or apply directly on League Inc.'s site. We never take the application ourselves.
Is this posting real?
- This role has been open
- 29 days League Inc.'s roles stay open a median of 24 days
- Reposted
- No
- Salary listed
- No 0% of League Inc.'s roles list one
- Ghost-job risk at League Inc.
- moderate 4 stale, 1 reposted of 18 open
- Hiring momentum
- 28 roles opened in the last 90 days ↑ up vs. the prior 90 days
- Last confirmed on the employer's board
- 2026-09-17
Measured from postings appearing on and disappearing from League Inc.'s own greenhouse board since 2026-08-03. Full hiring picture for League Inc..
About this role
As a Freelance Benefit SME at League, you will work remotely to validate and enhance the AI-driven Benefits Navigation Agent, ensuring it provides accurate and trustworthy guidance to members. Your responsibilities will include designing scenarios for evaluation, grading AI responses, and providing subject-matter expertise in areas such as benefits plan design and regulatory compliance. This role is ideal for benefits and insurance professionals seeking flexible, project-based work.
- benefits
- 1/5
- freshness
- 4/5
- career value
- 4/5
- role clarity
- 4/5
- pay transparency
- 0/5
Scored from the posting itself — how clearly the role is described, how much it says about pay and benefits, and how recently it was listed. Not a judgement of League Inc. as an employer.
What you need
- Meaningful hands-on experience in one or more of the specializations (benefits administration, plan design, payer or claims operations, benefits regulatory/compliance, member advocacy, or supplemental/point-solution expertise)
- Based in Canada or the United States, with working knowledge of the relevant benefits and insurance landscape
- Strong command of where accurate benefits guidance ends and regulated advice begins
- Reliable, detail-oriented, and dependable on deadline-driven async work
- Ability to access and operate within Google Workspace
Nice to have
- Prior experience with evaluation or validation of AI products, or structured content/quality review
- Familiarity with self-funded vs. fully-insured plan mechanics, accumulators, coordination of benefits, or claims adjudication
- Genuine curiosity and interest about the role of AI in benefits navigation
Worth weighing
- Contractor opportunity may not provide the same benefits as full-time employment
- Fully remote and async-friendly work may require strong self-motivation and time management skills
Summarised from League Inc.'s posting. Read the full original.
Listed by League Inc. on their greenhouse job board, last confirmed open on 2026-09-17. PitchMeAI is not the employer.
More roles at League Inc.
- Business Development RepresentativeToronto
- Freelance CliniciansCanada/US/UK
- Director, FP&AToronto
- Clinical Lead, Health SolutionsToronto, ON
- Security EngineerToronto, ON
- Clinical Lead, Health Solutions (United Kindom)United Kingdom
- Director, Platform Sales (US)United States
- Director, Platform SalesUnited States