Director of Sales, National Accounts at League Inc.

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:

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.

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: 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

US APPLICANTS ONLY: The US-specific compensation range below for this full-time position is exclusive of bonus, equity and benefits. This range reflects the minimum and maximum target for base salaries for the position across all US locations. The salary range is intentional to account for the performance and career progressions a Leaguer will experience in the role throughout their time at League. Where in the band you may land is determined by job-related skills/experience. Your recruiter can share more about the specific salary range specific to your skills and experience during the hiring process.

Compensation range for USA applicants only

$154,700—$232,100 USD

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 [email protected].

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 Notice
We 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 here.

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Director of Sales, National Accounts

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