Superintendent – Milton, WI

Job Description

The School District of Milton is seeking a Superintendent beginning on July 1, 2026, with a base salary range expected to be $181,000 to $211,000; other benefits to be negotiated. 

The School District of Milton, located in south-central Wisconsin, serves nine municipalities spanning across two counties. The District uniquely encompasses both urban and rural communities, with strong connections to both industry and agriculture. Five of Milton’s seven schools are located within the City of Milton. Two schools, Harmony Elementary and Consolidated Elementary, serve areas of significant residential growth within the greater community of Janesville, Wisconsin. The District’s central proximity to major markets and productive work force have made it a dynamic location for economic success in Southern Wisconsin. Milton is only 1.5 hours from Chicago, 30 minutes from Madison, and 1 hour from Milwaukee. Families are drawn to the District for the schools’ “small town feel” paired with easy access to urban amenities. Campgrounds, lakes, unique locally owned shops, historic attractions, and beautiful farmland surround the district, while nearby Janesville offers expanded recreation, arts, shopping, and event venues, offering both charm and opportunity. Modern conveniences and a strong sense of community pride come together to create the quality of life that many only dream of.

The School District of Milton has a high school, middle school, intermediate school, four elementary schools, and an early childhood program serving ~3,400 (PK-12) students. The District has 658 employees and a budget of approximately $64 million.

District Vision Statement: We believe in Opportunities, Achievement, and Community for All.

District Mission: The School District of Milton, in partnership with the community, prepares our students for achievement and lifetime readiness by providing opportunities for all. 

The District’s Five Strategic Objectives focus on: 

• Teaching and Learning 
• Relationships, Climate, and Culture 
• High Quality Staff
• Community Engagement
• Operations and Facilities 
  

District Highlights:

• The School District of Milton is a destination district in southern-Wisconsin, serving a growing community with a rich history, valued traditions, and a forward-thinking approach to education.
• Milton’s schools are widely recognized for excellence in academic achievement, commitment to community building, and leadership in school-to-career readiness. Milton’s Career Pathways model empowers students to curate their educational experiences to align with their post-graduation goals.
• Deeply rooted community partnerships support learning beyond the classroom, with 100+ local business partnerships and apprenticeship opportunities available to students.
• Rich tradition in the arts, including outstanding choral and instrumental music programs and a comprehensive K-12 visual arts curriculum. 
• Sustained community investment in the schools, including a successful recurring operational referendum in November 2024 and a capital referendum in 2019 that expanded classroom space at Milton East, Milton West, Harmony Elementary, and Milton Middle School. The capital referendum also supported the addition of a state-of-the-art STEM wing and field house facilities at Milton High School.
• Strong engagement and pride stretch across generations, with families, students, alumni, and community members deeply engaged with the school system. 90% of families agreed that they were “Proud to be Red Hawks”
• Milton maintains a supportive, student-focused, and mission-driven staff culture. 92% of staff reported they were proud to work for the School District of Milton.

Visit the District Website for more information:  School District of Milton Website

INCLUDE IN YOUR FRONTLINE APPLICATION:

1. Cover letter 
   • Stating specific and detailed interest in the Milton Superintendent position
   • Qualifications for the position
2. Full resume/vitae
3. Three current letters of recommendation
4. Contact information of three additional references different than the reference letters

For questions regarding the  School District of Milton Superintendent search, contact:

Mike Richie, Vice President, Hazard, Young, Attea & Associates
Email: mikerichie@hyasearch.com

Scott Winch, Senior Associate, Hazard, Young, Attea & Associates
Email: scottwinch@hyasearch.com 

How to apply for this job?

1. Register for an account on the HYA website. Or, log in to the HYA website if you already have an account created. Click the Login/Register button at the top of the page to get started.
2. After logging in, click the Apply Now button at the top of this page.
3. You will be redirected to the Frontline Education website. This website is where you will submit your application. This website also will require its own unique login and password.