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 robust candidates)

Strong analytical and problem-solving skills

Excellent attention to detail and communication skills

Work Style and Expectations

Work is primarily asynchronous, allowing for versatile 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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📌 Policy Administrator (Manitoba)
🏢 Crossing Hurdles
📍 Manitoba