Senior Insurance & Underwriting Evaluation Specialist

🔥 0 minutes ago

🗽 New York – Remote

🗽 New York – Remote

💵 $55 - $75 / hour

⏰ Full Time

🟠 Senior

📋 Underwriter

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24-MAG

WebsiteLinkedInAll Job Openings

2 - 10 employees

🤝 B2B

💼 Consulting

B2B • Consulting

24-MAG is a commercial strategy and execution firm that helps B2B organizations design and implement systems, workflows, and operating rhythms for sales, client management, and cross-functional projects. They focus on transforming scattered processes into aligned, measurable, and scalable commercial functions—covering pipeline structure, account management frameworks, and operational discipline for teams seeking efficient, intentional growth.

📋 Description

• 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