Insurance Operations Analyst

Crossing Hurdles; Canada; On-site; CAD 187,940 - 234,925; Part time

Job summary

Crossing Hurdles in Canada is seeking an Insurance Operations Analyst (Claims and Operations) for a freelance role. You will translate insurance workflows into structured tasks for AI, evaluate outputs for accuracy, and work on use cases in underwriting and claims. The candidate must have a minimum of 5 years' experience in the insurance sector and be comfortable working independently in a fast-paced remote environment. Competitive hourly compensation between $100 and $125 is offered.

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.

Responsibilities

• Translate real-world insurance workflows into structured tasks for AI systems.
• Evaluate AI-generated outputs for accuracy and relevance.
• Work on use cases including underwriting, claims, and actuarial analysis.

Skills

Professional experience in the insurance sector

Experience as an Underwriter, Risk Specialist, or Actuary

Detail-oriented evaluation of real-world scenarios

Ability to work independently in a remote environment

Experience with asynchronous work and Slack

Job description

Role: Insurance Operations Analyst (Claims and Operations)

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 flexible 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.