Business Development Representative

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: This is a build-your-craft role at the front of League's enterprise motion. You will work alongside two to three Account Directors, prospecting into their assigned book of business as the first point of contact between League and healthcare executives owning digital, member experience, AI initiatives, and innovation across North America. Your core responsibility is conducting deep account research to map League's value proposition to real organizational challenges, then deploying agentic outreach sequences across email, LinkedIn, and direct calls to create discovery meetings and pipelines. League is an AI-first company and this role is built that way. You will have the tools to research and sequence at a depth that used to take a team, and the support to keep improving how you use them. Your central mandate is to run League's go-to-market system with rigor, and to make it better from the inside. What You'll Own Account research and point of view Research accounts in your Account Directors' book at the level of their actual business: quality performance, digital and AI roadmaps, recent leadership changes, earnings commentary, public filings and app store reviews. Map League's value proposition to account-specific challenges to build points of view that drive early engagement. Bring League executives and subject matter experts into accounts where a peer-level conversation opens a door that a rep cannot. Outreach and pipeline creation Build and deploy agentic outreach sequences on League's technology stack, across email, LinkedIn and direct calls. Generate discovery meetings and pipeline while providing Account Directors with high-context research for first calls. Support marketing events, campaigns and initiatives where League's prospects are a good fit, and follow up on the interest they generate. The system itself Execute the go-to-market system with discipline while refining underlying AI workflows, skills, and agents, and share what works with the rest of the team. Partner with the Marketing team to analyze and iterate on market messaging. Keep Salesforce accurate and current, because pipeline decisions above you are made from what you record. Learn the enterprise sales motion end to end, from first touch through opportunity progression. Security-related responsibilities: Ensure access management is performed in compliance with your role and responsibilities. Execute League's policies and procedures within your team and engagements. Notify HR, Legal, Compliance & Security of any incidents, breaches, or policy violations. Comply with Information Security Policies. What You'll Bring Two+ years of outbound sales experience into large enterprises (ideally healthcare). We are hiring for trajectory, not tenure. A genuine, organic interest in building a sales development career. Track record of reaching and engaging executive-level buyers. Fluency with Claude or other AI-native tools, and evidence you fold them into your day-to-day rather than treating them as an add-on. Strong written communication. Real curiosity about healthcare and how it is changing. You do not need to know the US healthcare system on day one; you do need to be the kind of person who goes and learns it. Experience with long, committee-driven enterprise sales cycles. Experience working alongside senior sellers on account strategy. Helpful, not required Exposure to payers, health systems, benefits administrators or consumer health organizations. Familiarity with Star Ratings, HEDIS, care gaps, benefits navigation and digital front door. Experience with Salesforce, sales engagement platforms, Artisan or LinkedIn Sales Navigator. Experience building your own AI workflows, skills or agents. How You Work Beyond the functional bar, this seat calls for a specific way of operating: You listen as well as you talk. You are comfortable picking up the phone and going outbound, and equally able to sit back, hear what is actu