Live Oak’s new superintendent has a plan — and it starts with 15 minutes with every teacher

Figurines and images of cows, sheep, hedgehogs, Australian shepherds and school buses adorn Live Oak School District Superintendent Jennifer Baldwin’s walls and the desk of her office in Live Oak. 

The trinkets aren’t just decoration, but also serve as daily reminders of her mission. Like a farm, where the rancher or grower raises cattle and produce, Baldwin and her leadership team’s vision for the elementary school district is to help its nearly 1,500 students to grow. 

“That is so perfect for Live Oak because of the farm, the Life Labs and the focus of having great food for our kids,” she said. “No matter who you are in the district, you can gravitate to and enact the vision in some way.” 

One of the district’s schools, Del Mar Elementary, is home to the district’s farm – which celebrated its first full year of vegetable production this spring: 4,800 pounds of organic fruits, vegetables and herbs harvested for school meals and educational programs. 

Since her first day on the job in July, the longtime Santa Cruz resident has been meeting with staff, teachers, union leaders and the wider community to learn about the district, its strengths and weaknesses. Now, she’s starting to chart out community engagement to develop a five-year plan for the district that aligns with its vision of student growth. 

Baldwin, 53, is stepping into the role after the district experienced several years of instability stemming from financial crises, layoffs and turnover in its leadership teams under two superintendents. Former superintendent Daisy Morales resigned in 2024, and Morales’ successor, Pat Sanchez, left the position this past summer. During an interview on Monday, Baldwin told Lookout she would like to retire in her Live Oak role after working in schools over the hill during the past two decades. 

Raised in the small town of Yankton outside of Saint Helens, Oregon, Baldwin spent her childhood riding “horses in the strawberry fields” before she was recruited to play basketball on a full-ride scholarship at Santa Clara University. After living in Santa Clara County for about a decade, she made her way back to a greener landscape and moved to Felton, where she lived for 17 years. About five years ago, she moved to the Westside of Santa Cruz. 

Still, she and her family have strong country roots. Part of Baldwin’s philosophy comes from her grandmother, whom she was very close to growing up. She lived on a farm in central Oregon, where she raised sheep that she rescued from farms that left them to die after deciding that they wouldn’t survive or were abandoned by their mothers. She raised and cared for the sheep before selling them to pay for different needs on their farm. 

“That’s kind of been my north star, my mission, that I want to make a difference for the people that maybe haven’t had all the opportunities in the world,” she said. “As educators, we’re difference-makers; we provide opportunity that people wouldn’t have if it wasn’t for education.” 

As she and her leadership team begin their year of outreach to the community to start developing a five-year strategic plan, Baldwin is focused on getting a cohesive, districtwide approach to their purpose. She asked the school board trustees and leadership team – which includes her chief business officer, assistant superintendent of educational services and executive director of human resources – to read a book she’s encouraged prior teams to read as well. 

The book, “The Energy Bus: 10 Rules to Fuel Your Life, Work, and Team with Positive Energy” by Jon Gordon, focuses on positive leadership around a vision. 

“I think we all need to get on the bus and be heading in the same direction,” she said. “That doesn’t mean we all agree, but it means that we believe in Live Oak.” 

As for outreach and engagement with families and staff, Baldwin has big goals. She plans to host forums with school parent groups and the Live Oak Education Foundation, and forums in Spanish for Spanish-speaking families in the district on a recurring basis. The education foundation raises money for visual and performing arts and STEM opportunities for the district’s students. Baldwin was to host her first forum with the parent groups and education foundation on Tuesday. 

She calls them the “Live Oak Forums,” and says they’ll be an opportunity for guardians and parents to bring their concerns and ideas to Live Oak officials, and to hear about the direction of the district. 

“I think people have a misnomer that the public board meeting is a venue for discourse, and it is actually not,” Baldwin said. “It is a public meeting, but it doesn’t avail itself for rich and deep conversation amongst the people.” 

School board meetings, similar to government agency meetings, are governed by strict laws to promote transparency but often restrict engagement between community members and the elected officials running the meetings. 

Baldwin has also committed to meeting with most district employees, including all 102 teachers in the district for one-on-one, 15-minute meetings. During the meetings, she’ll get to know the educator and ask them for ideas for goals and the district’s five-year strategic plan. 

In the midst of Baldwin’s forums, meetings and strategic planning, she’s also leading the district through the spending of a $44 million bond measure passed in 2024, and declining enrollment and its impact on the budget. Chief Business Officer Jenny Im said the district finished the year on a better financial footing than expected, but officials are still cautious about future years if declining enrollment continues as projected. 

With Measure H bond funding, Im said the district worked on about 20 infrastructure improvement projects at its four sites this past summer, with its largest undertaking being the ongoing renovation of Shoreline Middle School’s gym. Live Oak and Green Acres elementary schools had new flooring and roofing installed, while Del Mar Elementary will have those improvements done next summer. The district expects to spend all the funds over the next two to three years, with one of the largest pending projects including a brand new central kitchen at Del Mar Elementary. 

Infrastructure improvements are being done at all of the school sites as the district is no longer considering beginning a discussion of school closures in the near future, as it was in prior years. After a demographic study in January showed signs of improvement for enrollment, the district postponed a discussion of school closures. 

“Based on what we were seeing from that demographic study, the discussion to potentially close schools has been put off,” said Im. “Because of the growth in our [transitional kindergarten] program this year, we were actually able to add our brand-new TK class and this has slowed our rate of decline.” 

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