Underwriter | Remote

Underwriter - Remote Freelance AI Evaluation Placed by Crossing Hurdles | On behalf of a US AI Frontier Lab About the Role Crossing Hurdles is partnering with a leading US-based AI frontier lab to source experienced insurance professionals for a remote freelance engagement. The company is building out a specialized team of domain experts to evaluate and improve AI systems used in insurance operations. This is a paid, flexible, long-term opportunity designed for working professionals who want to contribute to AI development without leaving their field. What You Will Do Review and assess AI-generated outputs related to claims handling, coverage decisions, and operational workflows Identify errors, gaps, or misalignments in AI reasoning against real-world insurance standards Provide expert written feedback to help train and refine AI models Evaluate scenarios involving claims investigation, documentation, reserving, and resolution Flag compliance or procedural issues based on your professional experience Domain Focus Property and casualty claims operations Liability and subrogation processes Claims documentation and reserving Coverage interpretation and policy analysis Regulatory compliance in claims handling What We Are Looking For 5 or more years of experience in insurance claims or operations Background in roles such as Claims Manager, Claims Analyst, Insurance Operations Analyst, Subrogation Specialist, or similar CPCU, ARM, ACAS, or FCAS designation is a strong plus Solid understanding of claims lifecycle, coverage analysis, and industry best practices Strong written communication skills and ability to give structured, clear feedback Comfortable working independently in a remote, asynchronous environment Work Style and Expectations This is a remote, self-managed engagement. You will complete evaluation tasks on your own schedule within agreed weekly hour targets. No meetings-heavy workflow. Onboarding is fast, typically within 24 hours of acceptance. The company values quality of feedback over volume, so attention to detail and professional rigor matter here. Compensation Rate: $100-125/hr (USD) Payment: Via Deel, fortnightly Commitment: 15-20+ hours/week (minimum 10+ hours/week) Type: Long-term engagement, retainer opportunities for strong performers You May Be a Good Fit If You are an experienced claims professional looking to apply your expertise in a new way, want flexible remote work that fits around existing commitments, are curious about AI and how it is being developed for insurance use cases, and want to be paid competitively for your domain knowledge without taking on a full-time role change. To express interest, send your resume to Crossing Hurdles and we will be in touch to discuss next steps. No lengthy applications or interviews required.

The underwriter will review and assess AI-generated outputs related to insurance claims and provide expert feedback to improve AI models. They will also identify errors and compliance issues based on their professional experience.

Candidates should have at least 5 years of experience in insurance claims or operations, with a strong understanding of the claims lifecycle and industry best practices. Relevant designations such as CPCU or ARM are preferred.

Identified from the job description. Confirm important requirements above.

• Claims Handling
• Coverage Decisions
• Operational Workflows
• Compliance
• Claims Investigation
• Documentation
• Reserving
• Policy Analysis
• Regulatory Compliance
• Written Communication
• Attention to Detail
• AI Evaluation
• Insurance Standards
• Feedback
• Insurance Operations
• Subrogation

• Finance & Accounting
• Data & Analytics
• Consulting
• Science & Research

Minimum experience

5+ years

Posting language

English

Working hours

20 hours per week

Seniority

Executive

Application method

Direct apply is available