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Weekday

Insurance Expert – AI Training, Evaluation

Weekday

. Design complex underwriting scenarios with clear, defensible model answers .

Posted 10/8/2026contractRemote • IndiaMid-LevelSenior💰 ₹20,000 - ₹25,000 per dayWebsite

Core Competencies

Role fit
Core Competencies

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Demonstrates expertise in underwriting and claims evaluation, with a strong focus on risk assessment, policy interpretation, and the integration of AI in insurance processes. Capable of producing clear rationales and maintaining precision in writing while meeting deadlines.

Highest-signal resume keywords
Underwriting ExperienceRisk AssessmentClaims EvaluationPolicy InterpretationAI Integration in Insurance

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills
UnderwritingRisk AssessmentClaims AnalysisPolicy ReviewModel EvaluationFraud DetectionCoverage DeterminationAdjudicationWriting RationaleDeadline Management
Soft Skills
Attention to DetailCuriosityReliabilityCritical ThinkingPrecision in Writing
Industry Keywords
Life InsuranceHealth InsuranceGeneral InsuranceSpecialty LinesExclusionsEndorsementsRisk PricingAI in Insurance

About the role

Key responsibilities & impact
  • 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

What you’ll need
  • 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

Comp & perks
  • 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