Two Candidates Vie for Vacant Flagler County School Board Seat in August Election

Flagler County voters will decide August 18 who fills the District 1 seat on the county school board, left vacant when former member Derek Barrs was confirmed by the U.S. Senate in 2025 as administrator of the Federal Motor Carrier Safety Administration. The nonpartisan race pits retired federal executive Cathy Moon against Jill Woolbright, a former teacher and school board member, in an election open to all voters regardless of party affiliation.

Both candidates responded to a News4JAX questionnaire as part of a statewide partnership of 27 newsrooms and universities working to help Florida voters make informed decisions in the 2026 school board elections. The race centers on kindergarten readiness, teacher recruitment and retention, and fiscal management during a period of uncertain state and federal funding.

What's happening

Cathy Moon, 68, is a retired federal program and project manager who moved to Flagler County in 2017 after nearly 30 years with multiple federal agencies, culminating in an executive leadership role in Washington, D.C. She operated a small business from 2018 through 2024 before retiring again. Moon holds a bachelor's degree in health and safety education, a graduate certificate in human resources, and a master's degree in business administration. This is her first run for public office.

Jill Woolbright, 68, taught in Flagler County schools for 28 years and previously served on the Flagler County School Board representing District 1 from 2020 to 2022. She holds a bachelor's degree in elementary education from the University of Central Florida and was named Florida's top sixth-grade math teacher for student academic growth in 2016. Woolbright has lived in the community since 1989 and raised three children who graduated from Flagler schools.

The election takes place August 18, 2026. The District 1 seat represents a portion of Flagler County, which lies between St. Johns County to the south and Volusia County to the north along Florida's Atlantic coast.

Kindergarten readiness emerges as central issue

Both candidates identify early childhood education as a critical challenge, though they frame the issue differently. Moon has made kindergarten readiness the centerpiece of her campaign, citing district data showing that only 37 percent of Flagler County children arrive at kindergarten ready to learn.

According to figures Moon cites from Flagler County Schools, 35 percent of kindergartners in 2024-2025 did not attend the state's free Voluntary Pre-Kindergarten (VPK) program. Of those who completed VPK, 65 percent tested kindergarten-ready, compared to just 36 percent of those who did not attend. In fall 2025, overall kindergarten readiness scores dropped to 37 percent.

Moon argues that the primary barrier keeping families from accessing VPK is lack of transportation. While VPK is free, the state does not fund transportation to the program. Moon frames the issue as a cost-benefit analysis: the expense of providing transportation versus the cost of thirteen years of intervention and remediation services for students who arrive unprepared.

"When a child misses VPK and arrives at kindergarten unprepared, our school system invests additional resources in intervention, remediation, and support services for that child across all thirteen years of their K-12 education," Moon stated in her response. "The cost of inaction far exceeds the cost of a solution."

Moon also identifies other barriers to VPK access: the program operates only half a day, and aftercare costs approximately $80 per week, which she says is out of reach for many families. She notes that Florida requires only booster seats for four-year-olds rather than full car seats, making transportation logistics more manageable than some assume. Moon pledges to convene parents, educators, transportation officials, and community partners to find solutions and to advocate at the state level for VPK transportation funding.

Woolbright does not focus specifically on VPK transportation in her responses, instead identifying academic achievement in reading and math as her top priority to maintain the district's A rating. She emphasizes using data to identify successful instructional practices and supporting teachers with evidence-based resources.

Teacher retention and compensation

Both candidates highlight teacher recruitment and retention as a critical issue, though they approach it from different angles.

Moon, who holds an MBA and a graduate certificate in human resources, says retaining great teachers requires competitive compensation, affordable health insurance, meaningful administrative support, and a school culture where educators feel respected and empowered. She says she is advised by a team of retired Flagler County educators.

Woolbright addresses the issue through the lens of fiscal responsibility and workforce support. She specifically mentions working to equalize steps on the teacher pay schedule, noting that nine years were compressed to the same pay level. "Each year, I hope we can make gains in equalizing the steps on the teacher pay schedule," Woolbright stated, adding that the district needs to prioritize classroom spending and partner with the local business community to strengthen classroom-to-career programs.

Teacher retention challenges are not unique to Flagler County. Districts across Florida face competition for qualified educators amid concerns about compensation levels relative to cost of living and administrative workload. School boards have limited control over base salary structures, which are largely determined by state funding formulas and collective bargaining agreements, but can influence supplemental pay, benefits, and working conditions.

Contrasting backgrounds and governance approaches

The candidates present starkly different professional backgrounds and governance philosophies.

Moon emphasizes her executive leadership experience managing large federal budgets and her full-time availability as a retiree with no other professional commitments. She says her career involved leading teams that saved the federal government hundreds of millions of dollars without layoffs or service cuts. Moon positions herself as bringing sophisticated financial literacy and strategic planning expertise to complement her education degree. She describes herself as having no ideological agenda and not being a career politician.

Woolbright emphasizes her 28 years of classroom experience in Flagler County and her previous school board service from 2020 to 2022. She argues that her combination of teaching experience, board governance experience, and long-term community ties—she has lived in Flagler County since 1989—gives her a unique understanding of how board decisions affect students, teachers, parents, and taxpayers. Her top priorities include rebuilding trust through transparency, ensuring compliance with Florida law regarding parental rights, and clear communication about curriculum, policies, and spending.

The different emphases reflect a fundamental question in school governance: whether boards are best served by deep educational expertise and institutional knowledge of the specific district, or by executive leadership experience and fresh perspectives from outside the education sector. Florida school board candidates are not required to have education backgrounds; boards typically include members from diverse professional backgrounds.

What happens next

The election takes place August 18, 2026. Because the race is nonpartisan, all registered voters in Flagler County School Board District 1 may participate regardless of party affiliation. If no candidate receives more than 50 percent of the vote, Florida election law would typically require a runoff, though with only two candidates in this race, one will necessarily receive a majority.

The winning candidate will join a five-member school board that governs Flagler County Schools. School boards in Florida have authority over district budgets, personnel policies, facilities, and academic programs within the framework of state law and regulations. Major spending decisions, such as whether to provide VPK transportation using local funds, would require board approval.

Voters can find additional information about the candidates at their campaign websites: cathymoon4flaglerschoolboard.com for Moon and jill4kids.com for Woolbright. News4JAX's complete voter guide is available at news4jax.com/voters-guide.

The race reflects broader tensions in Northeast Florida education policy as districts navigate rapid growth, teacher shortages, and debates over curriculum transparency and parental involvement. Flagler County has experienced significant population growth in recent years, with families moving from higher-cost areas, placing pressure on school capacity and services. The winner of this race will help determine how the district addresses those pressures and positions itself for the coming decade of growth.