Director, Platform and AI 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 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. In This Role, You Will: 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 new industry verticals. Surface product needs and feedback from Powered by League prospects and industry verticals to executive and product leadership. Ensure smooth account handoffs from the sales process into customer strategy and delivery. About You: 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 env…