Insurance Expert – AI Training, Evaluation
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Job Description
Insurance experts creating underwriting and claims tasks for Weekday's AI training project. Evaluating advanced models and explaining errors with rigorous insurance judgment.
Responsibilities:
- Design complex underwriting scenarios with clear, defensible model answers
- Build claims cases involving coverage determination, policy interpretation, exclusions, or fraud indicators, along with the right adjudication
- Review AI-generated underwriting and claims decisions line by line
- Grade model outputs on accuracy, reasoning, and completeness
- Identify misread policy wording, missed exclusions, incorrect risk calls, and plausible but incorrect decisions
- Write clear rationales explaining evaluation results
- Complete tasks on time
- Create and judge tasks used to train and evaluate advanced AI models
Requirements:
- 3+ years of hands-on experience in underwriting, risk assessment, or claims — life, health, general, or specialty lines
- Deep working knowledge of how risk is assessed and priced, and how claims actually get decided
- Comfort reading policy wordings closely — conditions, exclusions, endorsements — and knowing what they mean in practice
- Precision in writing
- Low tolerance for plausible-sounding nonsense
- Reliable on deadlines
- Curiosity about how AI is going to change insurance work
- Preference for shaping AI's development
Benefits:
- Remote, flexible work you can fit around a full-time role
- Flexible and task-based hours with no fixed working days
- Front-row seat to how frontier AI models are trained and evaluated on insurance work
- Opportunity to help improve frontier AI models
- YC-backed team that moves fast and keeps things direct
- More tasks and larger projects if work is consistently strong
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