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Remote Underwriting & Actuary Expert - Freelance

Remote / Online - Candidates ideally in
Oakville, Ontario, B8B, Canada
Listing for: Crossing Hurdles
Contract, Remote/Work from Home position
Listed on 2026-08-30
Job specializations:
  • Insurance
    Insurance Risk / Loss Control, Actuary, Underwriter, Insurance Analyst
Job Description & How to Apply Below
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.
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