Role: Insurance Experts (Underwriting & Actuary)

Engagement Type: Freelance/ 1099 Contractor, Remote

Compensation: $100–$125 per hour

Commitment: Minimum 10+ hours/week (Ideally 15–20 hours, depend upon interest and availability)

Start: Immediate | 24-hour fast-track onboarding required

Key Responsibilities

- Translate real-world insurance workflows into structured tasks for AI systems
- Evaluate AI-generated outputs for accuracy, logical reasoning, and business relevance
- Work on use cases including underwriting, claims, actuarial analysis, and insurance operations
- Identify gaps, edge cases, and failure modes in model performance
- Clearly document assumptions, thought processes, and decisions
- Provide structured feedback to improve AI performance and outputs

Required Qualifications

- Minimum 5 years of professional experience in the insurance sector.
- Recent,



hands-on experience as an Underwriter, Risk Specialist, or Actuary.
- Strong understanding of real-world insurance workflows and processes
- Detail-oriented with the ability to evaluate nuanced, real-world scenarios
- Comfortable working independently in a fast-paced, remote environment
- Work is primarily asynchronous, allowing for adaptable scheduling
- Minimal required meetings (typically optional office hours)
- Seamless day-to-day collaboration and task management handled via Slack and internal platforms.
- Candidates must be prepared to complete the onboarding process and initiate communication with the project team within 24 hours of receiving an offer.

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📌 Insurance Expert (Actuarial & Underwriting) | Remote (Canada)
🏢 Crossing Hurdles
📍 Canada