Policy Administrator

Crossing Hurdles; Canada; On-site; CAD 188,428 - 235,535; Part time

Job summary

Crossing Hurdles is seeking an Insurance Expert (Claims and Operations) for a freelance, remote, long-term engagement. The ideal candidate should possess strong experience in insurance operations and relevant qualifications, with at least 5-10 years in the field. Responsibilities include translating insurance workflows into structured tasks for AI and evaluating AI outputs for accuracy. This role offers flexible scheduling, with a commitment of a minimum of 10 hours per week. Compensation ranges from $100-125 per hour (USD).

Qualifications

• 5-10 years of relevant experience in claims management, underwriting, or insurance operations.
• Experience in claims adjudication, policy administration, or risk analysis (at least three).
• Strong analytical and problem-solving skills required.
• Excellent attention to detail and communication skills needed.

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

Underwriting

Risk Analysis

Analytical skills

Problem-solving

Attention to detail

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