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.

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

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