Business Development Representative

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 will run those sequences on League’s own technology stack, reaching people across email, LinkedIn and direct calls.

The work does not stop at the meeting. 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.

What earns a first conversation is rarely in a pitch deck. 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.

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.

In this role, you will:

• 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.
• Support marketing events, campaigns and initiatives where League’s prospects are a good fit, and follow up on the interest they generate.
• 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.
• Give Marketing honest feedback on what messaging is landing and what is not.
• 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

  • Compliance with Information Security Policies
  • Ensure access management is performed in compliance with the employee's role and responsibilities
  • 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

We're looking for:

• Two to four years of outbound sales experience into large enterprises, ideally healthcare.
• Track record of reaching and engaging executive-level buyers.
• Experience with Claude or other AI-native tools.
• Strong written communication.
• Experience with long, committee-driven enterprise sales cycles.
• Experience working alongside senior sellers on account strategy.
• Interest in healthcare and how it is changing.
• Nice to have:
• 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.

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 recruitinginfo@league.com.

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:

• Learn about our platform, leadership team and partners
• 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

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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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. Privacy Policy Review our Privacy Policy for information on how League is protecting personal data.