Complex Claims & Coverage Director

Weekday; United States; On-site; USD 83,000 - 166,000; Part time

Benefits offered by this job

$80/hour

Flexible part-time hours

Immediate start

Accommodations on request

Job summary

RemoteLeads seeks a part-time insurance claims strategist to design and evaluate complex, high-severity scenarios and settlements. You will develop multi-party strategies, assess coverage issues across jurisdictions, and escalate to counsel when needed.

Strong written reasoning and detail orientation are essential as you help train models and improve claim processes. You will also grade AI responses against policy standards, identify gaps, and contribute to onboarding and calibration sessions.

Qualifications

• 2+ years handling complex, litigated, high-severity or coverage-sensitive claims.
• Experience evaluating coverage issues across multiple parties, layers, policies, or jurisdictions.
• Knowledge of insurer duties, reservation-of-rights practices, litigation management, and escalation to counsel.
• Ability to distinguish operational coverage positions from legal advice and identify when legal review is needed.
• Exceptional written reasoning and defensible judgment.
• Ability to review incomplete records and separate facts, assumptions, and next steps.

Responsibilities

• Design realistic dispute scenarios involving coverage, rights reservation, excessive exposure, multiple insureds and carriers, and settlements.
• Create complex claim strategies, coverage-position analyses, authority requests, and litigation-management plans.
• Write senior-level reference responses for model training.
• Grade AI-generated responses using policy, strategy, and escalation rubrics.
• Identify inconsistent or unsupported claim-handling positions.
• Provide written feedback to improve model behavior and participate in onboarding/calibration sessions.

Skills

Complex claims handling

Litigation awareness

Coverage evaluation

Attention to detail

Written reasoning

Education

CPCU or similar

Job description

Description

• Design realistic scenarios involving disputed coverage, reservations of rights, excess exposure, multiple insureds and carriers, allocation, litigation, mediation, bad-faith risk, and high-severity settlements.
• Create complex claim strategies, coverage-position analyses, authority requests, litigation-management plans, reserve rationales, and escalation recommendations.
• Write senior-level “golden” reference responses for model training.
• Grade AI-generated responses using rubrics covering policy analysis, strategic judgment, factual support, stakeholder awareness, and escalation discipline.
• Identify inconsistent, unsupported, operationally unrealistic, or unauthorized claim-handling positions.
• Provide written feedback to help the research team improve model behavior.
• Participate in onboarding office hours and calibration sessions.

Requirements

• 2+ years of professional experience handling complex, litigated, high-severity, or coverage-sensitive insurance claims.
• Experience evaluating coverage issues and developing strategies involving multiple parties, layers, policies, or jurisdictions.
• Knowledge of insurer duties, reservation-of-rights practices, litigation management, settlement authority, and escalation to counsel.
• Ability to distinguish operational coverage positions from formal legal advice and identify when legal review is required.
• Exceptional written reasoning, defensible judgment, and attention to detail.
• Ability to review incomplete records and separate facts, assumptions, open issues, and recommended next steps.
• CPCU, AIC, SCLA, ARM, or comparable insurance designation preferred.
• Experience with complex lines such as excess casualty, professional liability, D&O, cyber, environmental, or construction defect preferred.
• Experience managing mediations, trials, coverage disputes, extra-contractual exposure, TPAs, adjusters, experts, or panel counsel preferred.
• Availability for at least 20 hours per week, ideally 40+; immediate start preferred.

Benefits

• Compensation of $80 per hour.
• Flexible part-time engagement with a minimum of 20 hours per week.
• Immediate start with rolling application review.
• Reasonable accommodations available upon request.