Dedication to the District
Kevin Chak’s 30-Year Journey of Service, Storytelling, and Support
August 28th, 2025
Written by Mila Yoch
In the heart of Skyline College’s bustling bookstore, Kevin Chak is more than a manager—he’s a living archive, a mentor, and a quiet force behind student success. With over three decades of service to the San Mateo County Community College District (District), his story is woven into the very fabric of the campuses he’s helped shape.
“I started as a student in 1994,” he recalls, seated in his office in Building 6—a space that once served as a visitor drop-off loop in front of Building 5. “I always joke that my desk now sits in the driveway entrance to that loop.”
From student assistant to store manager, Kevin’s career has mirrored the District’s own evolution. He has held roles at both Skyline and the College of San Mateo (CSM) and currently serves as interim co-store manager at CSM while continuing to lead operations at Skyline. But his impact reaches far beyond inventory and invoices.
Kevin’s connection to the District is more than professional—it’s deeply personal. His wife, nephew, chosendaughter Alexa Padilla, brother, sister-in-law, and brother-in-law are all Skyline alumni. “It’s a family thing,” he says with pride. “Skyline has been part of our lives for generations.”
That deep-rooted loyalty fuels Kevin’s belief in the power of community colleges—not just as stepping stones, but as destinations in their own right. “Why pay two or three times more for the same general ed class elsewhere?” he asks. “If you live in San Mateo County, it’s free. That allows students to succeed both in the classroom and in their lives off campus.”
Student success is a driving force behind everything Kevin does. He’s a fierce advocate for Career Technical Education (CTE) programs across the District—especially Barbering, Cosmetology, and Esthetics (BCE). And he’s not just a supporter; he’s a participant.
“I was going to be customer number one for the barbering program,” he laughs. “COVID delayed it, but I still sit in the chair and talk to students while they cut my hair.”
His mentorship is hands-on. He advises students on how to maximize book vouchers, encourages cosmetology students to invest in extra mannequin heads for practice, and even holds impromptu “resource briefings” mid-haircut. “Use your resources,” he tells them. “Don’t leave money on the table.”
For many students, Kevin is the first person to point them toward support services they didn’t know existed. “I’ve had student employees who are first-gen and didn’t know about financial support,” he says. “I’d drag them by the ear—literally—and introduce them to the program coordinators.”
He regularly connects students to TRIO—a program offering academic, personal, and social support—and SparkPoint, which helps reduce financial barriers. It’s this kind of grassroots advocacy that makes Kevin indispensable. He doesn’t just manage a store; he manages relationships, opportunities, and hope.
His commitment to student success is also reflected in his participation in the Employee Giving Program. Through payroll deduction, Kevin supports scholarships, such as the David Galan Fund for cosmetology students, and cultural programs, including Kababayan at Skyline.
His philosophy is simple: give what you can and give consistently. “It’s not just about money,” he says. “It’s about showing students that we believe in them.”
Kevin Chak’s story is one of quiet leadership, deep loyalty, and relentless advocacy. Whether he’s mentoring students, supporting scholarships, or dreaming up District-wide collaborations, his impact is unmistakable. In a world that often celebrates flash over substance, Kevin reminds us that legacy is built one student, one haircut, one book voucher at a time.
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