[Hiring] Multiline P&C Underwriter @Weekday AI

Role Description

We are partnering with a leading AI lab to train frontier models on high-quality insurance reasoning data. We're hiring Multiline Property & Casualty Underwriters to:

• Design realistic risk-selection and underwriting scenarios.
• Evaluate model outputs against established underwriting standards.
• Help shape how the next generation of AI reasons about insurability, pricing, coverage terms, and portfolio fit.

We welcome carrier, MGA, MGU, and program underwriters with experience across personal, commercial, or specialty P&C products. Candidates should have direct authority or meaningful responsibility for evaluating and selecting risks.

What You'll Do

• Design realistic underwriting scenarios involving new business, renewals, exposure analysis, loss history, inspections, classification, pricing, limits, deductibles, exclusions, and referral decisions.
• Create work products such as underwriting assessments, quote rationales, information requests, declination explanations, renewal strategies, and risk-improvement requirements.
• Write "golden" reference responses at experienced underwriter quality.
• Grade AI-generated responses against structured rubrics for technical accuracy, consistency, risk judgment, and adherence to underwriting guidelines.
• Identify unsupported assumptions, inadequate risk differentiation, incorrect use of policy terms, and inappropriate acceptance or declination decisions.
• Provide written feedback the research team uses to improve model behavior.
• Participate in onboarding office hours and calibration sessions.

Qualifications

• 2+ years of professional P&C underwriting experience.
• Experience underwriting at least one major segment, such as personal lines, commercial property, general liability, commercial auto, package, umbrella/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.
• Strong written reasoning, sound risk judgment, and high attention to detail.
• Ability to separate underwriting decisions from claims handling, brokerage advice, and actuarial portfolio analysis.

Bonus Qualifications

• 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.
• Experience with small commercial, middle-market, national-account, or high-net-worth segments.

Role Highlights

• Minimum 20 hours per week (ideally 40+).
• Role starts immediately, applications reviewed on a rolling basis.

We consider all qualified applicants without regard to legally protected characteristics and provide reasonable accommodations upon request.