Campaign Director and Senior Major Gift Officer

Winter 2020 | Boston, MA
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The Winsor School seeks nominations and expressions of interest for the newly created position of Campaign Director and Senior Major Gift Officer.

About The Winsor School

Winsor-School-students-in-treeThe 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 Campaign Director and Senior Major Gift Officer has been created to play a significant role in the strategic planning and coordination of the campaign and ongoing major gift success.

About the Position

Reporting directly to the Chief Advancement Officer (CAO), the Campaign Director and Senior Major Gift Officer (Campaign Director) will work closely with senior-level development volunteers, trustees and other key stakeholders. The Campaign Director will plan and implement strategies for identification, cultivation, solicitation, closure and stewardship of major prospects and donors; will help establish fundraising goals and objectives; and will play a strategic role in strengthening the relationship between Winsor and its constituencies. The Campaign Director will also carry a personal portfolio of prospects and donors and will be expected to meet ambitious fundraising goals.

Key Responsibilities

Campaign Management

  • Winsor-School-students-in-classDirect campaign planning and execution in collaboration with the CAO and other stakeholders to develop and execute a campaign calendar to ensure the achievement of key milestones.
  • Work with CAO to implement recommendations of soon-to-be-completed campaign feasibility study (Note: feasibility study already in progress.).
  • In collaboration with the CAO, provide critical support and staffing for the Campaign Steering Committee and other campaign subcommittees, including managing solicitations and preparing marketing materials.
  • Manage stewardship for campaign leadership donors.
  • Manage the solicitation process and pipeline for the CAO and Head of School.
  • Lead strategic efforts for campaign pipeline movement, gift proposals, campaign policy development, and goal setting.
  • Manage campaign budget and develop campaign tracking systems and reports.
  • Coordinate campaign events.
  • Direct and oversee prospect research.

Major Gift Portfolio Management

  • 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.
  • Enhance operational efficiency for Winsor’s major giving program and help ensure that all systems and processes—from gift documentation to systems reporting—are accurate and tailored to align with the needs of the Advancement Office and requirements of the Business Office.
  • Prepare and present written and oral briefings, follow-up materials, and contact reports on major gift prospects/donors in a timely manner.
  • Write, edit, and proofread proposals, letters, and other correspondence.
  • Work collaboratively with Advancement staff to devise and recommend cultivation and solicitation strategies; serve as a resource for staff and volunteers.
  • Lead the development and implementation of cultivation and stewardship for major gifts donors in collaboration with colleagues.
  • 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 all 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

  • Deep commitment to independent school education.
  • Keen understanding of Winsor’s mission and goals, and the ability to articulate the School’s 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’ experience in major gifts fundraising and campaign management in a college, independent school, or other mission-driven nonprofit institution.
  • Proven record of closing major gifts.
  • Demonstrated ability to handle multiple competing priorities and meet established personal and team goals.
  • Highest level of integrity, discretion, and respect for donor confidentiality and handling of sensitive information, tasks, and relationships.
  • Experience with budgets, reporting tools, and best practices for tracking campaign and major gifts moves management.
  • Skill in proofreading and editing, attention to detail, and follow-through. Computer literacy, particularly in word processing, PowerPoint, using internet resources, and using databases required. Comfort with online fundraising and social media.
  • Bachelor’s degree required, and Master’s 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

Interested in this position or other new career opportunities?