Insurance Expert – AI Training, Evaluation

Weekday (YC W21)

. Design complex underwriting scenarios involving applications, risk profiles, eligibility, or pricing decisions .

Posted 10/9/2026contractRemote • IndiaMid-LevelSenior💰 ₹20,000 - ₹25,000 per monthWebsite

Core Competencies

Role fit

Core Competencies

Use this summary to align your resume positioning with the role.

Demonstrates expertise in underwriting and risk assessment, with a strong focus on claims decision-making and policy interpretation. Capable of producing high-quality evaluations and rationales while leveraging AI insights to enhance insurance processes.

Highest-signal resume keywords

Underwriting ExperienceRisk Assessment KnowledgeClaims Decision-MakingPolicy InterpretationAI Development Engagement

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

UnderwritingRisk AssessmentClaims AnalysisPolicy ReviewPricing DecisionsCoverage DeterminationFraud IndicatorsEvaluation WritingAccuracy GradingExclusion Identification

Soft Skills

Precision in WritingReliability on DeadlinesCuriosity about AI

Industry Keywords

Life InsuranceHealth InsuranceGeneral InsuranceSpecialty InsurancePolicy WordingsConditionsEndorsements

About the role

Key responsibilities & impact

Design complex underwriting scenarios involving applications, risk profiles, eligibility, or pricing decisions
Build claims cases involving coverage determination, policy interpretation, exclusions, or fraud indicators
Review AI-generated underwriting and claims decisions line by line
Grade AI outputs for accuracy, reasoning, and completeness
Identify misread policy wording, missed exclusions, incorrect risk decisions, and plausible-sounding errors
Write clear rationales explaining evaluation results
Produce high-quality, rigorous submissions reviewed by the team

Requirements

What you’ll need

3+ years of hands-on experience in underwriting, risk assessment, or claims
Experience in life, health, general, or specialty insurance lines
Deep working knowledge of risk assessment and pricing
Knowledge of claims decision-making
Comfort reading policy wordings, including conditions, exclusions, and endorsements
Precision in writing
Ability to identify plausible-sounding inaccuracies
Reliability on deadlines
Curiosity about how AI will change insurance work
Preference for shaping AI development
Ability to work on project-based, task-based contract work

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 AI models
YC-backed team environment
More tasks and larger projects if work is consistently strong