About this role
Role Overview
Help train advanced AI systems to reason through real-world property and casualty underwriting decisions. You will develop realistic risk-selection scenarios, assess AI-generated underwriting analyses against established standards, and contribute to better reasoning on insurability, pricing, coverage terms, and portfolio fit across personal, commercial, and specialty P&C business.
Key Responsibilities
- Create underwriting scenarios covering new business, renewals, exposure analysis, loss history, inspections, classification, pricing, limits, deductibles, exclusions, and referral decisions.
- Produce underwriting assessments, quote rationales, information requests, declination explanations, renewal strategies, and risk-improvement requirements.
- Write high-quality reference responses reflecting experienced underwriter judgment.
- Evaluate AI responses using structured rubrics for technical accuracy, consistency, risk judgment, and compliance with underwriting guidelines.
- Identify unsupported assumptions, insufficient risk differentiation, incorrect policy-term usage, and inappropriate acceptance or declination decisions.
- Provide written feedback to support improvements in model behavior.
- Take part in onboarding office hours and calibration sessions.
Qualifications
- At least 2 years of professional P&C underwriting experience, with direct authority or meaningful responsibility for evaluating and selecting risks.
- Experience underwriting at least one major segment, including personal lines, commercial property, general liability, commercial auto, package, umbrella/excess, professional liability, cyber, or another specialty line.
- Understanding of the full 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 influence underwriting decisions.
- Strong written reasoning, sound risk judgment, and close attention to detail.
- Ability to distinguish underwriting decisions from claims handling, brokerage advice, and actuarial portfolio analysis.
Preferred Qualifications
- CPCU, AU, ARM, or a comparable insurance designation.
- Multiline underwriting authority.
- Experience in E&S, MGA/MGU, Lloyd''s, or program business.
- Experience with catastrophe-exposed property or high-severity casualty risks.
- Experience serving small commercial, middle-market, national-account, or high-net-worth segments.
Work Terms
- Remote hourly engagement open to candidates located in the United States, Canada, or the United Kingdom.
- Minimum commitment of 20 hours per week, with 40 or more hours preferred.
- The role is available to begin immediately, and applications are reviewed on a rolling basis.
- Successful completion of the onboarding process is required. Onboarding is estimated to take approximately 10 hours and includes office hours and calibration participation.
Compensation
- A flat $800 is paid upon successful completion of onboarding.
- After onboarding is successfully completed, compensation is $80 per hour.