Jobs at League

Lead post-sales value realization by turning pre-sales ROI commitments into measurable outcomes. Build measurement frameworks, track KPIs, run executive value reviews, identify expansion signals, create reusable value playbooks, and feed outcome data into product and solution design to support renewals and growth.

Create and scale GTM and sales assets (decks, one-pagers, battlecards), use AI to accelerate content production, maintain the field asset library, translate portfolio messaging for audiences and segments, localize and tailor content for deals and campaigns, run PMM intake and triage, and partner with solutions, sales engineering, and ops to ensure field-ready launches and accurate, up-to-date materials while complying with security and information access policies.

Freelance benefits experts review and evaluate an AI benefits-navigation agent. Responsibilities include designing scenarios, validating evaluation rubrics, grading generated guidance for accuracy and coverage, identifying regulatory or advice-boundary issues, and providing written improvement feedback. Engagements are remote, asynchronous, flexible, and project-based, with opportunities for recurring work. Candidates should have hands-on benefits, claims, regulatory, advocacy, or supplemental health expertise in Canada or the United States.

The Principal of Solution Engineering leads pre-sales efforts, designs digital healthcare experiences using League's platform, and collaborates across teams to deliver AI-driven solutions while ensuring compliance with security policies.

Builds a roster of licensed clinicians for flexible, remote, project-based engagements supporting digital health products. Work may include evaluating AI-generated health responses, developing clinical rubrics, reviewing care pathways and medical content, validating alignment with evidence and standards of care, and providing expert feedback on safety and utility. Candidates need an active Canadian or U.S. clinical license, hands-on patient care experience, strong scope-of-practice judgment, reliability, deadline discipline, and Google Workspace proficiency.