Career Coach

i.c.stars•Chicago, IL

1d•Hybrid

About The Position

i.c.stars is seeking qualified independent contractors to serve as Career Coaches in Chicago, Milwaukee, and Kansas City. The Career Coach will support interns and recent graduates during the latter weeks of their training program and the first 90 days following completion. The role focuses on helping participants translate their learning into demonstrable skills, craft their professional narratives, navigate the job search effectively, build their networks, and enter the workforce with confidence. The goal is to align participants' early career decisions with their skills, goals, and values, ultimately preparing them for rewarding careers in technology and breaking cycles of generational poverty. i.c.stars is a 25-year-old nonprofit workforce development organization with over 35 professionals, committed to bridging the gap between diverse talent and the tech industry.

Requirements

Experience coaching early-career professionals or adult interns through job search and career transitions
Strong understanding of entry-level tech roles, hiring processes, and employer expectations
Ability to coach confidence without inflating readiness—helping interns see what they’ve built clearly
Strong communication and feedback skills
Comfort holding boundaries and naming hard truths with care
Alignment with strengths-based, effort-driven learning models
Existing network in the local tech ecosystem or a demonstrated ability to build one quickly
Familiarity with technical roles and project-based portfolios
Ability and willingness to learn

Nice To Haves

Experience in workforce development or nontraditional education pathways
Experience coaching first-generation professionals
Knowledge of salary negotiation and early-career workplace dynamics

Responsibilities

Coach interns to clearly articulate what they built, the decisions they made, the challenges they navigated, and the skills they developed.
Support development of interns/graduates professional narratives, and clear explanations of technical and leadership contributions.
Provide feedback focused on clarity, credibility, and alignment with employer expectations.
Help strong interns avoid underselling themselves or freezing in interview settings.
Support interns with career goal setting and planning.
Support interns with resume refinement and framing using business and industry language.
Guide LinkedIn profile optimization and utilization of hiring platforms.
Conduct interview practice using realistic scenarios aligned to entry-level tech roles.
Coordinate timing and emphasis with the Program Director so career work is sequenced appropriately.
Support interns to develop a focused job search strategy and identify roles aligned to their skills, interest, readiness, and career goals.
Support interns with applications, networking outreach, and interview preparation.
Normalize job search timelines and variance.
Support interns with decision-making and evaluation with respect to hiring opportunities.
In collaboration with the Program Director, organize cycle mock interviews and job shadows.
Prepare interns to research companies, anticipate role-specific questions, and speak confidently about their learning and growth.
Debrief real interviews to extract learning, adjust strategy, and strengthen subsequent attempts.
Coach interns through offer comparison, salary and benefits research, and basic negotiation strategies.
Reinforce intern agency and self-advocacy.
Coordinate closely with the Program Director to understand intern context, readiness, and growth.
In collaboration with the Program Director, take lead on creating intern skills profiles.
Align messaging and expectations with other program staff.
Support strong communications/information-sharing to the Residency Coordinator, Program Director, and city’s program team.
Use national program team tracking tools to capture data + growth from your engagement with interns.