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Freelance Benefit SME

Canada, UK, USA🌐 Remote💼 Contract🗓 2026-09-25 → 2026-09-26

Core

Validating rubrics, grading AI-generated benefits guidance, and pressure-testing scenarios to ensure accuracy and regulatory compliance for League's Benefits Navigation Agent.

Role type

Freelance Subject Matter Expert (Benefits/Insurance)

Builds

The infrastructure and evaluation framework for League's AI Benefits Navigation Agent.

Domain

Health insurance, benefits administration, and AI product validation.

Deliverable

Production ML models (via rubric validation and scenario design)

Required skills

Benefits plan design and administration, Payer/claims operations, Regulatory and compliance knowledge, Member navigation and advocacy, Supplemental health solutions expertise

Preferred skills

AI product evaluation experience, Self-funded vs fully-insured plan mechanics, Claims adjudication knowledge

Technologies

Google Workspace

Responsibilities

Design and stress-test member scenarios for AI evaluation, Grade AI responses against accuracy and coverage standards, Provide subject-matter input on regulatory boundaries and hard-fail conditions

Seniority

Individual Contributor (Freelance/Contractor)

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