At Monday night’s School Board meeting, Superintendent Drill was honored with a surprise announcement that he has been named the 2024 Oregon Superintendent of the Year. This is a joint award by the Oregon Association of School Executives (OASE) and the Coalition of Oregon School Administrators (COSA), and demonstrates the strong respect Mr. Drill has from his peers across the state.
“Mr. Drill believes that school climate and culture are key to a great school experience and leads by example,” wrote School Board Chair Karen Ramseyer in her letter of support. “Put simply, he cares about every student and family here and he works hard to improve upon that every day.” Currently in his sixteenth year as Superintendent, Mr. Drill has made Cascade his home for 28 years, serving as a teacher, coach, Director of Human Resources, and high school principal before becoming Superintendent in 2008.
“We wouldn’t be here if it wasn’t for all these people,” Mr. Drill said at the board meeting, nodding over to the many staff in the room. “I’ve said it for a long time: find really good people and try to get out of the way.” This leadership style of equipping the school leaders who are closest to the students and who know best what students need has transformed Cascade’s Career Technical Education (CTE) pathways to be a model for the rest of the state, made our special education program one where students thrive, and consistently brought about a graduation rate that is near the top of the state.
This award automatically places Mr. Drill in the running for National Superintendent of the Year. “Superintendent Drill has led the Cascade School District with his vision of excellence for students and his commitment to the district has stood the test of time, “said COSA Executive Director Craig Hawkins. “He empowers leaders who in turn empower school teachers and staff, and has set a standard of improvement which has led to the strengthening of relationships in schools and the community, and stronger graduation outcomes for students. COSA is honored to have Darin Drill as Oregon’s 2024 Superintendent of the Year.”