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.Leadership Responsibilities And OpportunitiesReporting 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:Strategic Advancement LeadershipDevelop and implement a comprehensive advancement strategy aligned with Westside’s mission and strategic prioritiesServe as a strategic partner and trusted advisor to the Head of School on matters related to philanthropy, community engagement, and long-term sustainabilityLead all fundraising efforts, including annual giving, leadership giving, alumni engagement, stewardship, and future campaign initiativesEstablish clear advancement goals, benchmarks, and operational systemsStrengthen advancement infrastructure, donor management systems, and long-term sustainability practicesDonor Cultivation, Solicitation, and StewardshipPersonally cultivate, solicit, and steward leadership and major donorsBuild meaningful relationships across parents, alumni, grandparents, trustees, faculty, staff, and community partnersStrengthen donor participation, retention, and stewardship effortsRebuild and sustain a vibrant alumni engagement programExpand 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 supportersPartner closely with Dr. Wright in donor strategy, relationship-building, and philanthropic storytellingTeam Leadership and Community EngagementSupervise and support the Development SpecialistPartner closely with the Westside Family Association and advancement volunteersFoster a collaborative, inclusive, and mission-aligned advancement cultureMaintain a visible and relationship-centered presence within the school communityCommunications and StorytellingStrengthen the school’s case for support through compelling storytelling and strategic communicationsHelp articulate the impact of philanthropy on Westside’s students, faculty, programs, and long-term sustainabilitySupport advancement-related communications and community engagement initiatives with authenticity and claritySkills, Experience, And Leadership AttributesWestside School seeks a Director of Development who brings both advancement expertise and a genuine commitment to community-building and mission-driven leadership. The ideal candidate will demonstrate many of the following qualities and experiences:Demonstrated success leading advancement or fundraising programs within independent schools or nonprofit organizationsExperience creating and implementing comprehensive advancement strategies aligned with institutional goalsStrong donor cultivation, solicitation, and stewardship experienceExperience with annual giving, leadership gifts, foundation relations, grants, and community fundraising initiativesProven ability to strengthen alumni engagement and alumni-relations programsStrong organizational, operational, and systems-thinking skillsExperience supervising advancement staff and supporting volunteer engagementExcellent communication, storytelling, interpersonal, and strategic planning abilitiesCollaborative leadership style and ability to partner effectively with school leadership and trusteesThe ability to serve as a trusted strategic thought partner to the Head of SchoolHigh emotional intelligence, integrity, discretion, and professionalismCommitment to fostering an inclusive and mission-aligned school culture grounded in belonging and authentic community engagementFlexibility to work evenings and weekends as required in independent school advancement workAbove all, the successful candidate will be inspired by the opportunity to help advance a joyful, inclusive, and deeply mission-driven school community while partnering closely with Dr. Wright and school leadership to shape Westside’s future for generations to comeHow To ApplyPosition Start Date: January 2027 (or earlier, as soon as July/ August 2026 by mutual agreement)Westside School is committed to fostering a diverse, equitable, inclusive, and welcoming community and encourages applications from candidates whose experiences and perspectives will contribute to and strengthen that commitment.This is a full-time, salaried position, benefits-eligible contract. Based on qualifications and prior experience this position offers a salary range between $140,000 and $150,000 annually.Westside School does not discriminate on the basis of sex, race, creed, color, national origin, age, veteran or military status, sexual orientation, gender expression or identity, or disability.Applications Will Be Reviewed As They Are Received. Candidates Interested In This Position Are Asked To Submit The Following Materials In a Single Merged PDF Document, In The Order Listed EC Candidate Summary Sheet (you’ll be asked to make a copy upon opening) Letter of interest addressed to the Head of SchoolCurrent résuméA list of five or more professional references with contact information, including phone numbers and email addresses Disclosure Form (you’ll be asked to make a copy upon opening) Please send applications and inquiries to: Carol Santos, Partner, Educators Collaborative csantos@educatorscollaborative.com