Spring 2026 Recipient: Jeff Gilbert

August 27, 2026: Hillsdale High School Principal Jeff Gilbert Named Spring 2026 Recipient of Robert H. Griffin Leadership Award

Watch a recording of the award presentation.

The San Mateo Union High School District is proud to recognize Jeff Gilbert as the Spring 2026 recipient of the Robert H. Griffin Leadership Award; an award that recognizes leadership grounded in excellence, equity, and an unwavering commitment to student success. 

Few leaders embody these values as fully, as consistently, or as profoundly as Mr. Gilbert. His impact on students, families, colleagues, and the broader community is extraordinary, deeply human, and transformative. Jeff Gilbert’s leadership at Hillsdale High School embodies the very spirit of this award.

Those who work alongside Jeff describe a leader who is visionary without seeking the spotlight, deeply principled while remaining open to others, and ambitious for his school while never losing sight of the individual student or
teacher. His colleagues describe Hillsdale as being “forever changed for the better” because of his leadership. In a single week, members of the Hillsdale community heard Jeff praised for his visionary leadership, his care for students, and his humility as an administrator and colleague; three qualities that together capture the breadth of his influence.

At the center of Jeff’s leadership is a conviction that the experiences of students and classroom teachers should guide the work of a school. He has consistently grounded decision-making at Hillsdale in the school’s Cornerstones of Equity, Shared Decision-Making, Personalization, and Rigor, approaching leadership as something to be practiced collaboratively rather than exercised individually. His commitment to shared decision-making, Hillsdale’s governance structures, and teacher leadership reflects both his humility and his belief in the democratic promise of public education.

One of Jeff’s most significant contributions has been his sustained stewardship of Hillsdale’s Small Learning Communities. School reform is difficult to begin and even more difficult to sustain. Hillsdale has maintained
this transformative approach for more than two decades, developing teacher leadership and continually examining issues ranging from equity and assessment to Advisory, facilities, budgets, and instructional practice. Jeff’s
colleagues are careful to note that this success belongs to an entire community, yet they also recognize that his long tenure as Lead Principal and his unwavering commitment to this work have been instrumental in its endurance.

Under Jeff’s leadership, Hillsdale has remained at the forefront of high school redesign. He trusts teachers with meaningful autonomy while maintaining high expectations for innovation, collaboration, student-centered instruction,
and thoughtful assessment. His admiration for educators is evident in the way he leads them: with confidence in their professionalism and a belief in their ability to create extraordinary experiences for students. That sustained work has earned attention beyond Hillsdale and beyond our District. Educational leaders including Linda Darling-Hammond and Deborah Meier have recognized Hillsdale’s work and looked to Jeff and the school community as examples of thoughtful school redesign and democratic education.

Perhaps the most meaningful expression of Jeff’s leadership can be found in a simple belief frequently heard at Hillsdale: every student is known. At a comprehensive high school serving approximately 1,600 students,
making that belief real requires far more than good intentions. Through structures such as Advisory, championed and supported by Jeff, students have an adult who knows them, cares about them, and can help connect them to the larger school community. Jeff has helped allocate resources and build systems so that personalization and belonging become part of the everyday experience of school.

His commitment to equity is similarly evident in his support for initiatives such as Empowerment Through Action, and additionally, Empowerment San Mateo; accessible project-based assessments; coherent professional
learning; and MTSS work centered on improving outcomes for multilingual learners and historically underserved students. His colleagues describe this as lasting equity work; work embedded into practice and culture rather than
limited to individual initiatives.

Jeff’s accomplishments are significant, but the nomination submitted by the Hillsdale team makes clear that his influence comes just as powerfully from how he leads.

Jeff listens deeply. He meets people where they are. He makes students, staff members, and families feel heard and valued. He understands both the structures necessary to sustain long-term change and the human relationships necessary to make people believe that change is possible. His leadership of Hillsdale’s shared governance processes illustrates his ability to hold a long-term vision while inviting others to help shape and ultimately own that vision.

He also continues to see himself fundamentally as an educator. Jeff refers to members of his administrative team as “lead teachers,” and he models that philosophy by remaining close to the instructional life of the school, serving
as an advisor, collaborating with teaching teams, creating curriculum, connecting with families, and maintaining the belief that school leadership must always remain connected to students and classrooms. There is a wonderful alignment between the values represented by the Robert H. Griffin Leadership Award and the leadership Jeff Gilbert has demonstrated throughout his years at Hillsdale.

Excellence is evident in the school community he has helped nurture and sustain. Leadership is evident in the people around him who have been trusted, encouraged, and empowered to lead themselves. Equity is evident in a school designed around the promise that every student deserves to be known, challenged, supported, and valued.

And maybe most importantly, Jeff’s example reminds us that enduring leadership is not measured only by what a leader accomplishes personally. It can also be measured by what becomes possible in other people because
that leader was there.

Jeff Gilbert has spent his career creating those possibilities, for students, teachers, colleagues, families, Hillsdale High School, and for the broader educational community.

The San Mateo Union High School District is proud to celebrate Jeff Gilbert as the Spring 2026 recipient of the Robert H. Griffin Leadership Award and to thank him for the vision, generosity, humility, courage, and enduring belief in
public education that he brings to our District.