Freelance Benefit SME

About League

League is one of the fastest-growing technology companies in Canada and the leading healthcare experience platform. Getting healthcare is often the easy part — finishing it is where things fall apart: people book the appointment and skip the follow-up, fill the prescription and stop taking it, get the referral and never make the call. That gap costs health plans and health systems money, and it costs people their health.

League closes that gap — identifying what each person needs to do next, clearing what’s in their way, and getting it done, for the 70 million+ people whose care already runs through our platform. Health plans and health systems trust us to do this at scale. Organizations like Manulife, SCAN, Geisinger, and Medibank on the payer side, and Baptist and Shoppers Drug Mart on the provider side.

Position Summary:

League is building the infrastructure behind our Benefits Navigation Agent — the AI that helps members understand and use their health benefits — and we're growing our panel of expert reviewers. The through-line is domain judgment: the situational, real-world reasoning that determines the guidance of our agent gives members is accurate, complete, and trustworthy.

You'll help validate the rubrics we use to assess the agent's answers, grade responses against accuracy and coverage standards, and pressure-test the scenarios that keep benefits guidance correct and trustworthy. This is a great fit for benefits and insurance professionals who want flexible, remote work — and who want their expertise to shape a product while it's still being built.

The kind of work you might do:

Engagements vary, but could include:

• Scenario design and pressure-testing
• — building and stress-testing the member scenarios the agent is evaluated against, so the rubric reflects the questions members actually ask and the failure modes that matter most.
• AI agent evaluation
• — supporting the development and validation of rubrics, grading AI-generated benefits guidance against structured accuracy and coverage standards, flagging where the agent misstates coverage or oversteps into advice it shouldn't give, and providing written feedback on how responses can be improved.
• Subject-matter input
• — bringing a benefits, claims, or regulatory perspective to how we define correctness, coverage, and the hard-fail boundaries the agent must never cross.
• Specializations we're looking for: We're building a multidisciplinary panel. You don't need to cover all of these — we're looking for depth in one or more of the following areas:

What this means in practice:

• Use AI tools as part of your daily workflow to enhance productivity, problem-solving, and decision-making (e.g., drafting, analysis, coding, research, or process automation)
• Apply judgment and accountability when using AI by reviewing outputs for accuracy, bias, and quality before use
• Continuously learn and adapt as new AI tools and capabilities emerge, incorporating them into your ways of working
• Identify opportunities to improve how work gets done from personal productivity to team-level workflows by leveraging AI effectively
• Operate with strong data responsibility and security awareness
• , especially when working with sensitive or regulated information

How this scales by level:

Individual Contributors:

Use AI to improve personal productivity and quality of output

Senior ICs / Managers:

Integrate AI into team workflows and improve processes

Leaders:

Drive AI adoption at the organizational level and shape how work is done across teams

What we look for:

• Demonstrated experience using AI tools in a practical, responsible way
• Curiosity and openness to experimenting with new technologies
• Ability to balance efficiency with quality and sound judgment
• Our employees come from different backgrounds, and we celebrate those differences. We are looking for the best candidates for our open roles, but do not expect applicants to meet every qualification in order to be considered. If you are excited about what you could accomplish at League and believe you can add value to our team, we would love to hear from you.

We are committed to equal employment opportunity regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity or Veteran status

. If you are an individual in need of assistance at any time during our recruitment process, please contact us at recruitinginfo@league.com.

Our Application Process:

Applying to a role you love can be exhausting, and understanding the next steps can feel vague and uncertain. You have done the hard part of submitting your application; let's do ours by sharing potential next steps

You should receive a confirmation email after submitting your application.

A recruiter (not a computer) reviews all applications at League.

If we see alignment with League's needs, a recruiter will reach out to learn more about your goals. The recruiter will also share the team-specific interview process depending on the roles you are exploring.