City Year

Learning and Mentorship Specialist

Location : Winnetka, IL, 60093

Job Type : Full Time

Date Posted : 19 February 2026

Company Overview:

City Year is a nationwide nonprofit dedicated to helping students remain in school and achieve graduation. As an Learning and Mentorship Specialist, you will join a committed team focused on both academic and social-emotional support. Your contributions will directly advance City Year’s mission by delivering dependable mentorship and focused educational assistance.

Role and Responsibilities:

You will work to strengthen students’ academic skills while promoting personal growth. This role includes providing classroom assistance, individualized tutoring, and mentorship that drives measurable student success.

Deliver one-on-one and small group tutoring in core subjects including reading, math, and science.
Demonstrate positive behavior and model social-emotional skills to students.
Develop trusting relationships to encourage both academic and personal development.
Collaborate with teachers and staff to identify student needs and monitor progress.
Design and implement strategies to boost student engagement and achievement.
Track and analyze student data to inform instructional planning.

Required Skills and Experience:

High school diploma or equivalent required; Bachelor’s degree preferred.
Experience working with youth in educational or mentorship programs.
Strong communication and interpersonal skills for effective student engagement.
Organizational skills and ability to plan and deliver targeted academic support.
Dedication to fostering student growth and advancing educational equity.

Preferred Qualifications:

Prior experience tutoring or mentoring students in academic settings.
Understanding of strategies supporting diverse learning needs and social-emotional development.
Experience utilizing data-driven methods to monitor and enhance student progress.

Compensation and Benefits:

Competitive stipend or salary based on experience and role responsibilities.
Opportunities for professional development and mentorship training.
Eligibility for education awards.
Health coverage options, paid time off, and wellness programs.
Supportive team environment centered on collaboration, impact, and growth.

About City Year:

City Year is committed to equity, inclusion, and making a meaningful impact in communities. The organization emphasizes collaboration, continuous learning, and meaningful contributions to students’ lives. Joining City Year means becoming part of a mission-driven team dedicated to educational success and community empowerment.