AI GenAI Insurance Underwriter & Model Evaluator

Obsidian; New York (NY); Remote; USD 120,000 - 180,000; Full time

Job summary

Obsidian is seeking Insurance domain SMEs to join a cutting-edge AI training program. You will evaluate AI model outputs against real underwriting practice and rubrics, guiding research and engineering teams to close knowledge gaps in underwriting, claims, and risk assessment.

The role requires 8+ years in insurance at a top-tier firm and hands-on experience with AI model evaluation. Strong communication and problem-solving skills are essential for success in this W-2 position with Cincinnatus

Qualifications

• 8+ years of professional experience in insurance at a top-tier organization (e.g., AIG, Chubb, Allstate, Progressive, MetLife, Marsh McLennan, or equivalent).
• Hands-on experience evaluating LLM/AI model outputs against rubrics or structured scoring criteria - mandatory; describe this in the application.
• Demonstrable career progression (e.g., Underwriter -> Senior Underwriter -> VP of Underwriting).
• Ability to engage reliably for at least 35 hours/week during weekdays.
• Verbal and written communication skills, problem-solving skills, and interpersonal skills.

Responsibilities

• Guide research and engineering teams to close knowledge gaps in underwriting, claims, and risk-assessment reasoning.
• Design challenging, domain-relevant insurance tasks and write accurate, well-reasoned solutions grounded in real underwriting/claims practice.
• Evaluate AI model outputs against structured rubrics and provide clear, written feedback on correctness, judgment, and reasoning quality.
• Develop and refine evaluation guidelines and scoring rubrics specific to insurance tasks.
• Collaborate with other subject matter experts to ensure consistency and accuracy in training data.

Skills

Underwriting

Claims

Actuarial

Risk management

Communication

Job description

Obsidian is seeking Insurance domain SMEs to join a cutting-edge AI training program. You will evaluate AI model outputs against real underwriting practice and rubrics, guiding research and engineering teams to close knowledge gaps in underwriting, claims, and risk assessment.

The role requires 8+ years in insurance at a top-tier firm and hands-on experience with AI model evaluation. Strong communication and problem-solving skills are essential for success in this W-2 position with Cincinnatus