Director of Development

Westside School seeks an experienced and community-centered advancement leader who understands fundraising not simply as revenue generation, but as mission stewardship, relationship-building, and long-term institutional sustainability. The successful candidate will bring strategic vision, operational discipline, and a collaborative leadership style that inspires confidence and engagement across all school constituencies.

The Director of Development will partner closely with the Head of School, Dr. Wright, the Board of Trustees, Advancement Committee, Westside Family Association (WFA), alumni, and parent volunteers to strengthen advancement systems, deepen donor engagement, and grow philanthropic participation and support over time. Particular emphasis will be placed on rebuilding alumni and alumni-family relationships, strengthening stewardship practices, and ensuring that Westside’s advancement efforts are aligned with the school’s mission, values, and future aspirations.

In addition to stewarding and growing support from current families, alumni, grandparents, and community supporters, Westside sees a meaningful opportunity to expand its philanthropic reach through stronger engagement with local and national foundations, grantmaking organizations, and mission-aligned philanthropic partners. The school’s strong enrollment momentum, compelling educational mission, and deep commitment to joyful learning, inclusion, and community engagement position it well to cultivate broader philanthropic investment in its future.

This role presents an exceptional opportunity for a leader who values authentic relationships, visible community engagement, and strategic thinking. Dr. Wright is seeking a thought partner who can contribute meaningfully at the leadership table—someone who brings advancement expertise, thoughtful perspective, and the ability to collaboratively shape institutional priorities while guiding fundraising strategy with confidence and clarity.

Reporting directly to the Head of School and partnering closely with the Board of Trustees and Advancement Committee, the Director of Development will hold responsibility for the following areas:

• Develop and implement a comprehensive advancement strategy aligned with Westside’s mission and strategic priorities
• Serve as a strategic partner and trusted advisor to the Head of School on matters related to philanthropy, community engagement, and long-term sustainability
• Lead all fundraising efforts, including annual giving, leadership giving, alumni engagement, stewardship, and future campaign initiatives
• Establish clear advancement goals, benchmarks, and operational systems
• Strengthen advancement infrastructure, donor management systems, and long-term sustainability practices

• Personally cultivate, solicit, and steward leadership and major donors
• Build meaningful relationships across parents, alumni, grandparents, trustees, faculty, staff, and community partners
• Strengthen donor participation, retention, and stewardship efforts
• Rebuild and sustain a vibrant alumni engagement program
• Expand and diversify the school’s donor base, including opportunities with local and national foundations and grant‑making organizations, while honoring and strengthening relationships with current supporters
• Partner closely with Dr. Wright in donor strategy, relationship‑building, and philanthropic storytelling

• Supervise and support the Development Specialist
• Partner closely with the Westside Family Association and advancement volunteers
• Foster a collaborative, inclusive, and mission‑aligned advancement culture
• Maintain a visible and relationship‑centered presence within the school community

• Strengthen the school’s case for support through compelling storytelling and strategic communications
• Help articulate the impact of philanthropy on Westside’s students, faculty, programs, and long‑term sustainability
• Support advancement‑related communications and community engagement initiatives with authenticity…