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Weekday AI

Insurance Specialist

RemoteUnited States only
Published
Experience
Lead
Employment
Contract
$60–$80/hr
Check eligibility

Open to US only. Set where you work from to check your eligibility.

No BS summary

Experienced insurance specialist with 8+ years in underwriting, claims, actuarial science, or risk management. Must have hands-on experience evaluating LLM or AI outputs with structured rubrics and be able to commit 35+ weekday hours. H-1B or STEM OPT sponsorship candidates are not eligible.

What you'll do

  • Partner with research and engineering teams to improve AI understanding of insurance concepts, including underwriting, claims processing, risk assessment, and policy evaluation.
  • Design realistic, domain-specific insurance tasks and develop accurate, well-reasoned reference solutions based on industry best practices.
  • Evaluate AI-generated outputs against structured scoring rubrics, providing detailed written feedback on accuracy, reasoning, and professional judgment.
  • Develop, refine, and maintain evaluation guidelines and scoring criteria tailored to insurance-related tasks.
  • Collaborate with fellow subject-matter experts to ensure consistency, accuracy, and quality across AI training and evaluation datasets.

What they require

  • 8+ years of professional experience in the insurance industry, including areas such as underwriting, claims, actuarial science, or enterprise risk management within a leading insurance organization.
  • Demonstrated hands-on experience evaluating LLM or AI-generated outputs using structured rubrics or formal scoring frameworks.
  • Candidates should clearly describe this experience as part of their application.
  • Proven career progression demonstrating increasing responsibility and subject-matter expertise (for example, Underwriter → Senior Underwriter → Underwriting Manager or similar leadership progression).
  • Ability to commit reliably to 35 or more hours per week during standard weekdays.
  • Excellent verbal and written communication skills, analytical thinking, problem-solving ability, and collaboration skills.
  • Preferred: Experience designing evaluation rubrics, quality assurance frameworks, or assessment methodologies.
  • Preferred: Familiarity with AI training, model evaluation, human-feedback workflows, or data annotation projects.
  • Preferred: Expertise in multiple insurance disciplines, including commercial or personal lines, property and casualty, life and health, reinsurance, actuarial modeling, or enterprise risk management.
  • Applicants requiring H-1B or STEM OPT sponsorship are not eligible for this opportunity.

Benefits

  • Fully remote with flexible working hours.
  • Weekly payments are processed through supported payment platforms.
  • Reasonable accommodations are available throughout the application and engagement process upon request.

Weekday AI is a Y Combinator-backed startup transforming the hiring landscape with outreach tools and a database of white-collar talent, delivering recruitment solutions.

RecruitmentStartup

Details

Visa sponsorshipNo
$60–$80/hr