Oregon School District, Oregon, WI - Superintendent presso McPherson & Jacobson, LLC

Position Description for Superintendent for Oregon School District, Oregon, Wisconsin

The Oregon School District Board of Education in Oregon, Wisconsin, is seeking a highly quali?ed leader to serve as Superintendent. The Board wishes to have the successful candidate assume the responsibilities of the position by July 1, 2026.

McPherson & Jacobson, L.L.C., Executive Recruitment and Development, has been engaged as the consultant in a search for outstanding candidates. They will assist the Board in identifying and screening the candidates.

Enrollment: 4,100

Location: The District is located in the Oregon, Wisconsin area, a vibrant and actively supportive community just 15 minutes south of Madison, Wisconsin 

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. 

Essential Quali?cations

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.

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

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:

• Closing date for applications: November 16, 2025
• Board of Education selects candidates for interview: November 19, 2025
• Round One Interviews with the Board of Education: December 3 & 8, 2025
• Engagement Sessions with Candidates: Week of December 8, 2025
• Round Two Interviews: December 16 & 18, 2025
• Selection of new Superintendent: January 2026

Contact Information:

            McPherson & Jacobson, L.L.C.

            11725 Arbor Street, Suite 220

            Omaha, NE  68144

            888-375-4814

Email:  [email protected]

School Website: https://www.oregonsd.org/

Consultant: Dr. Dennis Pauli           [email protected]

The Oregon School District is an Equal Opportunity Employer. The district does not discriminate on the basis of race, religion, color, sex, age, national origin, or disability and, when needed, will provide reasonable accommodations to applicants and employees. Anyone requesting reasonable accommodation in the application or recruitment process please contact McPherson & Jacobson at the address/phone/email above.