Insurance Specialist

Posted 2 Days Ago
Be an Early Applicant
Hiring Remotely in United States
Remote
60-80 Hourly
Senior level
Artificial Intelligence • HR Tech • Professional Services • Software
The Role
Provide insurance subject-matter expertise to improve generative AI models: design insurance tasks, create reference solutions, evaluate AI outputs with structured rubrics, refine scoring guidelines, and collaborate with research and engineering teams to produce high-quality training and evaluation data. Commitment of 35+ hours/week and proven senior insurance experience required.
Summary Generated by Built In

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.


RequirementsKey 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.

Skills Required

  • 8+ years professional experience in the insurance industry (underwriting, claims, actuarial science, or enterprise risk management)
  • Hands-on experience evaluating LLM or AI-generated outputs using structured rubrics or formal scoring frameworks
  • Proven career progression demonstrating increasing responsibility and subject-matter expertise
  • Ability to commit 35 or more hours per week during standard weekdays
  • Excellent verbal and written communication, analytical thinking, problem-solving, and collaboration skills
  • Independent contractor engagement (must be able to work as an independent contractor)
  • Applicants requiring H-1B or STEM OPT sponsorship are not eligible
  • Experience designing evaluation rubrics, quality assurance frameworks, or assessment methodologies
  • Familiarity with AI training, model evaluation, human-feedback workflows, or data annotation projects
  • Expertise across multiple insurance disciplines (commercial/personal lines, P&C, life and health, reinsurance, actuarial modeling, enterprise risk management)
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The Company
Year Founded: 2021

What We Do

Weekday is an AI-powered recruitment platform that helps startups hire top-tier engineering and product talent. By leveraging a massive database of white-collar professionals and advanced outreach tools, the company streamlines the hiring process through automated sourcing, AI-driven resume screening, and white-glove contingency services. Their mission is to modernize recruitment by enabling companies to discover and engage passive candidates efficiently, ensuring high-quality hires for critical roles.

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