OSCEOLA COUNTY, Fla. — It was an evening filled with gratitude, reflection, applause and emotional farewells Tuesday, October 27, as the Osceola County School Board honored departing board members Teresa “Terry” Castillo of District 1 and Jolene Sheive of District 3 during their final board meeting, recognizing their individual contributions and celebrating a period of leadership marked by cooperation, mutual respect and a shared commitment to students.
The special recognition meeting brought together district leaders, educators, students, families and community partners to celebrate academic excellence and outstanding contributions to education. But one of the evening’s most meaningful moments came as Superintendent Dr. Mark Shanoff and fellow board members thanked Castillo and Sheive for their dedication to Osceola County’s schools, teachers, staff and families.
Beyond the accomplishments celebrated throughout the evening, one of the defining characteristics of the current School Board has been its collaborative approach to leadership. Board members have demonstrated a commitment to listening to differing perspectives, respecting one another’s contributions and finding common ground on decisions affecting Osceola County’s schools. That spirit of cooperation and mutual respect has been especially meaningful following earlier years when disagreements and divisions sometimes overshadowed the board’s shared responsibility to serve students, educators and families.
Under the leadership of Board Chair Heather Kahoun, the board has emphasized cooperation, professionalism and a focus on the responsibilities its members were elected or appointed to fulfill. Rather than allowing differences of opinion to become obstacles, members have worked to keep students, educators and district employees at the center of their decisions while supporting efforts to improve the efficiency, effectiveness and academic performance of Osceola County schools.
That spirit of cooperation was evident Tuesday evening as board members spoke warmly about their colleagues, acknowledged one another’s strengths and reflected on the relationships that helped shape their work together.
For Castillo, the evening marked the conclusion of eight years of service that began in 2018 and included a historic milestone when she became the first Hispanic woman to chair the Osceola County School Board in 2021. For Sheive, appointed by Governor Ron DeSantis earlier this year following the departure of former District 3 board member Anthony Cook, the meeting marked the conclusion of a shorter but meaningful chapter of public service.
Terry Castillo: Eight Years of Leadership, Advocacy and Student-Centered Service
A graduate of Gateway High School and longtime advocate for educational opportunities, Castillo has spent the past eight years helping guide one of Central Florida’s growing school districts through significant challenges, including the COVID-19 pandemic, changes in district leadership and ongoing efforts to improve student achievement.
Born in Hialeah, Florida, Castillo moved to Osceola County during her junior year of high school. She later attended Valencia College, Barry University and Rollins College, earning her MBA from the Crummer Graduate School of Business in 2021.
Her professional background in education, organizational development and employee training helped shape her approach to school board leadership, emphasizing accountability, educational opportunities and student success.
During Tuesday’s ceremony, Shanoff praised Castillo’s commitment to students throughout the district, emphasizing that her advocacy frequently extended well beyond the boundaries of District 1.
“No one has worked harder on behalf of their students and on behalf of their community as much as Miss Castillo,” Shanoff said.
He credited her with making a lasting difference in the district that helped raise her and where she later raised her own daughter.
“You have left an indelible mark on the School District of Osceola County,” Shanoff told Castillo.
Castillo’s leadership also extended beyond Osceola County through her involvement with the Florida School Boards Association, where she held several statewide leadership positions, including vice president and treasurer, and served on committees focused on advocacy and equity.
During her farewell remarks, Castillo reflected on the responsibilities of school board members, referencing the Florida Constitution and the legal obligations of elected education leaders.
“That’s the job. That’s what I was elected to do,” Castillo said. “And I have tried to do every single part of that job faithfully for the past eight years.”
She also reflected on her historic chairmanship and the district’s academic progress during her tenure.
“District 1 sent me here twice. My colleagues elected me in 2021 to be the first Hispanic woman to hold the seat as chair, and I served for two consecutive years,” Castillo said.
She described her commitment to reviewing contracts, questioning policies and advocating for vulnerable students while celebrating what she characterized as historic improvements in student achievement.
“I didn’t do this alone,” Castillo emphasized, repeatedly acknowledging the contributions of fellow board members, district administrators, educators and community supporters.
Her remarks also reflected the close relationships developed among the current board members and her confidence in their ability to continue moving the district forward.
Castillo thanked her daughter, Autumn, for supporting her public service and providing valuable insight from a student’s perspective.
She concluded by encouraging her colleagues and incoming board members to continue asking questions, challenging themselves and remaining focused on the district’s future.
“Continue the work. Keep asking questions. Keep elevating this district and leave your own mark,” Castillo said.
Jolene Sheive: Answering the Call to Serve District 3
While Sheive’s tenure on the School Board was considerably shorter, district leaders praised her willingness to step into a demanding public leadership position and her commitment to representing families in District 3.
A lifelong Osceola County resident and graduate of Osceola High School, Sheive was appointed to the board in 2026 by Governor Ron DeSantis following the departure of Anthony Cook.
Professionally, Sheive is the broker and owner of Legacy Realty of Central Florida and a partner at SLS Investments of Central Florida. Her extensive community involvement includes service with the Osceola County Education Foundation, Osceola County Planning Commission, local chambers of commerce and the Rotary Club of Kissimmee.
During Tuesday’s recognition, Shanoff highlighted Sheive’s advocacy for families in District 3, particularly those living in communities geographically distant from the district’s central administrative offices.
“You have been here a short time, but have made a very substantial impact,” Shanoff said.
He praised Sheive for ensuring that District 3 families were represented and their concerns received attention.
“You have made sure that they are heard, that they are seen, and that they are important,” he said.
Sheive received a commemorative shadow box containing challenge coins representing the school board members and superintendent, recognizing her service to Osceola County students.
