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. 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