Dean of Students - Boys (2025-2026)

Dexter Southfield School; Chicago (IL); On-site; USD 80,000 - 100,000; Full time

Job summary

An established industry player seeks a dedicated individual to support student success in a vibrant educational environment. This role involves providing guidance on academic and personal issues, overseeing student life activities, and collaborating with faculty and parents to address behavioral concerns. The ideal candidate will have a Master's Degree and at least five years of experience, demonstrating strong organizational and communication skills. Join a dynamic team committed to fostering an inclusive and engaging atmosphere where students thrive and grow. This position offers a unique opportunity to make a meaningful impact in the lives of students.

Qualifications

• Master's Degree with 5+ years of experience in educational roles.
• Strong communication and organizational skills are essential.

Responsibilities

• Support students on academic and personal issues while promoting a positive environment.
• Manage student attendance and behavioral concerns effectively.

Skills

Organizational Skills

Communication Skills

Teamwork

Flexibility

Experience with Learning Management Systems

Education

Master’s Degree

Job description

In performing assigned tasks and duties, all employees of Dexter Southfield are expected to demonstrate quality work and meet deadlines (with or without direct supervision); interact professionally with students, parents, faculty, staff, and others; work effectively as individual and team contributors on all assignments; and communicate and coordinate efforts with colleagues and other stakeholders that align with the School’s mission and values. Those working in teaching roles are also expected to demonstrate effective classroom management skills and deliver quality academic instruction to ensure student success.

Essential Job Functions:

• Provide support and guidance to students on school, social, and personal issues
• Oversee student life activities planning while encouraging a positive and inclusive school environment, including key events done as a member of the Senior Parent Committee
• Uphold and enforce the school’s code of conduct, managing discipline matters in a consistent, fair, and developmentally appropriate manner
• Collaborate with teachers and parents to address student behavioral concerns, developing individualized plans when necessary
• Monitor student attendance, addressing patterns of absenteeism, and working with students and families to improve attendance
• Coordinate with the Upper School administrative team to identify and support at-risk students, implementing interventions as needed
• Serve as the primary contact for student-related emergencies, coordinating with families, faculty, and administration in response
• Administer advisory program, including the training and coaching of advisors; proofread advisor comments bi-annually
• Manage the four class deans; lead weekly class dean meetings
• Oversee student leadership offerings, including student government and peer advisor program; direct student clubs, including staffing and scheduling
• Coordinate Class 9 and Class 10-12 New Student Orientations with Admissions and Head of Upper School
• Collaborate with Middle School Student Deans on Class 8 to 9 student transition
• Be a visible and prominent presence around campus and at significant school events, which include evenings and weekends from time to time.
• Stay informed on trends in education and adolescent development, applying best practices in support of student success
• Part of the Upper School Dean of Student's role is to teach one academic course year-round, coach two sports seasons, or the equivalent thereof, and do other auxiliary supervision such as advisory, extra help for students, and other activities that require adult supervision
• Other duties as assigned by the Head of the Upper School

Skills and Qualifications:

• Master’s Degree with a minimum of Five years of experience
• Adept at using Learning Management Systems (LMS)
• Willingness and ability to work as a team player and individual contributor
• Strong organizational skills with the capacity to multitask and meet deadlines with maximum precision and minimal supervision
• Excellent communication skills (oral, written, non-verbal) to build trust among constituencies
• Commitment to actively promote and contribute to an engaging and inclusive workplace
• Ability to be flexible, effectively manage stress, and adapt to changing work priorities in a fast-paced work environment

Requirements:

This job requires one to lift, carry, push, and/or pull materials and equipment weighing up to 20 pounds as well as the ability to stand, sit, walk, and effectively use extremities to reach, hold, touch, push, pull, lift, and carry. Incumbents must also effectively communicate (oral, written, non-verbal) with others. This job typically requires 35% sitting, 35% walking, and 30% standing and is performed under minimal temperature variations in a generally hazard-free environment. Depending on classroom assignment, this role may require one to relocate classrooms throughout the day and require ascending and descending stairs. Incumbents will occasionally be required to work extended hours, including after school, during evenings, and on weekends.

Dexter Southfield’s 36-acre campus is composed of several buildings, playing fields, and outdoor learning spaces, which are accessible via internal and external walkways, stairs, nature paths, hills, and uneven terrain. This position requires one to transfer between these areas in all weather conditions.

All employees of Dexter Southfield are required to verify employment eligibility and successfully complete CORI, SORI, and fingerprint-based background checks as a condition of employment.