Career Navigator (Chicago IL

THE OPPORTUNITY

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 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.

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

Specifically, the Career Navigator will:

• 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 graduation requirements within the two-year program.
• Proactively raise and document any high-risk or concerning situations (academic, personal, or professional) through established reporting channels.

• Plan, coordinate, and facilitate monthly in-person professional development sessions, in collaboration with the Summer Search team.
• Coordinate event logistics including scheduling, and on-site arrangements such as booking rooms and sending invites to apprentices.
• Track apprentice participation in professional development sessions to support progress documentation.

• Provide occasional support for recruiting and engagement activities for Apprentice program, including career fairs, open houses, final round apprentice interviews, graduation celebrations, or other local program needs.

The Career Navigator position calls for a strong relationship builder who is consistent and reliable in their communication and project management. Specifically, this hire will bring:

• EXPERIENCE: 3-5+ years of experience in workforce development or career advising, preferably working with early career individuals.
• ACCOUNTABILITY: Holds self and others responsible for process, decisions, actions and commitments to results and to drive high-quality outcomes for students, is responsive to needs of stakeholders (students, donors, community partners, staff members, alumni, volunteers).
• TEAMWORK AND
  
  COLLABORATION:
  
  Inspires and fosters commitment, connection, enthusiasm, and trust, facilitates cooperation and motivates people to accomplish goals, manages, and resolves conflicts and handles interpersonal issues constructively.
• PROJECT MANAGEMENT: Strong organizational and project management skills, including the ability to juggle multiple workflows and easily adapt to shifting priorities in a fast-paced environment. Prior experience leading project teams and managing external partners/vendors.
• CRITICAL…