Director of Sales, National Accounts

• Own the end-to-end sales process for target Strategic National Accounts (Health Plans, Health Systems, and Pharmacy Chains).
• Build and nurture a pipeline of high-value prospects by leveraging your network within the healthcare C-Suite (CIOs, CDOs, Heads of Product/Innovation).
• Articulate and sell the value of AI-driven personalization and predictive modeling, demonstrating how League’s AI solutions can drive hyper-personalized member engagement and automate next-best-actions for patients.
• Drive the "Powered by League" strategy, positioning our platform as the underlying infrastructure that enables Payers and Providers to launch their own best-in-class digital member experiences.
• Collaborate with Marketing and Business Development to execute Account-Based Marketing (ABM) campaigns targeting specific industry giants.
• Negotiate complex partnership agreements and multi-year platform contracts, navigating intricate procurement, security, and technical due diligence cycles.
• Work with Go-to-Market leadership to refine the buyer journey for healthcare infrastructure buyers, ensuring our value proposition resonates with technical and strategic decision-makers.
• Proactively identify market signals and product requirements specific to the Payer/Provider verticals and communicate these to the Product and Engineering leadership teams.
• Successfully achieve budgeted revenue targets and maintain an accurate forecast of long-cycle enterprise deals.

• 10+ years of experience in enterprise sales, with a specific focus on selling technology or consulting services to US Payers, Health Systems, or large Pharmacy Retailers.
• Experience selling AI, Machine Learning, or Data Analytics solutions is highly preferred; you must be comfortable discussing how AI transforms health outcomes and operational efficiency.
• Deep understanding of "Platform-as-a-Service" (PaaS), digital transformation, and the API economy. You understand how to sell "infrastructure," not just an app.
• Existing relationships with C-Level executives in the target verticals (e.g., Chief Digital Officers, Chief Information Officers, Chief Strategy Officers, and VPs of Member Experience).
• Knowledge of the healthcare tech stack (EHRs, Claims Engines, CRM) and the interoperability challenges (FHIR, HL7) that Payers and Providers face.
• A history of successful quota attainment in a complex, consultative sales environment with deal sizes in the 7-figure range.
• Ability to lead cross-functional deal teams (Solution Engineering, Product, Legal) to close large-scale partnerships.
• Proficiency with Salesforce and sales acceleration tools.
• Bachelor's degree in Business, Computer Science, or equivalent experience.

• 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

• Individual Contributors: Use AI to improve personal productivity and quality of output
• Senior ICs / Managers: Integrate AI into team workflows and improve processes
• Leaders: Drive AI adoption at the organizational level and shape how work is done across teams

• 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

• Comprehensive Health Benefits: We prioritize your well-being with complete medical, dental, and vision coverage
• Bonus Program: Be rewarded for your contributions with our performance-based bonus program
• Employee Stock Option Program: Become an owner and share in our success through our stock option program
• Unlimited Paid Time Off: Take the time you need to recharge and maintain a healthy work-life balance
• Spending Accounts: Manage your healthcare and dependent care expenses with tax-advantaged spending accounts
• Wellness Days: Prioritize your mental and physical health with dedicated wellness days throughout the year
• Growth Opportunities: We invest in your future with abundant opportunities for professional development and advancement
• Mentorship Program: Benefit from guidance and support from experienced leaders in your field
• Flexible Ways of Working: Enjoy the freedom to work in a way that suits your life and boosts your productivity

• →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 

We have a mix of office-centric roles based in our vibrant Toronto office, and remote-eligible roles based anywhere in Canada or 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. We are committed to fostering a meaningful work environment and connections for all Leaguers regardless of location.