Jill Woolbright is one of two candidates running for the Flagler School Board’s District 1 seat. Her opponent is Cathy Moon. The seat is currently vacant; Sally Hunt was elected in 2022 before resigning in 2024. Her appointed replacement, Derek Barrs, resigned in 2025 to accept an appointment to the U.S. Department of Transportation.
Woolbright served on the Flagler School Board previously for two years. She was elected in 2020 to fill the remainder of Andy Dance’s term after he ran for County Commission. In her 2022 re-election bid she was defeated by Sally Hunt.
The 2026 primary election is on Tuesday, August 18. Flagler County voters will be able to vote for the District 1, District 2, and District 4 seats. School Board races are nonpartisan and open to all county voters. Woolbright and Moon’s race will be decided in the primary, as a runoff would require three or more filed candidates.
Other Candidate Interviews
Flagler School Board:
Palm Coast City Council:
Interview Criteria
- The object of the interview is not to grill the candidate, nor to give them softballs. Ideally, in their answers the candidates provide to voters a useful insight into their ideology, their priorities, and their knowledgeability and preparedness for office.
- These questions are sent to each declared candidate in Flagler County’s local elections. All candidates running for the same office received the same exact questions.
- The only edits made are for spelling, formatting and basic grammar (i.e., ‘their’ when it should be ‘there’). Censorship of profanity may also be applied if it were applicable. Otherwise, answers are presented in their full form as the candidate provides them.
- Answers are subject to fact-checking if they contain information that’s blatantly misleading or untrue (misrepresenting factually verifiable information, misquoting a statistic, etc). Clarifications will be added underneath the candidate’s answer if applicable. The answers will still be presented as given even if a fact-check or clarification is needed.
Candidate Interview
Date of Birth: November 23, 1957
Hometown: Flagler County, FL
Career/Educational Resume: “Jill Woolbright has called Flagler County home since 1989 and has dedicated her career to serving local students and families. She earned a Bachelor of Science degree in Elementary Education from the University of Central Florida and holds certifications in Elementary Education, Exceptional Student Education, and an ESL Endorsement.
“Jill taught in Flagler County for 28 years, serving students in general education, special education, and advanced learning environments. During her teaching career, she was recognized as a High Impact Teacher and earned the #1 state-ranked Math Value-Added Model (VAM) score in Florida in 2016.
“She served on the Flagler County School Board from 2020–2022, bringing classroom experience and a commitment to transparency, accountability, school safety, parental engagement, and academic excellence. She has also been involved in the community through organizations including the Flagler Education Foundation, Kiwanis Club, Guardian ad Litem, church volunteer work, and international service teaching ESL in Hungary and Vacation Bible School in Togo.
“Jill is a mother of three children, all graduates of Flagler Palm Coast High School.”
1) Order these three groups according to how strongly you feel a School Board member is tasked with serving them: students, teachers, and parents.
“I respectfully disagree with the premise that these groups should be ranked. A successful public school system depends on students, parents, and teachers working together, and a School Board member has a responsibility to support all three.
“After teaching in Flagler County for 28 years, I witnessed firsthand that the greatest student success occurred when parents and teachers worked together as partners. Open communication, mutual respect, and shared accountability create the strongest learning environment for children.
“The School Board’s mission is to ensure every student has the opportunity to receive a high-quality education and reach his or her full potential. Achieving that mission requires engaging parents as valued partners in their children’s education and supporting teachers with safe schools, effective leadership, appropriate resources, and the respect they deserve as professionals.
“These are not competing priorities. Students, parents, and teachers are strongest when they work together, and that partnership should guide every decision a School Board member makes.”
2) Describe any career experience you have in which you directly worked in or with the public education system. If none applies, explain how any other experience you have would directly apply to the education aspects of School Board duties.
“For 28 years, I worked directly in Flagler County’s public education system as an elementary and special education teacher. During my career, I taught general education, exceptional student education, and advanced learners, earned an ESL endorsement, and was recognized as a Florida High Impact Teacher. In 2016, my sixth-grade math students achieved the highest Value-Added Model (VAM) score in the state of Florida.
“I also served on the Flagler County School Board from 2020 to 2022, where I gained firsthand experience in school governance, budgeting, policy development, strategic planning, collective bargaining, student achievement, school safety, and compliance with state and federal education laws.
“I am the only candidate in this race with both decades of classroom experience in Flagler County Schools and prior service on the Flagler County School Board. That unique perspective allows me to understand how Board decisions affect students, teachers, parents, administrators, and taxpayers, and to contribute effectively from day one.
“If elected, I will use that experience to keep students at the center of every decision, support teachers, respect parents’ rights, ensure fiscal responsibility, and continue improving academic achievement for every child in Flagler County.”
3) How would you assess the School Board’s productivity and decorum over the past two years?
“The School Board has made progress in several important areas, including maintaining strong fiscal oversight and supporting school operations. At the same time, there have been instances where public confidence has been affected by unnecessary conflict and inconsistent decorum. Healthy debate is essential, but it should always be conducted with professionalism, mutual respect, and a shared commitment to serving students.
“The Board has also faced the challenge of operating with vacancies following resignations, which at times made it more difficult to build consensus and maintain continuity. An effective School Board works best when every elected member has an equal opportunity to ask questions, share perspectives, and contribute to the discussion. No single member should dominate deliberations, because the community benefits when all voices are heard before decisions are made.
