Leadership Gift Officer

Administrator / Full-Time

The Winsor School, Boston, MA


The Winsor School seeks a Leadership Gift Officer (LGO) to manage and further cultivate a strong group of existing donors to support the ambitious and strategic fundraising growth of the School. The LGO will be responsible for identifying, cultivating, soliciting, and stewarding major gift donors and prospects. Key to success in this role will be identifying and building relationships with new prospects, as well as strengthening relationships with existing donors to maximize philanthropic support. In addition to soliciting major gifts, the LGO will develop ways in which donors can support the future of The Winsor School through transformational campaign gifts.

Reporting directly to the Director of Advancement, the Leadership Giving Officer will work closely with the Director of Advancement, senior-level Advancement volunteers, and other key stakeholders to expand and grow the fundraising efforts of The Winsor School. The Winsor fundraising team secures philanthropic resources that propel the work of our faculty, establish access, equity, and belonging for our students, and empower Winsor to realize its fullest potential, securing the School into the future.

Major Gift Portfolio Management

  • Grow and manage a portfolio of 150-175 major gift prospects capable of making six and seven-figure commitments.
  • Identify and qualify new major gift prospects and create a comprehensive strategy for donor cultivation, solicitation, and retention.
  • Directly solicit major gifts and partner with senior staff and/or volunteers on solicitations by providing prospect briefings, strategic guidance, and assistance with donor communications.
  • Ensure that key prospects are actively managed by meeting and corresponding regularly with them; communicate fundraising goals and move prospects through the major gifts pipeline.
  • Enhance the operational efficiency of Winsor’s major giving program by developing, implementing, and ensuring that all systems and processes—from tracking prospect activity to gift documentation to reporting—are accurate and align with the needs and requirements of the Advancement Office and the Business Office.
  • Work strategically, as assigned, with the Head of School, other senior administrators, faculty, staff, and volunteer leaders to communicate fundraising priorities.

Prospect Cultivation and Donor Stewardship

  • Liaise with the Engagement team to develop, plan, and participate in donor engagement events.
  • Develop a high-quality donor experience through regular correspondence, professional proposals, and timely acknowledgements.
  • Lead the development and implementation of cultivation and stewardship for your portfolio of major gift donors.
  • Personally acknowledge all gifts from assigned prospects.
  • Visit specified regions across the country to cultivate prospective donors and build relationships.
  • Establish a plan, including specific goals and timetable, to cultivate and solicit prospective planned gifts and maintain up-to date planned giving knowledge.

Advancement Responsibilities and General Operations

  • Ensure relationships are developed with alumnae and families through engagement tactics that complement fundraising activities.
  • Partner with the Director of Annual and Leadership Giving to ensure the growth and development of all fundraising efforts at Winsor. Work together to identify, steward, and cultivate major giving prospects.
  • Manage the fundraising team. Help hire, train, and evaluate persons in direct report position(s).
  • Engage with the Winsor community beyond Advancement initiatives in order to represent the school authentically. Be an active member of the broader Winsor community.


  • A belief in all-girls independent school education, keen understanding of Winsor’s mission and goals, and the ability to articulate its uniqueness and relevance.
  • Minimum of 7 to 10 years’ experience in major 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. Proven record of closing major gifts.
  • The ability to serve as senior member of the Advancement Team, providing thoughtful insights and high-level strategic input in all areas of fundraising and prospect management.
  • A working knowledge of constituent management systems with an emphasis in Raiser’s Edge for Windows, NXT, and Microsoft Windows suite of products.
  • A solution-oriented mindset, a demonstrated sensitivity in handling confidential information, strong skills in diplomacy, communication, collaboration, and a sense of humor.
  • Some travel and weekend and after-hours work required.


This full-time, benefits-eligible position offers a salary commensurate with experience and the opportunity to work in a school environment and make an impact.


Please visit the Winsor Careers page to apply for and submit your resume and cover letter explaining why you are interested in this role and what you will bring to the position at https://www.winsor.edu/about/careers-at-winsor/open-positions

The hiring process includes:

  • Virtual interview with Erika McMahon, Director of Advancement
  • Virtual or in-person meeting with Advancement Team Members
  • Virtual or in-person interview with Sarah Pelmas, Head of School

Questions? Contact Erika McMahon at emcmahon@winsor.edu.

Winsor is committed to building a diverse and inclusive campus community. We welcome applications from underrepresented groups.

The Winsor School

Boston, MA
Elementary, Middle School, High School