League

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.

The Role

As a Sales Director at League, you're joining at a tipping-point moment in our growth. We've established product‑market fit, and we're accelerating pipeline conversion. This is a chance to be part of an incredible growth story and drive impact in helping people live healthier, happier lives. You'll be a key member of our growth team, scaling the business across League's priority healthcare segments — health plans, providers, pharmacy retailers, and digital health innovators. Payer accounts are a near‑term priority given current pipeline needs, but this role is fundamentally a healthcare market seat: the strongest sellers move fluidly across payer and provider as funding and demand shift, and your focus will evolve with League's go‑to‑market direction. You'll own complex, enterprise‑scale business development and sales initiatives, and will have the opportunity to design partnerships that power the digital transformation of your customers' consumer, member, or patient experience.

In This Role You Will

• Own the end‑to‑end sales process for target enterprise Platform strategic accounts.
• Generate new pipeline by capitalizing on your network, while collaborating with Marketing and the Business Development teams to execute Account‑Based Marketing initiatives.
• Negotiate complex partnership agreements through to completion.
• Successfully achieve budgeted sales objectives and maintain an accurate, thorough sales forecast.
• Ensure and monitor successful handoffs of accounts from the sales process into delivery.

Build the story and the system

• Work with League executives and go‑to‑market leaders to build the story and materials for prospective accounts.
• Partner with go‑to‑market leadership to create and improve persuasive, repeatable sales processes and buyer journeys, especially in new industry verticals.
• Proactively identify and communicate the product needs of prospects and industry verticals to executive leadership.
• Help foster a culture of success and ongoing goal achievement across League's go‑to‑market functions.

What You'll Bring

• 10+ years of experience in sales and sales management, with a history of successful quota attainment in a complex enterprise sales environment.
• Experience in Platform‑as‑a‑Service (PaaS), digital transformation, and/or consumer and patient engagement sales.
• Knowledge of the U.S. healthcare industry — payers (health plans, HCM, brokers), providers, and/or pharmacy retailers.
• Ability to win the support of key C‑suite stakeholders in large corporates.
• Proficiency with Salesforce and sales acceleration tools; experience developing polished documentation for client presentations and webinars.
• Bachelor's degree in Business or equivalent experience.

How You Work

• You're sharp and quick to learn. You understand how prospects make decisions and can explain how our solution solves their problems simply and clearly, keeping pace with League's rate of innovation.
• You have real drive. You have a high motor and a reason for doing this work that goes beyond money or recognition — the kind of purpose that outlasts a string of tough days and "no"s.
• You're a culture fit, not a lone wolf. You're collaborative and team‑oriented rather than someone who prefers to work independently. This is a team sale: you win over the broader organization, teach others, and show up as a positive teammate.
• You're ambitious with substance. Your ambition is grounded in a genuine sense of purpose, not surface‑level motivators — it's what keeps you going when the deal gets hard.
• You're structured, not freelance. You thrive inside a replicable, rules‑based sales process rather than working around it. The U.S. healthcare market rewards sellers who bring structure and control — buyers are wary of "market breakers."
• You communicate directly. You favor clear, straightforward communication, while still building genuine relationships along the way.
• You don't need to be the loudest person in the room. You don't need to be a classic extrovert to succeed here — some of the strongest sellers on this team aren't.
• You're self‑aware and coachable. You know your own strengths and blind spots, take feedback well, and adjust. You can hold both the big‑picture narrative and the granular detail of a deal without losing the thread.
• You're steady under pressure and ambiguity. You have a clear answer for what you do when you feel like you're losing control of a situation, and you don't need everything mapped out to keep moving.

What Success Looks Like

• You consistently hit or exceed sales targets while maintaining an accurate, thorough forecast.
• Accounts move through a structured, repeatable process across the healthcare market, with clean handoffs into delivery.
• Executive leadership and go‑to‑market peers see you as a trusted partner who brings clarity, not confusion, to deals.
• You build genuine trust with your team and stakeholders — people want to work with you, and you make others better in the process.

US APPLICANTS ONLY

The US-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 US 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 USA applicants only

$177,800—$217,300 USD

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

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.

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.