Insurance AI Evaluation Specialist

About OpenTrain

OpenTrain is the #1 platform for finding and building careers in AI training and data labeling. We connect experienced professionals with flexible, remote contract work that helps shape how modern AI systems behave. OpenTrain AI is the hiring organization for this role.

• Work remotely and build a portfolio of AI training projects.
• Opportunities span annotation, evaluation, content creation, and expert review.

About AI training and why it matters

AI training (data labeling, annotation, and human feedback) is the human side of building AI: people prepare, evaluate, and improve the examples models learn from. This work is highly accessible, often part-time and remote, and gives you direct impact on model behavior and safety.

Insurance expertise is especially valuable because models must reason about complex policy language, coverage triggers, exclusions, and compliance-aware recommendations.

• Contribute to industry-leading AI behavior in insurance scenarios.
• Flexible, cutting-edge work that rewards domain knowledge and clear writing.

The role

As an Insurance AI Evaluation Specialist you will evaluate AI-generated insurance content, craft gold-standard outputs, and provide detailed, plain-language feedback that improves model correctness and reliability. This is an hourly contractor role focused on coverage analysis, claims scenarios, underwriting decisions, policy communication, and compliance-aware reasoning.

• Hourly contractor, part-time engagement (20+ hours/week).
• Work with text tasks: evaluation ratings and text generation (gold outputs).
• Provide expert review that bridges insurance practice and model training needs.

What you'll do

Your day-to-day work will center on reviewing model responses, creating reference outputs, and documenting precise feedback. Expect to analyze ambiguous facts, edge cases, and internal reasoning quality to ensure recommendations are accurate and compliant.

• Review and evaluate AI-generated answers for insurance accuracy, clarity, and compliance awareness.
• Create detailed prompts and gold-standard outputs for coverage, claims, underwriting, and policy communication tasks.
• Compare multiple model responses and rank them by correctness and reasoning quality.
• Detect missing facts, incorrect assumptions, unsupported recommendations, and misleading guidance.
• Write plain-language explanations that demonstrate sound insurance methods and reasoning.
• Validate outputs across ambiguity, edge cases, and internal consistency from facts to coverage position.

Requirements

You must meet the core requirements below; preferred and helpful backgrounds are listed after the essentials. All substantive role facts come from this posting.

• 5+ years professional insurance experience in claims, underwriting, brokerage, actuarial support, risk management, compliance, or operations.
• Strong command of insurance fundamentals: policy structure, exclusions, endorsements, limits, deductibles, and coverage triggers.
• Experience evaluating claims or coverage decisions across commercial or personal lines.
• Clear written communication and ability to explain complex policy concepts simply.
• Minimum C1 English proficiency.
• Prior AI data training, claims QA, underwriting QA, policy drafting or review, or insurance editorial experience is strongly preferred.

Helpful background and credentials

While not required, the following qualifications make you a stronger candidate and help you move quickly into evaluation and gold-output work.

• Bachelor’s degree or higher in Business, Finance, Risk Management, Insurance, Law, or a related field.
• Professional designations such as CPCU, AINS, ARM, CIC, or AU are a plus.

Compensation, schedule, and eligibility

This is a contractor role paid hourly. Candidates must be located in one of the eligible countries listed below; the role is not worldwide.

• Pay: USD $40–$70 per hour (hourly contractor).
• Time: 20+ hours per week (part-time contractor).
• Employment type: Contractor, Part-time.
• Language: English (minimum C1).
• Eligible countries: Vietnam, Timor-Leste, Thailand, Singapore, Pakistan, Philippines, Nepal, Malaysia, Sri Lanka, Cambodia, Indonesia, Bhutan, Bangladesh, India, Brazil, Germany, United States.

How the work is done

Tasks are text-focused and use evaluation and text-generation workflows. You'll rate responses, produce gold-standard answers, and provide written rationales that model trainers use to improve system outputs. Clear, consistent feedback and reproducible reasoning are essential.

OpenTrain will onboard contractors, provide task guidelines, and supply the annotation/evaluation interface and examples you'll use; you will not be required to provide tools or proprietary platforms yourself.

• Data type: Text. Label types: Evaluation rating and text generation (gold outputs).
• Deliverables: rated responses, ranked comparisons, gold-standard answers, and explanatory feedback.
• Work remotely and submit tasks through the OpenTrain workflow after onboarding.

Who should apply

Apply if you are an experienced insurance professional who can translate deep subject-matter knowledge into clear, teachable explanations for AI systems. This role suits claims adjusters, underwriters, compliance officers, brokers, and insurance operations specialists who enjoy writing and quality assurance.

• You enjoy careful review, structured reasoning, and improving how AI communicates insurance decisions.
• You have the required experience and can commit to 20+ hours/week as a contractor.