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About the Role:

  • Build and validate the rubrics used to assess the AI agent's answers.
  • Grade AI-generated benefits guidance against accuracy and coverage standards.
  • Pressure-test member scenarios to ensure the agent's guidance is trustworthy.

What You'll Do:

  • Design and stress-test member scenarios that the agent is evaluated against.
  • Provide written feedback on how responses can be improved.
  • Bring a benefits, claims, or regulatory perspective to define correctness.

What We're Looking For:

  • Meaningful hands-on experience in benefits administration, plan design, or claims operations.
  • Strong command of where accurate benefits guidance ends and regulated advice begins.
  • Reliable, detail-oriented, and dependable on deadline-driven async work.

Engagement Details:

  • Fully remote and async-friendly.
  • Project-based with flexible hours.
  • Structured onboarding and calibration provided.

League

League is a healthcare experience platform that closes the gap between people and their health by identifying what each person needs to do next and getting it done. It is one of the fastest-growing technology companies in Canada, serving 70 million+ people, and fosters an AI-native, flexible, and remote-friendly culture.

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