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[Remote] AI Evaluator - Insurance Domain | Remote

Remote · Canada Full-time

Note: The job is a remote job and is open to candidates in USA. Crossing Hurdles is seeking Insurance Experts with a focus on underwriting and actuarial analysis. The role involves translating insurance workflows into structured tasks for AI systems and evaluating AI-generated outputs for accuracy and relevance.

Responsibilities

  • Translate real-world insurance workflows into structured tasks for AI systems
  • Evaluate AI-generated outputs for accuracy, logical reasoning, and business relevance
  • Work on use cases including underwriting, claims, actuarial analysis, and insurance operations
  • Identify gaps, edge cases, and failure modes in model performance
  • Clearly document assumptions, thought processes, and decisions
  • Provide structured feedback to improve AI performance and outputs

Skills

  • Minimum 5 years of professional experience in the insurance sector
  • Recent, hands-on experience as an Underwriter, Risk Specialist, or Actuary
  • Strong understanding of real-world insurance workflows and processes
  • Detail-oriented with the ability to evaluate nuanced, real-world scenarios
  • Comfortable working independently in a fast-paced, remote environment

Benefits

  • Work is primarily asynchronous, allowing for flexible scheduling
  • Minimal required meetings (typically optional office hours)
  • Seamless day-to-day collaboration and task management handled via Slack and internal platforms

Company Overview

  • Crossing Hurdles connects skilled professionals with opportunities across leading AI training platforms and high-growth companies. It was founded in 2022, and is headquartered in , with a workforce of 11-50 employees. Its website is https://www.crossinghurdles.com/.

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