Insurance Expert for AI Model Evaluation

Serve as an insurance subject-matter expert embedded with a GenAI team to design insurance-related tasks, apply real-world underwriting and claims judgment, and evaluate large language model outputs against structured rubrics to improve model reasoning and accuracy.

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

• Minimum 8 years of dedicated professional experience in insurance, such as underwriting, claims, actuarial, or risk management, at a recognized, top tier organization, for example AIG, Chubb, Allstate, Progressive, MetLife, Marsh McLennan, or equivalent employers.
• Prior hands on experience evaluating LLM or AI model outputs against rubrics or structured scoring criteria, this is mandatory, please describe this experience in your application.
• Demonstrable career progression, for example Underwriter to Senior Underwriter to VP of Underwriting, or equivalent advancement.
• Ability to engage reliably for at least 35 hours per week during weekdays.
• Strong verbal and written communication skills, problem solving ability, and interpersonal skills needed to collaborate with technical and nontechnical teams.

• Employment type: hourly, W 2 employment through Cincinnatus LLC, serving as the employer of record and placing employees within a client AI lab team.
• Location: United States, placement at a leading AI lab as part of an extended workforce.
• Schedule commitment: must be able to work at least 35 hours per week on weekdays.

• Pay range: $60 to $80 per hour.
• W 2 payroll, benefits, and compliance administration are provided by the employer of record.

• Candidates should be available to work in the United States under W 2 employment terms provided by Cincinnatus LLC.
• To apply, submit your resume and a written description of your hands on experience evaluating LLM or AI model outputs against rubrics or structured scoring criteria, including specific examples where possible. Also include employer names and evidence of career progression, and confirm availability to work at least 35 hours per week on weekdays.
• An Equal Employment Opportunity employer statement: the employer provides equal opportunity and does not discriminate based on legally protected characteristics.