Superintendent of Schools
Dr. Jon Isaacson
Dr. Jon Isaacson has served as Superintendent of the Hillsboro R-III School District for the past seven years and has been a member of the district’s administrative team since 2008. Prior to his current role, he served as the Assistant Superintendent of Human Resources.
With nearly 30 years of experience in education, Dr. Isaacson brings a collaborative leadership style focused on transparency, accountability, and continuous improvement. He holds a Bachelor of Education from Olivet Nazarene University, a Master of Education from Southwest Baptist University, and a Doctor of Educational Leadership degree from Missouri Baptist University.
Dr. Isaacson is a strong advocate for Career and Technical Education, early childhood development, and ensuring students have access to opportunities that align with their individual goals. He works in partnership with Jefferson College, business leaders, and community organizations to expand programs that support student readiness for both the workforce and post-secondary education.
Under Dr. Isaacson’s leadership, the Hillsboro R-III School District has invested in modern learning environments, expanded access to technology, improved school safety and student supports, and remained fiscally responsible. He leads the district’s strategic planning process and works closely with the Board of Education to ensure district goals reflect community priorities.
He has served during key periods of development, including the sale of the Highway A property and the purchase of the Bridle Ridge property in 2019. During the COVID-19 pandemic, he guided the district through complex and evolving challenges. He also led efforts to pass a major bond issue that funded secure entrances and classroom additions at the Junior High, Elementary, and Primary Schools, as well as the construction of a new Special Education Center.
Significant facility improvements have continued throughout his tenure. These include the purchase of the Diane Hall property, now home to the district’s Administrative Offices and Learning Center Annex, and the sale of the Ridgewood property in 2024. In 2024, the district also acquired and renovated the former Logo Daddy building, which will open as the new Learning Center and host the district’s Early Childhood Program beginning in fall 2025. The district completed its grade-level reconfiguration during the 2024–2025 school year.
Under Dr. Isaacson’s guidance, Hillsboro R-III has increased educator and support staff compensation while simultaneously reducing the district’s tax rate and overall debt—from $27.7 million in 2019 to approximately $6 million in 2025.
Dr. Isaacson is active in advocacy efforts at the state and federal levels and is involved in multiple professional organizations. He serves in a regional leadership role with the Missouri Association of School Administrators (MASA) and is the 2024–2025 Chair of the EducationPlus Board of Directors. He is a past President of the Missouri Association of School Personnel Administrators and participates in several local boards, including the Hillsboro Community Civic Club. He is also an active member of the Hillsboro Rotary Club, Chamber of Commerce, and Jefferson County Growth Association. He is a frequent presenter on topics related to educational leadership, human resources, and innovation in schools.
Dr. Isaacson and his wife Ashley are proud residents of Hillsboro. He values the relationships built with students, families, staff, and the broader community and remains committed to the success of every learner in the district. He is also proud of their two sons: Tyler, who works in Construction Management and holds an MBA from Olivet Nazarene University, and Drew, who will graduate in May 2025 with a degree in Heavy Equipment and Construction Management from State Technical College of Missouri. Drew is also a certified EMT and firefighter.