Insurance AI Model Evaluator

About OpenTrain

OpenTrain AI is the hiring and contracting organization for this role. OpenTrain is the #1 platform for finding and building careers in AI training and data labeling, helping experts discover projects, build a professional profile, and apply to cutting-edge work.

• Free account creation and a streamlined application process
• Opportunities to build a lasting career in AI training and data labeling

About AI Training Work

AI training is the human side of building modern artificial intelligence. Subject-matter experts review model outputs, create challenging examples, and provide structured feedback that helps AI systems reason more accurately in specialized fields such as insurance.

• Help shape how advanced AI models evaluate insurance scenarios
• Apply professional judgment to real-world model responses
• Work remotely in a fast-growing technology field

The Role

OpenTrain AI is seeking an Insurance AI Model Evaluator to support generative AI model improvement. You will apply expert knowledge from underwriting, claims, actuarial work, or risk management to design domain-specific tasks, assess model reasoning, and deliver precise feedback.

This is an expert-level contractor and part-time engagement for professionals based in the United States. The structured project requirement is 20+ hours per week, with reliable availability of at least 35 weekday hours expected for the role.

• Pay: $60–$80 per hour
• Engagement: Contractor, part-time
• Location: United States
• Primary language: English
• Data type: Text
• Work type: Evaluation and rating of AI outputs

What You'll Do

You will help research and engineering teams identify and close gaps in how AI models handle insurance reasoning. Your work will combine task design, expert review, rubric development, and written communication.

• Guide teams on knowledge gaps involving underwriting, claims, and risk-assessment reasoning.
• Design challenging, domain-relevant insurance tasks.
• Write accurate, well-reasoned solutions grounded in real underwriting or claims practice.
• Evaluate AI model outputs using structured rubrics.
• Provide clear written feedback on correctness, judgment, and reasoning quality.
• Develop and refine evaluation guidelines and insurance-specific scoring rubrics.
• Collaborate with other subject-matter experts to maintain consistency and accuracy in training data.

Required Qualifications

This role requires substantial professional insurance experience and demonstrated familiarity with evaluating large language model or AI outputs. Candidates should be able to communicate nuanced insurance judgment clearly and apply structured scoring criteria consistently.

• 8+ years of dedicated professional insurance experience at a recognized, top-tier organization.
• Background in underwriting, claims, actuarial work, risk management, or a related insurance function.
• Mandatory hands-on experience evaluating LLM or AI model outputs against rubrics or structured scoring criteria.
• Demonstrable career progression in insurance.
• Strong verbal and written communication skills.
• Strong problem-solving and interpersonal skills.
• Reliable availability for at least 35 hours per week during weekdays.

Who Should Apply

This opportunity is designed for experienced insurance professionals who want to use their industry judgment to influence how generative AI systems perform. It may suit senior practitioners with a strong record of progression and direct experience reviewing AI outputs in a structured way.

• Senior insurance specialists with deep practical expertise
• Professionals experienced in underwriting, claims, actuarial, or risk functions
• Experts comfortable writing detailed evaluations and reasoned solutions
• Candidates located in the United States who can meet the weekday availability requirement