Role Overview
Help train advanced AI systems to reason through real-world Property & Casualty underwriting decisions. You will apply your underwriting expertise to develop realistic risk-selection scenarios, assess model responses against established standards, and strengthen AI judgment on insurability, pricing, coverage terms, and portfolio fit.
Key Responsibilities
- Create underwriting scenarios covering new business, renewals, exposure analysis, loss history, inspections, classification, pricing, limits, deductibles, exclusions, and referral decisions.
- Develop underwriting assessments, quote rationales, information requests, declination explanations, renewal strategies, and risk-improvement requirements.
- Write high-quality reference responses reflecting experienced underwriting judgment.
- Evaluate AI-generated 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 or 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 affect 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, high-severity casualty, small commercial, middle-market, national-account, or high-net-worth segments.
Work Terms
Remote hourly engagement open to candidates in the United States, Canada, or the United Kingdom.
Minimum commitment of 20 hours per week, with 40 or more hours preferred.
Compensation
- A flat $800 is paid upon completion of onboarding, estimated to take approximately 10 hours.
- After onboarding is completed, compensation is $80 per hour.