Senior Insurance Specialist for AI Evaluation (Remote)

Weekday AI; United States; Remote; USD 83,000 - 110,000; Full time

Benefits offered by this job

Remote work

Job summary

Weekday AI is seeking an experienced Insurance Specialist to join our remote team and help train and evaluate AI models with insurance domain expertise. You will design insurance tasks, assess outputs against rubrics, and provide detailed feedback to improve AI judgment in underwriting, claims, and risk management.

The role is fully remote, requires 35+ hours per week, and offers hourly compensation of 60–80 USD. Prior leadership progression and strong communication are a plus.

Qualifications

• 8+ years of professional experience in the insurance industry.
• Hands-on experience evaluating AI outputs with structured rubrics.
• Clear career progression in underwriting or risk management.
• Ability to commit 35+ hours per week.
• Strong verbal and written communication, analytical thinking.

Responsibilities

• Partner with research and engineering 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.

Skills

Insurance underwriting

Claims processing

Actuarial science

Enterprise risk management

AI evaluation rubrics

Communication skills

Domain expertise

Leadership progression

Job description

Weekday AI is seeking an experienced Insurance Specialist to join our remote team and help train and evaluate AI models with insurance domain expertise. You will design insurance tasks, assess outputs against rubrics, and provide detailed feedback to improve AI judgment in underwriting, claims, and risk management.

The role is fully remote, requires 35+ hours per week, and offers hourly compensation of 60–80 USD. Prior leadership progression and strong communication are a plus.