Director of Planned and Major Giving

October 2019 | Boston, MA
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The Winsor School seeks nominations and expressions of interest for the newly created position of Director of Planned and Major Giving.

About The Winsor School

Winsor-School-STEM-ClassThe Winsor School, one of the nation’s leading independent schools, serves 470 academically promising and motivated girls in grades five through twelve. Located in the heart of Boston’s Longwood medical and academic area, Winsor School was founded in 1886 by Miss Mary Pickard Winsor with eight girls in a private home on Beacon Hill. The School grew quickly and today students benefit from its commitment to providing a superior education for girls, inspirational and dedicated faculty, and a talented community. Winsor strives to consciously create an environment of respect and inclusion and to support ethnic, racial, religious, and socio-economic diversity among all the constituencies of the School. Winsor supports this commitment through its more inclusive curriculum, success addressing a range of learning styles, the availability of a wide array of diversity efforts and programs, and by participating in the greater Boston community.

In keeping with the mission of the school to develop “responsible, generous-minded women,” Winsor affirms, teaches, and values:

  • Belief in the dignity and humanity of every person and a commitment to understanding individual and group differences.
  • Respect for oneself and for one another and responsibility for oneself and for community.
  • Generosity of spirit, thinking beyond one’s immediate self-interest, and sharing talents freely with others.
  • Openness to new ideas and rejection of stereotypical thinking.
  • Honesty, kindness, integrity, courage, and humor.
  • Empathetic understanding.

Ongoing philanthropic support from alumnae, parents, and friends of The Winsor School makes a significant impact on the daily life of students and faculty and the fulfillment of this vision. Winsor will launch its next major campaign in 2020, and the position of Director of Planned and Major Giving has been created to play a significant role in the campaign and ongoing individual giving support.

About the Position

Reporting directly to the Chief Advancement Officer (CAO), the Director of Planned and Major Giving (the Director) will work closely with senior-level development volunteers, trustees, and other key stakeholders. The Director will plan and implement strategies for identification, cultivation, solicitation, closure, and stewardship of major prospects; lead the planned giving program; help establish fundraising goals and objectives; serve as the lead planned giving officer; and strengthen the relationships between Winsor and its constituencies. The Director will also carry a portfolio of donors and prospects and will be expected to meet ambitious goals.

Key Responsibilities

Planned Giving

  • Winsor-School-Graduation-DayHold primary responsibility for gifts of estates, trusts, and various other financial venues that reflect financial planning and deferred giving opportunities.
  • Serve as planned giving fundraising liaison for Winsor and prepare written materials about the intricacies of financial, legal, and tax-related aspects of charitable gift planning in order to engage donors.
  • Proactively identify, cultivate, solicit, and steward planned giving prospects and serve as the planned giving advisor for all Winsor planned giving donors.
  • Train and support other staff members working with donors on deferred and planned gifts such as trusts, charitable annuities, life insurance, wills, and bequests.
  • Enhance operational efficiency in planned giving for the Winsor program. Ensure that all systems and processes from gift documentation to systems reporting are accurate and tailored to align with the needs of the Advancement and Business Offices.
  • Oversee the Lamp of Learning Society, Winsor’s planned giving program, including member events and stewardship.
  • Enhance donor gift planning and giving by remaining current in areas of gift possibilities available and the current laws and regulations governing such gifts.
  • Lead strategic efforts for planned giving pipeline movement, gift proposals, policy development, goal setting.
  • Manage planned giving prospects and donors; develop tracking systems and reports.
  • Direct and oversee planned giving prospect research.
  • Manage the solicitation process and pipeline for the CAO and Head of School, specific to planned giving.

Major Gifts

  • Grow and manage a portfolio of 150-200 prospects capable of making five- to seven-figure gifts.
  • Ensure that key prospects are actively managed with regular face-to-face meetings and outreach with prospects to communicate campaign goals and move prospects along the major gifts pipeline.
  • Prepare and present written and oral briefings, follow-up materials, and contact reports on major gift prospects/donors as needed in a timely manner.
  • Write, edit, and proofread proposals, letters and other correspondence as necessary.
  • Work collaboratively with development staff to devise and recommend cultivation and solicitation strategies; serve as a resource for development staff and volunteers.
  • Collaborate on and lead the development and implementation of cultivation and stewardship for major gifts donors.
  • Represent the school at alumnae, parent, and other constituent events.
  • Work strategically, as assigned, with the Head of School, other senior administrators, faculty, staff, and volunteer leaders to support fundraising priorities.
  • Acknowledge personally any gifts from assigned prospects.
  • Visit specified regions across the country to cultivate prospective donors, staff senior administrators at events, and coordinate logistics for strategic visits.
  • In collaboration with the CAO, provide critical support and staffing for the Board of Trustees, the Corporation, and the Advancement Committee.
  • Engage volunteers in a variety of roles, including identification, cultivation, solicitation, stewardship, and events.
  • Meet quarterly benchmarks and goals based on activity with prospects/donors and annual fundraising goals.

Key Qualifications

  • A deep commitment to an independent school education, a keen understanding of Winsor’s mission and goals, and the ability to articulate its uniqueness and relevance.
  • Strong organizational and time management skills with exceptional attention to detail.
  • Excellent communication skills, both verbal and written, with a strong ability to influence and engage a wide range of donors and build long-term relationships.
  • Minimum of 10 years’ related experience in major gifts fundraising, campaigns, planned giving in a college, independent school, or other mission-driven nonprofit institution.
  • Proven record of closing major gifts and directing planned giving programs.
  • Demonstrated ability to handle multiple competing priorities and meet established personal and team goals.
  • Possess the highest level of integrity, donor confidentiality, and discretion with sensitive information, tasks, and relationships.
  • Experience with planned giving, giving societies, reporting tools, and best practices for tracking and stewarding planned and major gifts moves management.
  • Skills in proofreading and editing, along with an attention to detail and follow-through. Computer literacy, particularly in word processing, using Internet resources, and using databases is required. Comfort with online fundraising and social media.
  • An understanding of current laws regarding taxability of donations, familiarity with deferred giving strategies, and knowledge of a diverse array of financial instruments are essential.
  • A Bachelor’s degree required and Master’s or Juris Doctorate degree preferred.
  • Some travel and weekend and after-hours work required.

All qualified candidates will receive consideration for employment without regard to race, color, religion, sex, national origin, disability, veteran status, or any other characteristic protected by law.

Please email your cover letter and resume in confidence to:

Tracy Marshall
Senior Vice President, Principal
Development Guild DDI

For more information about The Winsor School please visit

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