Jessica Gilmore Named Regional Director for Sierra Schools of Arizona

Jessica Gilmore brings more than 15 years of experience in education and school administration to her new role as regional director for Sierra Schools of Arizona. Her commitment to supporting educators and improving student outcomes will guide her as she expands her leadership across the region.

Building a Strong Foundation at Gateway

Gilmore joined Sierra School of Gateway in 2021 after a successful career in public education. At Gateway, she helped build strong systems, support staff development, and foster a positive school culture. Her leadership helped establish Gateway as a high-performing program. The school reached its highest academic growth and lowest rates of behavioral incidents. It also strengthened teacher certification pathways and internal career advancement opportunities.

Expanding Leadership Across Sierra Schools of Arizona

She will now oversee schools in Mesa, Scottsdale and Tucson, while supporting the development of a new campus in Casa Grande. She is especially energized by the opportunity to expand her impact beyond a single campus by empowering school leaders and helping them strengthen their programs to better serve students across Arizona.

“At my core, I love helping people grow,” Gilmore said. “When you empower educators, you ultimately impact more students.”

A Leadership Philosophy Built on Trust

Gilmore’s leadership philosophy centers on collaboration, intentionality, and trust. She looks forward to strengthening relationships with school directors, using data to guide decisions and creating space for leaders to solve problems and innovate.

Her hands-on experience as a school director provides valuable insight into the needs of the leaders she now supports. Having been “in their shoes,” she understands the classroom and operational aspects of running a school, from the importance of accurate data to the daily realities educators face.

One of the lessons she carries forward is the importance of autonomy in leadership. “Not everyone has to do things the same way to be effective,” she said. “Great outcomes can come from different approaches.”

Supporting Growth for Educators and Students

Gilmore is also a strong advocate for professional growth and internal advancement. She credits Sierra Schools’ investment in staff development, including tuition reimbursement and certification pathways, as a key driver of success for both educators and students.

As Gilmore begins this next chapter, she remains grounded in the mission that has guided her work from the beginning: ensuring every student receives support, every educator feels empowered and every school continues to grow.

We wish Gilmore the best of luck in her new role.

About Sierra Schools

Designed to nurture students’ academic, social and behavioral growth, Sierra Schools of Arizona provides individualized instruction in smaller, structured classrooms. Its six private day schools go beyond what typical classrooms provide, offering an evidence-based approach, a comprehensive range of specialized services and a team of highly trained educators to help students and their families shine.