Employment

Founded in 1926, Wooster School is a co-educational, 5-12, college preparatory day school with an enrollment of approximately 350 students, and a regional leader in student-centered education. The School is located in Danbury, Connecticut. By design and mission, it educates a student population diverse in academic ability, socioeconomic background, religious affinity, and race and ethnicity. Wooster is a member of the Connecticut Association of Independent Schools and the National Association of Independent Schools.

While Wooster’s traditions of Self-Help and relationship-building have long been recognized as strengths, our more recent commitment to innovative approaches to teaching and learning are making us a leader in the independent school world. We are committed to a learner-centered environment for our students, and to exploring the full potential of competency-based and personalized teaching and learning.

Wooster School is an Equal Opportunity Employer and we provide a work environment that welcomes diversity. In addition to a competitive salary, employees receive retirement, health insurance, tuition remission, short and long term disability and life insurance benefits.

All employees are subject to a criminal background check before any contractual offer is final.

Director of Development

Position Description

Wooster School seeks a Director of Development to start when available. This senior-level position reports to the Chief Development Officer (CDO) and plays a central role in advancing the School’s mission and philanthropic vision. The Director of Development will serve as a strategic partner in shaping and leading all aspects of fundraising, donor relations, and campaign planning. This role will focus on expanding Wooster’s base of support by identifying, engaging, and stewarding donors at all levels while also providing leadership in the design and execution of comprehensive campaigns, including capital, endowment, and planned giving initiatives.

The ideal candidate will be an innovative and forward-thinking leader—just like Wooster School. A strategic problem-solver and relationship builder, the Director of Development will be highly organized and skilled at research, planning, and execution. A passion for education, an affinity for young people, and a desire to be an active and visible member of a thriving school community are essential. The successful candidate will also be a collaborative teammate and inspiring leader, balancing confidence with humility and bringing a ready sense of humor to their work.

Responsibilities

Strategic Leadership & Planning

Partner with the CDO to design and execute a comprehensive development strategy aligned with Wooster’s mission, vision, and long-term goals.
Provide leadership for all fundraising initiatives, including the Annual Fund, major gifts, capital projects, endowment growth, and planned giving.
Develop and oversee donor pipelines, ensuring the successful identification, cultivation, solicitation, and stewardship of prospects.

Major & Planned Giving

Lead a robust portfolio of major and planned gift prospects, managing face-to-face solicitations and personalized stewardship strategies.
Work in close partnership with the Head of School, CDO, and Trustees to engage high-capacity donors and advance transformative philanthropic opportunities.

Community Engagement

Collaborate with Trustees, Parents’ Association leadership, alumni leaders, and other key volunteers to build a strong culture of philanthropy across the Wooster community.

Campaign & Program Oversight

Play a leadership role in the design, launch, and management of any upcoming capital or comprehensive campaigns.
Plan and manage fundraising events that strengthen donor engagement and expand Wooster’s visibility.
Stay current with industry best practices and proactively bring new ideas and innovations to Wooster’s advancement efforts.

Team Collaboration

Support, mentor, and work closely with advancement staff to foster a high-performing, collaborative, and creative development team.
Promote integration across communications, alumni relations, and fundraising to maximize impact and donor experience.

Qualifications

Bachelor’s Degree required; advanced degree preferred.
5–7+ years of progressively responsible development experience, preferably in independent schools or the nonprofit sector.
Proven success in major gifts fundraising and campaign leadership, with a strong track record of securing and stewarding five- and six-figure gifts.
Demonstrated leadership ability, with experience managing staff, volunteers, and/or boards in a mission-driven environment.
Excellent interpersonal, communication, and presentation skills, with the ability to engage diverse stakeholders warmly and effectively.
High emotional intelligence, curiosity, creativity, and a collaborative spirit.
Strong strategic planning and project management skills, with the ability to balance multiple priorities.
Proficiency with Raiser’s Edge or comparable CRM required; experience with event management tools a plus.
Commitment to diversity, equity, inclusion, and belonging, and to being an active and visible member of the Wooster community.

Salary & Benefits

This is a full-time, 12-month, exempt position. Salaries are competitive with local independent schools. A competitive benefits package includes retirement, health insurance, tuition remission, short-term and long-term disability, and life insurance. All employees are subject to a criminal background check before any contractual offer is final.