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Job type Full-Time

Salary CAD 175000–200000 / yearly

Posted 16 Oct 2026 (1 day ago)

Category Sales

Work mode Remote

League is one of the fastest-growing technology companies in Canada and the leading healthcare experience platform. That gap costs health plans and health systems money, and it costs people their health. Health plans and health systems trust us to do this at scale.

League is a leading Canadian healthcare AI company building the digital health experiences that make it easy for people to access, understand, and act on their health. Our platform powers personalized consumer, member, and patient experiences for some of the world's leading health insurers, providers, and pharmacy retailers, with a footprint that's scaling quickly across our core healthcare payor market and our fast-growing provider market in Canada and the US.

As we continue to expand our team in Canada, our Go-to-Market team is growing to power this next phase of growth — and we're looking for a Director, Platform & AI Sales to help lead the way.

As a Director, Platform & AI Sales, you'll be a core part of the Go-to-Market team, working across priority segments including public sector payors and providers, private insurers, retail healthcare, and digital health innovators. You'll lead complex, enterprise-scale business development and sales initiatives, and carry a quota for League's AI-powered consumer experience platform.

Working closely with other Go-to-Market functions — including Solution Engineering, Partnerships, and Product Marketing — you'll strategize, scope, and design impactful customer partnerships that power the digital transformation of the consumer, member, or patient experience.

Expand League's footprint in Canada, building on the strength of existing customer relationships.

Own the end-to-end sales process for target platform accounts — from sales strategy and pipeline development to closing revenue and growing customer relationships.

Build pipeline using your own network,



and partner with the Business Development and Marketing teams on account-based marketing campaigns that convert into closed revenue and quota attainment.

Meet and exceed sales objectives, and maintain accurate, up-to-date sales forecasts.

Negotiate complex software and professional services agreements from initial conversation through signature.

Create demand by pairing healthcare industry expertise with an understanding of C-level priorities — uncovering business problems and matching them to League's solutions, including our AI capabilities.

Partner with League executives and Go-to-Market leaders to build compelling narratives and tailored materials for meetings with prospective accounts.

Help shape and improve sales processes and buyer journeys, especially in current industry verticals.

Ensure smooth account handoffs from the sales process into customer strategy and delivery.

8+ years of experience selling PaaS or SaaS solutions, with a focus on digital transformation and/or consumer and patient engagement

Proven experience selling AI-powered solutions

Experience in a consulting role focused on digital health or consumer experience is a strong asset

Deep knowledge of the healthcare industry, particularly public healthcare services and provincial/territorial health plans A track record of consistent quota attainment in complex, enterprise sales environments

Proficiency with Salesforce and sales acceleration/enablement tools

Bachelor's degree in Business or equivalent experience The Canada-specific compensation range below for this full-time position is exclusive of bonus, equity and benefits. 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. 175,000—$200,000 CAD

AI Fluency & Ways of Working 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.

Use AI tools as part of your daily workflow drafting, analysis, coding, research, or process automation)

when using AI by reviewing outputs for accuracy, bias, and quality before use as new AI tools and capabilities emerge, incorporating them into your ways of working 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

Use AI to improve personal productivity and quality of output

Senior ICs / Managers: Integrate AI into team workflows and improve processes

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

Ability to balance efficiency with quality and sound judgment

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.

Highmark

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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. Director, Platform and AI Sales League Canada #

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