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About the job Remote | Senior Insurance & Underwriting Evaluation Specialist - $55-$75/hour
We are sharing a specialised full-time consulting opportunity for US-based insurance professionals with deep experience in underwriting, claims, actuarial analysis, risk management, and structured evaluation of AI-generated outputs.
This role supports a high-impact generative AI initiative focused on improving how advanced models reason through real-world insurance scenarios. Selected professionals will design rigorous domain-specific tasks, evaluate model outputs against structured criteria, develop scoring frameworks, and provide practical feedback grounded in senior-level underwriting, claims, and risk-assessment experience.
Key Responsibilities
Insurance Domain Guidance

• Guide research and engineering teams on underwriting, claims, actuarial analysis, policy interpretation, and risk-assessment concepts
• Identify gaps in model understanding across coverage decisions, loss evaluation, pricing, claims handling, and insurance operations
• Apply practical insurance judgment to complex scenarios involving policyholders, exposures, financial risk, and regulatory considerations
• Ensure insurance tasks reflect realistic professional decisions and industry standards

Insurance Task & Solution Development

• Design challenging, domain-relevant tasks grounded in real underwriting, claims, actuarial, or risk-management practice
• Write accurate, well-reasoned solutions covering insurance analysis and decision-making scenarios
• Develop problems requiring technical judgment, risk evaluation, policy interpretation, and assessment of competing considerations
• Ensure tasks are clear, internally consistent, and suitable for structured evaluation

AI Output Evaluation

• Evaluate AI-generated insurance responses against established rubrics and scoring criteria
• Assess correctness, professional judgment, reasoning quality, relevance, and practical applicability
• Compare alternative outputs and determine which response provides the stronger insurance analysis
• Identify factual errors, unsupported assumptions, weak risk reasoning, and incomplete conclusions
• Provide clear written feedback that supports improvements in model behaviour

Rubric Development & Quality Calibration

• Develop and refine evaluation guidelines for underwriting, claims, actuarial, and risk-management tasks
• Define scoring criteria covering technical accuracy, professional judgment, reasoning, and decision quality
• Participate in calibration activities with other insurance specialists
• Collaborate across teams to maintain consistency and accuracy throughout the training data

Ideal Profile
Strong candidates may have:

• At least 8 years of dedicated professional experience in insurance
• Senior-level expertise in underwriting, claims, actuarial work, risk management, or a related area
• Experience working within a recognised insurer, broker, consultancy, financial-services organisation, or comparable institution
• Prior hands-on experience evaluating LLM or AI-generated outputs using structured rubrics or scoring criteria
• Demonstrable career progression into senior, management, director, vice president, or comparable leadership responsibilities
• Strong professional judgment and the ability to assess complex insurance decisions
• Excellent written and verbal communication skills
• Reliable availability for at least 35 hours per week during weekdays

Educational Background

• A degree in insurance, actuarial science, finance, economics, mathematics, business administration, risk management, or a related field is highly relevant
• Graduate-level education in actuarial science, finance, business, analytics, or risk may be helpful
• Equivalent senior professional experience in underwriting, claims, or insurance operations may also be considered
• Professional credentials such as CPCU, ACAS, FCAS, ARM, AIC, or comparable qualifications may be valuable

Nice to Have

• Experience across property and casualty, life, health, commercial, specialty, or reinsurance markets
• Background in complex underwriting, claims investigation, pricing, reserving, or portfolio risk
• Experience creating structured scoring rubrics, evaluation guidelines, or quality frameworks
• Familiarity with model training, human-feedback workflows, annotation, or AI quality assurance
• Strong understanding of policy language, coverage interpretation, risk selection, and claims decision-making
• Experience reviewing underwriting files, claims assessments, actuarial analyses, or risk reports
• Previous collaboration with product, analytics, legal, compliance, research, or technical teams

Why This Opportunity

• Apply senior insurance expertise to an advanced generative AI initiative
• Influence how AI systems reason about underwriting, claims, and risk
• Design and assess challenging insurance problems grounded in practical industry experience
• Collaborate with technical teams and experienced insurance specialists
• Join a full-time remote engagement with competitive hourly compensation

Contract Details

• Full-time W-2 contingent employment arrangement
• Fully remote role available to candidates based in the United States
• Expected commitment of at least 35 hours per week during weekdays
• Competitive rates between $55-$75 per hour depending on expertise and project scope
• Prior experience evaluating AI or LLM outputs against structured rubrics is required
• Applicants should clearly describe relevant AI evaluation experience in their application
• Immediate availability is preferred
• Work may include onboarding, specialty calibration, task development, and ongoing quality review
• Project scope and duration may be adjusted according to programme requirements and performance

About the Platform
This opportunity is available through 24-MAG LLC. We connect experienced professionals with remote consulting opportunities across technical, evaluation, and project-based workstreams.
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