Remote | Senior Insurance & Underwriting Evaluation Specialist

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.

• 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

• 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

• 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…