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.

The Business Development

Representative works alongside two to three Account Directors, prospecting into their assigned book of business. You are the first point of contact between League and the executives who own digital, member experience, AI initiatives and innovation at the largest payers and health systems in North America. The job is account research, understanding where League’s value proposition meets an organization’s real challenges, and deploying agentic outreach sequences that create discovery meetings and early stage pipeline.

You stay in the account to help advance and co-develop qualification, shaping the discussion alongside your Account Directors until it is ready to align with more senior resources across Growth. It is usually something specific about that organization: a Star Ratings slip, three member apps that do not talk to each other, a redetermination backlog, a Chief Digital Officer six months into the job with a mandate and no platform. Finding that is the research half of the job, and it is the half that decides whether the outreach works.

Alongside net new campaigns, you will support marketing events and initiatives where League’s prospects are a good fit, and follow through on the interest they create. 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. 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 the specific challenges facing each account,



and build the point of view that earns a first conversation. Build and deploy agentic outreach sequences on League’s technology stack, across email, LinkedIn and direct calls. Create discovery meetings and early stage pipeline, and give your Account Directors the context to run a strong first call.

Help advance and co-develop qualification after the first meeting, until the account is aligned with more senior resources across Growth. Refine the AI workflows, skills and agents behind your outreach, and share what works with the rest of the team.

Bring

League executives and subject matter experts into accounts where a peer-level conversation opens a door that a rep cannot. Keep Salesforce accurate and current, because pipeline decisions above you are made from what you record. Compliance with Information Security Policies Responsibility and accountability for executing League's policies and procedures within the department/ team Notification of HR, Legal, Compliance & Security of any incidents, breaches or policy violation 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.

CANADA APPLICANTS ONLY: 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 We expect all employees regardless of role or level to thoughtfully leverage AI to improve the quality, speed, and impact of their work. 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 solid 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. We have a mix of office-centric roles based in our vibrant Toronto office, and remote-eligible roles based anywhere in Canada or US.

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