Director of Development - Hillbrook School

At a glance

Description: What you'll be doing

Another Source's client, Hillbrook School, is recruiting a Director of Development to join their team in Los Gatos and San Jose, California. 

Here's a little about Hillbrook School: 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. 

https://www.hillbrook.org/about/our-mission-vision  

About this role: 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. 

How you will spend your time: 

Strategic Leadership & Advancement Planning 

• 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  

Major & Leadership Giving 

• 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  

Team Leadership & Collaboration 

• 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  

Stewardship & Community Engagement 

• 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  

Data, Reporting, & Administration 

• 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  

Experience You Will Bring: 

• 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; advanced degree preferred  

Compensation & Benefits: The salary range for this role is $135,000–$150,000, depending on experience. 

Hillbrook offers a competitive benefits package that includes medical, dental, and vision coverage; retirement planning through TIAA; generous holidays; and robust professional development opportunities. 

https://www.hillbrook.org/connect/careers 

Diversity, Equity, Inclusion, Justice, & Action As noted in our Commitment to Community & Belonging, we strive to reflect the extraordinary diversity of Silicon Valley, believing that educational excellence and equity depend on the creation of a diverse and inclusive community where all students, families and employees feel a full sense of membership. To live up to our DEI Teaching Philosophy Statement, all employees contribute to developing culturally competent students and building an educational institution committed to social justice and reaching beyond. We offer a wide range of opportunities for all employees to engage in work that furthers these goals, from personal dialogues that help us understand different perspectives, to pedagogical training designed to support equitable instructional practices and build habits to disrupt bias whenever we see it. Ultimately, we hope that this work helps all of our constituents—employees, students, and families—be more aware, empathetic, globally-minded, and justice-oriented. 

A highly collaborative community, we use the following norms to guide our communication with each other: 

• Assume good will  

• Come from your own experience  

• Be more curious than certain  

• Hold yourself and others capable  

Our commitment to these norms makes it possible for us to partner meaningfully, disagree productively, and engage in conversations that are both challenging and generative. 

Equal Employment Opportunity Statement: Hillbrook School is an Equal Opportunity Employer and seeks candidates from diverse backgrounds. Hillbrook School is committed to fostering and sustaining a learning community and does not discriminate on the basis of race, color, religion, sex, gender, sexual orientation, national origin, ancestry, age, marital status, disability, or any other characteristic protected by law. This policy applies to, but is not limited to, educational policies, admission, financial aid, hiring and employment practices, use of school facilities, athletics, and other school-administered programs and activities. 

Another Source works with their clients, on a retained project basis. We are committed to building inclusive candidate pools as we partner with hiring teams. As you read through the job posting and review the list of qualifications (required and/or preferred), please do not self-select out if you feel you do not meet every qualification. No one is 100% qualified. We encourage you to apply and share your story with us. 

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