Insurance SME - Underwriting Expert

Obsidian; San Francisco (CA); On-site; USD 180,000 - 240,000; Full time

Job summary

Cincinnatus LLC is placing an Insurance SME at a leading AI lab in San Francisco to help evaluate AI outputs and ground them in underwriting expertise.

You will design tasks, write scoring rubrics, and collaborate with researchers to ensure high‑quality training data for foundation AI models.

Applicants should have 8+ years in insurance, experience evaluating LLM outputs, and be able to work ~35 hours/week during weekdays.

Qualifications

• 8+ years of dedicated professional experience in insurance at a top-tier organization.
• Hands-on experience evaluating LLM/AI outputs against rubrics or structured scoring criteria.
• Demonstrable career progression in underwriting leadership.
• Ability to engage reliably for at least 35 hours/week during weekdays.
• Strong verbal and written communication and problem-solving skills.

Responsibilities

• Guide research and engineering teams to close knowledge gaps in underwriting, claims, and risk assessment reasoning.
• Design 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

Risk management

Claims evaluation

AI evaluation

Rubrics

Interpersonal skills

Communication

Job description

Join a leading AI lab's cutting-edge GenAI team to be at the core of the AI revolution, where your expertise fuels the development of the most advanced Large Language Models.

1. Overview

Join a leading AI lab's cutting-edge GenAI team and help build foundational AI models from the ground up. We're seeking talented Insurance subject-matter experts (SMEs) with deep domain expertise and hands-on experience evaluating AI model outputs against rubrics to bring rigor and real‑world underwriting judgment to our AI training data.

This is a W-2 employment position with Cincinnatus LLC, with the opportunity to be placed at a leading AI Lab as part of their extended workforce.

2. Key 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.

3. Core Qualifications

• 8+ years of dedicated professional experience in insurance (e.g., underwriting, claims, actuarial, risk management) at a recognized, top‑tier organization (e.g., AIG, Chubb, Allstate, Progressive, MetLife, Marsh McLennan, or equivalent).
• Prior hands‑on experience evaluating LLM/AI model outputs against rubrics or structured scoring criteria — mandatory; please describe this experience in your 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.

About Cincinnatus LLC: Cincinnatus LLC is an enterprise staffing company that partners with leading technology companies to source and employ highly skilled professionals for contingent and contract‑based opportunities. Cincinnatus serves as the employer of record for these engagements, providing W-2 employment, payroll, benefits, and compliance, while placing employees directly within client teams to work on high‑impact initiatives.

Equal Employment Opportunity: Cincinnatus is proud to be an Equal Employment Opportunity employer. We do not discriminate based upon race, religion, color, national origin, sex (including pregnancy, childbirth, reproductive health decisions, or related medical conditions), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, genetic information, political views or activity, or any other legally protected characteristic.