Director, Platform Sales

United Statesexecutive

EngineeringMarketingSales

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Quick Summary

Key Responsibilities

The US-specific compensation range below for this full-time position is exclusive of bonus, equity and benefits.

Technical Tools

EngineeringMarketingSales

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 Sales Director 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 Health care such as Highmark Health, Telus and Manulife. We have established our product-market fit and we are accelerating pipeline conversion rates through improved pricing and packaging models. This is a chance of a lifetime to be part of an incredible growth story and drive impact in helping people live healthier, happier lives!

In this role, you will be a key member of our growth team who is scaling the business across priority segments including healthcare providers, payers, pharmacy retailers & digital health innovators. You will be accountable for leading complex, enterprise-scale business development & sales initiatives with prospective League customers - and will have the opportunity to scope and design customer partnerships to power the digital transformation of their consumer, member or patient experience.

Own the end-to-end sales process for target strategic platform accounts
Leverage your own relationships to build pipeline, and work in collaboration with the Business Development Manager - Platform and Marketing to run Account Based Marketing campaigns
Work collaboratively with League Executives and Go-to-Market leaders to build the story and materials for Powered by League prospective accounts
Work with the Go-to-Market leadership team to create and improve persuasive sales processes and buyer journeys, especially in new industry verticals
Be able to negotiate complex partnership agreements through to completion
Proactively identify and communicate product needs of Powered by League prospects / industry verticals to executive leadership
Successfully achieve budgeted sales objectives, and maintain sales forecast in an accurate and thorough manner
Ensure and monitor successful handoffs of accounts from the sales process and into delivery
Help foster a culture of success and ongoing business and goal achievement across the go-to-market functions at League

10+ years of experience in enterprise sales
Experience in ‘Platform as a service’, ‘digital transformation’ and/or consumer & patient engagement sales required
Knowledge of the healthcare industry (Providers, Pharmacy Retailers) and/or health benefits industry (Payers, HCM, Brokers) in the US
A history of successful quota attainment in a complex sales environment
Ability to win the support of key C-Suite stakeholders in large corporates
Proficiency with SalesForce and sales acceleration tools
Experience developing exceptional documentation for client presentations, webinars
Bachelor's degree in Business or equivalent experience

AI Fluency & Ways of Working

At League, we are an AI-native organization. We expect all employees regardless of role or level to thoughtfully leverage AI to improve the quality, speed, and impact of their work.

What this means in practice:

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

How this scales by level:

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

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

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✓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

Responsibilities

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→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

Requirements

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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.

Privacy Policy

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