Complex Claims and Coverage AI Evaluation Expert

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

About OpenTrain

OpenTrain is the #1 platform for finding and building careers in AI training and data labeling. OpenTrain AI contracts specialists to help improve advanced AI systems, while giving contributors a place to build a credible profile and grow a long-term portfolio.

• Remote contract work with a fast-growing AI training organization
• Create an OpenTrain profile and apply in minutes
• Build documented experience in specialized AI evaluation

About AI Training Work

AI training is the human side of building artificial intelligence. Specialists write examples, assess model responses, and provide detailed feedback so AI systems can reason more accurately and handle complex professional situations.

• Apply your insurance expertise to cutting-edge AI development
• Evaluate generated responses against clear quality criteria
• Help models improve their reasoning, judgment, and professional communication

The Role

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 involving disputed coverage, reservations of rights, excess exposure, multiple insureds and carriers, allocation, litigation, mediation, bad-faith risk, and major-loss settlement strategy.

You will also create senior-level reference responses and evaluate model-generated work for sound policy analysis, strategic judgment, factual support, stakeholder awareness, and appropriate escalation.

• Contract role available remotely in the United States, Canada, the United Kingdom, Australia, New Zealand, Ireland, Malta, the Netherlands, Sweden, Denmark, Norway, Finland, Germany, Austria, and Belgium
• Expected commitment of at least 20 hours per week, ideally 40 or more
• English-language work
• Part-time contractor engagement

What You’ll Do

You will produce and review complex insurance claims content with a focus on defensible senior-level judgment. When records are incomplete, your work should clearly separate known facts, assumptions, open issues, and recommended next steps.

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

Required Experience and Judgment

This role requires professional experience handling complex insurance matters and the ability to reason carefully across incomplete records, multiple stakeholders, and competing coverage considerations. You must be able to distinguish operational coverage analysis from formal legal advice.

• 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
• Working knowledge of insurer duties, reservation-of-rights practices, litigation management, settlement authority, and escalation to internal or external 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

Helpful Insurance Background

The following experience or credentials is helpful for evaluating the range of scenarios covered by this work, but the core requirements are your complex claims experience, coverage knowledge, and professional judgment.

• CPCU, AIC, SCLA, ARM, or a comparable insurance designation
• Excess casualty or professional liability
• Directors and officers, cyber, environmental, or construction-defect claims
• Mediations, trials, coverage disputes, or extra-contractual exposure
• Claim governance, third-party administrators, independent adjusters, experts, or panel counsel

Compensation and Commitment

Compensation includes a flat $800 payment upon successful completion of onboarding, which is estimated at approximately 10 hours. After onboarding, the rate is $80 per hour.

• $800 flat payment upon successful onboarding completion
• Onboarding estimated at approximately 10 hours
• $80 per hour after onboarding
• At least 20 hours per week expected, with 40 or more hours preferred