Director Platform Sales

About League Founded in 2014, League is the leading healthcare consumer experience (CX) platform, powered by artificial intelligence (AI), reaching more than 63 million people around the world and delivering the highest level of personalization in the industry. Payers, providers, and consumer health partners build on League’s platform to deliver high‑engagement healthcare solutions proven to improve health outcomes. League has raised over $285 million in venture capital funding to date, powering the digital experiences for some of healthcare’s most trusted brands, including Highmark Health, Manulife, Medibank, and Shoppers Drug Mart. Position Summary League’s footprint is strategically scaling. Building on the proven success among our market‑leading customers and partners in Canada and the US, our Go‑to‑Market team is expanding and seeking a Director, Platform Sales to help us achieve this next phase of growth. As a Director, Platform Sales, you will be a core part of the Go‑to‑Market team working across priority segments including public sector, healthcare providers, insurers, pharmacy retailers and digital health innovators. In This Role You Will • Focus on expanding League’s footprint in Canada and building on the success of existing customer relationships. • Lead and own the end‑to‑end sales process for target platform strategic accounts, including formulating sales strategy, driving revenue growth and developing new customer relationships. • Leverage your own relationships to build pipeline, and work in partnership with the Business Development and Marketing teams to run account‑based marketing campaigns that lead to closed revenue and quota attainment. • Successfully achieve and exceed budgeted sales objectives, and maintain sales forecast in an accurate and thorough manner. • Negotiate complex software and professional services agreements from initial stages through to completion. • Create demand by leveraging healthcare industry expertise and the priorities of C‑level executives, uncovering business problems and matching them to our solution. • Work collaboratively with League Executives and Go‑to‑Market leaders to build the story and tailored materials for meetings with prospective accounts. • Work with the Go‑to‑Market leadership team to create and improve sales processes and buyer journeys, especially in new industry verticals. • Proactively identify and communicate product needs of Powered by League prospects and industry verticals to executive and product leadership. • Ensure and monitor successful handoffs of accounts from the sales process into customer strategy and delivery. About You • 8+ years of experience in ‘Platform as a Service’ (PaaS) or ‘Software as a Service’ (SaaS), digital transformation and/or consumer & patient engagement sales required. • Previous experience in a consulting role focusing on digital health and consumer experience is a significant asset. • Knowledge of the healthcare industry, especially public healthcare services and provincial/territorial health plans. • A history of successful quota attainment in a complex sales environment. • Ability to win the support of key C‑Suite stakeholders in large corporations. • Proficiency with Salesforce and sales acceleration tools. • Experience developing exceptional documentation for client presentations and webinars. • Bachelor’s degree in Business or equivalent experience. AI Fluency & Ways of Working • Use AI tools as part of your daily workflow to enhance productivity, problem‑solving, and decision‑making (e.g., drafting, analysis, coding, research, or process automation). • Apply judgment and accountability when using AI by reviewing outputs for accuracy, bias, and quality before use. • Continuously learn and adapt as new AI tools and capabilities emerge, incorporating them into your ways of working. • Identify opportunities to improve how work gets done 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. What We Look For • Demonstrated experience using AI tools in a practical, responsible way. • Curiosity and openness to experimenting with new technologies. • Ability to balance efficiency with quality and sound judgment. What We Offer • Total OTE for Sales Director (Canada): • Base Pay: $175K‑$200K CAD • On‑Target Earnings: $350K‑$400K CAD based on hitting commission targets • Comprehensive Health Benefits: Complete medical, dental, and vision coverage. • Employee Stock Option Program: Opportunity to become an owner and share in our success. • Unlimited Paid Time Off. • Spending Accounts: Manage healthcare and dependent care expenses with tax‑advantaged accounts. • Wellness Days: Dedicated days throughout the year to prioritize mental and physical health. • Growth Opportunities: Invested in your professional development and advancement. • Mentorship Program: Guidance and support from experienced leaders. • Flexible Ways of Working: Freedom to work in a way that suits your life and boosts productivity. Security‑Related Responsibilities • Compliance with Information Security Policies. • Ensure access management is performed in compliance with the employee's role and responsibilities. • Responsibility and accountability for executing League's policies and procedures within the department/team. • Notification of HR, Legal, Compliance & Security of any incidents, breaches or policy violations. Work Location We have a mix of office‑centric roles based in our vibrant Toronto office and remote‑eligible roles based anywhere in Canada or the 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. Equal Employment Opportunity 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. If you are an individual in need of assistance at any time during our recruitment process, please contact us at recruitinginfo@league.com.

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