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

About OpenTrain

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

About AI Training Work

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

The Role

OpenTrain 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

What You'll Do

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 counterparty 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 counterparty exposure
• Assess carrier, MGA, reinsurer, broker, cedent, and insured responsibilities
• Provide written feedback to improve model performance and support calibration

Required Qualifications

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

Helpful Background

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 ceded or assumed reinsurance
• Experience with treaty wording, recoverables, claims, program audits, or bordereaux management
• Experience with captives, large deductibles, retrospective rating, or risk sharing

Schedule and Compensation

Successful completion of onboarding is compensated at a flat $800, with onboarding estimated at approximately 10 hours. After onboarding, the ongoing contractor rate is $80 per hour.

• Paid onboarding: $800 flat
• Estimated onboarding time: approximately 10 hours
• Ongoing rate: $80 per hour
• Part-time contractor schedule with 20 or more hours expected weekly
• English-language work

Why Work With OpenTrain

AI training gives experienced professionals a way to apply their expertise to the development of modern AI systems. OpenTrain helps you manage that work in one place, build a credible portfolio, discover projects aligned with your skills, and grow toward a long-term career in AI training and data labeling.

If you understand reinsurance and program business and can explain complex insurance reasoning clearly, your expertise can directly improve how AI systems handle specialized professional questions.

• Work from home with a computer and internet connection
• Apply specialized insurance knowledge to cutting-edge AI development
• Build a reusable OpenTrain profile and professional AI training portfolio
• Apply through OpenTrain in minutes