Director, Platform Sales (US)

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.

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.

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.

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.

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 violations

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.

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

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

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

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.

Learn about our platform, leadership team and partners

Highmark Health, Google Cloud, League: new digital front door to seamless care

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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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