Remote 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 actually being said, and take it in. Neither mode is a stretch for you.
• You keep up. You process new information fast: new market, new structure, new process; and you can hold pace with a team that moves quickly..
• You run the play. You buy into the system that has been built for you and execute it with discipline. You surface your ideas rather than quietly launching your own version of the stack.
• You grind, then you think. You genuinely enjoy the daily rhythm of the work. Within it, you connect dots and find creative angles that the process alone would not produce.
• You do the thing every day. You are consistent and process-oriented. Results here come from showing up the same way every morning.
• You are discerning with your time. You will be pulled by several Account Directors at once. You know what to say yes to, what to sequence, and what to push back on.
• You ask the hard question. You are supportive and easy to work with, and you still challenge assumptions. This team is optimistic by nature and benefits from someone willing to press constructively.
• You are self-directed. When something is unfamiliar, you go read, listen and dig until you can hold your own on it. You share your ideas and learnings with others on the team.
• You want to win. You lead yourself, you compete, and you bring the energy to keep up with the people around you.

What Success Looks Like

• 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.

CANADA APPLICANTS ONLY: 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 range for Canada applicants only

$55,000—$65,000 CAD

AI Fluency & Ways of Working

At League, we are an AI-native organization . We expect all employees regardless of role or level to thoughtfully leverage AI to improve the quality, speed, and impact of their work.

What this means in practice:

• Use AI tools as part of your daily workflow to enhance productivity, problem-solving, and decision-making (e.g., drafting, analysis, coding, research, or process automation)
• Apply judgment and accountability when using AI by reviewing outputs for accuracy, bias, and quality before use
• Continuously learn and adapt as new AI tools and capabilities emerge, incorporating them into your ways of working
• 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

How this scales by level:

• Individual Contributors: Use AI to improve personal productivity and quality of output
• Senior ICs / Managers: Integrate AI into team workflows and improve processes
• Leaders: Drive AI adoption at the organizational level and shape how work is done across teams

What we look for:

• Demonstrated experience using AI tools in a practical, responsible way
• Curiosity and openness to experimenting with new technologies
• Ability to balance efficiency with quality and sound judgment

Our employees come from different backgrounds, and we celebrate those differences. We are looking for the best candidates for our open roles, but do not expect applicants to meet every qualification in order to be considered. If you are excited about what you could accomplish at League and believe you can add value to our team, we would love to hear from you.

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 View email address on us.fitly.work .

Our Application Process:

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:

Work Location:

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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