Out of School Time (OST) Group Leader

NORTHWESTERN SETTLEMENT • Chicago, IL

5d • $19 - $19 • Onsite

About The Position

Since 1891, Northwestern Settlement has nurtured, educated, and inspired children and families in need within Chicago’s West Side. Our programs—from early childhood education and afterschool programs to family services and adventure-based learning — are rooted in our commitment to disrupting generational poverty and building community. We are seeking dedicated and energetic Out of School Time Group Leaders to join our Youth Services team. This position is ideal for individuals passionate about working with youth and committed to helping young people grow academically, socially, and emotionally in a safe, engaging environment. The Out of School Time (OST) Group Leader plays a key leadership role within Northwestern Settlement's expanded learning programs, which serves youth outside of regular school hours - including before and after school, school holidays, and breaks. Group Leaders are responsible for leading a classroom group of children, implementing daily enrichment activities, managing behavior, and ensuring a safe, engaging, and supportive environment. This position is ideal for individuals passionate about youth development and social equity, and who are ready to lead by example.

Requirements

• High School diploma or GED required; some college coursework in education, child development, or social work strongly preferred.
• Minimum 1-2 years experience working with children in a structed setting (OST, classroom, summer camp, etc.).
• Demonstrated leadership experience (leading activities, mentoring peers, managing a classroom).
• Strong communication, conflict resolution, and youth engagement skills.
• Ability to work collaboratively in a fast-paced, community-focused environment.
• Must pass background checks and meet DCFS licensing requirements (CPR/First Aid, Mandated Reporter, TB test, etc.)

Nice To Haves

• Experience with trauma-informed care, restorative practices, or SEL frameworks.
• Bilingual (Spanish/English or other relevant language) is a plus.
• Familiarity with Chicago Public Schools or urban education environments.

Responsibilities

• Supervise and lead a group of 10-20 students in grades K-8 during out-of-school time hours.
• Plan and facilitate structured activities that align with program goals (academic enrichment, SEL, recreation, arts, STEM, etc.).
• Model and uphold expectations for behavior, cooperation, and respect.
• Support students' social-emotional and academic development through positive guidance and mentoring.
• Implement daily lesson plans and schedules provided by the Director of Afterschool.
• Adapt programming to meet the needs of diverse learners.
• Encourage creativity, problem-solving, and collaboration through engaging, hands-on learning experiences.
• Maintain a safe, clean, and organized classroom environment.
• Conduct regular attendance checks, headcounts, and follow safety procedures during transitions and emergencies
• Complete required documentation, including incident reports, behavioral logs, and lesson reflections.

Benefits

• Compensation will be commensurate with experience and qualifications.
• Benefits are offered to our part-time employees accordance to organizational policies.
• In addition, all staff members are equipped with the tools needed to succeed, including a dedicated workspace, iPad, email, high-speed internet access, and all necessary supplies.

What This Job Offers

• Job Type: Part-time
• Career Level: Entry Level
• Education Level: High school or GED