Director, Platform Sales

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

League’s digital health footprint is strategically scaling. Building on the proven success among our market-leading customers and partners in Canada and the US, our Go-to-Market team is expanding and seeking a Director, Platform Sales to help us achieve this next phase of growth. As a Director, Platform Sales , you will be a core part of the Go-to-Market team working across priority segments including public sector, healthcare providers, insurers, pharmacy retailers and digital health innovators. You will be responsible for leading complex enterprise-scale business development and sales initiatives with prospects and carry a quota for our consumer experience platform sales. Working in collaboration with other parts of the Go-to-Market team (including Solution Engineering, Partnerships, Product Marketing), you will strategize, scope and design impactful customer partnerships that power the digital transformation of their consumer, member or patient experience.

In this role you will:

• Focus on expanding League’s footprint in Canada and building on the success of existing customer relationships.
• Lead and own the end-to-end sales process for target platform strategic accounts including formulating sales strategy, driving revenue growth and developing new customer relationships.
• Leverage your own relationships to build pipeline, and work in partnership with the Business Development and Marketing teams to run account-based marketing campaigns that lead to closed revenue and quota attainment.
• Successfully achieve and exceed budgeted sales objectives, and maintain sales forecast in an accurate and thorough manner.
• Negotiate complex software and professional services agreements from initial stages through to completion.
• Create demand by leveraging healthcare industry expertise and what the priorities from C-level executives are, uncovering business problems and matching them to our solution.
• Work collaboratively with League Executives and Go-to-Market leaders to build the story and tailored materials for meetings with prospective accounts.
• Work with the Go-to-Market leadership team to create and improve sales processes and buyer journeys, especially in new industry verticals.
• Proactively identify and communicate product needs of Powered by League prospects and industry verticals to executive and product leadership.
• Ensure and monitor successful handoffs of accounts from the sales process and into customer strategy and delivery.
• 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.

About you

• 8+ years of experience in ‘Platform as a Service’ (PaaS) or ‘Software as a Service’ (SaaS), digital transformation and consumer & patient engagement sales within the Healthcare industry required Selling AI-powered solutions is also a requirement Previous experience in a consulting role focusing on digital health and consumer experience is a significant asset Knowledge of the healthcare industry, especially public healthcare services and provincial/territorial health plans A history of successful quota attainment in a complex sales environment Ability to win the support of key C-Suite stakeholders in large corporations Proficiency with Salesforce and sales acceleration tools Experience developing exceptional documentation for client presentations and webinars Bachelor's degree in Business or equivalent experience.
• 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. Where in the band you may land is determined by job-related skills/experience.
• Compensation range for Canada applicants only $160,000 — $200,000 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 click.appcast.io .

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 .

Privacy Policy

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

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.