Director of Sales, National Accounts

League; Canada; Hybrid; CAD 154,000 - 233,000; Full time

Job summary

A leading healthcare technology provider is seeking an experienced enterprise sales professional to manage Strategic National Accounts. The role requires over 10 years in technology sales, emphasizing relationships with C-Level executives in healthcare. Candidates should have experience in AI and be capable of negotiating complex agreements. The position offers comprehensive health benefits, stock options, and growth opportunities, all while supporting a flexible work environment across Canada.

Benefits

Comprehensive Health Benefits

Performance-based bonus program

Employee Stock Option Program

Unlimited Paid Time Off

Tax-advantaged healthcare accounts

Dedicated wellness days

Investment in professional development

Mentorship Program

Flexible working arrangements

Qualifications

• 10+ years of experience in enterprise sales focused on technology.
• Experience selling AI or Data Analytics solutions is preferred.
• Deep understanding of 'Platform-as-a-Service' sales.

Responsibilities

• Own the end-to-end sales process for Strategic National Accounts.
• Build and nurture a pipeline of high-value prospects.
• Negotiate complex partnership agreements.

Skills

Enterprise sales experience

Relationship building with C-Level executives

Knowledge of healthcare tech stack

Proficiency with Salesforce

Education

Bachelor's degree in Business or Computer Science

Tools

Sales acceleration tools

Job description

Position Summary

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. With $250 million in investment and a product‑market fit that enables us to accelerate pipeline conversion rates, League partner with major names such as Highmark Health, Telus, and Manulife.

In this role you will:

• 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.

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: Complete medical, dental, and vision coverage.
• Bonus Program: Performance‑based bonus program.
• Employee Stock Option Program: Share in our success through equity.
• Unlimited Paid Time Off: Recharge with flexible PTO.
• Spending Accounts: Tax‑advantaged healthcare and dependent care accounts.
• Wellness Days: Dedicated days for mental and physical health.
• Growth Opportunities: Investment in professional development and advancement.
• Mentorship Program: Guidance from experienced leaders.
• Flexible Ways of Working: Freedom to work in a way that supports productivity.

Security‑Related Responsibilities

• Compliance with Information Security Policies.
• Ensure access management complies with the employee's role and responsibilities.
• Responsible and accountable for executing League's policies and procedures within the department/team.
• Notify HR, Legal, Compliance & Security of any incidents, breaches or policy violations.

US Applicants Only

• Compensation range for USA applicants only: $154,700 – $232,100 USD (base salary; exclusive of bonus, equity and benefits).
• Salary depends on job‑related skills/experience and will be discussed during the hiring process.

Our Application Process

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

Location & Work Arrangements

We have a mix of office‑centric roles based in our Vancouver office and remote‑eligible roles based anywhere in Canada or the US. Each posting indicates the role’s location. Regardless of location, all Vancouver‑area Leaguers collaborate in‑office Monday through Thursday, with flexible remote days available each quarter.

Equal Employment Opportunity Statement

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 need assistance at any time during our recruitment process, please contact us at [e-mail].