Policy Processing Specialist

Crossing Hurdles; Canada; On-site; CAD 188,350 - 235,438; Part time

Job summary

Crossing Hurdles is looking for an Insurance Expert (Claims and Operations) for a freelance, remote opportunity. The ideal candidate will translate insurance workflows into structured tasks for AI systems and evaluate outcomes for accuracy. Candidates should have strong experience in insurance operations, with a focus on claims management, underwriting, or risk analysis, preferably with 5-10 years of experience. This role allows for asynchronous work with minimal meetings, enabling proactive and flexible engagement.

Qualifications

• Strong experience in Insurance Operations, Claims Management, Underwriting, or Risk.
• Proven experience in claims adjudication, underwriting, and policy administration.
• 5-10 years of relevant experience, flexible for strong candidates.
• Strong analytical and problem-solving skills.
• Excellent attention to detail and communication skills.

Responsibilities

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

Skills

Insurance Operations

Claims Management

Underwriting

Risk Analysis

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