Product Manager – AI Career Evaluation Specialist

Product Manager – AI Career Evaluation Specialist

About the Role

What if your years of product management experience could help ensure that AI provides career guidance worth actually following? We're looking for experienced Product Managers in Chicago to evaluate AI-generated career advice — identifying what's accurate, what's missing, and what only a seasoned professional would know to say.

This is a fully remote, flexible contract role open to working professionals across all product management backgrounds. No AI experience required.

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

What You'll Do

• Review career questions posed by professionals at different stages of their PM journey
• Write expert-level "golden answers" providing practical, accurate career guidance for product professionals
• Develop evaluation rubrics that objectively assess the quality of AI-generated career advice
• Spot AI responses that are misleading, overly generic, or disconnected from how product work actually operates
• Apply your field knowledge to meaningfully improve AI career coaching at scale
• Work independently and asynchronously — on your own schedule, at your own pace

Who You Are

• Experienced Product Manager with solid real-world credentials
• Strong command of product strategy, roadmap planning, prioritization, and cross-functional stakeholder management
• Experience mentoring or supporting Associate Product Managers or junior professionals
• Clear, confident written communicator capable of giving structured, actionable career advice
• No prior AI, tech evaluation, or annotation experience required

Nice to Have

• Experience in technology companies, fintech, or enterprise software — all common in Chicago's growing tech scene
• Senior or leadership-level PM experience
• Record of taking products from concept to launch
• Close working relationships with engineering and design partners
• Background in professional development, coaching, or mentoring

Why Join Us

• Help define how AI guides product professionals through their careers
• Fully remote and flexible — work when it works for you
• Freelance autonomy with meaningful, well-defined work
• Contribute to cutting-edge AI career guidance projects
• Potential for ongoing work and long-term contract opportunities as projects expand