Senior Insurance & Underwriting Evaluation Specialist

This is a fully remote position, open to applicants in New York.

📋 Description

• Provide guidance to research and engineering teams on topics such as underwriting, claims, actuarial analysis, policy interpretation, and concepts of risk assessment.

• Identify deficiencies in model comprehension regarding coverage decisions, loss assessments, pricing, claims processing, and insurance operations.

• Utilize practical insurance judgment in complex situations involving policyholders, exposures, financial risk, and regulatory matters.

• Ensure that insurance-related tasks mirror realistic professional decisions and adhere to industry standards.

• Create challenging, domain-relevant tasks based on real practices in underwriting, claims, actuarial work, or risk management.

• Produce precise and well-reasoned solutions that address insurance analysis and decision-making scenarios.

• Develop problems that necessitate technical judgment, risk evaluation, policy interpretation, and assessment of competing factors.

• Ensure that tasks are clear, internally consistent, and appropriate for structured evaluation.

• Evaluate AI-generated insurance responses using established rubrics and scoring criteria.

• Assess the accuracy, professional judgment, reasoning quality, relevance, and practical applicability of responses.

• Compare different outputs to determine which provides a more robust insurance analysis.

• Identify factual inaccuracies, unsupported assumptions, flawed risk reasoning, and incomplete conclusions.

• Provide clear written feedback that facilitates improvements in model behavior.

• Develop and refine evaluation guidelines for underwriting, claims, actuarial, and risk management tasks.

• Define scoring criteria that encompass technical accuracy, professional judgment, reasoning, and decision quality.

• Engage in calibration activities alongside other insurance specialists.

• Collaborate across teams to ensure consistency and accuracy throughout the training data.

⛳️ Requirements

• Must be a US-based insurance professional.

• A minimum of 8 years of dedicated professional experience in the insurance field.

• Senior-level expertise in underwriting, claims, actuarial work, risk management, or a related domain.

• Experience with a recognized insurer, broker, consultancy, financial services organization, or similar institution.

• Prior hands-on experience evaluating LLM or AI-generated outputs using structured rubrics or scoring criteria.

• Demonstrated career progression into senior, management, director, vice president, or similar leadership roles.

• Strong professional judgment with the capacity to assess complex insurance decisions.

• Excellent written and verbal communication skills are required.

• Reliable availability for a minimum of 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 advantageous.

• Equivalent senior professional experience in underwriting, claims, or insurance operations may also be considered.

• Professional credentials such as CPCU, ACAS, FCAS, ARM, AIC, or similar qualifications may be beneficial.

• Experience across property and casualty, life, health, commercial, specialty, or reinsurance markets.

• Background in complex underwriting, claims investigation, pricing, reserving, or portfolio risk.

• Experience in 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 in 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 mandatory.

🏝️ Benefits

• Full-time W-2 contingent employment arrangement.

• Fully remote position.

• Competitive hourly rates ranging from $55 to $75, depending on expertise and project scope.

• Expected commitment of at least 35 hours per week during weekdays.

• Immediate availability is preferred.

• Opportunities for onboarding, specialty calibration, task development, and ongoing quality review.