Dean of Students

Milton-Academy; Milton Center (MA); On-site; USD 110,000 - 150,000; Full time

Job summary

Milton Academy is seeking a Dean of Students for the Upper School to oversee the Office of Student Life for 700+ boarding and day students, including international students. The role emphasizes wellness, student programs, and community standards within a demanding independent school setting.

Ideal candidates bring passion, empathy, and strong communication skills, plus experience partnering with families and school leadership.

Qualifications

• Minimum 5 years as a dean of students (or comparable role) in an independent boarding high school.
• Experience leading and managing teams; strong crisis management.
• Excellent verbal and written communication; ability to work with families.
• Willingness to be on-campus resident and participate in evening/weekend duties.
• Knowledge of student programs, policies, and advisory practices.

Responsibilities

• Oversee the Office of Student Life.
• Partner with counseling and school physician on student health.
• Oversee Milton's Accounting for Students policy.
• Oversee student discipline processes with dean of academics.
• Open school programming with Upper School Admin Team.
• Lead student leadership programming with Equity & Inclusion and SGA.
• Collaborate on hiring, housing, onboarding of new faculty.
• Coordinate with restorative practices for student support.
• Supervise co-curricular program directors and advisors.

Skills

Leadership

Communication

Team management

Emergency management

Collaboration

Tools

Google Workspace

Microsoft Office

Adobe Creative Cloud

Reach

Veracross

Job description

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.”

Summary of 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 of residential life in the hiring, housing, onboarding/orientation, and mentoring of new faculty.
• Partnership with the director of restorative practices regarding Milton’s relational support process.
• Supervision of several co-curricular program directors.
• Supervision of colleagues managing faculty advisors and class deans.
• Oversight of the annual review and update of the student handbook.
• Participation in the annual review and revision of the faculty handbook.
• Participation in the weekly creation of the upper school family newsletter and other US communications.
• Oversight of the OSL budget.
• Membership on various committees.
• Participation in weeknight and weekend administrative/supervisory duties as an on-campus resident and an AOD (administrator on duty).
• Fulfillment of core Upper School responsibilities, including serving as an advisor; contributing actively to student life and the broader school community; and meeting all professional expectations related to collaboration, communication, school programming, and institutional policies. Additional details regarding advising, community engagement, and professional responsibilities are outlined in the Upper School Faculty Handbook.
• Other responsibilities as assigned.

Supervision to be received:

The dean of students will report to the Upper School principal as a member of the Upper School Administrative Team, comprising the dean of faculty, dean of academics, dean of operations, dean of college counseling, Upper School director of equity & inclusion, Upper School director of athletics, director of residential life, director of health services, and the principal's executive assistant/project manager.

Supervision to be exercised:

The dean of students will supervise the director of residential life, the director of activities & student life, the student trips coordinator, and the administrative coordinator (in collaboration with the dean of academics).

Education/Certification/Licensure:

Valid driver's license and ability to pass an insurance and driver's record check.

Experience:

Required: Experience as a dean of students (or a comparable position) working with colleagues, adolescents, and parents/guardians in an independent boarding high school (preferably) for a minimum of 5 years.

Preferred: Proven leadership and management experience in an independent boarding high school (preferably) for 10+ years as a dean of students (or a comparable position).

• Demonstrated ability to lead and manage teams and implement initiatives.
• Demonstrated ability to navigate emergencies and manage conflicts effectively, both internally (employees and students) and externally (families).
• Excellent verbal and written communication skills.
• Ability to prioritize multiple projects and tasks in a fast-paced work environment.
• Experience in developing and administering student programs, services, and policies.
• Demonstrated computer expertise, including proficiency in Google Workspace, Microsoft Office, and Adobe Creative Cloud, with a willingness to learn new tools/systems such as Reach and Veracross.
• Ability to work collaboratively with internal and external constituencies.
• Understanding of confidentiality and related issues.
• Receptive to supervision and professional development.
• Commitment to be a part of a dynamic educational community.

Physical Abilities Required:

• Must be able to work at a computer for up to 8 hours each day in conjunction with OSHA requirements.
• Must be able to move around the Milton Academy campus without restriction, including accessing all residential houses on Milton's campus.
• Must be able to drive various school vehicles.
• Must be able to lift up to 10 pounds.

The essential functions and basic skills have been included in this job description; it is not intended to be construed as an exhaustive list of all functions, responsibilities, skills and abilities. Additional functions and requirements may be assigned by supervisors as deemed appropriate. This position description is subject to change at any time.

Milton Academy is an equal opportunity employer. All qualified applicants will receive consideration for employment and will not be discriminated against on the basis of any category protected by federal, state, or local law, including but not limited to race, color, sex, sexual orientation, gender identity, gender expression, religion, disability, age, genetic information, veteran status, ancestry, citizenship or national or ethnic origin.