Weekday 1

Complex Claims & Coverage Director

Germany remote Mid Salary not listed
remote Mid level Technology & IT Curated
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About the role

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.
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Interview prep

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Mid
Technology & IT Complex Claims Coverage Director Technology Mid level

Likely questions

  1. Tell us about work you have done that is close to the Complex Claims & Coverage Director role.
  2. How would you approach your first 30 days at Weekday 1?
  3. Which of Complex, Claims and Coverage have you used recently, and what did it help you achieve?
  4. Describe a time you solved a problem without waiting to be told exactly what to do.
  5. How do you stay organised and communicate clearly when working remotely?

Prepare before the call

  • A recent example that proves your experience with Complex, Claims and Coverage.
  • One short story with a problem, your action, and the result.
  • Two examples that show the strengths listed on your CV.
  • A clear reason why this role and company interest you.
  • Your availability, preferred work style, and salary expectations.

Ask them

  • What would success look like in the first 90 days?
  • What are the main problems this hire should help solve?
  • How does the team give feedback and measure good work?
  • What does a normal working week look like for this role?
Practice line

I am interested in the Complex Claims & Coverage Director role because I can bring practical experience in Complex, Claims and Coverage, learn the team quickly, and contribute to the outcomes Weekday 1 needs from this hire.

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