Insurance Specialist
Weekday AI (YC W21) · United States · 2 days ago
RemoteRemoteOTHR$60–$80/hrPart-time
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)
- Able 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