The Winsor School
A leading school for academically promising girls in grades 5-12
Director of Planned and Major Giving

The Winsor School is an independent girls' school for academically promising and motivated students in grades five through twelve. Our diverse, vibrant community values intellectual curiosity, authentic engagement, and personal integrity, and prepares young women to pursue their aspirations and contribute to the world. Winsor strives to create an environment of respect and inclusion. The Advancement Office supports The Winsor School by raising the necessary funds to meet the school's needs and further its mission. We are currently seeking a Director of Planned and Major Giving. Please email your cover letter and resume to

Reporting 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.

Planned Giving

·        Hold 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.

For more information about The Winsor School please visit

For more information about Development Guild DDI, please visit