Director of Platform Sales, League
$160-200k
Salesforce
Expert level
Remote from US
Consumer experience platform for healthcare
Be an early applicant
Consumer experience platform for healthcare
501-1000 employees
HealthcareB2BPersonal healthSaaSData Analysis
Be an early applicant
$160-200k
Salesforce
Expert level
Remote from US
501-1000 employees
HealthcareB2BPersonal healthSaaSData Analysis
Company mission
To power next-generation healthcare experiences with a platform built to enable CX transformation.
Role
Who you are
- 10+ years of experience in sales and sales management, with a history of successful quota attainment in a complex enterprise sales environment
- Experience in Platform-as-a-Service (PaaS), digital transformation, and/or consumer and patient engagement sales
- Knowledge of the U.S. healthcare industry — payers (health plans, HCM, brokers), providers, and/or pharmacy retailers
- Ability to win the support of key C-suite stakeholders in large corporates
- Proficiency with Salesforce and sales acceleration tools; experience developing polished documentation for client presentations and webinars
- Bachelor's degree in Business or equivalent experience
- You're sharp and quick to learn. You understand how prospects make decisions and can explain how our solution solves their problems simply and clearly, keeping pace with League's rate of innovation
- You have real drive. You have a high motor and a reason for doing this work that goes beyond money or recognition — the kind of purpose that outlasts a string of tough days and “no”s
- You're a culture fit, not a lone wolf. You're collaborative and team-oriented rather than someone who prefers to work independently. This is a team sale: you win over the broader organization, teach others, and show up as a positive teammate
- You're ambitious with substance. Your ambition is grounded in a genuine sense of purpose, not surface-level motivators — it's what keeps you going when the deal gets hard
- You're structured, not freelance. You thrive inside a replicable, rules-based sales process rather than working around it. The U.S. healthcare market rewards sellers who bring structure and control — buyers are wary of “market breakers.”
- You communicate directly. You favor clear, straightforward communication, while still building genuine relationships along the way
- You don't need to be the loudest person in the room. You don't need to be a classic extrovert to succeed here — some of the strongest sellers on this team aren't
- You're self-aware and coachable. You know your own strengths and blind spots, take feedback well, and adjust. You can hold both the big-picture narrative and the granular detail of a deal without losing the thread
- You're steady under pressure and ambiguity. You have a clear answer for what you do when you feel like you're losing control of a situation, and you don't need everything mapped out to keep moving
What the job involves
- As a Sales Director at League, you're joining at a tipping-point moment in our growth. We've established product-market fit, and we're accelerating pipeline conversion. This is a chance to be part of an incredible growth story and drive impact in helping people live healthier, happier lives
- You'll be a key member of our growth team, scaling the business across League's priority healthcare segments — health plans, providers, pharmacy retailers, and digital health innovators
- Payer accounts are a near-term priority given current pipeline needs, but this role is fundamentally a healthcare market seat: the strongest sellers move fluidly across payer and provider as funding and demand shift, and your focus will evolve with League's go-to-market direction
- You'll own complex, enterprise-scale business development and sales initiatives, and will have the opportunity to design partnerships that power the digital transformation of your customers' consumer, member, or patient experience
- Own the end-to-end sales process for target enterprise Platform strategic accounts
- Generate new pipeline by capitalizing on your network, while collaborating with Marketing and the Business Development teams to execute Account-Based Marketing initiatives
- Negotiate complex partnership agreements through to completion
- Successfully achieve budgeted sales objectives and maintain an accurate, thorough sales forecast
- Ensure and monitor successful handoffs of accounts from the sales process into delivery
- Work with League executives and go-to-market leaders to build the story and materials for prospective accounts
- Partner with go-to-market leadership to create and improve persuasive, repeatable sales processes and buyer journeys, especially in new industry verticals
- Proactively identify and communicate the product needs of prospects and industry verticals to executive leadership
- Help foster a culture of success and ongoing goal achievement across League's go-to-market functions
- What Success Looks Like:
- You consistently hit or exceed sales targets while maintaining an accurate, thorough forecast
- Accounts move through a structured, repeatable process across the healthcare market, with clean handoffs into delivery
- Executive leadership and go-to-market peers see you as a trusted partner who brings clarity, not confusion, to deals
- You build genuine trust with your team and stakeholders — people want to work with you, and you make others better in the process
- 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
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
Our take
Health benefits are a top requirement for anyone seeking a new job in the US today, but classic one-size-fits-all plans are no longer regarded fit for service. League's platform - for payers, providers, consumer health businesses, and employees - connects all benefits in one HIPAA-compliant place, to enable all bodies involved with health benefits to provide better customer healthcare experiences.
League is already one of the bigger players in the employee wellness space, having capitalised on the recently accepted correlation between employee health and productivity to secure huge clients like Uber, Shopify and Unilever. The company has seen significant investment, which will support the scaling of its platform-as-a-service offering. With more than 63 million contracted users, it is securing its position as the leading digital infrastructure for an integrated health ecosystem.
Freddie
Company Specialist at Welcome to the Jungle
Insights
Top investors
-4% employee growth in 12 months
Company
Funding (last 2 of 4 rounds)
Feb 2022
$95m
SERIES C
Jul 2018
$47.1m
SERIES B
Total funding: $171.1m
Company benefits
- Flexible medical and dental plans
- 401(k) and RRSP matching programs
- Health, lifestyle, learning and family spending accounts
- Employee stock option program (ESOP)
- Generous leaves (including parental and sabbatical)
- Flexible time off
Company HQ
Entertainment District, Toronto, ON
Leadership
Michael Serbinis
(Founder & CEO)Founder of DocSpace and Kobo. Experience as CEO for Three Angels Capital and Board Director for Vector Insitute, among other prominent business leadership roles.
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