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Project Manager – AI Career Coaching Evaluator

Alignerr

AI & Data Training Contractor
Remote (Global) $25 – $50/hr June 16, 2026

Job description

Project Manager – AI Career Coaching Evaluator

About the Role

What if your hands-on project management experience could directly influence how AI guides thousands of aspiring and mid-career PMs? We're looking for experienced Project Managers in the Chicago area to evaluate and improve next-generation AI career coaching systems — helping ensure the advice they give is grounded, practical, and true to how the profession actually works.

This is a fully remote, flexible contract role. No AI background required — just deep project management expertise and strong written communication skills.

  • Organization: Alignerr
  • Type: Hourly Contract
  • Location: Remote
  • Commitment: 10–40 hours/week

What You'll Do

  • Review career-related questions from professionals at different stages of their project management journeys
  • Write high-quality "golden answers" reflecting expert-level career guidance within your field
  • Build objective evaluation rubrics to assess AI-generated career advice
  • Flag inaccurate, unrealistic, or incomplete recommendations produced by AI systems
  • Bring your real-world industry knowledge to improve AI career coaching capabilities
  • Complete task-based assignments independently on your own schedule

Who You Are

  • Solid professional experience as a Project Manager in any industry or sector
  • Strong grasp of career progression, hiring practices, and professional development within project management
  • Experience mentoring, managing, interviewing, or advising other professionals is a real advantage
  • Excellent written communication skills with the ability to translate complex ideas into clear, practical guidance
  • Self-directed and reliable when working independently
  • No prior AI or tech experience required

Nice to Have

  • PMP, PRINCE2, Agile, Scrum, or other recognized PM certifications
  • Experience with cross-functional team leadership or large-scale project delivery
  • People management or leadership experience
  • Background in coaching, mentoring, or career development
  • Knowledge of the Chicago and Midwest job market for project management professionals

Why Join Us

  • Shape how AI systems provide career guidance to project management professionals
  • Fully remote and flexible — work when and where it suits you
  • Freelance autonomy with the structure of meaningful, task-based work
  • Contribute your professional expertise to cutting-edge AI evaluation projects
  • Potential for ongoing work and long-term opportunities as new projects launch
Apply now

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