Director, Platform and AI Sales

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 environments
• Ability to build trust and win support from C-suite stakeholders at large organizations
• Proficiency with Salesforce and sales acceleration/enablement tools
• Experience creating polished documentation for client presentations and webinars
• Bachelor's degree in Business or equivalent experience

• You should receive a confirmation email after submitting your application.
• A recruiter (not a computer) reviews all applications at League.
• If we see alignment with League's needs, a recruiter will reach out to learn more about your goals. The recruiter will also share the team-specific interview process depending on the roles you are exploring.
• The final step is an offer, which we hope you will accept!
• Prior to joining us, we conduct reference and background checks. Additional checks could be required for US Candidates, depending on the role you are exploring.