Remote Reinsurance AI Evaluation Specialist

OpenTrain AI; Northern (KY); Hybrid; USD 70,000 - 95,000; Part time

Benefits offered by this job

Paid onboarding

Remote work

Flexible schedule

OpenTrain portfolio

Job summary

OpenTrain seeks a Reinsurance and Program Business AI Evaluation Specialist to develop high-quality insurance reasoning data and evaluate AI-generated responses. You will work on treaty and facultative reinsurance, MGAs, MGUs, and alternative risk solutions, applying experienced judgment to determine structural accuracy and market realism.

The role offers remote contractor work with flexible scheduling around your availability, starting with onboarding and then ongoing at $80 per hour for at

Qualifications

• 2+ years in reinsurance, program business, delegated authority, fronting, captive insurance, or ART
• Experience with treaty or facultative reinsurance, MGA/MGU, Lloyd's arrangements
• Ability to analyze risk transfer structures, layers, limits, retentions and recoverables
• Strong written reasoning and attention to detail

Responsibilities

• Design and evaluate AI-generated insurance responses for contract logic and market realism
• Analyze treaty and facultative reinsurance, margins, and risk participation
• Create reference materials and scenarios reflecting reinsurance transactions
• Grade AI outputs for structural accuracy and financial understanding
• Provide feedback to improve model performance and calibration
• Identify errors in layering, attachments, and counterparty exposure

Skills

Reinsurance

Program business

Delegated authority

Fronting

Captives

Alternative risk transfer

Tools

Lloyd's structures

Job description

OpenTrain seeks a Reinsurance and Program Business AI Evaluation Specialist to develop high-quality insurance reasoning data and evaluate AI-generated responses. You will work on treaty and facultative reinsurance, MGAs, MGUs, and alternative risk solutions, applying experienced judgment to determine structural accuracy and market realism.

The role offers remote contractor work with flexible scheduling around your availability, starting with onboarding and then ongoing at $80 per hour for at