Director of Development

Director of Development

Start Date: July 1, 2026 (Flexible June 15 - August 1)

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VISION: Inspire students to achieve their dreams and reach beyond themselves to make a difference in the world.

MISSION: Hillbrook provides an extraordinary educational experience that fosters a love of learning in our students and helps them develop the knowledge, skills, and confidence to achieve their highest individual potential in school and in life. At Hillbrook, students are known, respected and valued as individuals and every day is a journey of self-discovery, imaginative thinking, creative problem solving, laughter and friendship.

CORE VALUES: Be kind. Be curious. Take risks. Be your best.

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The Position: What Will You Do & How Will We Collaborate?

The Director of Development is responsible for developing and executing a comprehensive, integrated fundraising strategy that strengthens philanthropic support, deepens community engagement, and advances the school’s long-term strategic priorities. This role provides leadership across major gifts, annual giving, donor stewardship, and development operations, collaborating closely with the Director of Annual Giving and other members of the Office of Advancement and Enrollment.

Reporting to the Chief Institutional Advancement Officer, the Director of Development designs and implements strategies that grow a sustainable culture of philanthropy across the JK–12 community. This role requires strategic vision, strong management capability, emotional intelligence, discretion, and the ability to inspire confidence among donors, volunteers, and colleagues.

In addition to leading strategy and team execution, the Director of Advancement manages a portfolio of high-capacity families and partners with the Head of School, Chief Institutional Advancement Officer and Board Advancement Committee in modeling best practices in cultivation, solicitation, and stewardship.

The Director of Development works across both the Los Gatos and San Jose campuses. Given the highly relational and community-facing nature of the work, occasional evening and weekend commitments are expected.

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The Hillbrook Employee: Who Are You?

Do our Core Values – Be kind. Be curious. Take risks. Be your best. – align with how you show up as a professional? Are you committed to building and bridging inclusive communities? Do you believe learning should be an active and relational process? Do you thrive in small collaborative environments? Are you entrepreneurial? Do you pursue impact and equity in your work? Do you enjoy connecting with people, understanding their stories, and aligning passions with purpose? A Hillbrook employee will emphatically say yes to each of these questions.

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Specific Duties and Responsibilities

Strategic Leadership & Advancement Planning

• In partnership with the Chief Institutional Advancement Officer, develop and implement a comprehensive fundraising strategy aligned with Hillbrook’s mission and strategic plan
• Establish annual and multi-year fundraising goals across major gifts, leadership annual giving, alumni giving and other priority initiatives
• Lead forecasting, pipeline development, and revenue projections in collaboration with Chief Institutional Advancement Officer and the Finance team
• Serve as a strategic thought partner to the Chief Institutional Advancement Officer and Head of School on philanthropic trends, donor engagement, and campaign readiness

Major & Leadership Giving

• In collaboration with Chief Institutional Advancement Officer, develop and manage a portfolio of 40-50 high-capacity current and past families capable of making leadership and major gifts
• Develop individualized cultivation, solicitation, and stewardship strategies
• Support complex gift conversations in partnership with the Chief Institutional Advancement Officer, Head of School, and volunteer leaders
• Prepare compelling proposals, gift agreements, donor briefings, and stewardship plans
• Partner closely with the Director of Annual Giving to ensure seamless pipeline development from broad-based participation to leadership and major gifts

Team Leadership & Collaboration

• Provide day-to-day leadership and strategic oversight to the advancement team, specifically the Director of Annual Giving and other Office of Advancement and Enrollment team members providing support for database management and events
• Foster a collaborative, accountable, and mission-aligned team culture
• Collaborate with Office of Advancement and Enrollment team members including the Communications team, the Finance team, and academic leaders to translate institutional priorities into compelling philanthropic opportunities
• Engage and support Board Advancement Committee members and key volunteers in fundraising strategy and execution, including collaborating with the Chief Institutional Advancement Officer on preparing Board Advancement materials and attending regularly scheduled committee meetings

Stewardship & Community Engagement

• Oversee a comprehensive stewardship program that ensures timely, personalized, and impact-driven donor communications
• Design, implement and participate in high-level donor engagement opportunities, including small gatherings, cultivation events, and strategic campus experiences
• Ensure donors experience meaningful connection to Hillbrook’s mission, students, and programmatic impact
• In collaboration with the Director of Annual Giving and Director of College Counseling, provide strategic oversight of the growth of our Alumni Connection opportunities and fundraising imperatives.
• In collaboration with the Chief Institutional Advancement Officer and Director of the Scott Center, provide strategic oversight of outside fundraising and sponsorship potential through Scott Center partnership and events such as Conversations for Good.

Data, Reporting, & Administration

• In close collaboration with the Advancement and Enrollment Coordinator and Director of Annual Giving, ensure accurate portfolio management, contact reporting, and pipeline tracking within the advancement database
• Monitor and report progress toward fundraising goals to the Chief Institutional Advancement Officer and Board Advancement Committee
• In close collaboration with the Advancement and Enrollment Coordinator and Director of Annual Giving, partner with Finance to oversee pledge documentation, payment schedules, and reconciliation processes
• Maintain confidentiality and integrity in all donor-related matters

Other Responsibilities

• Attend evening and weekend events as needed
• Support and attend engagement initiatives led by the Office of Advancement and Enrollment, Programs, and the Head of School office as they relate to the broader strategic goals of the school
• Perform other responsibilities as assigned by the Chief Institutional Advancement Officer

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Qualifications

• 5+ years of progressive experience in fundraising, with demonstrated success in major gifts and/or comprehensive fundraising programs; independent school experience preferred
• Proven ability to cultivate, solicit, and close leadership-level and major gifts
• Experience managing volunteers and cross-functional teams
• Strategic thinker with strong analytical and planning skills
• Exceptional relationship-building capacity and emotional intelligence
• Outstanding written, verbal, and interpersonal communication skills
• Strong organizational skills and attention to detail, with the ability to manage multiple priorities
• Sound judgment and discretion in handling confidential information
• Commitment to anti-racism and designing inclusive, equitable donor and community experiences
• Proficiency with Google Suite and fundraising databases (e.g., Raiser’s Edge, NXT, iWave, GiveSmart)
• Ability to occasionally work evenings and weekends
• Bachelor’s degree required; advanced degree preferred

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Diversity, Equity, Inclusion, Justice, & Action

Commitment to Diversity, Equity, Inclusion, Justice, & Action

As noted in our Commitment to Community & Belonging, Hillbrook values a diverse and inclusive community that reflects the richness of Silicon Valley. All employees contribute to creating an environment where students and families feel respected, supported, and connected.

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To Apply

Salaries are competitive. Benefits include full medical, dental, and vision coverage; retirement planning; generous holidays; and robust professional development.

The salary range for this role (full-time equivalent) is $135,000–$150,000 dependent on experience.

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.

Please submit your application materials through Another Source recruiting here!

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About Hillbrook School

Hillbrook School is an independent Junior Kindergarten - 12th grade school located on two campuses in San José and Los Gatos, California. The JK - 8th grade is located on 14 acres in Los Gatos and the 9th-12th grade is in two historic buildings in downtown San José. Founded in 1935, Hillbrook is known for its student centered approach to education where students are known as individuals and learning is active and engaging. You can learn more about Hillbrook at https://www.hillbrook.org/.

Benefits include full medical, dental, and vision coverage; tuition remission, student loan assistance, commuter stipend, retirement planning; generous holidays; and robust professional development.