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
• Evaluate AI model outputs against structured rubrics and provide 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

Requirements
• 8+ years of professional experience in insurance at a top-tier organization such as AIG, Chubb, Allstate, Progressive, MetLife, or Marsh McLennan
• Prior hands-on experience evaluating LLM or AI model outputs against rubrics or structured scoring criteria is mandatory
• Demonstrable career progression in insurance such as Underwriter → Senior Underwriter → VP of Underwriting
• Ability to engage reliably for at least 35 hours per week during weekdays
• Strong verbal and written communication, problem-solving, and interpersonal skills

How to Apply
Click "Apply" to be taken to the Cincinnatus LLC application. This is a W-2 contingent role with the opportunity to be placed at a leading AI lab.