Lead Career Navigator (Chicago IL

At Summer Search, we believe in 'No Ceilings' and envision a world in which young people, regardless of circumstances, can chart their own destiny. In the United States, students from underserved communities - disproportionately BIPOC and first-generation - face systemic inequities in school, in the workforce, and in life. Nevertheless, these young people possess unique strengths, resilience, and limitless potential.

Since 1990, Summer Search has partnered with young people during their transition from adolescence into adulthood by connecting them to expansive opportunities, professional mentoring, and a community of support. Summer Searchers recognize their potential and build a toolkit to navigate and challenge systemic barriers, break new ground for their families and communities, and achieve economic equity and a life of purpose.

The Summer Search Business Development team partners with client organizations to support the implementation of their mentorship and apprenticeship programs. Summer Search has partnered with Aon since 2021 providing professional support to their apprentices. The Lead Career Navigator will provide individualized coaching and mentoring to apprentices and guidance to managers supervising early-career employees, in partnership with program leadership at Aon and a robust team of part- and full-time colleagues at Summer Search.

The Lead Career Navigator supervises a team of two (2) Career Navigators, based out of the Chicago and Bannockburn offices, providing coaching and support to these team members in collaboration with team leadership and other Lead Career Navigators.

Reporting to the Senior Business Development Associate, the Career Navigator ensures consistent, high-quality support for apprentices and their managers at Aon.

Specifically, the Lead Career Navigator will:

• Supervise, coach, and support a team of Career Navigators; partner with direct-reports and colleagues to address unique and challenging issues involving their caseloads.
• Provide professional development and training for team members on effective mentoring, trauma-informed practice, and equity-centered workforce development.
• Travel as needed to partner regional offices to support partners and part-time staff.

• Supervise, coach, and support a team of Career Navigators; partner with direct-reports and colleagues to address unique and challenging issues involving their caseloads.
• Provide professional development and training for team members on effective mentoring, trauma-informed practice, and equity-centered workforce development.
• Travel as needed to partner regional offices to support partners and part-time staff.

• Conduct initial one-on-one intake assessments with apprentices and their managers to understand career and academic goals, employment background, and support needs.
• Meet regularly with apprentices (weekly or biweekly) to support their workplace readiness, foundational skill development, and professional growth.
• Provide coaching and referrals for apprentices facing barriers such as childcare, transportation, housing, or other personal needs impacting participation.
• Maintain consistent communication with apprentices to track academic standing, work-based learning, and overall well-being.
• Track apprentice engagement, attendance, and case notes using tracking tools and templates provided.
• In collaboration with apprentices, managers, Summer Search, and the Aon Program Team, develop individualized Success Agreement Plans, or intervention plans when required.
• Connect with apprentice managers monthly via email, Teams, or through in-person meetings to discuss progress, share feedback, and provide guidance on supporting apprentices.
• Encourage and facilitate balanced feedback between managers and apprentices, emphasizing positive reinforcement alongside constructive guidance, using Summer Search and Aon frameworks.
• Remind managers to complete required Apprentice Status Reports and competency check-ins.

• Partner with the Aon Program Team to support all apprentices in meeting…