Another Source’s client, Hillbrook School, is recruiting an Advancement and Alum Engagement Manager to join their team in Los Gatos, CA and San Jose, CA.


Internally this will be titled Director of Capital Campaign and Alum Engagement


About Hillbrook School:

For almost 90 years, Hillbrook School has been a junior kindergarten-8th grade independent school located on 14 acres of oak woodland in Los Gatos, CA – and in the fall of 2023, we opened the doors to the founding class of our high school. Founded in 1935, the school remains deeply connected to its historical roots as a place where children are known, learning is authentic and active, and success is measured one child at a time. Over the years, we have grown and evolved from a small boarding school serving wards of the state to one of the leading independent schools in the Bay Area, and yet our vision remains the same—to inspire children to achieve their dreams and reach beyond themselves to make a difference in the world.


We are now embarking on one of the school’s most ambitious strategic initiatives ever: the expansion to a JK-12 with the addition of a new high school in downtown San José. We are driven by a foundational belief – that our 8th graders and other students deserve an extraordinary educational experience in high school that builds upon the exceptional foundation we provide our JK-8 students. The core differentiators for our current program – the placement of choice and engagement at the center of the learning experience, integrated, real world education that challenges students to reach beyond and make a difference, and a deep commitment to diversity, equity and inclusion – will translate seamlessly into a 9-12 environment, allowing us to extend our innovative approach into a market in need of a new model of secondary school education.


To learn more about the school: https://www.hillbrook.org/


Anticipated Salary: $80,000 – $110,000 per year, depending on years of experience.



full medical, dental, and vision coverage; ample retirement planning with TIAA-CREF; a generous holiday schedule, including over five scheduled weeks off during the year (this is over and above the three weeks of additional personal vacation); shortened work days throughout the summer months; religious holidays following each employee’s faith; and a strong commitment to engaging and personalized professional development.



About the role:

The Director of Capital Campaign and Alum Engagement will play a pivotal role in cultivating relationships with alums, parents of alums, community partners, and current parents while strategically advancing fundraising efforts to support the organization’s mission and goals.


The Director of Capital Campaign and Alum Engagement is expected to actively participate in a collaborative employee culture that is committed to being at the leading edge of JK – 12th grade education. The Director of Capital Campaign and Alum Engagement reports to the Chief of Institutional Advancement and Enrollment and is part of a highly collaborative team of advancement and enrollment professionals all tasked with filling and funding the school. This individual works with highly confidential, personalized and proactive processes that hold families from the Admission experience through their tenure as current families and then into a deepening alum experience. Interpersonal skills, networking, attention to detail, and discretion are of utmost importance.


The Director of Capital Campaign and Alum Engagement will create meaningful ways for alums, alum families, and current families to engage with and support Hillbrook School. The ideal candidate understands the benefits of an independent school education and can articulate Hillbrook’s unique vision, mission, and extraordinary educational experience in a compelling way. The Director of Capital Campaign and Alum Engagement manages the day to day operations of the Hillbrook Capital Campaign, currently 75% through the quiet phase and assumes responsibility for developing a comprehensive alum and alum parent engagement plan and cultivation, solicitation, and stewardship strategies for these stakeholders.


Specific Duties and Responsibilities:

Actively participate in a collaborative employee culture that is committed to being at the leading edge of JK – 12th grade education.
Report to the Chief of Institutional Advancement and Enrollment
Collaborate closely on all fundraising priorities with the Director of Annual Fund and Advancement team to ensure Hillbrook families have a holistic and deeply meaningful experience engaging with and supporting the school
Collaborate with the entire Office of Advancement and Enrollment team in fulfilling the goals and objectives outlined by school leadership
Partner with the marketing and communication team, with support from the Chief of Institutional Advancement and Enrollment to develop compelling alum, alum parent, and capital campaign materials for prospective donors
Oversee the school’s capital campaign in close collaboration with the Chief of Institutional Advancement and Enrollment
Support the development and implementation of a comprehensive alum and alum parent engagement program, including coordinating and implementing alum and alum parent donor cultivation and recognition events
Alum and Alum Parent Engagement

