Director of Advancement

May 2026 | Ashburnham, MA
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Cushing Academy seeks an enthusiastic and strategic Director of Advancement to lead a strong and evolving advancement program, deepen alumni and donor engagement, and inspire philanthropic support that advances Cushing Academy’s mission.

About Cushing Academy

Cushing Academy is a coeducational, college preparatory boarding and day school in Ashburnham, Massachusetts, serving students in grades 9–12 and post-graduate. Founded in 1865, Cushing Academy is guided by its mission to develop “curious, creative, and confident learners and leaders,” placing students at the center of a dynamic, supportive, and diverse community.

Cushing offers a rigorous and personalized academic experience, with small class sizes, a strong student-faculty ratio, and a wide range of programs across disciplines including STEM, visual and performing arts, and global studies. Dedicated faculty provide close mentorship and academic support, helping students build confidence, think critically, and prepare for success in college and beyond. Graduates attend a distinguished range of four-year colleges and universities, a reflection of Cushing’s rigorous college preparatory program and its focus on developing students who are prepared to excel beyond Cushing.

Life at Cushing extends well beyond the classroom, with robust opportunities in athletics, the arts, and student-led clubs and activities. Students participate in competitive sports teams, creative arts programs, and a wide array of organizations, from Model United Nations to a cappella, while also enjoying a vibrant residential life filled with campus events, leadership opportunities, and weekend excursions. This breadth of experiences, combined with a strong sense of community, empowers students to explore their passions, form lasting relationships, and thrive as engaged, well-rounded individuals.

About Philanthropy at Cushing Academy

Philanthropy plays a vital role in sustaining and advancing Cushing Academy’s mission, supporting both the immediate student experience and the school’s long-term priorities. Cushing fosters a strong culture of giving among alumni, parents, and friends, whose collective generosity ensures continued investment in academic programs, faculty excellence, financial aid, and student life. This shared commitment reflects a deep belief in the value of a Cushing education and its impact on students’ growth and success.

The Cushing Fund annual giving program provides flexible, unrestricted support for core operations. Contributions to The Cushing Fund help bridge the gap between tuition and the full cost of educating each student, enabling enhancements across classrooms, co-curricular offerings, and residential life. Additional philanthropic support strengthens the endowment and advances strategic initiatives, ensuring that Cushing can remain both innovative and accessible.
Cushing’s advancement program prioritizes meaningful, long-term engagement with its community through annual, major, and planned giving, as well as advancing an alumni engagement program with strong institutional support and growth potential. By cultivating relationships and offering multiple pathways for involvement, donors are inspired to invest in the future of Cushing and is essential to delivering on Cushing’s promise of a dynamic, well-rounded educational experience.

About the Position

The Director of Advancement (Director) will join a committed and growing advancement team and serve as a key member of Cushing Academy’s leadership team, working closely with the Head of School to advance the institution’s strategic priorities and philanthropic goals. The Director will provide leadership, oversight, and strategic direction for all areas of advancement, including fundraising, alumni engagement, stewardship, advancement operations, communications, and events.

The Director is responsible for fostering a collaborative, high-performing advancement program and supporting the continued growth and development of the team. In partnership with the Head of School, the Director will enhance alumni and donor engagement and build systems and strategies that support long-term success. The Director will conduct prospect analysis, cultivate and solicit donors, and provide thoughtful and tailored donor stewardship and recognition.

Key Responsibilities

• Lead and manage the Advancement Office
• Fostering a highly collaborative relationship with the Head of School to advance strategic priorities while sustaining and enhancing Cushing’s mission.
• Supervise and develop a team of administrative and professional staff, overseeing hiring, performance management, and professional development.
• Direct all Advancement Office operations, including gift processing and acknowledgement, stewardship, prospect management, and the maintenance of donor and financial records.
• Lead the Advancement Office budgeting and planning process, including revenue forecasting and development of a major gifts pipeline.
• Design and execute comprehensive fundraising strategies, including annual giving, major gifts, corporate and foundation relations, and campaign initiatives.
• Grow and strengthen the annual fund through data-informed strategies, donor segmentation, and multi-channel engagement.
• Build and sustain strong working relationships with the senior leadership, trustees, and volunteer leaders.
• Cultivate, solicit, and steward a portfolio of high-net-worth individuals, foundations, and corporate partners.
• Develop and implement strategies to engage the alumni community, overseeing all alumni relations programs and alumni-related events.
• Expand the reach and impact of Cushing’s philanthropic programs through innovative engagement and outreach strategies.
• Provide leadership and creativity in prospect identification, qualification, and moves management.
• Ensure consistent, compelling, and coordinated communications with donors and prospects; lead development-related marketing and communications across print, digital, and multimedia platforms.
• Engage board members, staff, and parent volunteers in the fundraising process.
  Represent Cushing Academy at internal and external events, cultivation opportunities, and community functions.
• Serve on the Head of School’s Leadership Team and act as a key liaison, along with the Head of School, to the Advancement Committee of the Board of Trustees.

Key Qualifications

• Minimum of seven years of increasingly responsible experience, with a track record of success in major and special gifts fundraising.
• Experience working in advancement at the assistant director, director, or chief advancement officer level.
• Proven experience working closely with nonprofit boards and board committees, including supporting trustees in fundraising and engagement roles.
• Demonstrated success leading alumni relations programs and engagement events.
• Track record of growing and strengthening fundraising programs, with working knowledge of institutional fundraising best practices and ethical standards.
• Ability to build, manage, and steward long-term donor and volunteer relationships aligned with Cushing’s priorities.
• Strategic thinker with the ability to design, implement, and scale programs for growth.
• Strong written and verbal communication skills, with the abilities to communicate persuasively and authentically with a broad range of constituencies.
• Broad professional experience and sound judgement to navigate challenges, mitigate obstacles, and achieve results.
• Confident, collaborative leader with experience planning and executing strategic plans with clear goals and performance metrics.
• Entrepreneurial mindset, with demonstrated success in leveraging innovation and best practices to address resource needs.
• A deep commitment to the mission, values, and community of Cushing Academy.

Compensation

The salary range for this position is $165,000–$195,000 per year, commensurate with experience.

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.