“If elected, I will work to foster a collaborative and respectful Board culture where differing viewpoints are welcomed, discussions remain focused on facts and solutions, and every decision is guided by what is best for students. My goal is to help build public trust through civility, transparency, accountability, and effective leadership.”
4) In recent years the School Board has navigated multiple issues which became political lightning rods. How does an effective School Board member remain focused on students when the situation attracts mass political attention from the county and beyond?
“An effective School Board member remains focused by remembering who the Board ultimately serves: the students of our community. Political controversy may come and go, but our responsibility is constant; to make decisions that improve student learning, protect student safety, respect parents’ rights, and faithfully carry out the duties assigned to us under Florida law.
“My approach is straightforward. I listen respectfully to everyone, even when opinions differ. I review the facts, follow the law, consider district policy, and ask one simple question: “What decision is in the best interest of students?”
“After 28 years as a Flagler County teacher and serving on the School Board, I’ve learned that leadership is not about chasing headlines or responding to the loudest voices. It’s about staying principled, transparent, and willing to make difficult decisions based on facts rather than politics.
“Our community deserves a School Board that is focused on academic excellence, fiscal responsibility, safe schools, and strong partnerships with parents and teachers. If we keep students at the center of every decision, political distractions become just that… distractions.”
5) Florida passed universal school choice in 2023. As someone who hopes to be a leader within the school district, do you believe Flagler Schools is the best choice available to parents? Why or why not?
“Florida’s universal school choice law recognizes an important principle: parents should have the freedom to choose the educational setting that best meets their child’s needs. I support that right.
“As a School Board member, however, my responsibility is to ensure Flagler Schools are a district that families want to choose. We should strive to offer outstanding academics, safe and orderly schools, exceptional teachers, career and technical education opportunities, fine arts, athletics, and strong support for every student.
“After teaching in Flagler County for 28 years and serving on the School Board, I know our district has many strengths and dedicated educators. At the same time, we should never become complacent. Families have more educational options than ever before, and that challenges us to continuously improve.
“Success should not be measured by limiting parents’ choices, it should be measured by earning their confidence. My goal is to help make Flagler Schools the first choice for as many families as possible by focusing on academic excellence, transparency, fiscal responsibility, and strong partnerships with parents.”
6) On a similar note, educators and other faculty may view Flagler Schools as one option among several other school districts. What will you advocate for to make Flagler Schools a more attractive place to work?
“As someone who taught in Flagler County for 28 years, I understand what educators want. Competitive compensation matters, but people also want to work in a district where they feel respected, supported, and able to focus on teaching.
“As a School Board member, I will advocate for responsible compensation and benefits that help us recruit and retain outstanding employees while being good stewards of taxpayer dollars. Just as importantly, I will support safe and orderly classrooms, reduce unnecessary bureaucracy whenever possible, provide teachers with the resources they need to be successful, and recognize the professionalism and expertise they bring to our schools.
“I also believe support staff are essential to a successful school district. Bus drivers, paraprofessionals, custodians, food service employees, clerical staff, and maintenance personnel all contribute to student success and deserve to be valued and supported.
“The best recruiting tool is a district with a strong reputation. When educators know they will be respected, listened to, supported by school leadership, and part of a district committed to academic excellence, Flagler Schools become a destination where talented professionals choose to build their careers.
“A School Board member’s first responsibility is to be a responsible steward of taxpayer dollars. Before seeking additional revenue, we must ensure that current resources are being used effectively, efficiently, and where they have the greatest impact on student success.”
7) Are there any new or underutilized revenue streams you can name that Flagler Schools might tap into to support its budget? If so, expand upon your proposal for implementation.
“Flagler Schools already have excellent Classroom to Career programs that provide students with valuable opportunities and connections to future careers. As our community grows, I believe we should build on that success by expanding the programs that are working and creating additional opportunities aligned with local workforce needs.
“One way to do that is through continuing to build stronger partnerships with our business community, nonprofits, and industry leaders. These partnerships can help provide mentorships, internships, certifications, equipment, and real-world experiences that prepare students for success after graduation. Our local businesses have a vested interest in developing the future workforce of Flagler County, and our schools benefit when those partnerships grow.
“We should also continue pursuing appropriate grants and outside funding opportunities that support student programs without placing additional burdens on taxpayers.
“The goal is not simply to find more money. The goal is to maximize every resource available to give students more opportunities, strengthen our workforce pipeline, and ensure Flagler Schools remains a district where students are prepared for college, careers, and life.”
8) How would you define a successful working relationship between the School Board and the superintendent?
“A successful working relationship between the School Board and the Superintendent is built on trust, communication, mutual respect, and a clear understanding of their respective roles.
“The School Board is responsible for setting policy, establishing direction, and providing accountability, while the Superintendent is responsible for the day-to-day operations of the district and implementing the Board’s policies. Both roles are essential, and the district is strongest when they work together toward the same goal: improving outcomes for students.
“Effective leadership does not mean that everyone will always agree. Healthy organizations welcome thoughtful discussion, different perspectives, and respectful debate. However, once decisions are made, the Board and Superintendent must work together professionally and remain focused on serving students, supporting teachers and staff, and maintaining the trust of parents and the community.
“Having served on the School Board and spent 28 years as a classroom teacher in Flagler County, I understand the importance of collaboration, communication, and accountability. A strong Board-Superintendent relationship is not about personalities or politics, it is about leadership, transparency, and doing what is best for the students we serve.”
