Overview
Underwriter | Remote Jobs in Canada at Crossing Hurdles
Title: Underwriter | Remote
Company: Crossing Hurdles
Location: Canada
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.
