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League is a leading Canadian healthcare AI company building digital health experiences for major health insurers, providers, and pharmacy retailers. The company powers personalized consumer, member, and patient experiences for organizations like Manulife, SCAN, Geisinger, Medibank, Baptist, and Shoppers Drug Mart, with a rapidly scaling footprint across North America.
As Director of Platform and AI Sales, you will lead complex, enterprise-scale business development and sales initiatives across priority segments including public sector payors and providers, private insurers, retail healthcare, and digital health innovators. You'll own the end-to-end sales process for target platform accounts, from strategy and pipeline development through closing revenue and growing customer relationships.
Key responsibilities include expanding League's footprint in Canada by building on existing customer relationships; owning sales strategy, pipeline development, and revenue closure for enterprise accounts; building pipeline through your network and partnering with Business Development and Marketing on account-based campaigns; meeting and exceeding sales objectives with accurate forecasting; negotiating complex software and professional services agreements; creating demand by pairing healthcare expertise with C-level priorities; partnering with executives to build compelling narratives and tailored materials; shaping sales processes and buyer journeys in new verticals; surfacing product feedback from prospects to leadership; and ensuring smooth handoffs from sales to customer strategy and delivery.
You bring 8+ years selling PaaS or SaaS solutions focused on digital transformation and consumer/patient engagement, with proven experience selling AI-powered solutions. Deep knowledge of the healthcare industry—particularly public healthcare services and provincial/territorial health plans—is essential. You have a track record of consistent quota attainment in complex enterprise sales, the ability to build trust with C-suite stakeholders, proficiency with Salesforce and sales acceleration tools, and experience creating polished client presentations. A Bachelor's degree in Business or equivalent is required. Experience in digital health consulting or healthcare consulting is a strong asset.
