School-Based Group Mentor; Part-Time

School-Based Group Mentor

The School-Based Group Mentor delivers structured, small-group mentoring to high school youth (ages 12–21) at Wendell Phillips Academy High School under the KLEO L.I.F.T. Mentoring Program. Working directly on-site, each mentor guides an assigned cohort of 8 to 10 students through evidence-informed social-emotional, leadership, and relationship-building activities. Primary responsibilities include direct youth mentorship, consistent curriculum delivery, attendance tracking, and regular collaboration with school and program leadership.

Direct Mentoring & Student Engagement

• Maintain consistent, supportive mentoring relationships with assigned youth cohorts throughout the school year, adhering to a mentor-to-student ratio not exceeding 1:10.
• Facilitate weekly small-group mentoring sessions (at least four sessions monthly per group, lasting 1–2 hours each), scheduled primarily during lunch periods or other designated non-instructional blocks.
• Conduct structured session components: welcome and check-ins, icebreakers/team-building, interactive lessons, skill-building activities, reflection/goal setting, and closing circles.
• Facilitate restorative conversations, promote positive peer interactions, and guide experiential learning, community service, and youth-led initiatives.

Curriculum Delivery & Program Implementation

• Deliver the evidence-informed L.I.F.T. curriculum across core areas:
  Leadership Development, Identity Formation, Social-Emotional Learning (SEL), Healthy Relationships, Academic Success/Postsecondary Readiness, and Civic Engagement.
• Utilize trauma-informed, culturally responsive practices and positive youth development principles during all group facilitations.
• Distribute and manage session materials, activity resources, and student snacks.

Attendance Monitoring, Administration & Retention

• Record and monitor accurate student attendance for every mentoring session.
• Conduct timely outreach, send reminders, and implement re-engagement strategies for absent or disengaged students in coordination with school staff and families.
• Assist with student intake, enrollment paperwork, parent/guardian consent collection, and orientation activities.
• Administer student surveys, collect evaluation feedback, and maintain strict confidentiality of all student records and data.

School Collaboration & Professional Compliance

• Partner closely with the L.I.F.T. Program Coordinator, Program Director, and Wendell Phillips Academy personnel to align schedules and minimize disruption to core academic instruction.
• Attend required program staff meetings, supervisory check-ins, and ongoing professional development workshops.
• Adhere strictly to Chicago Public Schools (CPS) partnership guidelines, mandated reporting policies, and agency safety protocols.

Other

• Performance of all other duties as needed and assigned.

Education

• High School/GED or four-years of equivalent experience. Bachelor's degree preferred but not required.

Experience

• Proven experience working with adolescents or high school youth in mentoring, youth development, out-of-school time, or educational settings.
• Demonstrated ability to facilitate small-group discussions and manage adolescent group dynamics effectively.

Core Competencies

• Familiarity with social-emotional learning (SEL), trauma-informed care, restorative practices, and conflict de-escalation techniques.
• Strong interpersonal, active listening, and verbal communication skills.
• Reliable administrative tracking skills for session logs and student attendance data.
• Deep commitment to community empowerment, equity, and student advocacy.
• Strong crisis intervention, leadership, and organizational skills.
• Exceptional organizational,…