“Improving literacy outcomes for every learner in Wisconsin is one of our highest priorities, and Kaylee brings both the expertise and urgency this work requires,” Dr. Underly said. “Throughout her career, she has been a tireless advocate for students and schools, particularly those serving children who have too often been denied equitable opportunities to succeed. Her unwavering commitment to ensuring every child becomes a confident reader makes her exceptionally well-suited to lead this work across Wisconsin.” 

Jackson has served as a teacher, instructional coach, principal, and district executive across both charter and traditional public school systems, including as executive director of curriculum and instruction for the Madison Metropolitan School District. She began her career teaching and leading in charter schools, where she developed a deep commitment to high expectations, strong school culture, and ensuring that every student has access to excellent instruction and support. 

Jackson has led large-scale literacy initiatives, supported educator professional learning, and guided the adoption and implementation of high-quality instructional materials aligned to the science of reading. Jackson has also worked in the private sector, partnering with school systems across the country to support literacy improvement, curriculum implementation, and instructional leadership.  

“My passion for literacy comes from seeing the profound impact reading has on a student’s confidence, opportunities and future,” Jackson said. “I am excited to serve Wisconsin in this role and to work alongside educators, families, school leaders, libraries and community partners to strengthen literacy outcomes across our state. Together, we can ensure that every student develops the skills they need to thrive as readers, learners and citizens.” 

Jackson, who started in the role in May, leads the DPI’s work in the continued implementation of 2023 Wisconsin Act 20. More information about the Office of Literacy and the implementation of Act 20 is available on the DPI’s website. A photo of Jackson is available upon request.  

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