Develop cultivation, solicitation, and stewardship strategies for alums and alum parents to grow and improve our donor base giving, retention, and engagement
Maintain database of annual grant makers (prospects and donors), including individuals, corporations, and foundations that can be used for all Hillbrook fundraising campaigns and activities
Plan and implement targeted fundraising campaigns, including direct mail, email, phone, and digital strategies in coordination with Director of Annual Giving and Parent Engagement
Organize and implement a diverse range of events aimed at fostering alumni engagement and community building including but not limited to: mentoring programs, the Loukas Angelo Alumni Basketball Game, class reunions, Scott Center for Social Entrepreneurship’s Conversations for Good
Work strategically with Division Heads and volunteers to encourage them to activate their networks to help Hillbrook School develop stronger relationships with alumni and current students
Cultivate alum and alum parent volunteers for future leadership roles on Hillbrook School’s boards, committees, councils, and task forces
Capital Campaign

Manage our portfolio of Capital Campaign prospects at various stages of their relationship with Hillbrook School
Qualify and cultivate newly identified prospects and evaluate major gift potential and next steps
Lead the volunteer Capital Campaign Committee by providing meaningful engagement for volunteers in meeting the goals of the Capital Campaign
Draft, update, and prepare all campaign proposals and other meeting materials with guidance from the Chief of Institutional Advancement and Enrollment and Director of Communications as needed
Prepare Campaign Agreements, enter gifts into the development database, and work closely with the advancement and finance teams to ensure proper gift and pledge fulfillment
Plan and implement meaningful stewardship of campaign donors to ensure long-lasting engagement with the school
Events: Conversations for Good, Alum and Campaign events (large and small)

Create invitations, manage RSVPs and fields questions related to events
Create and facilitate event programming
Secures event sponsorships in collaboration with school leadership
Secures and manages event vendors
Tracks and manages event budgets
Attend and provide onsite management of all alumni and campaign events
Strategize and conduct all event follow-up
Set up, manages, and troubleshoots event software
Track donations and underwriting in coordination with Finance team
Manage and facilitate outreach with all constituents
Recruit volunteer event committees and schedules/leads all event committee meetings

Desire and ability to work in a collegial, highly collaborative environment
Demonstrated commitment to teaching and learning in a diverse, dynamic, and progressive school community
A commitment to anti-racism and demonstrated skill designing equitable and inclusive educational experiences and learning environments that incorporate themes of diversity and justice
Strong passion for the role and the school, and an understanding of how the position supports the school’s ability to meet its mission and vision every day
Three or more years of relevant professional experience in fundraising or transferable experience; independent school experience preferred
Natural networking instincts that make one adept at building and nurturing relationships with all types of constituent groups
Excellent interpersonal, written and verbal communication skills to articulate and explain complex issues to stakeholders responsible for making informed and effective strategic decisions
Strong project management skills, especially as related to event management
Strong attention to detail for guiding gifts through transactions in collaboration with the finance team
Ability to work both independently and collaboratively under tight deadlines
Exhibit sound judgment related to confidential conversations, projects, and information related to the School or any of its constituents, including effective communication regarding such matters to the appropriate individuals
Strong active listening skills, including an ability to ask sensitive questions with tact
Must be able to deal effectively and politely with people from all types of backgrounds and experiences and in all types of difficult or challenging situations
A growth mindset, sense of humor, and warm personality
Ability to work in a collegial, collaborative environment and to develop the necessary trust and credibility to work with a broad range of constituents.
An entrepreneurial spirit with the ability to think strategically and creatively
Availability on nights and occasional weekends
Availability to regularly work in person and travel between Los Gatos and San Jose campuses
Mandarin/Spanish proficiency is a plus
Proficiency in Google Suite, particularly Google Sheets, and utilizing fundraising database software such as Raiser’s Edge, GiveSmart, iWave, and similar.
Bachelor’s degree
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




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. Veterans, women, people of color, LGBTQIA+, and people with disabilities are encouraged to apply. 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.