In her farewell remarks, Sheive expressed appreciation for the opportunity to serve, thanking fellow board members, district staff, Shanoff, Governor DeSantis and her family.
She acknowledged that she accepted the position knowing her time on the board would be limited, but said she was determined to make a difference.
“I came into this position knowing that my time here would be short, but I wanted that time to matter,” Sheive said.
“I wanted to listen, learn, ask questions, and always remember that the decisions we make at this table ultimately affect a child, a family, a teacher, or someone in the community.”
Sheive described the experience as a blessing and said she would leave the position grateful for the relationships, experiences and knowledge she gained.
“It has truly been an honor to serve Osceola County District 3 and most importantly, our students,” she said.
A Board Built on Respect, Teamwork and Shared Purpose
Perhaps one of the most memorable aspects of Tuesday’s ceremony was the genuine appreciation board members expressed for one another.
The tributes went beyond recognizing individual accomplishments, highlighting a working environment in which board members supported one another, shared experiences and approached their responsibilities with a common commitment to public education.
Several members praised Castillo for mentoring newer colleagues, helping them understand their responsibilities and encouraging them to develop their own leadership styles.
One board member credited Castillo with providing guidance through difficult periods, including the pandemic and times when the board faced significant disagreements.
“You led through COVID and through a board that was often divided, and you stayed focused on our number one priority, the students and their education,” the board member said.
Others described Castillo as a positive and encouraging leader who offered guidance without overshadowing the contributions of her colleagues.
Sheive was remembered for bringing enthusiasm, humor, thoughtful perspectives and a collaborative spirit to the board while demonstrating a strong commitment to the families she represented.
During the ceremony, one board member reflected on how the group had developed close friendships, even recalling how members sometimes wore matching shoes and spent time together during conferences and professional development events.
Those personal relationships reflected the broader spirit of teamwork that has characterized the board’s recent work.
Under Kahoun’s chairmanship, the board has placed an emphasis on working together and keeping the district’s educational mission at the forefront. The relationships celebrated Tuesday demonstrated how mutual respect and a willingness to consider differing opinions can strengthen the work of a public governing body.
For a district serving more than 70,000 students and supported by more than 8,000 employees, that shared sense of purpose carries significant responsibility.
Shanoff acknowledged those responsibilities while thanking both departing members for their willingness to serve.
“The job of a board member is not easy and the job of a board member is never done,” Shanoff said.
He reminded those attending that school board members commit themselves to public service because they want to make a difference in their communities.
The departing members were presented with commemorative gifts, and board members gathered for photographs marking the occasion.
Students, Educators and Community Partners Also Celebrated
Before the farewell tributes, Tuesday’s meeting featured numerous recognitions highlighting student achievement, educational excellence and community partnerships throughout Osceola County.
Among the evening’s notable honors was the recognition of Lakeview Elementary School educator Megan Han, who was named one of just three worldwide finalists for AVID Elementary Teacher of the Year.
The award recognizes educators who demonstrate exceptional dedication to academic achievement, critical thinking and preparing students for future success. Winners will be announced during AVID’s national conference in Atlanta in December.
The district also celebrated 13 students who earned perfect scores on multiple statewide assessments during the 2025–2026 school year. Two students achieved perfect scores on three assessments, while 11 earned perfect scores on two assessments.
Board members additionally recognized National Merit Scholars, educators, school volunteers and community organizations for their contributions to local schools.
During her final District 1 recognitions, Castillo honored the Celebration Foundation for its scholarships, donations and Learning Without Hunger program, along with the Mercy Foundation for its educational advocacy and assistance to families, particularly during the COVID-19 pandemic. She also recognized National Merit Scholars from Celebration High School.
Sheive used her final District 3 recognitions to honor Reedy Creek Elementary educators for excellence in early childhood education, a longtime Horizon Middle School educator for celebrating cultural diversity, and representatives of Royal St. Cloud Golf Course for supporting student opportunities.
Other recognitions included Tohopekaliga High School’s NJROTC STEM drone team, which earned four first-place trophies in its first regional STEM competition, along with educators and community organizations supporting literacy, career education and student development.
The board also approved proclamations recognizing National School Bus Safety Week, National Military Family Month, Holocaust Education Week and Celebrate Literacy Week.
Looking Ahead With a Continued Commitment to Students
The departure of Castillo and Sheive marks a transition for the Osceola County School Board as newly elected members prepare to assume the District 1 and District 3 seats.
Greg Filak is set to succeed Castillo in District 1, while Alyssa Noel will take over the District 3 seat previously held by Sheive.
While Tuesday’s meeting celebrated the contributions of two departing members, it also highlighted the importance of continuing the district’s focus on student achievement, effective leadership and cooperation among those entrusted with overseeing public education.
The collaborative relationships established among current board members provide an example of how public officials with different backgrounds, experiences and perspectives can work together toward shared goals. As the board welcomes new members, that commitment to respectful discussion and student-centered decision-making remains an important part of the district’s path forward.
For Castillo and Sheive, the evening provided an opportunity to reflect on the people, partnerships and shared commitment to students that defined their service.
For their fellow board members, it was a chance to recognize the importance of collaboration and the relationships that helped shape their work together.
And for the School District of Osceola County, the occasion served as a reminder that behind the policies, budgets and difficult decisions made by school board members are the students, educators, employees and families whose futures are influenced by those decisions.
As Castillo offered her final words of encouragement to the incoming board, she expressed confidence that the next generation of leaders was prepared to continue the district’s work.
“To our incoming board, you are ready on day one because you have already started doing the work,” Castillo said.
Then, with a smile and a lighthearted reminder that her interest in the district’s future would continue even after leaving office, she added:
“I will be watching.”
Her comment drew laughter and applause, bringing an evening of appreciation, reflection and celebration to a fitting close.
