Insurance Expert – AI Career Coaching Evaluator
$25-50/hr Remote Freelance Other
About the Role
What if your hands-on experience in the insurance industry could directly improve how AI coaches professionals through their careers? We're looking for experienced Insurance Agents, Brokers, and Producers in the Chicago area to evaluate AI-generated career guidance — ensuring it reflects the real standards, challenges, and opportunities of working in insurance.
This is a fully remote, flexible contract role. No AI background required — just genuine industry expertise and a commitment to quality.
• Organization: Alignerr
• Type: Hourly Contract
• Location: Remote
• Commitment: 10–40 hours/week
What You'll Do
• Review career-related questions from insurance professionals at various stages of their careers
• Write high-quality "golden answers" that reflect expert-level, practical career guidance within the insurance field
• Develop objective evaluation rubrics to assess AI-generated career advice
• Flag AI outputs that are inaccurate, incomplete, or unrealistic for working insurance professionals
• Apply your knowledge of the Midwest and broader US insurance market to improve AI coaching capabilities
• Work independently and asynchronously — fully on your own schedule
Who You Are
• Professional experience as an Insurance Agent, Broker, Producer, or Account Executive
• Strong understanding of insurance sales, client acquisition, policy management, and Illinois licensing requirements
• Excellent written communication skills
• Ability to translate real industry experience into clear, actionable career advice
• Self-motivated and consistent when working independently
• No prior AI or tech experience required
Nice to Have
• Active insurance license in Illinois or multi-state
• Experience across life, health, property, casualty, or commercial insurance lines
• Experience mentoring junior agents or managing a book of business
• Sales leadership or agency management background
Why Join Us
• Help shape how AI systems provide career guidance to insurance professionals nationwide
• Fully remote and flexible — work when and where it suits you
• Freelance autonomy with meaningful, task-based work
• Contribute your real-world expertise to cutting-edge AI evaluation projects
• Potential for ongoing work and long-term opportunities as new projects launch