Director, Platform Sales

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 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.

In this role you will:

• 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

About you:

• 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 Sales Force and sales acceleration tools

• Experience developing exceptional documentation for client presentations, webinars

• Bachelor's degree in Business 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…