Overview

Role: Insurance Expert (Claims and Operations) Engagement Type: Freelance, Remote, Long-Term Compensation: $100-125/hour (USD) Commitment: Minimum 10+ hours/week (20+ hours/week preferred) Start: Immediate | Fast onboarding within ~24 hours Key Responsibilities

Translate real-world Insurance workflows into structured tasks for AI systems Evaluate AI-generated outputs for accuracy, logical reasoning, and domain correctness Work on use cases including claims review, underwriting analysis, policy administration, and risk evaluation Analyze claims data, policy documents, and risk reports to identify trends, risks, and opportunities Clearly document assumptions, thought processes, and decisions Provide feedback to improve AI performance and outputs Required Qualifications

Strong experience in Insurance Operations, Claims Management, Underwriting,



or Risk Proven experience in claims adjudication, underwriting, policy administration, subrogation, risk analysis (at least three of these) 5-10 years of relevant experience (flexible for solid candidates) Strong analytical and problem-solving skills Excellent attention to detail and communication skills Work Style and Expectations

Work is primarily asynchronous, allowing for flexible scheduling Minimal required meetings (typically optional office hours 1-2x per week) Day-to-day collaboration happens via Slack and internal tools Candidates are expected to engage consistently and proactively communicate progress

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📌 Risk Management and Claims Specialist (Winnipeg)
🏢 Crossing Hurdles
📍 Winnipeg