High School Dean of Students

Distinctive Schools of IL; Chicago (IL); On-site; USD 72,000 - 88,000; Full time

Benefits offered by this job

25+ Paid holidays

12 weeks family paid leave

Comprehensive Healthcare (Medical, Den

talenta match to 3%

Job summary

Distinctive Schools of IL is seeking a High School Dean of Students at CICS Longwood High School, Chicago, IL, starting November 2026. This regular full-time role reports to the Principal and focuses on creating a safe, positive learning environment and district-wide operations.

The ideal candidate holds a Bachelor's in a relevant field, has K-12 urban experience and 3–5 years in leadership/discipline roles, and is proficient with GoogleSuite to support classroom and school-wide initiatives.

Qualifications

• Bachelor's Degree in Human Service, Mental Health, School Counseling, or Social Work.
• K-12th Grade Education Experience.
• 3-5 years of experience; 1 year in urban setting; proficient with GoogleSuite.

Responsibilities

• Cultivate a positive climate and learning atmosphere; train staff on classroom management and school culture strategies; respond to Student Code of Conduct incidents.
• Provide proactive leadership to engage stakeholders in programs to support student achievement and development.
• Oversee attendance tracking, data reporting, and adherence to handbook policies.

Skills

Discipline management

Communication

Education

Bachelor's Degree in Human Service, Mental Health, School Counseling, Social Work

Tools

GoogleSuite

Job description

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Title: High School Dean of Students
Location: CICS Longwood High School- 1309 W 95th St, Chicago, IL 60643
Reports To: Principal
Salary: Starting $79,987, commensurate with experience
Employee Type: Regular Full Time
Start Date: November 2026

Distinctive Schools creates diverse, joyful, welcoming communities rooted in social justice and rigorous learning. We support all learners to be engaged, curious, and to achieve their full potential. Our students become confident advocates, creative problem-solvers, and collaborative leaders.

Position Overview

The Dean of Students will work closely with the Principal to ensure that the school campus is a safe, comfortable and positive learning environment for all students to be able to reach their goals. The Dean of Students will act as a part of the leadership team to provide operational support and to handle all discipline related incidents as well as provide support and direction to teachers for classroom management interventions and strategies. The Dean of Students will also take on multiple tasks and responsibilities as assigned by the School Principal to support school wide operations.

Responsibilities

Culture

• Be an expert at responding to the challenges presented by today’s diverse student population
• Maintain a positive climate and learning atmosphere for all students so that they can achieve their academic and personal goals
• Train staff on classroom management, student- staff relationships, crisis response, and school culture strategies
• Implement, monitor and coach the community on the Distinctive Schools philosophy and model for responding to Student Code of Conduct violations
• Ensure 100% resolution of all Student Code of Conduct incidents

Leadership

• Supervise, manage, and evaluate the members of the School Culture Team to ensure training, professional development and goal setting in alignment with school goals
• Provide proactive leadership to engage all stakeholders in the delivery of programs and services to support the students’ academic achievement, social and emotional development
• Lead cooperative work cooperatively with the students, staff and families towards a positive school climate
• Oversee specific teams of teachers or staff as assigned by the School Principal
• Drive coordinated response to school culture data

Administrative

• Monitor and track student attendance by following mandates and demands for notifying parents and families about absences. Assist teachers with absence tracking and parent conferences as needed to discuss attendance and tardiness concerns
• Oversee attendance data stored in school database systems to ensure accuracy
• Prepare monthly reports that categorize the total number of suspensions, discipline code violations, recidivism and percent changes. Track discipline data in all systems
• Enforce the school handbook procedures and policies including dress code guidelines
• Ensure 100% resolution of all Student Code of Conduct incidents in alignment with the DS model and necessary communication to all stakeholders for each event
• Develop and progress monitor student safety and behavior plans

Safety

• Follow all safety procedures and track/file all documents required
• Oversee the School Security officer and motivate that person to support the Principal, Dean and Team Leader’s and the safety/climate of the school

Professionalism

• Maintain clear boundaries and professional demeanor with students, staff, and families when conducting/administering disciplinary consequences to students
• Complete additional duties assigned by the School Principal
• Problem solve with teachers on issues regarding student challenges to identify antecedents of poor behavior and develop plans for positive behavior
• Informally observe teachers on a regular basis and provide feedback on classroom management and interventions that may be needed for specific students or whole classes
• Model best practices in the classroom for classroom management strategies and tools to ensure student success and positive student teacher relationships
• Support teachers and staff to problem solve in their classroom with management plans before sending students to the office
• Collaborate daily with school site Leadership Team to complete leadership tasks such as planning and communicating school needs
• Collaborate with Student Services Staff to monitor behavioral needs in classrooms and create/document plans for success. Support IEP/504 meetings with research and information from the student’s files. Support and monitor all behavioral RTI data

Requirements (minimum)

Education: Bachelor's Degree (in Human Service, Mental Health, School Counseling, Social Work)

Qualifications

• K-12th Grade Education Experience
• 1 year experience working in urban setting
• 3-5 years of experience
• Technology demands: Proficient with cloud based software solutions ( GoogleSuite)

Occasional lifting, carrying, pushing, and/or pulling; some stooping, kneeling, crouching, and/or crawling; and significant fine finger dexterity. Generally, the job requires 30% sitting, 50% walking, and 20% standing

• 25+ Paid holidays
• 12 weeks family paid leave
• Comprehensive Healthcare (Medical, Dental, Vision)
• 403b match
  • Fully match up to 3%
  • 50% match up to 5%
• Professional development including tuition reimbursement
• Gym and wellness discounts
• And more

Description Disclaimer:

Since no job description can detail all the duties and responsibilities that may be required from time to time in the performance of a job, duties and responsibilities that may be inherent in a job, reasonably required for its performance, or required due to the changing nature of the job shall also be considered part of the jobholder's responsibility.

EEO:

Distinctive Schools is an equal opportunity employer and does not discriminate against any employee or applicant for employment on the basis of race, color, religion, sex, gender, national origin, age, disability, veteran status, marital status, sexual orientation, gender identity, gender expression, or any other personal characteristic protected by applicable law.

Distinctive Schools is committed to the full inclusion of all qualified individuals. In keeping with our commitment, Distinctive Schools will take the steps to assure that people with disabilities are provided reasonable accommodations. Accordingly, if reasonable accommodation is required to fully participate in the job application or interview process, to perform the essential functions of the position, and/or to receive all other benefits and privileges of employment, please contact [e-mail] or call 773.828.4191