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Home Flexible Job Board Insurance Specialist

$60–80/hr 56d ago

Insurance Specialist

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Weekday AI

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Summary

The Insurance Specialist will partner with research and engineering teams to improve AI understanding of insurance concepts by designing domain-specific tasks. They will also evaluate AI-generated outputs against structured rubrics and provide detailed feedback to ensure accuracy and professional judgment.

Job Description

This role is for one of our clients

Compensation: $60-$80 per hour

Join a leading AI lab at the forefront of Generative AI and contribute to building the next generation of foundational AI models. We are seeking experienced Insurance Specialists with deep expertise in underwriting, claims, actuarial science, or risk management, along with hands-on experience evaluating AI model outputs against structured rubrics. In this role, you will help improve AI systems by bringing real-world insurance judgment and domain expertise into high-quality training and evaluation data.

This is a fully remote engagement requiring approximately 35+ hours per week during weekdays.

Key Responsibilities

  • 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.

Core Qualifications

  • 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 Qualifications

  • Experience designing evaluation rubrics, quality assurance frameworks, or assessment methodologies.
  • Familiarity with AI training, model evaluation, human-feedback workflows, or data annotation projects.
  • Expertise in multiple insurance disciplines, including commercial or personal lines, property and casualty, life and health, reinsurance, actuarial modeling, or enterprise risk management.

Equal Opportunity

We are committed to providing equal employment opportunities to all qualified applicants. Employment decisions are made without regard to legally protected characteristics, and reasonable accommodations are available throughout the application and engagement process upon request.

Contract & Payment Terms

  • Independent contractor engagement.
  • Fully remote with flexible working hours.
  • Projects may be extended, shortened, or concluded based on business requirements and individual performance.
  • Weekly payments are processed through supported payment platforms.
  • Applicants requiring H-1B or STEM OPT sponsorship are not eligible for this opportunity.

About the company

Weekday AI

Recruitment agency

Finding a great startup job should not feel like a second job.

Weekday AI brings the most exciting roles from premium YC and VC-backed startups into one place. Our team hand-picks every listing, so you skip the agency spam and the dead links and go straight to companies building things that matter.

Why people use Weekday AI?

Curated roles from premium YC and VC-backed startups
Fresh jobs every week, picked by humans
AI that helps you apply in minutes
Free to join

Your next role should come from a company you are proud to work at. We help you find it.
Browse live roles at jobs.weekday.works

Founded

2022

Company size

11-50 employees

Industry

Technology, Information and Internet

Org type

Privately Held

Apply Now

About the company

Weekday AI

Recruitment agency

Finding a great startup job should not feel like a second job.

Weekday AI brings the most exciting roles from premium YC and VC-backed startups into one place. Our team hand-picks every listing, so you skip the agency spam and the dead links and go straight to companies building things that matter.

Why people use Weekday AI?

Curated roles from premium YC and VC-backed startups
Fresh jobs every week, picked by humans
AI that helps you apply in minutes
Free to join

Your next role should come from a company you are proud to work at. We help you find it.
Browse live roles at jobs.weekday.works

Founded

2022

Company size

11-50 employees

Industry

Technology, Information and Internet

Org type

Privately Held

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