Insurance Risk Analyst

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

Job summary

Crossing Hurdles is seeking an Insurance Expert (Claims and Operations) to join their team. The role is remote and freelance, requiring a commitment of at least 10 hours per week. Responsibilities include translating insurance workflows for AI, evaluating AI outputs for accuracy, and analyzing claims data. The ideal candidate should have 5-10 years of experience in insurance operations or claims management, with strong analytical and communication skills. Salary ranges from $100 to $125 per hour.

Qualifications

• Strong experience in Insurance Operations, Claims Management, Underwriting, or Risk.
• Proven experience in claims adjudication, underwriting, policy administration, or risk analysis.
• 5-10 years of relevant experience, flexible for strong candidates.

Responsibilities

• Translate insurance workflows into structured tasks for AI systems.
• Evaluate AI-generated outputs for accuracy and logical reasoning.
• Work on claims review, underwriting analysis, and risk evaluation.

Skills

Insurance Operations

Claims Management

Underwriting

Risk Analysis

Job description

Overview

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 strong candidates)
• Strong analytical and problem-solving skills
• Excellent attention to detail and communication skills

Work Style and Expectations

• Work is primarily asynchronous, allowing for flexible 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