Cascade School District Superintendent Darin Drill has been named Superintendent of the Year for Oregon.
Drill, who has spent 16 years running the Cascade district, was honored by the Oregon Association of School Executives (OASE) and the Coalition of Oregon School Administrators (COSA) at a Cascade district board meeting on Sept. 11.
The award automatically places Drill in the running for the national superintendent honor that is awarded annually by the American Association of School Administrators (AASA).
COSA Executive Director Craig Hawkins, and Deputy Executive Director Dr. Krista Parent made the official announcement at the Cascade School District Board meeting.
“Darin is a leader of leaders,’ said Parent, at the board session. “He really is the go-to superintendent for just about any issue his peers might be working on. With the average tenure of a superintendent in any one district at 2.9 years, Darin’s tenure at 16 years is truly incredible.
“We know stable district leadership is critical to ensure the success of all kids in a school district and Darin’s leadership has done just that. Darin Drill is in the top 5 for current superintendent tenure in Oregon and his leadership is felt well beyond the boundaries of Cascade School District.”
Drill has spent the majority of his career at Cascade, serving as a teacher, coach, director of human resources and high school principal. He has served as superintendent since the 2008-2009 school year.
Key achievements cited by the OSAE and the COSA in a press release about the honor include:
• Drill worked with high school administrators to redesign 9th grade on-track initiatives for all incoming high school students. Drill and his team examined instructional and school counselor practices and created a system in which the 9th grade students in most need of assistance received additional support for the full school year. This shift resulted in higher on-track graduation rates for all 9th-graders. Cascade High has a 97% on track graduation rate for 9th graders.
• Drill worked to make coming to kindergarten more successful. For the past several years, Drill’s elementary administrative team has done community outreach to identify as many incoming kindergarteners as possible. Families are invited to the school in the spring to meet the teachers, become familiar with the school, meet other families, and receive educational materials to assist in preparing their children for the fall.
• Drill has invested in district CSD staff through ongoing professional development with late-start Wednesdays, which have afforded staff an additional 32 hours of professional learning throughout the school year.
“What is conveyed more than anything else is how welcoming and inclusive our schools are because Mr. Drill believes that school climate and culture are key to a great school experience and (he) leads by example,” wrote Karen Ramseyer, Cascade School Board chair in a letter of support of Drill’s nomination.
“Put simply, he cares about every student and family here and he works hard to improve upon that every day.”
Drill, who received his undergraduate education at Western Oregon and his law degree at Willamette University, served as COSA president for the 2022-2023 school year.
He was OASE president in 2017-2018 and served on the AASA National Superintendents organization Delegate Assembly for six years.
Drill’s award will be noted at the 2023 Oregon School Boards Association Convention in November, the 2024 OASE Winter Conference in January, the 2024 AASA National Conference in February, and the 2024 COSA Annual Conference in June.
