In November, voters will elect trustees for the San Mateo Union High School District from areas one, three and five. Trustees are elected to represent their community and govern the district body as a whole over four-year terms. Their main responsibilities include setting district policy, hiring and overseeing the superintendent and approving the budget.
In area one, covering San Bruno and part of Millbrae, incumbent Teri Chavez is running unopposed.
HARRIS VS. JACOBSON
In area three, which includes the Hillsborough and Highlands areas, incumbent Jennifer Jacobson is running against Diana Harris, a San Mateo-Foster City School District teacher.
Jacobson is the current vice president on the board, and is running for her second term after winning an uncontested race in her first term.
“I’ve learned so much [and have gained so] much institutional knowledge,” Jacobson said. “It takes a long time to ramp up and learn the system, [learn] who all the people are and what are all of the initiatives that the school board is involved in and working on … so that’s why I want to run for a second term.”
In her first term, Jacobson worked alongside the other board members to accomplish tasks such as establishing athletic study hall for sophomores, instituting Measures of Academic Progress as a districtwide academic proficiency testing method to better measure students’ academic proficiency, pushing for an AI task force, an increase in career pathway related courses and the district-wide phone ban.
In February 2025, the San Mateo Daily Journal reported that SMUHSD Teachers Association President Craig Childress had called for Jacobson to be censured for advising community members at a board meeting who were concerned about content in Ethnic Studies to report it to administrators or the Office of Civil Rights.
In 2025, the SMDJ reported that Jacobson delayed a SMUHSD board meeting where the trustees put in place districtwide policy in compliance with a state law that allows transgender student athletes to compete in sports categories consistent with their gender. At the meeting, she mentioned the Hillsdale girls lacrosse team losing to a team whose star player she called a boy, though Jacobson ultimately voted for the policy.
“That’s not something our school board has jurisdiction over because it’s a state law,” Jacobson said. “That’s our district policy and I have no say as a single board member to change this. I voted yes to approve that policy, and I want all of our students regardless of their gender identity to feel that they belong on our campuses.”
Jacobson’s goal for her next term is to continue working to continue or expand those initiatives, such as continuing the Empowerment Through Action program and increasing career pathways.
Jacobson has been endorsed by former SMUHSD trustees Peter Hanley and Linda Lees Dwyer, and the North Coast States Carpenters Union.
Meanwhile, Harris hopes to bring both the perspectives of an educator and a parent involved in the SMFCSD Parent Teacher Association to the Board of Trustees.
“There’s no one [on the current board] who’s a teacher and knows what it’s like when [board] decisions come down and affect the classroom,” Harris said. “A lot of times the people making decisions don’t think of how it will actually look, and they overlook a lot [of things. A] teacher’s point of view would be very helpful and help us smooth out some potential bumps in decision making.”
Harris also wants to continue existing programs and establish them as more permanent means of supporting students, and also aims to bridge the gap between the board, parents and students.
“I’m really focused on [engaging] people who don’t have access to the school board and that kind of information,” Harris said. “[I’d] really like to set up regular [meetings] like listening sessions at different high schools to talk with students, teachers and parents [to] get a sense of what their concerns are [and] what their questions are.”
Harris has been endorsed by current trustees Greg Land and Ligia Andrade Zúñiga, the SMUHSD teacher’s union, SMUHSDTA, the San Mateo Democratic Party and other organizations.
“[Harris is] really connected [to] the community,” said Giancarlo Corti, Aragon SMUHSDTA representative and Advanced Placement Psychology teacher. “It’s nice to have an educator on the board, so the fact that she’s a teacher, even though it’s elementary or middle school, is a good voice to have. She understands educational issues, and we don’t have a teacher on the board [currently].”
PROCTOR VS. ROSENBAUM
In area five, which covers Foster City, former two-term SMFCSD trustee Alison Proctor is running against parent Kimo Rosenbaum for the position after longstanding trustee Robert Griffin decided not to run for reelection.
Rosenbaum hopes to bring the perspective of a parent to the board. He said the decision to run came as he felt the time was right. Rosenbaum’s campaign is centered around technology and use of technology in schools, and he advocates for a looser cell phone policy.
“I’ve been going to the meetings,” Rosenbaum said. “Almost every time, [I’ve made] public comments about how the cell phone policy cuts off a lot of things without the district having an answer. I [didn’t] like … the way the board decided on the cell phone policy and the way they’re talking about AI. [Speaking] at the board meetings isn’t enough, [so] if I get on the board, maybe I can make [the policy] better.”
Proctor brings the perspective of a parent as well.
“I’m mainly focused [on] ensuring that every student knows there’s a path to success,” Proctor said. “When I was in high school, the only path anyone talked about was going to a four-year college, [but] there’s so many different ways that [students] can be successful in life, and I want to make sure that every student knows that.”
Proctor takes a different perspective on the cell phone ban to Rosenbaum.
“Overall, the idea is right,” Proctor said. “Sometimes what’s best for us isn’t always what we love the most, but having a distraction-free environment is what is the best environment for [students’ learning and social life].”
Proctor is also endorsed by the SMUHSDTA, as well as the San Mateo Labor Council and Trustee Greg Land.
“She’s really well respected,” Corti said. “[SMFCSD has] a very difficult district. It’s big. There’s lots of diversity in their district, especially economically, and they’ve had to handle some difficult things that she handled really well. She’s always been a good communicator and a good listener.”
Students highlighted what they would like to see in the trustee candidates.
“Students are the people who are being directly affected by all of these rules,” said senior Catherine Tsao. “Whoever is chosen [should be] able to reflect the students’ needs and wants, [as well as] able to actually make a difference that supports everyone.”
Trustee terms for areas 2, encompassing Burlingame and parts of Millbrae, and 4, covering southeastern San Mateo, will expire in 2028.
