Dean of Students
Listed on 2026-11-01
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Education / Teaching
Education Administration, Academic, University Professor, Professional Development -
Management
Education Administration, Professional Development
Hours: Full-time with the flexibility to work nights and weekends
FLSA: Exempt
Classification: Staff (12-month)
Residential Status
:
Housed Position -- On-campus residency required
Salary Range: $110,000 to $150,000 annually, based on experience and qualifications
Milton Academy is an independent college preparatory K–12 school, boarding and day in grades 9–12, located just outside of Boston.
Milton Academy cultivates in its students a passion for learning and a respect for others. Embracing diversity and the pursuit of excellence, we create a community in which individuals develop competence, confidence and character. Our active learning environment, in and out of the classroom, develops creative and critical thinkers, unafraid to express their ideas, prepared to seek meaningful lifetime success and to live by our motto, “Dare to be true.”
Summaryof Position:
The dean of students oversees and directs the key elements of the Upper School's Office of Student Life for 700+ students, comprised of both boarding and day students, including international students. The Office of Student Life serves as a hub - both literally and figuratively - of student culture & norms, services, policies, programming, and accountability, centrally located on campus and ultimately responsible for both the day-to-day management of the student experience and the overarching wellness of the community.
In partnership with other members of the Upper School administrative team generally, and the dean of operations and dean of faculty specifically, the dean of students also helps to build the framework of support and expectations for the adults working most closely with Milton students. At its best, the work of the dean of students is student-facing, proactive, and energizing, including situations requiring students to take ownership for their missteps and move forward.
At its most challenging, the work of the dean of students is central to the immediate and long-term management of student crises. Ultimately, the dean of students must embrace work that is immersed in the complexities of adolescent development and buoyed by each student’s journey and growth. To that end, the dean of students will join Milton at a time of self-reflection, bold vision, and strategic thinking regarding the student experience both within, and beyond, the classroom.
Ideal candidates will be passionate, empathetic, steady, and student-centered; thrive as an eminently present community member; have strong communication skills; have broad and deep experience working with students’ families; find joy in 24/7 community; and draw inspiration and energy from teenagers.
A member of the Upper School administrative team and the Office of Student Life, the dean of students reports to the Upper School principal and collaborates closely with the dean of operations, Upper School director of equity & inclusion, director of counseling, dean of academics, dean of faculty, director of restorative practices, and director of athletics.
Essential Functions and Responsibilities :- Management of the Office of Student Life.
- Partnership with the director of counseling and school physician regarding the comprehensive health of students (including programming, student medical leaves, kidwatch).
- Oversight of Milton's Accounting for Students policy.
- Oversight of student discipline processes in collaboration with the dean of academics.
- Oversight of opening of school programming, in close partnership with members of the Upper School Administrative Team.
- Oversight of student leadership programming/training, in close partnership with the Office of Equity & Inclusion and the student Self Governing Association (SGA).
- Partnership with the dean of faculty, dean of academics, and director…
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