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League Inc.
Toronto
Source: League Inc. careers · View original posting
From League Inc.'s posting. “We” and “our” refer to the employer.
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.
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.
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.
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.
Meetings that hold.
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.
The system gets sharper.
Your AI workflows and sequences improve measurably over your first two quarters, and other people on the team adopt what you built.
You know the market.
Within months you can hold a credible conversation about US payer and health system dynamics with someone who does it for a living.
You are trusted with more.
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. This range reflects the minimum and maximum target for base salaries for the position across all Canadian locations. 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. Where in the band you may land is determined by job-related skills/experience.
Your recruiter can share more about the specific salary range specific to your skills and experience during the hiring process.
Compensation
. We expect all employees regardless of role or level to thoughtfully leverage AI to improve the quality, speed, and impact of their work.
Use AI to improve personal productivity and quality of output
Integrate AI into team workflows and improve processes
Drive AI adoption at the organizational level and shape how work is done across teams
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
. If you are an individual in need of assistance at any time during our recruitment process, please contact us at recruitinginfo@league.com.
Applying to a role you love can be exhausting, and understanding the next steps can feel vague and uncertain. You have done the hard part of submitting your application; let's do ours by sharing potential next steps
You should receive a confirmation email after submitting your application.
A recruiter (not a computer) reviews all applications at League.
If we see alignment with League's needs, a recruiter will reach out to learn more about your goals. The recruiter will also share the team-specific interview process depending on the roles you are exploring.
The final step is an offer, which we hope you will accept!
Prior to joining us, we conduct reference and background checks.
Additional checks could be required for US Candidates, depending on the role you are exploring.
Here are some additional resources to learn more about 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. 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.
We are committed to fostering a meaningful work environment and connections for all Leaguers regardless of location.
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Use of AI Notice
We are committed to ensuring fairness and transparency throughout our hiring process. League may use Artificial Intelligence (AI) tools to assist in the screening of applicants for this position. Please check out our stance on using AI in recruitment here.
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