League is one of the fastest-growing technology companies in Canada and the leading healthcare experience platform. That gap costs health plans and health systems money, and it costs people their health. Health plans and health systems trust us to do this at scale.

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. 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. Keep Salesforce accurate and current, because pipeline decisions above you are made from what you record.

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. A genuine, organic interest in building a sales development career. Track record of reaching and engaging executive-level buyers.





Experience working alongside senior sellers on account strategy. 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. You are comfortable picking up the phone and going outbound, and equally able to sit back, hear what is actually being said, and take it in. Within it, you connect dots and find creative angles that the process alone would not produce.

Results here come from showing up the same way every morning. You will be pulled by several Account Directors at once. You consistently create discovery meetings with the right executives, and your Account Directors walk in with context they did not have to build themselves.

Pipeline that progresses. Opportunities you source advance past first meeting because you stayed in the account and helped shape qualification. Within months you can hold a credible conversation about US payer and health system dynamics with someone who does it for a living.

You have the fundamentals of the enterprise sales motion under you and a clear path toward owning accounts. The Canada-specific compensation range below for this full time position is exclusive of bonus, equity and benefits. The salary range is intentional to account for the performance and career progressions a Leaguer will experience in the role throughout their time at League. 55,000—$65,000 CAD drafting, analysis, coding, research, or process automation) Apply judgment and accountability when using AI by reviewing outputs for accuracy, bias,



and quality before use 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 Individual Contributors: Use AI to improve personal productivity and quality of output Senior ICs / Managers: Ability to balance efficiency with quality and sound judgment 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.

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

Highmark

Health, Google Cloud, League: new digital front door to seamless care Former Providence President and Workday EVP of Corporate Strategy join League Board of Directors League raises $95 million USD in Series C to build world’s leading healthcare CX platform Forbes x League: The Platformization Of Healthcare Is Here Fast Company x League: If we want better innovations in healthtech, we need more competition We have a mix of office-centric roles based in our vibrant Toronto office, and remote-eligible roles based anywhere in Canada or US. Each job posting will indicate where the role will be based. Regardless of the role’s posted location, all Toronto-area Leaguers (living within 65 km of our downtown HQ) collaborate in‑office Monday through Thursday.

Depending on your distance to the office, you’ll enjoy 10 or 20 Flexible Remote Days each quarter for focus and deep-work time. Scammers are getting craftier and leveraging fake job postings to get personal information. League may use Artificial Intelligence (AI) tools to assist in the screening of applicants for this position.

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📌 Remote Technology Business Development Representative (Toronto)
🏢 League
📍 Toronto