Internship Tech Support Jobs in Chicago, IL (NOW HIRING)

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Technology Facilitator 

i.c.stars  |  Contract Position

We are a 25-year-old nonprofit workforce development organization dedicated to preparing individuals from underserved communities for rewarding careers in technology. With a passionate team of 35+ professionals, we're committed to bridging the gap between diverse talent and the tech industry. We find talent, train talent, and place talent in rewarding careers that end cycles of generational poverty and yield long-term success. Our program operates in Chicago, Milwaukee and Kansas City, Missouri. 

At our core, we believe that innovation thrives when people are empowered, supported, and allowed to grow. If you're someone who is energized by people-first leadership and is passionate about making a lasting impact, you may want to be a part of our journey as we continue to shape the future of tech professionals.

2026 Program Cycle Calendar

Each cycle is followed by a 3-week break before the next cycle begins.

i.c.stars is seeking qualified independent contractors to serve as tech instructors for each of our three program cities. The Technology Facilitator is responsible for helping interns build foundational technical awareness and growth, scope and execute on a client tech project that can be successfully executed in 13 weeks, and develop the skills/mindset to be a continuous tech learner.

This position prioritizes interns' learning processes and deliverables. The instructor guides interns to understand fundamental concepts, ask insightful questions, and overcome obstacles.

The Tech Facilitator works alongside-but is distinct from-the Technology Fellow, who supports client project delivery and sprint execution, foundational tech learning, and small group differentiated learning supports. These roles coordinate closely.

*i.c.stars interns are emerging professionals from underestimated communities participating in an intensive 14-week training program to develop technical, business, and leadership skills for entry-level careers.

• Deliver foundational technical instruction aligned to i.c.stars' curriculum and program standards

• Reinforce core concepts including programming logic, data fundamentals, and APIs

• Teach interns how to read documentation, debug effectively, and break down unfamiliar problems

• Establish explicit quality benchmarks, clearly differentiating baseline competency from advanced or exemplary performance across each phase of learning

• Serve as the primary technical liaison with the project client; Manage scope and expectations to protect learner experience

• Provide targeted coaching to tech fellows who are early in their career, with special attention/care to responsive tech learning facilitation

• Normalize confusion and learning curves without lowering expectations

• Help interns develop question-asking skills, persistence strategies, and technical confidence

• Avoid rescuing or solving problems for interns-support their capacity to work through challenges with scaffolded support

• Explicitly teach learning strategies such as time-boxing, distinguishing practice from perfection, and using peers as resources

• Help interns recognize patterns in their own learning

• Support reflection on growth over time so interns can articulate how they learned, not just what they built

• Lead tech instructional planning in collaboration with the technology fellow

• Align foundational instruction with the needs of active client projects

• Use consistent language, expectations, and feedback approaches

• Share insights about tech fellow and  intern learning strengths and areas of growth

• Avoid duplicative or conflicting guidance; ensure alignment between Tech Facilitator and Tech Fellow is strong

• Participate in weekly/biweekly 1:1 and team check-ins

• Track and communicate intern learning progress

• Support responsive interventions in coordination with program leadership

• Align learning supports to program-wide expectations and timelines

• Submit a simple monthly activity log documenting hours worked, instruction delivered, and coaching activities; a template will be provided by i.c.stars

To set clear expectations, the Tech Facilitator is not responsible for:

• Full-time mentoring or case management

• Employment placement or job search support

• Replacing the need for interns to develop self-directed learning skills

• Strong technical foundation in relevant technologies (e.g., JavaScript, SQL, APIs, web development fundamentals)

• Experience teaching or coaching beginning adult learners in technical domains

• Ability to explain complex ideas simply and clearly

• Patience, emotional intelligence, and calm under pressure

• Comfort setting boundaries and resisting the urge to rescue learners from productive struggle

• Alignment with adult learning and strengths-based instructional models

• Ability and willingness to learn

• Experience in community college instruction, workforce development education/training/preparation

• Familiarity with JavaScript, databases, and API development

• Experience supporting nontraditional or adult learners in technical environments

• Experience with project-based technical teams

The following outcomes will guide performance evaluation:

1. Interns demonstrate impressive growth in foundational technical skills

2. Interns increasingly self-direct and take control of their learning by week 7.

3. Interns meet/exceed client project expectations

4. Interns can articulate how they thought through the solution, not just what they built

5. The cohort's 14-week tech learning is fully planned out in advance of the cycle launch, in alignment with program requirements

6. The tech fellow operates with clarity and confidence in supporting both the foundational tech curricula and the project tech learning

7. Ability to collaborate with the local program team and national program team

Interested individuals should submit the following:

1. A brief statement of interest (1-2 pages) describing your experience and approach to teaching technical concepts to adult learners, including how you handle learner confusion and build independence/confidence

2. A current resume or summary of relevant teaching and technical experience

3. The city or cities for which you are applying (Chicago, Milwaukee, or Kansas City)

4. When you are available to start

5. Two professional references who can speak to your instructional and/or coaching work

Submit materials to: Dawn Foye, Director of People + Culture (dfoye@icstars.org) 

Submission deadline: May 29, 2026

Questions may be directed to: Dawn Foye, dfoye@icstars.org

i.c.stars is committed to diversity and inclusion in all aspects of its work. We encourage applications from individuals of all backgrounds, particularly those with lived experience in the communities we serve.

i.c.stars reserves the right to modify, suspend, or cancel this RFQ at any time. This RFQ does not obligate i.c.stars to award a contract or to pay any costs incurred in the preparation of a response.