Lead Career Navigator (Chicago IL)

Summer Search•Chicago, IL

7d•Onsite

About The Position

Summer Search partners with young people during their transition from adolescence into adulthood by connecting them to expansive opportunities, professional mentoring, and a community of support. The Summer Search Business Development team partners with client organizations to support the implementation of their mentorship and apprenticeship programs. 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.

Requirements

5-7+ years of experience in workforce development or career advising, preferably working with early career individuals.
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).
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.
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.
Recognizes sociopolitical barriers and understands the systems of oppression that operate in day-to-day lives of stakeholders e.g. students/participants, staff members, community partners, and alumni. Applies critical thinking and takes action against the oppressive aspects of reality
Basic proficiency with Microsoft Suite.
Commitment to Summer Search's mission of unleashing students’ potential through mentoring and transformative experiences.
Ability to thrive in an environment that values excellence, gratitude, well-being, diversity, authenticity, and collaboration.

Responsibilities

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 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.

Benefits

Medical insurance with up to 90% employer contribution
Dental, vision, FSA, life and disability insurance plans
401 (K) and Employer Match up to $2,000 annually
15 vacation days
10 sick days
18 holidays (2 floating holidays of your choice, a birthday day-off, 10 company-wide holidays, and a 1-week December closure)
Refresh Friday’s – a paid day off the first Friday of every month!
A comprehensive Employee Recognition Program (years of service awards, spot awards, and professional development funding).
A four-week paid sabbatical after five years of continuous employment.
Individual, local, regional and national training
A commitment to developing leaders from within the organization.
An organizational culture that supports staff well-being and holistic self-care/community care
Ample opportunities to connect with the students and communities we serve.