Underwriting Expert | Remote

Crossing Hurdles; Canada; On-site; CAD 188,401 - 235,502; Part time

Job summary

Crossing Hurdles is seeking Insurance Experts to translate insurance workflows into tasks for AI systems and evaluate AI outputs. Candidates should have at least 5 years of experience in the insurance field and recent roles as Underwriters or Actuaries. The position is freelance/contractor and remote, offering flexible scheduling with a commitment of 10+ hours per week. Onboarding is required within 24 hours of an offer, facilitating immediate engagement.

Qualifications

• Minimum 5 years of professional experience in the insurance sector.
• Recent, hands-on experience as an Underwriter, Risk Specialist, or Actuary.
• Comfortable working independently in a fast-paced, remote environment.

Responsibilities

• Translate real-world insurance workflows into structured tasks for AI systems.
• Evaluate AI-generated outputs for accuracy and business relevance.
• Provide structured feedback to improve AI performance and outputs.

Skills

Detail-oriented

Understanding of insurance workflows

Ability to evaluate scenarios

Independent work skills

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 hoursof receiving an offer.