About the Role Mercor is partnering with a leading AI lab to train frontier models on high-quality insurance reasoning data. We're hiring Complex Claims and Coverage Directors to design high-severity and coverage-sensitive claim scenarios, evaluate model outputs against established senior claims standards, and help shape how the next generation of AI reasons about disputed coverage, litigation strategy, allocation, and major-loss resolution.

We welcome senior carrier claims professionals, complex-claims leaders, coverage specialists, and technical claim directors. This is an insurance-practitioner role and does not require a law degree or license to practice law.

What You'll Do

Design realistic scenarios involving disputed coverage, reservations of rights, excess exposure, multiple insureds, multiple carriers, allocation, litigation, mediation, bad-faith risk, and high-severity settlement strategy

Create work products such as complex claim strategies, coverage-position analyses, authority requests, litigation-management plans, reserve rationales, and escalation recommendations

Write "golden" reference responses at senior technical claims quality

Grade AI-generated responses against structured rubrics for policy analysis, strategic judgment, factual support, stakeholder awareness, and escalation discipline

Identify claim-handling positions that are internally inconsistent, unsupported by the record, operationally unrealistic, or outside the authority of a non-lawyer claims professional





Provide written feedback the research team uses to improve model behavior

Participate in onboarding office hours and calibration sessions

You're a Good Fit If You

Have 2+ years of professional experience handling complex, litigated, high-severity, or coverage-sensitive insurance claims

Have evaluated coverage issues and developed claim strategies involving multiple parties, layers, policies, or jurisdictions

Understand insurer duties, reservation-of-rights practices, litigation management, settlement authority, and escalation to internal or external counsel

Can distinguish an operational coverage position from formal legal advice and recognize when specialized legal review is required

Demonstrate exceptional written reasoning, defensible judgment, and high attention to detail

Are comfortable reviewing incomplete records and clearly separating facts, assumptions, open issues, and recommended next steps

Bonus Qualifications

CPCU, AIC, SCLA, ARM, or comparable insurance designation

Experience with excess casualty, qualified liability, directors and officers, cyber, environmental, construction-defect, or other complex lines

Experience managing mediations, trials, coverage disputes, or extra-contractual exposure

Home-office technical claims or claim-governance experience

Experience overseeing TPAs, independent adjusters, experts, or panel counsel

Role Highlights

Minimum 20 hours per week (ideally 40+)

Role starts immediately, applications reviewed on a rolling basis

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📌 Complex Claims Director - Insurance (Winnipeg)
🏢 Mercor
📍 Winnipeg