Insurance Expert - Remote Contract Position
Listing checked September 22, 2026 · pay as published by AfterQuery
Overview
AfterQuery, a YC-backed startup, creates training content for AI systems that need real insurance judgment. As a contract Insurance Expert, you will write and review scenarios that push AI models through underwriting decisions, claims adjudication, policy reading, risk checks, compliance calls, and actuarial ideas. The work runs remote and asynchronous, with about 15 hours each week. You will partner with insurance and technical experts to raise question difficulty and keep every item accurate, educational, and tied to industry practice.
What You'll Do7
- 1Craft insurance questions and case studies that test AI models on underwriting analysis, claims adjudication, policy interpretation, risk assessment, regulatory compliance, and actuarial principles.
- 2Review model responses and validate each answer against insurance standards, industry best practices, and the facts in the prompt.
- 3Write detailed feedback that points out errors in coverage analysis, exclusion handling, claim decisions, or risk grading.
- 4Work with insurance specialists and technical team members to tune question difficulty and confirm each item teaches the right concept.
- 5Build scenarios from real insurance operations, including commercial, property and casualty, life and health, or claims workflows.
- 6Check source material for compliance issues and flag content that could misstate policy language or regulatory rules.
- 7Keep a consistent review process so questions remain clear, fair, and challenging for the model.
Requirements9
- 1Bachelor's degree in risk management, finance, business, or a related field, or equal professional experience.
- 2Hands-on work in insurance operations, underwriting, claims management, or risk assessment.
- 3Knowledge of multiple insurance products and how carriers, brokers, and regulators use them.
- 4Strong analytical skills and clear written and verbal communication.
- 5Close attention to detail when reading policy forms, claims files, or underwriting guidelines.
- 6Several years in the insurance industry, with work across property and casualty, life and health, commercial lines, or other diverse business areas.
- 7Experience with insurance publications, regulatory projects, or insurtech work.
- 8Professional designations such as CPCU, CLU, ChFC, ARM, or AINS.
- 9Familiarity with AI or technology-driven insurance applications.
Who Should Apply
The best fit is an insurance professional who has spent years inside underwriting, claims, or risk teams and can explain policy decisions in plain language. That person holds or can obtain an Insurance Producer License in Life, Health, or P&C and enjoys turning messy claim facts into clear review notes. The role suits someone who wants a flexible 15-hour week and can work without constant supervision. Candidates who only know insurance theory, or who cannot give precise written feedback on coverage and compliance, tend to score lower. Missing the requested license can also slow an application, so list it upfront if you have it.
Salary Insight
The listing sets pay at $60.00 to $100.00 per hour. That range matches senior insurance practitioners who can review underwriting, claims, or risk material with minimal ramp-up. The contract covers about 15 hours each week, and the source does not mention benefits, so treat the hourly rate as the main cash figure.
Pay and demand for Insurance & Risk Management roles
AggregatedTypical pay
$78/hour
This role
$60–$100/hr
Most Insurance & Risk Management roles pay $70–$80 per hour. This role's pay falls inside that range.
Based on 12 similar roles that publish pay · 2 publish only a top rate; those count at the rate they gave
Rates shown per hour. Yearly and monthly pay converted; one-time fees and non-USD pay are not included.
- Live similar roles
- 14
- Listed in last 30 days
- 10
- Remote
- 93%
Hiring most right now: Mercor (6) · AfterQuery (3) · SME Careers (2)
Most requested skills · share of roles
- arm36%
- cpcu36%
- ains36%
- reinsurance36%
Figures from Insurance & Risk Management roles live on NearSkill when this page loaded. A role can close before you apply, so check the listing itself.
Compare your resume against these rolesLocation
Compensation
$60–100/hr
Required Skills
Application Tip
Lead with the requested Insurance Producer License (Life, Health, or P&C) and name your strongest lines, such as property and casualty or life and health. Pair that with one short example of an underwriting or claims case you reviewed, the issue you caught, and the outcome you recommended. Specific case detail shows the analytical and written judgment the reviewers need.
See NearSkill jobs more often in your search
Application & verification flow
1Instant rubric match
Your resume is scanned against this role’s requirements to check qualification fit.
2Screened before the employer sees it
Only profiles that clear screening are passed on.
3Outcome by email
We notify you at the address on your resume once the screening is reviewed.
Similar open positions
Explore active roles that match your skills and interests.
SME Careers
VerifiedInsurance Expert for AI Training Content (Remote)
This remote, hourly contractor role places you as an Insurance Expert dedicated to AI-driven training content. You review AI-generated insurance responses and craft expert material that clarifies policy interpretation, coverage analysis, and risk assessment. You’ll assess step-by-step reasoning for accuracy and regulatory awareness, delivering precise explanations and model solutions. Your work fuels training data for major AI systems and supports content across lines like P&C, auto, and homeowners.
Mercor
VerifiedInsurance Expert - AI Lab Project (Remote)
Mercor partners with a leading AI lab on a project that turns real insurance work into training material for AI systems. You will apply your own practice in underwriting, claims, actuarial analysis, or a related specialty to write realistic scenarios and assess model outputs. The engagement is remote and paid by the hour, and you can focus on the area where your expertise runs deepest.
Mercor
VerifiedInsurance Underwriting Specialist (Remote)
Mercor partners with a frontier AI lab to improve how large models handle insurance reasoning. The team needs underwriting specialists to create realistic risk scenarios and judge model answers against industry standards. You will shape training data around risk selection, policy provisions, pricing, and coverage calls. Underwriters from life, health, property, casualty, commercial, personal, specialty, marine, surety, and reinsurance backgrounds can apply. Work happens remote on an hourly basis.
Mercor
VerifiedInsurance Domain Expert
Insurance and actuarial professionals with deep practice experience will shape how frontier AI models reason about real insurance work. You will review model outputs and insurance knowledge tasks for professional accuracy, write the instruction specs and golden answers that define correctness, and design benchmarks that track model progress. The position is full-time W-2 employment with Cincinnatus LLC, with placement inside a leading AI lab's research and program management teams. Work is hybrid in the Bay Area, California, with on-site presence required multiple days each week. The role is not remote.
AfterQuery
VerifiedInsurance Policy Analyst - Remote Contract
AfterQuery, a Y Combinator-backed research lab, needs an Insurance Policy Analyst for a remote contract project. You will review policy language, coverage forms, endorsements, and exclusions across several lines of business. The work runs on an asynchronous schedule over the next two to three weeks, with 10 to 20 hours per week assigned on a project basis. Your analysis will cover coverage determinations, policy comparisons, gap assessments, and compliance with filing and regulatory rules. Expect a part-time schedule that fits alongside other commitments.
Mercor
VerifiedInsurance Experts
We're looking for senior insurance professionals to help train AI systems that operate in the high-stakes world of Fortune 500 enterprise insurance and risk management. You'll design realistic scenarios, craft reference answers, and build scoring rubrics that reflect how experienced underwriters, claims leaders, and actuaries actually think. This is a remote, hourly role with flexibility to apply your domain expertise to AI evaluation work.