# Complex Claims & Coverage Director

**Company:** [Weekday AI](null/companies/pxG9rDgnvZm2c86JUchT1j.md)
**Location:** Remote
**Workplace:** remote
**Employment type:** Contract
**Department:** AI Training

[Apply for this job](null/view/bd3aa4e3-2cb1-485a-b17b-97cee9ca76e0)

## Description

**This role is for one of our clients**

**Compensation: $80 per hour**

We are 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.

## Requirements

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, professional 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

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