School, High School
All Gender