Senior Insurance & Underwriting Evaluation Specialist
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Job Description
Senior insurance specialist evaluating AI-generated outputs for underwriting, claims, actuarial, and risk decisions. Designing domain-specific tasks and scoring frameworks for a generative AI initiative.
Responsibilities:
- 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
- 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
- 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
- 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
Requirements:
- US-based insurance professional
- 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 ability to assess complex insurance decisions
- Excellent written and verbal communication skills
- Reliable availability for at least 35 hours per week during weekdays
- 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
- 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
- Prior experience evaluating AI or LLM outputs against structured rubrics is required
Benefits:
- Full-time W-2 contingent employment arrangement
- Fully remote role
- Competitive rates between $55–$75 per hour depending on expertise and project scope
- Expected commitment of at least 35 hours per week during weekdays
- Immediate availability preferred
- Onboarding, specialty calibration, task development, and ongoing quality review opportunities
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