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 Robust 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 strong 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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📌 Insurance Risk Analyst (Manitoba)
🏢 Crossing Hurdles
📍 Manitoba