Lead Career Navigator (Chicago IL)

Summer Search
Summer Search

Columbia, MD, USA

USD 82,500-86k / year

Posted on Aug 6, 2026
Position: Lead Career Navigator (Chicago IL)
Location: Chicago, IL
Job Id: 861
# of Openings: 1
LEAD CAREER NAVIGATOR
SUMMER SEARCH, NATIONAL (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 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 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.
WHAT YOU’LL DO
Specifically, the Lead Career Navigator will:
Supervision (20%)
  • 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.
Apprentice Support & Coaching (30%)
  • 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.
Manager Engagement (15%)
  • 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.
Program Monitoring & Communication (15%)
  • 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.
Professional Development Program (15%)
  • 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.
Other Duties (5%)
  • 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.
WHO YOU ARE
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: 5-7+ 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 CONCIOUSNESS: 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
  • TECHNOLOGY SKILLS: Basic proficiency with Microsoft Suite.
In addition, all Summer Search staff bring a commitment to our mission of unleashing students’ potential through mentoring and transformative experiences, as well as the ability to thrive in an environment that values excellence, gratitude, well-being, diversity, authenticity, and collaboration.
LOCATION AND OTHER REQUIREMENTS
This position will work in-person out of the Aon office in Chicago IL. In addition regular travel, 10%-20% of the time may be required to support Aon in regional offices in Bannockburn, IL. Summer Search will cover the cost of travel, per-diem, and accommodations (if necessary) for all work-related travel.
COMPENSATION AND BENEFITS
Competitive and transparent salaries. This is an exempt position with an annual salary ranging from $82,500 - $86,000. Summer Search is committed to transparent, equitable compensation practices. Salaries are benchmarked using current market data and salary bands are created to demonstrate the growth potential within the band. Typically, offers are made at the starting place of the salary band. The Hiring Manager partners with the Talent Team to ensure offers are appropriate, competitive and maintain internal equity.
Well-being, flexibility, and ongoing learning and development are pillars of our culture. We value our staff and are committed to creating an environment where every individual feels seen, heard and valued. Investments in our staff include:
  • 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
  • Generous time off including 15 vacation days, 10 sick days, and 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.
OUR COMMITMENT TO EQUITY, DIVERSITY, AND INCLUSION
With a staff that cares deeply about social justice and racial justice, we believe that diverse perspectives and backgrounds create a rich work environment and enhance our ability to pursue our mission. We are committed to building an organization with critical consciousness in order to impact how we work with students, as well as how we work together as a team. We hope you will join us as we continue to build a justice-centered organization that fosters a work environment where people from all backgrounds are welcomed and valued.

TO APPLY
Select "Apply for this Position" below to submit a resume and targeted cover letter, addressed to Shawn Bradley, Lead Business Development Associate, that answers the question, “Why are you interested in the Career Navigator opportunity at Summer Search?".
The application deadline is August 19th.

SUMMER SEARCH IS AN EQUAL OPPORTUNITY EMPLOYER.

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