Jobs at League

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.

Own end-to-end management of League CONNECT and year-round community programs: event operations, digital demand generation, vendor and venue management, budget tracking, and member experience design. Lead programming (roundtables, thought leadership), cultivate executive relationships, and align cross-functional teams to drive engagement and pipeline. Blend large-scale event execution with membership-style community strategy and AI-enabled digital tactics.

Prospect enterprise healthcare accounts, research account-specific challenges, build targeted outreach sequences across email/LinkedIn/calls, create discovery meetings and early pipeline, support qualification alongside Account Directors, refine AI-driven outreach workflows, and maintain accurate Salesforce records.

Build and maintain internal security tooling, automation, and cloud-native services to improve secure software delivery, secrets and identity management, vulnerability detection, and runtime protection. Partner with Platform, Infrastructure, and Product teams to integrate security into CI/CD, Kubernetes, and AI-enabled workflows and support incident response and remediation.

Lead security architecture and technical direction across encryption/key management, IAM, cloud and application security, and AI/agentic systems. Partner with product and engineering teams to embed secure-by-default designs, mentor security engineers, advise on complex technical escalations, and translate technical risk for leadership and compliance stakeholders.

Lead enterprise platform and AI sales across healthcare segments, own end-to-end sales cycle and quota, build pipeline and C-level relationships, negotiate complex agreements, collaborate with Solution Engineering and Product Marketing, surface product feedback, improve buyer journeys, and ensure smooth handoffs to delivery teams.

The Senior Account-Based Marketing Manager at League will lead the ABX strategy for key markets, driving engagement and revenue through integrated marketing programs and collaboration with sales and content teams.

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.

Own and optimize demand generation to drive demos and pipeline. Design, execute, and A/B test integrated programs across paid search, paid social, SEO, email, content, and events. Manage marketing tech stack and attribution, analyze performance and unit economics, partner with Sales/Product/Revenue Ops, direct agencies, and apply AI tools to accelerate workflows and AEO strategies.