Superintendent – Milton, MA

Job Description

Milton Public Schools in Milton, Massachusetts, located just south of Boston, seeks an experienced and visionary leader to serve as its next Superintendent of Schools. This is a unique opportunity to lead a high-performing PreK–12 school district serving approximately 4,350 students across six schools. Our community deeply values educational excellence, equity, collaboration, and the holistic development of all students.

The Community of Milton 
Incorporated in 1662, Milton is a vibrant suburban community in eastern Massachusetts that prides itself on its rich diversity, historic charm, distinctive character, and natural surroundings. 

Milton’s geography is unique – it borders the City of Boston and is home to significant portions of the Blue Hills Reservation, giving it the most privately and publicly held conservation land within 20 miles of Boston. This combination gives the town a bucolic atmosphere and close-knit community feel in close proximity to the cultural, educational, and professional opportunities in the Greater Boston area. Milton residents have convenient access to major highways such as Route 128, Interstate 93 and Interstate 95, as well as access to the Red Line T into Boston via the Mattapan Trolley. 

Families and community members are actively involved in the life of the town and its schools. Active parent-teacher organizations, youth sports leagues, enrichment programs, and civic groups contribute to a welcoming and supportive environment for students and families across the district.

The Milton Public School District
Milton Public Schools envision a district with excellent instruction in every classroom, where learning experiences are aligned with students’ individual strengths and needs, and where attention to academic and social-emotional growth are balanced so that every child achieves at high levels and develops a strong sense of self and belonging in schools that are safe and supportive for all. We see a district of intellectual discourse and learning at all levels – students, faculty, and administration – with systems and processes for continual reflection, innovation, and data-driven decision-making. We know that such a district is achievable if: we facilitate instruction that instills a passion for learning, curiosity, and critical thinking skills; we are committed to cultural competency; we foster a positive approach to the behavioral health of children; and we build strong partnerships with families and the community. 

Serving approximately 4,350 students across four elementary schools, one middle school, and one high school, Milton Public Schools employs approximately 518 employees, with an annual budget in FY27 of $75,613,973.00. The district has a strong record of student success and is committed to providing a supportive, inclusive, and academically challenging learning environment for all students. The district serves students with a wide range of backgrounds, strengths, interests, and learning needs, with approximately 17% of students receiving special education services and 28% identified as high needs. In Milton Public Schools, we know that our diversity is our strength. Dedicated to educational equity, continuous improvement, whole-child development, data-informed decision-making, and strong social-emotional support, Milton Public Schools works to prepare every student to succeed in higher education, careers, and global citizenship.

Milton offers a developmental preschool, engaging before- and after-school programs, and summer school and camp programs. One distinctive aspect of the Milton Public Schools is its well-established French Immersion choice program beginning in first grade at all elementary schools. Another unique opportunity for the next Superintendent of Milton Public Schools is advancing a school building project, as the district is currently engaged through the MA School Building Authority in a process to address overcrowding in the schools.

Milton Public Schools benefits from engaged families, dedicated educators and staff, and a community that places a high value on its schools, with the Superintendent playing a lead community role engaging our residents. The district actively fosters strong collaboration among families, staff, and local community stakeholders.

The Opportunity & Leadership Profile
The next Superintendent of Milton Public Schools will be an experienced, collaborative, and student-centered educational leader who can build upon the district’s strengths while providing a clear vision for its future. We seek a leader who is motivated to serve in this role for a sustained period of time, making a lasting positive impact on our district. The successful candidate will support high-quality teaching and learning, advance opportunities for all students, foster strong relationships across the school community and town, and effectively navigate the operational and financial issues facing the district.

The Superintendent will be expected to listen and engage thoughtfully with stakeholders, communicate transparently, build trust, support and develop staff, and work collaboratively with the School Committee to ensure that Milton Public Schools continues to provide an outstanding educational experience for every student.

The deadline to apply is November 24, 2026.

Equal Opportunity Employer 
The Milton Public School system does not and shall not discriminate on the basis of race, color, religion (creed), gender, gender expression, gender identity, transgender status, gender transitioning, age, national origin (ancestry), disability, pregnancy/parenting status, marital status, sexual orientation, homelessness, or military status, in any of its programs, activities or operations. These include, but are not limited to, admissions, equal access to programs and activities, hiring and firing of staff, provision of and access to programs and services, as well as selection of volunteers, vendors and employers recruiting at the Milton Public Schools. We are committed to providing an inclusive and welcoming environment for all members of our staff, students, volunteers, subcontractors, and vendors. The following person has been designated to handle inquiries regarding the non-discrimination policies: Danielle Whitmore, Director of Student Services, 617-696-5040, X5574.

Qualifications & Candidate Profile

• Demonstrated collaborative and inclusive leadership prioritizing instructional excellence, equity, and constructive relationship management among all stakeholders.
• Experience managing tight budgets and complex organizational systems.
• Proven commitment to diversity and inclusion.
• Track record of meaningfully improving instructional and organizational culture through implementation of cutting-edge instructional leadership practices.
• Licensed or eligible for licensure as a Superintendent of Schools in Massachusetts.
• Master’s degree in education or a related field required; Doctorate preferred.
• Minimum of 10 years in education, including teaching, central office, and/or administrative leadership experience; extensive district central office leadership experience preferred.
• Experience with MSBA or other major school building projects preferred.

Additional information is available on the Superintendent Search Page on the Milton Public Schools website www.miltonps.org. Questions can be directed to Dr. George Perry at georgeperry@hyasearch.com or Caryn Shaw at carynshaw@hyasearch.com

Position Details & Compensation
Start Date: July 1, 2027

Compensation: The anticipated base salary range is $220,000 to $280,000, commensurate with experience and qualifications. A competitive benefits package and contract terms will be negotiated with the successful candidate. 

How to apply for this job?

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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.