Senior Insurance Expert for AI Training & Evaluation - Remote

Weekday AI; United States; Remote; Part time

Benefits offered by this job

Remote work

Flexible hours

Job summary

Weekday AI is recruiting insurance experts to design and judge underwriting and claims tasks for AI model training. This remote, contract-based role focuses on creating complex scenarios, evaluating model outputs, and providing precise rationales. You’ll work on depth over volume and help steer frontier AI in insurance judgment.

The role emphasizes high accuracy, defensible decisions, and timely delivery, with pay per task and flexible scheduling to complement other commitments.

Qualifications

• 3+ years of hands-on underwriting, risk assessment, or claims in life/health/general/specialty lines.
• Deep knowledge of how risk is assessed and priced and how claims get decided.
• Comfort reading policy wordings—conditions, exclusions, endorsements— and their practical meaning.
• Precision in writing: state what’s wrong and why, without padding.
• Low tolerance for plausible-sounding nonsense from models or people.
• Reliability on deadlines; task-based work requires timely delivery.
• Curiosity about how AI will change insurance work and a desire to shape it.

Responsibilities

• Design complex underwriting scenarios with defensible model answers.
• Build claims cases focusing on coverage determination, policy interpretation, exclusions, or fraud indicators.
• Review AI-generated underwriting and claims decisions line by line for accuracy and reasoning.
• Catch misread policy wording, missed exclusions, wrong risk calls, or dubious conclusions.
• Write clear rationales to help the model learn from evaluations.

Skills

Underwriting

Claims

Policy wording

Risk assessment

Writing clarity

Deadlines

Curiosity about AI

Job description

Weekday AI is recruiting insurance experts to design and judge underwriting and claims tasks for AI model training. This remote, contract-based role focuses on creating complex scenarios, evaluating model outputs, and providing precise rationales. You’ll work on depth over volume and help steer frontier AI in insurance judgment.

The role emphasizes high accuracy, defensible decisions, and timely delivery, with pay per task and flexible scheduling to complement other commitments.