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