AI Evaluator - Insurance Domain | Remote

Crossing Hurdles; Canada; On-site; CAD 137,760 - 172,200; Part time

Job summary

Crossing Hurdles is seeking Insurance Experts (Underwriting & Actuary) for a remote freelance position. The role demands a minimum of 5 years in the insurance sector and includes responsibilities like translating workflows into tasks for AI, evaluating outputs, and ensuring effective collaboration. The position offers flexible scheduling with a commitment of at least 10 hours per week. Immediate start is required, with fast-track onboarding expected. The compensation ranges from $100 to $125 per hour, depending on experience.

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 underwriting, claims, and actuarial analysis use cases.

Skills

Experience in the insurance sector

Underwriting and Risk Analysis

Attention to detail

Independent work

Evaluating nuanced scenarios

Job description

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 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.