Bend-La Pine Schools has selected new principals for High Desert Middle School and Cascade Middle School for the 2025-26 school year.
Heather Bailey joins Bend-La Pine Schools as the new principal of High Desert Middle School, bringing over two decades of experience in K–8 education to the new role. Heather has a strong track record of leading school improvement through student-centered, systems-based, relationship-driven leadership.
“In Heather, we found a leader who brings both the systems thinking and the heart that High Desert needs right now,” Dr. Steven Cook, Superintendent of Bend-La Pine Schools, said. “Her experience in middle school leadership, focus on creating opportunities for student success, and proven ability to build structures that support staff and students align directly with what the community told us they were looking for in a new leader – a steady, thoughtful leader ready to build upon the strengths the talented HDMS staff has built to continue to move the school forward.”
Most recently the Principal of Kraxberger Middle School in the Gladstone School District, Bailey led the school out of state-mandated improvement status by implementing data-informed support structures and expanding opportunities for multilingual learners and students with disabilities. Her career reflects a deep commitment to instructional excellence, inclusive practices, and building collaborative school communities.
Bailey has over 12 years of experience as a school leader and 14 years as a classroom teacher, where she taught kindergarten, 4th and 5th grades with a focus on early literacy and differentiated instruction.
She will begin her role July 1, 2025, and is taking over for current Principal Jessica Reilly, who will be moving to another administrative role within Bend-La Pine Schools.
Kelly Schmidt has been hired to serve as the next Principal at Cascade Middle School, bringing a record of successful school leadership to Bend-La Pine Schools. Kelly has a depth of experience leading a variety of populations across grades 6-12.
“In Kelly, Cascade is getting a principal with extensive secondary school leadership experience,” Dr. Cook said. “She has a strong reputation as a leader who is student-centered and works to build systems to ensure all students can achieve their fullest potential.”
Most recently the Principal at Wilsonville High School in the West Linn-Wilsonville School District, Schmidt previously worked as a middle school Principal in West-Linn Wilsonville and Oregon City School Districts and as a middle school Assistant Principal in Oregon City and Canby.
She has over 15 years of experience as a school leader and ten years as a classroom teacher.
Schmidt will begin her role July 1, 2025, and is taking over for current Principal Gabe Pagano, who will be moving the Director of District Activities & Athletics with Bend-La Pine Schools.
