GenAI Insurance SME — Risk & Underwriting Evaluation

Obsidian; New York (NY); On-site; USD 140,000 - 220,000; Full time

Job summary

Cincinnatus LLC is seeking an Insurance Subject-Matter Expert to join a leading GenAI team, helping evaluate AI model outputs against real underwriting practice. You will guide research and engineering teams to close knowledge gaps in underwriting, claims, and risk assessment, and design tasks grounded in real-world underwriting.

The role requires 8+ years in insurance with hands-on rubric-based evaluation of AI outputs; ability to commit to 35 hours per week; W-2 employment with an extended

Qualifications

• 8+ years of professional insurance experience at top‑tier organizations.
• Hands‑on experience evaluating AI model outputs against rubrics or structured scoring criteria.
• Demonstrated 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 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

Insurance domain expertise

Experience evaluating AI outputs

Communication skills

Reliability for 35 hrs/wk

Job description

Cincinnatus LLC is seeking an Insurance Subject-Matter Expert to join a leading GenAI team, helping evaluate AI model outputs against real underwriting practice. You will guide research and engineering teams to close knowledge gaps in underwriting, claims, and risk assessment, and design tasks grounded in real-world underwriting.

The role requires 8+ years in insurance with hands-on rubric-based evaluation of AI outputs; ability to commit to 35 hours per week; W-2 employment with an extended