Director of Development - Hillbrook School

Another Source•Los Gatos, CA

1d•$135,000 - $150,000

About The Position

Another Source’s client, Hillbrook School—an innovative, nearly 90-year leader in independent education in Silicon Valley—is now in its 4th year of expansion into a full JK–12 experience and hiring a Director of Development to help fuel that growth. This is a rare opportunity to shape a culture of philanthropy, partner closely with senior leadership, and build momentum at a school redefining what modern education can be. You’ll play a visible, strategic role in driving fundraising efforts during a pivotal chapter of growth and innovation.Another Source's client, Hillbrook School, is recruiting a Director of Development to join their team in Los Gatos and San Jose, California. For nearly 90 years, Hillbrook School has been a leader in independent education in Silicon Valley, known for its student-centered approach and commitment to developing confident, curious, and purpose-driven learners. Originally founded in 1935, Hillbrook has evolved from a small boarding school into a highly regarded JK–8 institution, and recently expanded with the launch of a new high school campus in downtown San José in 2023. This expansion is in its fourth year and marks a transformative moment in the school’s history. With a strong foundation and bold vision for a JK–12 experience, Hillbrook is redefining what secondary education can look like—blending academic rigor with real-world learning, social impact, and a deep commitment to diversity, equity, inclusion, and belonging. Situated in the heart of Silicon Valley, Hillbrook offers a dynamic and innovative environment where education is both meaningful and future-focused. This is a pivotal opportunity to shape and grow a culture of philanthropy at a school in the Multidisciplinary Studies (MDST) of exciting expansion. Reporting to the Director of Capital Campaign, the Director of Development will lead a comprehensive fundraising strategy that supports Hillbrook’s strategic priorities and long-term vision. You’ll play a highly visible and influential role—partnering closely with senior leadership, engaging deeply with the community, and building meaningful relationships with donors and volunteers. This role is ideal for a strategic and relationship-driven fundraising leader who is energized by building momentum, strengthening infrastructure, and making a lasting impact on an institution during a period of growth.

Requirements

5+ years of progressive fundraising experience, with demonstrated success in major gifts or comprehensive campaigns
Proven ability to cultivate, solicit, and close leadership-level gifts
Experience managing volunteers and working across cross-functional teams
Strong strategic thinking, planning, and analytical skills
Exceptional relationship-building skills and emotional intelligence
Outstanding written, verbal, and interpersonal communication skills
Highly organized with the ability to manage multiple priorities effectively
Sound judgment and discretion in handling confidential information
Commitment to building inclusive, equitable, and community-centered fundraising practices
Experience with fundraising systems such as Raiser’s Edge, NXT, iWave, or GiveSmart, and proficiency with Google Suite
Ability to work occasional evenings and weekends for events and engagement activities
Bachelor’s degree required

Nice To Haves

Advanced degree preferred

Responsibilities

Develop and execute a comprehensive fundraising strategy aligned with Hillbrook’s mission and strategic plan
Establish and drive annual and multi-year fundraising goals across major gifts, annual giving, and alumni engagement
Lead forecasting, pipeline development, and revenue projections in partnership with Advancement and Finance leadership
Serve as a strategic advisor on donor engagement, philanthropic trends, and campaign readiness
Manage a portfolio of 40–50 high-capacity donors, including current and past families
Design and implement tailored cultivation, solicitation, and stewardship strategies
Partner with senior leaders and volunteers on complex gift conversations
Develop compelling proposals, agreements, and donor communications
Build a strong pipeline from annual giving into leadership and major gifts
Provide leadership and direction to the advancement team, including the Director of Annual Giving
Foster a collaborative, accountable, and mission-aligned team culture
Partner cross-functionally with communications, finance, and academic leaders to align fundraising priorities
Engage with Board Advancement Committee members and support fundraising strategy and execution
Oversee a comprehensive donor stewardship program focused on meaningful, personalized engagement
Design and participate in donor events, campus experiences, and cultivation opportunities
Strengthen alumni engagement and connection strategies
Support external partnerships and sponsorship opportunities tied to key programs and initiatives
Ensure accurate donor tracking, portfolio management, and reporting within the advancement database
Monitor progress toward fundraising goals and report to leadership and the Board
Partner with Finance on pledge tracking and reconciliation
Maintain confidentiality and integrity in all donor-related matters