Insurance Compliance Analyst

Crossing Hurdles; Canada; On-site; CAD 187,556 - 234,445; Part time

Job summary

Crossing Hurdles is seeking an Insurance Expert (Claims and Operations) for a freelance, remote position in Canada. This role requires 5-10 years of relevant experience in insurance operations and claims management. Responsibilities include translating workflows into AI tasks, evaluating outputs for accuracy, and analyzing claims data. The ideal candidate will have strong analytical skills and the ability to document processes clearly, with minimal required meetings. The expected commitment is a minimum of 10 hours per week.

Qualifications

• 5-10 years of relevant experience in Insurance Operations, Claims Management, or Risk.
• Proven experience in at least three areas: claims adjudication, underwriting, policy administration, subrogation, or risk analysis.
• Strong analytical and problem-solving skills with excellent attention to detail.

Responsibilities

• Translate real-world Insurance workflows into structured tasks for AI systems.
• Evaluate AI-generated outputs for accuracy and logical reasoning.
• Analyze claims data and policy documents to identify trends and risks.

Skills

Insurance Operations

Claims Management

Analytical skills

Communication skills

Job description

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