Senior Remote Complex Claims & Coverage AI Evaluator

OpenTrain AI; Northern (KY); Hybrid; USD 83,000 - 166,000; Part time

Job summary

OpenTrain AI is seeking a Complex Claims and Coverage AI Evaluation Expert to train advanced models on insurance reasoning data. You will design realistic, high-severity claim scenarios and create senior-level reference responses for sound policy analysis, strategic judgment, and escalation when needed.

You will also produce and review complex insurance claims content, ensuring clear separation of known facts, assumptions, open issues, and recommended next steps, while evaluating model-generated

Qualifications

• At least two years handling complex, litigated, high-severity, or coverage-sensitive insurance claims.
• Experience evaluating coverage issues across multiple parties, layers, policies, or jurisdictions.
• Knowledge of insurer duties, reservation-of-rights practices, litigation management, settlement authority, and escalation to counsel.
• Ability to separate facts, assumptions, open issues, and recommendations in incomplete claim records.
• Exceptional written reasoning, defensible senior claims judgment, and close attention to detail.
• Ability to distinguish operational coverage positions from formal legal advice.

Responsibilities

• Develop complex claim strategies and coverage-position analyses.
• Prepare authority requests, litigation-management plans, reserve rationales, and escalation recommendations.
• Write reference responses reflecting senior technical claims quality.
• Grade AI-generated responses against structured evaluation criteria.
• Identify positions that are inconsistent, unsupported by the record, or outside a non-lawyer claims professional’s authority.
• Provide written feedback to help improve model behavior.
• Recognize when specialized legal review is needed.

Skills

Complex insurance claims experience

Senior-level judgment

Written reasoning

Defensible analysis

Attention to detail

Education

CPCU / AIC / SCLA / ARM or comparable designation

Job description

OpenTrain AI is seeking a Complex Claims and Coverage AI Evaluation Expert to train advanced models on insurance reasoning data. You will design realistic, high-severity claim scenarios and create senior-level reference responses for sound policy analysis, strategic judgment, and escalation when needed.

You will also produce and review complex insurance claims content, ensuring clear separation of known facts, assumptions, open issues, and recommended next steps, while evaluating model-generated