Description
The Oregon School District Board of Education is seeking a highly qualified leader to serve as District Superintendent. The Board has engaged McPherson & Jacobson, L.L.C., Executive Recruitment and Development, as the consultant in a search for outstanding candidates to assist the Board in identifying and screening the candidates. Please apply online to www.macnjake.com. You may direct questions to Dr. Dennis Pauli at D_Pauli@macnjake.com.
Position Summary
The District Superintendent serves as the chief executive of the Oregon School District, providing visionary leadership, strategic management, and operational oversight for all district functions. This role is responsible for ensuring high-quality educational opportunities and the development of the whole child for approximately 4,100 amazing students. The District employs ~1,000 high quality staff members across seven school buildings, partners with seven early childhood / 4-year kindergarten centers and over a dozen school transportation contractors , and is home to a Community Pool. The District has an operating budget of approximately $60 million. The Superintendent works closely with the Board of Education, staff, students, families, the Oregon Education Association, the school community and local, state and federal agencies to promote academic excellence, social emotional learning, educational equity, fiscal responsibility, and continuous improvement. The District is located in the Oregon, Wisconsin area, a vibrant and actively supportive community just 15 minutes south of Madison, Wisconsin.
Essential Qualifications
Aligned with Our Five Core Values
A leader who embraces and is dedicated to our District’s established five core values: Relevant & Empowering Learning Experiences, Caring & Professional Educators, Educational Equity, Strong Family & Community Partnerships, and Whole Child Emphasis. You can learn more here: https://www.oregonsd.org/district/about
Community-Focused Leader & Collaborator
A superintendent who builds strong, authentic relationships and trust with staff, students, families and the community. Values input, and creates a unified school culture grounded in mutual respect and shared purpose. Proactively promotes and supports public education within the school community and beyond.
Decisive & Visionary Strategic Leader
Demonstrated experience leading effective, results-driven organizations and diverse teams. Provides clear, decisive direction to achieve strategic goals and embraces innovation while maintaining focus on student achievement and district goals. Ability to make data-driven decisions to ensure academic excellence and financial sustainability, even when those decisions are difficult.
Effective Communicator & Relationship Builder
A superintendent with strong interpersonal skills who communicates clearly, listens actively, builds trust, develops strong partnerships and fosters a school climate of openness, encouragement, and shared responsibility.
Equity & Inclusion Champion
A leader who champions equity for every student and staff member, ensuring inclusion, fairness, and belonging are at the heart of all decisions. They lead with compassion, approachability, and authenticity—creating environments where all voices are heard and valued.
Compensation & Benefits
The salary range for this position is $210,000 - $230,000, commensurate with experience. The District offers a comprehensive benefits package including health, dental, and vision insurance; post-retirement benefits; and professional development opportunities. The Oregon School District is an equal opportunity employer. Qualified applicants are considered for employment without regard to sex; age; race; religion; color; national origin; ancestry; creed; pregnancy; marital status; parental status; sexual orientation; gender identity; disability; or any other legally-protected status or classification. In compliance with the Americans with Disabilities Act, the District will provide reasonable accommodations to qualified individuals with disabilities.
Search Timeline:
Round One Interviews: December 3 and 8, 2025
Engagement Sessions with Candidates: Week of December 8, 2025
Round Two Interviews: December 16 and 18, 2025
Selection of New Superintendent: January 2026
Requirements
Education & Experience
-Master’s degree in Educational Leadership, Administration, or related field (Doctorate preferred)
-Valid Wisconsin District Administrator License
-Progressive leadership experience in public education, including as a building or district office administrator
-Proven record of improving student outcomes and leading organizational change
