Reinsurance AI Evaluation Specialist

About Open Train

Open Train is the hiring and contracting organization for this remote AI training opportunity. It helps specialists build careers in AI training and data labeling by creating a profile, finding relevant projects, and developing a durable record of their work.

• Remote contractor work through Open Train
• A profile designed to showcase specialized AI training experience
• Flexible part-time work with a minimum commitment of 20 hours per week

AI training is the human side of building modern artificial intelligence. Subject-matter experts create realistic examples, write reference answers, and evaluate model outputs so AI systems can reason more accurately and respond in ways that reflect real professional standards.

In this role, your insurance judgment will help shape how AI models understand risk transfer, contracts, financial responsibilities, and the operational relationships among insurance stakeholders.

• Contribute to cutting-edge generative AI evaluation
• Apply professional expertise to realistic insurance scenarios
• Work remotely with flexible scheduling around your availability

Open Train is seeking a Reinsurance and Program Business AI Evaluation Specialist to develop high-quality insurance reasoning data and evaluate AI-generated responses. The work covers treaty and facultative reinsurance, MGAs and MGUs, fronting arrangements, captives, Lloyd's structures, and alternative risk solutions.

You will use experienced reinsurance and program-business judgment to determine whether model outputs are structurally accurate, commercially sound, contractually logical, and realistic for the market.

• Expected commitment: at least 20 hours per week
• Preferred commitment: 40 or more hours per week
• Remote contractor opportunity
• Work available to eligible residents of the United States, Canada, the United Kingdom, Australia, New Zealand, Ireland, Malta, the Netherlands, Sweden, Denmark, Norway, Finland, Germany, Austria, and Belgium

You will create challenging, realistic scenarios and reference materials that reflect how reinsurance and program-business professionals analyze transactions, responsibilities, and risk structures. You will also review model responses and provide written feedback that supports more accurate AI behavior and evaluator calibration.

• Design scenarios involving treaty and facultative reinsurance, attachment and exhaustion, cessions, and recoverables
• Analyze bordereaux, delegated authority, program governance, fronting, captives, and risk participation
• Create structure comparisons, submission analyses, contract summaries, program reviews, and counter party assessments
• Write reference responses that reflect experienced reinsurance and program-business judgment
• Grade AI-generated responses for structural accuracy, contract logic, financial understanding, stakeholder responsibilities, and market realism
• Identify errors involving layers, limits, retentions, commissions, claims control, collateral, and counter party exposure
• Assess carrier, MGA, reinsurer, broker, cedent, and insured responsibilities
• Provide written feedback to improve model performance and support calibration

At least two years of professional experience in reinsurance, program business, delegated authority, fronting, captive insurance, or alternative risk transfer is required. You should be comfortable applying commercial judgment to complex insurance structures and explaining your reasoning in writing.

• Experience with treaty or facultative reinsurance, MGA or MGU programs, Lloyd's arrangements, captives, or fronted programs
• Ability to analyze risk transfer, layers, limits, retentions, recoverables, collateral, commissions, and claims responsibilities
• Ability to assess the economic and operational responsibilities of cedents, reinsurers, brokers, MGAs, fronting carriers, and insureds
• Strong written reasoning and attention to detail
• Ability to distinguish reinsurance decisions from direct underwriting and ordinary claim adjudication
• Ability to evaluate AI-generated insurance responses for contract logic, financial understanding, stakeholder roles, and market realism

Professional credentials and additional experience can strengthen your application. Relevant expertise may come from underwriting support, reinsurance broking, claims, program operations, delegated-authority oversight, or risk-sharing arrangements.

• CPCU, ARe, ARM, ACAS, FCAS, or a comparable designation
• Experience with…