Complex Claims and Coverage Director

Weekday (YC W21)

. Design realistic scenarios involving disputed coverage, reservations of rights, excess exposure, multiple insureds, multiple carriers, allocation, litigation, mediation, bad-faith risk, and high-severity settlement strategy .

Posted 9/17/2026contractRemote • United States, Australia, Canada, New Zealand, United Kingdom, GermanyLead💰 $80 per hourWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates expertise in handling complex insurance claims, including coverage evaluations and litigation management, while providing exceptional written reasoning and attention to detail. Capable of developing strategic claim approaches and training AI models with high-quality insurance data.

Highest-signal resume keywords

Complex Claim HandlingCoverage EvaluationLitigation ManagementExceptional Written ReasoningInsurance Designation (CPCU, AIC, SCLA, ARM)

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Claim Strategy DevelopmentCoverage-Position AnalysisLitigation-Management PlanningReserve Rationale CreationEscalation RecommendationsDisputed Coverage ScenariosHigh-Severity Settlement StrategyClaim-Handling Position IdentificationAI Model TrainingFact Separation and Analysis

Soft Skills

Attention to DetailDefensible JudgmentStakeholder Awareness

Certifications & Qualifications

CPCUAICSCLAARM

Industry Keywords

Excess CasualtyProfessional LiabilityDirectors and OfficersCyber InsuranceEnvironmental InsuranceConstruction-DefectMediation ManagementTrial ManagementCoverage DisputesExtra-Contractual Exposure

About the role

Key responsibilities & impact

Design realistic scenarios involving disputed coverage, reservations of rights, excess exposure, multiple insureds, multiple carriers, allocation, litigation, mediation, bad-faith risk, and high-severity settlement strategy
Create complex claim strategies, coverage-position analyses, authority requests, litigation-management plans, reserve rationales, and escalation recommendations
Write “golden” reference responses at senior technical claims quality
Grade AI-generated responses against structured rubrics for policy analysis, strategic judgment, factual support, stakeholder awareness, and escalation discipline
Identify claim-handling positions that are internally inconsistent, unsupported by the record, operationally unrealistic, or outside the authority of a non-lawyer claims professional
Provide written feedback to improve model behavior
Participate in onboarding office hours and calibration sessions
Train frontier AI models using high-quality insurance reasoning data

Requirements

What you’ll need

2+ years of professional experience handling complex, litigated, high-severity, or coverage-sensitive insurance claims
Experience evaluating coverage issues and developing claim strategies involving multiple parties, layers, policies, or jurisdictions
Understanding of insurer duties, reservation-of-rights practices, litigation management, settlement authority, and escalation to internal or external counsel
Ability to distinguish an operational coverage position from formal legal advice and recognize when specialized legal review is required
Exceptional written reasoning, defensible judgment, and high attention to detail
Comfortable reviewing incomplete records and clearly separating facts, assumptions, open issues, and recommended next steps
CPCU, AIC, SCLA, ARM, or comparable insurance designation is a bonus qualification
Experience with excess casualty, professional liability, directors and officers, cyber, environmental, construction-defect, or other complex lines is a bonus qualification
Experience managing mediations, trials, coverage disputes, or extra-contractual exposure is a bonus qualification
Home-office technical claims or claim-governance experience is a bonus qualification
Experience overseeing TPAs, independent adjusters, experts, or panel counsel is a bonus qualification
Law degree or license to practice law is not required

Benefits

Comp & perks

Minimum 20 hours per week (ideally 40+)
Role starts immediately
Reasonable accommodations upon request