[Hiring] Insurance Specialist @Weekday AI

Role Description

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.

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.