Senior Complex Claims & Coverage Director

Weekday 1; United States; Remote; USD 94,000 - 127,000; Part time

Job summary

Weekday 1 is seeking a part-time Complex Claims Director to design and evaluate high-severity coverage scenarios for AI training data. You will shape litigation strategy, allocate resources, and assess claim-position quality against senior standards.

Ideal candidates have extensive experience in complex insurance claims, coverage disputes, and multi-party scenarios. This role emphasizes rigorous reasoning, clear documentation, and escalation to counsel when needed.

Qualifications

• 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.
• Understand insurer duties, reservation-of-rights practices, litigation management, settlement authority, and escalation to internal or external counsel.

Responsibilities

• 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 work products such as 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 or outside the authority of a non-lawyer claims professional
• Provide written feedback the research team uses to improve model behavior
• Participate in onboarding office hours and calibration sessions

Skills

Complex claims

Coverage analysis

Litigation management

Policy analysis

Escalation discipline

Education

CPCU / AIC / SCLA / ARM or comparable designation

Job description

Weekday 1 is seeking a part-time Complex Claims Director to design and evaluate high-severity coverage scenarios for AI training data. You will shape litigation strategy, allocate resources, and assess claim-position quality against senior standards.

Ideal candidates have extensive experience in complex insurance claims, coverage disputes, and multi-party scenarios. This role emphasizes rigorous reasoning, clear documentation, and escalation to counsel when needed.