About the Role

Mercor is partnering with a leading AI lab to train frontier models on high-quality insurance reasoning data. We're hiring

Insurance Underwriting Specialists

to design realistic underwriting and risk-selection scenarios, evaluate model outputs against established industry standards, and help shape how the next generation of AI reasons about risk assessment, policy provisions, pricing, and coverage decisions. We welcome underwriters across all lines, including life, health, property, casualty, commercial, personal, specialty, marine, surety, and reinsurance — from carriers, MGAs, and reinsurers. What You'll Do

Design realistic scenarios involving risk selection, exposure analysis, policy terms and conditions, exclusions, endorsements, pricing, and coverage determinations

Create work products such as underwriting decisions, risk assessments, rating and pricing rationales, coverage analyses, and referral write-ups

Write "golden" reference responses at experienced underwriting-professional quality

Grade AI-generated responses against structured rubrics for risk-selection accuracy, provision interpretation, pricing correctness, and sound judgment

Identify misread policy language, flawed risk classifications, incorrect pricing math, and gaps in documented rationale





Provide written feedback the research team uses to improve model behavior

Participate in onboarding office hours and calibration sessions

You're a Valuable Fit If You

Have 2+ years of professional experience in insurance underwriting (any line)

Understand how policy provisions, exclusions, endorsements, and rating factors determine coverage and price

Can weigh risk, exposure, and financial evidence and articulate a defensible decision with a documented rationale

Demonstrate excellent written analysis, balanced judgment, and high attention to detail

Can distinguish underwriting decisions from sales/agent recommendations and from formal legal advice

Bonus Qualifications

CPCU, CLU, AINS, ARM, AU, FALU, or comparable industry credential

Experience across multiple lines of business or specialty risks

Reinsurance, treaty, or facultative underwriting experience

Actuarial, pricing, or catastrophe-modeling exposure

Experience with regulatory filings, compliance, or audit review

Role Highlights

Minimum 20 hours per week (ideally 40+)

Role starts immediately, applications reviewed on a rolling basis

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📌 Insurance Underwriter - Risk Specialist (Winnipeg)
🏢 Obsidian
📍 Winnipeg