Dean of Students

Milton Academy•Milton, MA

2d•Onsite

About The Position

The Dean of Students oversees and directs key elements of the Upper School Office of Student Life, which serves more than 700 boarding and day students, including international students. The office supports student culture, services, policies, programming, accountability, day-to-day student experience, and the overall wellness of the community. Working with the Upper School administrative team, the Dean of Students also helps establish support and expectations for adults who work closely with students. The position addresses both proactive student development and student crises, with a focus on adolescent development, student growth, and a student-centered community. The Dean of Students is a member of the Upper School administrative team and Office of Student Life and reports to the Upper School principal. The role collaborates closely with other school leaders and requires broad experience working with students and families, strong communication, and active participation in a 24/7 residential community. This is a full-time, 12-month, exempt staff position requiring on-campus residency, with flexibility to work nights and weekends. The Dean of Students manages the Office of Student Life; partners on student health and wellness; oversees student accountability, discipline, leadership programming, and student-life policies; and supports faculty hiring, onboarding, and mentoring. The role supervises residential life and student activities staff and other colleagues, serves as an advisor, participates in school committees and communications, and fulfills broader Upper School community and professional responsibilities. The position is based at Milton Academy’s campus in Milton, Massachusetts. The salary range is $110,000 to $150,000 annually, based on experience and qualifications.

Requirements

Bachelor’s degree.
Experience as a dean of students or in a comparable position working with colleagues, adolescents, and parents or guardians in an independent boarding high school (preferably), for at least 5 years.
Valid driver’s license and ability to pass an insurance and driver’s record check.
Demonstrated ability to lead and manage teams and implement initiatives.
Demonstrated ability to navigate emergencies and manage conflicts effectively with employees, students, and families.
Excellent verbal and written communication skills.
Ability to prioritize multiple projects and tasks in a fast-paced work environment.
Experience developing and administering student programs, services, and policies.
Computer expertise, including proficiency in Google Workspace, Microsoft Office, and Adobe Creative Cloud, and willingness to learn tools and systems such as Reach and Veracross.
Ability to work collaboratively with internal and external constituencies.
Understanding of confidentiality and related issues.
Receptiveness to supervision and professional development.
Commitment to being part of a dynamic educational community.
Ability to work at a computer for up to 8 hours each day in conjunction with OSHA requirements.
Ability to move around campus without restriction, including accessing all residential houses.
Ability to drive various school vehicles.
Ability to lift up to 10 pounds.

Nice To Haves

Graduate degree.
Proven leadership and management experience in an independent boarding high school (preferably) for 10 or more years as a dean of students or in a comparable position.
Passion, empathy, steadiness, and a student-centered approach; strong presence in a community; broad and deep experience working with students’ families; and enthusiasm for working with teenagers.

Responsibilities

Manage the Office of Student Life.
Partner with the director of counseling and school physician regarding comprehensive student health, including programming, medical leaves, and kidwatch.
Oversee Milton's Accounting for Students policy.
Oversee student discipline processes in collaboration with the dean of academics.
Oversee opening-of-school programming in partnership with the Upper School Administrative Team.
Oversee student leadership programming and training in partnership with the Office of Equity & Inclusion and the student Self Governing Association (SGA).
Partner with the dean of faculty, dean of academics, and director of residential life on hiring, housing, onboarding/orientation, and mentoring new faculty.
Partner with the director of restorative practices regarding Milton’s relational support process.
Supervise several co-curricular program directors.
Supervise colleagues managing faculty advisors and class deans.
Oversee the annual review and update of the student handbook.
Participate in the annual review and revision of the faculty handbook.
Participate in the weekly creation of the Upper School family newsletter and other Upper School communications.
Oversee the Office of Student Life budget.
Serve on various committees.
Perform weeknight and weekend administrative and supervisory duties as an on-campus resident and administrator on duty (AOD).
Fulfill core Upper School responsibilities, including serving as an advisor; contributing to student life and the broader school community; and meeting expectations related to collaboration, communication, programming, and institutional policies.
Supervise the director of residential life, director of activities & student life, student trips coordinator, and administrative coordinator in collaboration with the dean of academics.
Carry out other responsibilities as assigned.