by Sentinel Staff
Teamwork for 25-26
The 2025-2026 school year is underway and is led by a united administration team. Kyle Hebberd, Superintendent, Ren Olson, Middle School and High School Principal, and Sydney Benesch K-5 principal collectively bring decades of administration experience to the Custer County School District. Hebberd, achieved success and longevity as a Superintendent in both the Walsh and Swink school districts. With 22 years of administration in small rural school districts Hebberd believes, “Successful small school educators have the mindset that being in a small school is not just a job, it is a way of life.” Hebberd has held jobs outside of education as well. He refers to his many hats. He has built hundreds of miles of fence,built bridges, cut wheat and drilled for oil. His education hat seems to be the favorite, it is well worn and tattered in the best ways from with more than two decades of service to parents, students, and the rural community.
Ren Olson, is the principal for the middle and high schools. Olson previously served the Roaring Fork School District as an administrator and has more than four decades in public education. Prior to applying for the principal position at Custer County schools, she regularly attended school board and other meetings as an interested resident. She is fully invested in the public education of our kids. She finds the opening of the MS/HS principal position and her subsequent selection as “serendipitous”. Olson’s principal message states, “Our kids thrive – with higher grades, greater engagement, and maintaining a more positive outlook on learning – when we team together to actively support them.” She said she is excited about working with the high-quality staff. When asked about the year ahead, Olson said she is most grateful for the teamwork and collaboration she Benesch and Hebberd share. All agreed that they feel lucky to serve the students at Custer County Schools.
Sydney Benesch continues to serve Custer County schools in a mighty way. She returned to serve this year as the K-5 principal. Sydney is Custer County to her core. She attended school here K-12, left for college, and then returned to teach second grade at Custer County Elementary School. She rose quickly to serve as a Teacher on Special Assignment as Vice Principal. She weathered the storm of transition serving as the principal of all Custer County Schools and for a few months also served as Interim Superintendent. Benesch is considered by many to be the glue of our district. She has institutional knowledge. She is excited about the year and says she feels “fully supported and is excited to work alongside Kyle and Ren”.
A cohesive leadership team has the greatest potential to positively impact our students and their learning. The benefactors of this new aligned and cohesive administration are the more than 300 students in attendance and the seventy plus staff members. Under the leadership of Hebberd, Olson, and Benesch, CCHS students are taking advantage of college enrollment and STEM classes, extracurricular activities, and the support services available to all students who need a little extra help. The elementary students will be cared for each day by a mostly new teacher lineup shepherded by Benesch. These are considered positive adjustments to achieve the best outcomes for our students.
Hopeful is the feel of this new school year. The hallways are buzzing, and students are already looking forward to Homecoming activities. Whether you are a former Bobcat or a Bobcat supporter you are welcome to attend the volleyball and football games on September 13th. Times and details are available on the Custer County Schools website and on page 10 of the paper.
Go Bobcats!!