(Salem, Ore.) The Oregon Association of School Executives (OASE) and the Coalition of Oregon School Administrators (COSA) have named Darin Drill, Superintendent of the Cascade School District, (CSD), the 2024 Oregon Superintendent of the Year. The announcement was shared at the CSD School Board meeting on Monday, September 11, 2023, in front of a crowd of supportive staff, students, family members, and School Board members. This award automatically places Drill in the running for National Superintendent of the Year awarded annually by the American Association of School Administrators.

COSA Executive Director, Craig Hawkins, and Deputy Executive Director Dr. Krista Parent made the official announcement at the Cascade School District Board meeting on Monday night. Dr. Parent shared with the audience, “Darin is a leader of leaders. 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’s commitment to and the impact on the school community runs deep. He has spent the majority of his career at Cascade having been a teacher, coach, Director of Human Resources, High School Principal, and has served as Superintendent since the 2007-2008 school year. He believes in the power of supporting local schools and supports the school principals in the Cascade School District with both guidance and autonomy to do great work. With Measure 98 dollars, Drill placed much of the budget decision making with school leaders - those closest to the students and most knowledgeable about students’ needs. Measure 98 funding in CSD supports a variety of after school activities, tutoring and mentoring opportunities, and re-envisioned Career Technical Education (CTE) pathways and CTE summer camp for incoming 9th graders.

Drill worked with high school administrators to redesign 9th grade on track initiatives for all incoming highschool students. Drill knows 9th grade on track data is a key indicator of future high school graduation success. With his team, the High School examined instructional and school counselor practices and created a system where the 9th grade students in most need of support had additional support for the full school year. This shift resulted in higher ontrack graduation rates for all 9th graders. Cascade High School has a 97% on track graduation rate for 9th graders, inclusive of all students by gender, ethnicity, socioeconomics, and those receiving special education services.   

While 9th grade on track data is an important indicator for graduation, the youngest learners, the kindergarten students in Cascade, also have Mr. Drill’s eye on their needs. There are many social factors that influence how a child enters kindergarten. Drill sought to make coming to Kindergarten more successful for each child. For the past several years, Drill has asked the elementary administrative team to reach out in the community and identify as many incoming kindergarten students as possible. Families of incoming kindergartners are invited into the school in spring, prior to the start of kindergarten, for a night to meet the teachers, become familiar with the school, meet other families, and receive educational materials to assist in preparing their children for school in the fall. This important event helps families connect with their neighborhood school and form relationships with staff while the students get to make new friends and learn more about their school making it something to look forward to at the end of summer.

Drill has invested in the CSD staff through ongoing professional development. In 2007, he began late state Wednesdays which has afforded staff an additional 32 hours of professional learning throughout the school year. Staff regularly see him in the schools and know he values them as the key to student success and well-being.

Drill’s commitment to connection is seen throughout the district. He has prioritized engaging and communicating with families across the district by visiting each Parent Teacher Organization and regularly attends community meetings to share the progress CSD is making on many initiatives. Strong schools make a strong community. Drill is active at school and community events and school sports competitions. Students and families know he is approachable and connected to the district. Parents who Drill taught when they were in school frequently stop to say hello. “What is conveyed more than anything else is how welcoming and inclusive our schools are because Mr. Dill 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 of Drill’s nomination for the award. “Put simply, he cares about every student and family here and he works hard to improve upon that every day.”

In addition to leading in CSD, Drill has served as COSA president in 2022-2023, OASE President in 2017-2018, served on the AASA National Superintendents organization Delegate Assembly for six years, and regularly meets with state and national elected leaders keeping them informed of needs of schools and students in our state.

Drill will be honored 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.

"Superintendent Darin 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. 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," said COSA Executive Director Craig Hawkins. "COSA is honored to have Darin Drill as Oregon’s 2024 Superintendent of the year."