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Freelance AI Expert - AI Workshops and Masterclasses

Job in Chicago, Cook County, Illinois, 60290, USA
Listing for: Fired Up
Contract position
Listed on 2026-10-02
Job specializations:
  • Education / Teaching
    AI Business & Operations, AI Evaluation
Salary/Wage Range or Industry Benchmark: 95000 - 135000 USD Yearly USD 95000.00 135000.00 YEAR
Job Description & How to Apply Below
About us

At Fired Up GmbH, we are dedicated to supporting people currently in a career transition phase. We are a bootstrapped company, based in Berlin. Our mission is to break the stigma around unemployment and create a safe space where people have the opportunity to reorient themselves and find their (new) path. We believe in empathy and understanding as the foundation for real change - everyone deserves the chance to reinvent themselves professionally.

Your

Impact as an AI Expert in our Trainer Pool

Since June, our Project Management with AI course has run several cohorts with consistently strong feedback. Over 13 weeks, participants learn core project management methods while using AI as a thinking partner across the full project lifecycle - not just as an output machine.

We're building out a pool of AI experts to run the workshops and masterclasses that give students who want to go deeper technically the space to do so. This can mean one or more of the following:

  • You run dedicated masterclasses on AI tools and workflows for students who want to explore beyond the course's core curriculum - for example prompt design, AI-assisted research (Perplexity), or AI-assisted prototyping (Figma Make, Lovable, Replit, Firebase Studio).
  • You design and deliver workshops that show how to apply AI critically and responsibly to real project management tasks - planning, stakeholder prep, decision-making - rather than teaching AI in the abstract.
  • You bring current, hands-on experience of the fast-moving AI landscape and help our non-technical students build the confidence to keep exploring after the course ends.

Our program combines morning live sessions with guided self-study and project work support in the afternoons. Depending on your availability, you can run a single workshop, a short masterclass series, or take ownership of a recurring AI module. Your contribution helps people upskill, re-enter the workforce, or take the next step in their careers.

As a freelance trainer, you receive 73.33 EUR (gross) per hour.

Your profile
  • Solid, current, hands-on experience applying AI tools to real work - not just theoretical knowledge of the space.
  • University Degree required for compliance reasons. Bonus if you have additional certificates in teaching or adult education.
  • Comfortable across a range of tools beyond a single chatbot: e.g. Claude or ChatGPT, Perplexity, AI prototyping tools like Figma Make, Lovable, Replit, or Firebase Studio, automation tools like Zapier or n8n.
  • Able to explain AI concepts and workflows clearly to a non-technical, career-transition audience - didactic clarity matters more than technical depth for its own sake.
  • Able to teach agentic AI, from delegating goals to AI agents to designing workflows with human review.
  • A critical, responsible perspective on AI use - you can teach people to evaluate AI outputs, not just accept them.
  • Experience as a trainer, instructor, teacher, or mentor is a bonus but not required.
  • Team player - friendly and empathetic communication style.
  • Fluent in English, spoken and written (German is a plus).
  • Organized, efficient and independent working style.
  • Proactive problem-solving skills.

This isn't a role for building AI products, training models, or working with AI infrastructure - it's about helping project managers use AI well in their day-to-day work.

Your New Role

Your responsibilities as an AI expert - and the core capabilities you need to be effective in this role:

Designing Practical, Learner-Focused AI Workshops

You'll turn your AI expertise into hands-on learning experiences - explaining concepts clearly, demonstrating tools, and guiding participants through real AI-supported project tasks.

Skills:

AI tool fluency
- Didactic clarity
- Ability to break down complex…

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