Title: Insurance Specialist

Pay Rate: $100/hr

Hours: 20–40/week, flexible schedule (Pick your own hours!)

Location: Remote

Summary:

We are seeking experienced Insurance Specialists to support the development and evaluation of AI systems focused on real-world insurance workflows. In this role, you will apply your expertise in underwriting, claims, and risk analysis to evaluate AI-generated outputs and help model how insurance decisions are made in practice.

This is a unique opportunity to work at the intersection of insurance and emerging technology, translating complex risk and coverage decisions into structured frameworks that improve AI reasoning and performance. The ideal candidate is analytical, detail-oriented, and comfortable applying judgment in nuanced scenarios.

What You’ll Do:

· Evaluate AI-generated insurance outputs for accuracy, consistency, and completeness

· Translate underwriting, claims, and risk workflows into structured tasks for AI systems

· Analyze risk profiles, coverage decisions, and policy details

· Provide clear, well-reasoned explanations behind underwriting and claims decisions

· Support development of AI models by defining strong insurance judgment and best practices

· Provide feedback to improve AI performance and decision-making capabilities

What You Bring:

· 5–8+ years of experience in insurance (underwriting, claims, actuarial, or related fields)

· Strong understanding of risk assessment, coverage analysis, and policy structures

· Experience making or supporting underwriting or claims decisions

· Strong analytical and problem-solving skills

· Ability to clearly communicate complex decisions and reasoning

· High attention to detail and ability to evaluate edge cases

Bonus Points If You Have:

· Professional certifications such as CPCU or similar

· Experience with regulatory or compliance considerations in insurance

· Exposure to actuarial analysis, reserving, or loss estimation

· Interest in AI, data systems, or emerging technologies

Domain Focus:

Underwriting & Risk Selection

· Risk assessment and selection

· Policy pricing and guideline application

Coverage & Policy Analysis

· Coverage interpretation and policy structuring

· Regulatory and compliance considerations

Claims & Adjudication

· Claims intake, investigation, and resolution

· Subrogation and recovery processes

Loss & Risk Analysis

· Loss estimation and reserving

· Portfolio and exposure analysis

TCWGlobal is an equal opportunity employer. We do not discriminate based on age, ethnicity, gender, nationality, religious belief, or sexual orientation.

It is unlawful in Massachusetts to require or administer a lie detector test as a condition of employment or continued employment. An employer who violates this law shall be subject to criminal penalties and civil liability.

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