Risk Mentor

Chicago West | Ombudsman Educational Service
3210 W Roosevelt Rd
Chicago, IL 60624, USA

Ombudsman Educational Services
, a growing, dynamic organization with a social mission to offer hope, is seeking an At-Risk Mentor to join our award-winning Alternative Education team and perform meaningful work in a culture that welcomes innovation, encourages creative expression and offers limitless potential for personal and professional satisfaction!

As an At-Risk Mentor
, you will manage a focused portfolio of students identified through attendance, academic performance, and behavioral indicators. In this highly relational and impact-driven role, you will provide strategic case management and individualized support, building strong, growth-oriented relationships while partnering with families, educators, and support teams to drive measurable student success.

Leveraging targeted strategies such as home visits, collaboration with teachers and clinical professionals, and coordination of after school and community-based supports to develop a comprehensive understanding of each student’s academic, social, and home environment.

Building high-trust, accountability-centered relationships with students and key stakeholders while maintaining a self-directed, outcomes-focused approach to student growth.

Reviewing and analyzing student-level academic, attendance, and behavioral data to assess intervention effectiveness, identify trends, and communicate measurable progress.

Connecting students to appropriate supports and interventions while consistently following up and strengthening partnerships with families, educators, and internal teams.

Identifying and re-engaging students experiencing attendance challenges through proactive outreach, home visits, relationship-building efforts, and structured intervention planning to remove barriers to school participation.

Leading case management and re-entry planning for students returning from suspension, home stay, or extended leave, ensuring a structured, supportive, and successful transition back to campus.

Collaborating as an integral member of the Clinical Care Team to align strategies, share insights, and drive coordinated, student-centered action plans.

Facilitating cross-functional meetings with security and advocate associates to review student circumstances, align interventions, and ensure consistent, practical implementation.

Utilizing student information systems and data tools to monitor performance, track progress toward goals, and recommend timely, evidence-based interventions.

Supporting additional initiatives and responsibilities as assigned to meet evolving student, campus, and program needs.

• High school diploma or equivalent w/ passage of basic skills test.
• Associate's degree or higher in a closely related field of study preferred.
• Hold currently or have the ability to obtain a valid IL state driver's license.
• Ability to obtain and maintain certification in company approved crisis management training.
• Prior experience providing instruction, guidance and/or support to children; preferably in an alternative, special education and/or behavioral health program setting.
• Well-versed in alternative educational services for at-risk youth and working with students with diverse needs at various levels.
• Proficiency in providing motivation and having critical conversations with students that help move them toward realistic goals.
• Highly skilled in building relationships with students, parents, teachers and/or community partners.
• Proven ability to effectively prioritize tasks and meet deadlines while maintaining organization and attention to detail.
• Highly skilled in providing mentoring, coaching, administrative support and/or technical support functions.
• Advanced oral and written communication, organization, conflict resolution, multitasking, problem solving and decision-making ability.
• Knowledgeable in the use of relevant technology including experience with computers, Microsoft Office Suite, database entry and basic office equipment.
• Availability to work evening hours as needed.

Learn more about our history, our mission, and the program services we provide…