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 anizations like Manulife, SCAN, Geisinger, and Medibank on the payer side, and Baptist and Shoppers Drug Mart on the provider side.

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.

• 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.

• 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.…