Weekday (YC W21)

Complex Claims & Coverage Director

Weekday (YC W21)  •  $80/hr  •  United States (Remote)  •  17 hours ago
Apply
AI can make mistakes so check important info. Chat history is never stored.

Job 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.

Weekday (YC W21)

About Weekday (YC W21)

AI recruiter that runs outbound sourcing campaigns to find top talent. At Weekday, we have built the most accurate database of talent (250mn+ people in US & India with contact data), we run outbound campaigns to identify top talent for any role you might be hiring for. We generate the highest response rates (30-40%) on our campaigns making sourcing talent as easy as making a job posting. We are backed by Y-Combinator and were also ranked #1 on Product Hunt.

Industry
Consulting & Advisory
Company Size
51-200 employees
Headquarters
San Fransisco, CA
Year Founded
2021
Social Media