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.
As a Director of Sales, National Accounts at League, you are joining at a tipping point moment in our growth. With 63 million people contracted onto the platform and over $250 Million in investment so far, there has never been a better time to be part of League. We partner with some of the biggest names in healthcare, such as Highmark Health, Telus, and Manulife. We have established our product-market fit and are accelerating pipeline conversion rates through improved pricing and packaging models.
In this role, you will be a key member of our Platform Growth team, focused exclusively on the US Payer, Provider, and Pharmacy Retail verticals. You will be accountable for leading complex, enterprise-scale infrastructure sales with prospective partners. You will scope and design strategic partnerships to power the digital transformation of
their consumer, member, or patient experience using League's "Powered by League" architecture.
About you:
- 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.
What We Offer
- 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
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
Our employees come from different backgrounds, and we celebrate those differences. We are looking for the best candidates for our open roles, but do not expect applicants to meet every qualification in order to be considered. If you are excited about what you could accomplish at League and believe you can add value to our team, we would love to hear from you.
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.
Our Application Process:
Applying to a role you love can be exhausting, and understanding the next steps can feel vague and uncertain. You have done the hard part of submitting your application; let's do ours by sharing potential next steps
- 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.
Here are some additional resources to learn more about League:
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 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.
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Use of AI NoticeWe are committed to ensuring fairness and transparency throughout our hiring process. League may use Artificial Intelligence (AI) tools to assist in the screening of applicants for this position. Please check out our stance on using AI in recruitment
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