Job Description

The Cambridge School of Weston seeks a Leadership and Planned Giving Officer to cultivate and steward a group of loyal, high-capacity donors to advance the ambitious strategic fundraising growth of the school. Reporting to the Chief Development Officer, the Leadership and Planned  Giving Officer will be responsible for identifying, soliciting, and stewarding major and planned giving donors and prospects. Key to success in this role will be building relationships with new prospects, and strengthening relationships with existing donors to maximize philanthropic support. The Leadership and Planned Giving Officer will work closely with the Chief  Development Officer to expand and grow CSW’s fundraising efforts. 

Specific Responsibilities for This Position Include:  

Major & Planned Gift Portfolio Management:  

• Grow and manage a portfolio of 100-150 prospects capable of making five- to seven-figure philanthropic commitments and/or significant planned gifts. 
• Meet quarterly benchmarks and goals based on activity with prospects/donors and annual fundraising goals. 
• Identify and qualify new major and planned gift prospects and create a comprehensive strategy for donor cultivation, solicitation, and retention based on the donor’s giving history and capacity. 
• Directly solicit major gifts and partner with the Head of School, Chief Development  Officer, and/or volunteers on solicitations by providing prospect briefings, strategic guidance, and assistance with donor communications. 
• Track prospect activity by creating and sharing reports that accurately reflect donor relationships and support through the moves management system.  
• 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 CSW's major giving program by developing,  implementing, and ensuring that all systems and processes—from gift documentation to reporting—are accurate and align with the needs and requirements of the Development  Office and 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. 
• Manage CSW’s process for drafting written gift agreements, letters of intent, and other legal instruments pertaining to donor gifts.

Planned Giving Operations 

• Establish a plan, including specific goals and timetable, to cultivate and solicit prospective planned gifts.  
• Direct and manage CSW’s process for receiving realized bequests and comparable gifts from trusts, estates, and retirement plans; includes significant interface with estate attorneys/executors, trust and fiduciary representatives, and CSW’s Business Office. 
• Serve as a planned giving resource and maintain up-to-date planned giving knowledge. 

Prospect Cultivation and Donor Stewardship 

• In collaboration with team members, develop, plan, and participate in strategic donor engagement events. 
• Create a high-quality donor experience through regular correspondence, professional proposals, and timely acknowledgments. 
• Lead the development and implementation of cultivation and stewardship for major gift donors in collaboration with colleagues. 
• Engage prospects in volunteer activities (as appropriate) to further steward and cultivate those relationships.  
• Represent CSW at alumni, family, and other school events. 

Advancement Responsibilities 

• Partner with the Director of the CSW Fund to ensure the growth and development of  annual giving.  
• In collaboration with the Chief Development Officer, provide support and staffing as  needed for the Board of Trustees and the Development Committee. 
• Attend Development Committee meetings.  

Benefits of Working at CSW:  

• Collegial faculty and working environment 
• Curricular agency valuing creativity, innovation, and collaboration 
• Access to state-of-the-art fitness center  
• Wooded, 65-acre campus located just 12 miles from Boston and Cambridge, in close proximity to scenic walking trails and excellent local restaurants and shops. 
• Easy access to Kendal Green MBTA station, with on-campus parking and EV charging stations.  

To Apply for This Position:  

Please email a cover letter, resume, and the names and contact information of three to five references to: developmentjobs@csw.org. Please send pdf files only. No phone calls, please. 

Deadline for Application:  

Position will remain open until filled.  

Experience, Knowledge and Skills: 

• Keen understanding of CSW’s mission and values, and the ability to articulate its uniqueness and relevance as a leader in progressive education. 
• Minimum of 5 to 7 years experience in major and/or planned gifts fundraising in an independent school, college, or other mission-driven nonprofit institution.  
• Excellent communication skills, both verbal and written, 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 a senior member of the Development Team, providing thoughtful insights and high-level strategic input in all areas of fundraising and prospect management.  
• A working knowledge of constituent management systems; Raiser’s Edge experience preferred.  
• A strong understanding of best practices for tracking campaigns and major gifts.  
• A solution-oriented mindset and strong skills in diplomacy, communication,  collaboration, and a demonstrated sensitivity in handling confidential information. 
• Some travel and weekend and after-hours work required.

About The Cambridge School of Weston

A leader among America’s progressive independent schools, The Cambridge School of Weston (CSW) has been at the forefront of educational innovation since 1886. At this day and boarding high school located in Weston MA, creative, motivated students embrace challenging work and address complex questions — with curiosity and courage. Inspired by the diverse perspectives and high expectations of our justice-minded community, they find and develop what is extraordinary in themselves and in the world around them. CSW's mission is to provide a progressive education that emphasizes deep learning, meaningful relationships, and a dynamic program that inspires students to discover who they are and what their contribution is to their school, their community, and the world. The Cambridge School of Weston does not discriminate on the basis of race, color, religious creed, retaliation, national origin, ancestry, sexual orientation, gender, gender identity/expression, disability, mental illness, genetics, choice of health insurance, marital status, age, veteran status, or any other basis prohibited under applicable law. We are an equal opportunity employer and we encourage candidates who will in ... crease our diversity to apply. Other resources:

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