Multiline P&C Underwriter AI Training

About Open Train

Open Train AI is the hiring and contracting organization for this project. We connect experienced professionals with cutting-edge AI training work and help contributors build careers teaching artificial intelligence through high-quality human expertise.

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AI training is the human side of building modern artificial intelligence. Experts create examples, write strong responses, and evaluate model outputs so AI systems can learn accurate reasoning and make better decisions.

In this project, your insurance knowledge will help train frontier AI models to understand insurability, pricing, portfolio fit, and sound underwriting judgment.

Open Train is seeking a Multiline P&C Underwriter with at least two years of professional property and casualty underwriting experience and direct risk evaluation authority. You will design realistic underwriting scenarios, create experienced-underwriter-quality reference responses, and assess AI-generated outputs against structured standards.

This is a remote, part-time contractor role open to candidates in the United States, Canada, and the United Kingdom. The project starts immediately, and applications are reviewed on a rolling basis.

• Pay: $80 per hour
• Schedule:
  
  Minimum 20 hours per week, with the option to work up to 40 or more hours
• Onboarding payment:
  Flat $800 upon successful completion
• Work type:
  Contractor and part-time
• Primary language:
  English

You will produce and review insurance reasoning data that reflects real underwriting practice. Your written feedback will help the research team improve model behavior.

• Design scenarios covering new business, renewals, exposure analysis, loss history, inspections, classification, pricing, limits, deductibles, exclusions, and referral decisions
• Create underwriting assessments, quote rationales, information requests, declination explanations, renewal strategies, and risk-improvement requirements
• Write golden reference responses at the quality level expected from an experienced underwriter
• Grade AI-generated responses for technical accuracy, consistency, risk judgment, and adherence to underwriting guidelines
• Identify unsupported assumptions, inadequate risk differentiation, incorrect policy-term usage, and inappropriate acceptance or declination decisions
• Provide written feedback for model improvement
• Participate in onboarding office hours and calibration sessions

This role requires practical P&C underwriting experience and the ability to explain complex risk decisions clearly in writing. Candidates should be able to distinguish underwriting judgment from related functions such as claims handling, brokerage advice, and actuarial portfolio analysis.

• At least 2 years of professional P&C underwriting experience
• Underwriting experience in one or more major segments, such as personal lines, commercial property, general liability, commercial auto, package, umbrella or excess, professional liability, cyber, or another specialty line
• Understanding of the underwriting lifecycle from submission and assessment through quotation, binding, renewal, and nonrenewal
• Ability to explain how account characteristics, jurisdiction, peril, loss experience, and market conditions affect underwriting decisions
• Ability to design realistic underwriting scenarios and write golden reference responses
• Experience grading AI-generated outputs against structured rubrics
• Strong written reasoning, sound risk judgment, and close attention to detail

The following experience is helpful but not required:

• CPCU, AU, ARM, or comparable insurance designation
• Multiline underwriting authority
• E&S, MGA, MGU, Lloyd's, or program-business experience
• Catastrophe-exposed property or high-severity casualty experience
• Small commercial, middle-market, national-account, or high-net-worth underwriting experience

AI training offers flexible, remote work where specialized professional knowledge directly shapes how advanced models behave. Insurance experts can contribute meaningful domain judgment while building experience in a fast-growing technology field.

Open Train brings together opportunities to help professionals start and grow careers in AI training and data labeling. Your underwriting expertise can help make AI outputs more accurate, consistent, and useful.