League Inc.
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Principal, Strategic Partnerships
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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 Principal, Strategic Partnerships, you will be responsible for building and leading strategic partnerships on behalf of League and will report to the SVP of Customer & Partner Ecosystem. You will manage partnerships within a single portfolio or combination of partnerships across System Integrator & Enterprise Technology, and/or Product/ISV segments. You will be responsible for the strategy, execution, negotiation/contract management, and relationship management for your partnerships towards achievement of business objectives, prioritizing sourcing and influencing closed won revenue.
The ideal candidate will have demonstrated experience growing and managing partnerships with Systems Integrators, Cloud providers or ISVs & AI natives, with proven success in driving opportunities via complex partner networks. They will have shown the ability to think strategically, navigate complex partner ecosystems, and lead cross-functional teams to execute on revenue-generating KPIs. The ideal candidate must have experience in healthcare/digital health.
In this role, you will:
- Partnership strategy definition and alignment: Define success/KPIs, develop a plan to get there, and align support to achieve those targets independently (including cross functional stakeholders, external stakeholders, working team and leadership).
- Develop sales strategies and identify opportunities that align to League’s platform go-to-market segments (focus on payors by working closely with internal and external commercial teams.
- Continuously educating and enabling partners on League’s unique positioning and value proposition, and enabling internal teams on new partnerships.
- Collaborate with Product Marketing to develop ‘better together’ messaging for the partnership and enable our internal and partner commercial teams.
- Partner with Marketing on strategies to drive partnership awareness through joint blogs, podcasts, webinars, case studies, etc.
- Define and gain alignment on the partnership product roadmap internally and with the partner product development teams (e.g. technology integrations).
- Execution: Deliver on objectives at a high standard, on time, and meeting success criteria (e.g. partner-generated and partner-influenced KPI’s, sales qualified opportunities, revenue targets) independently.
- Responsible for driving execution on the strategy from start to finish, internally & externally, cross functionally, and with all levels of leadership.
- Effectively consider dependencies and mitigate risks when planning work.
- Manage partnerships to the partnership health framework.
- Proactively raise and address issues, such that the resulting impact is minimized.
- Partnership Structuring & Negotiation: Responsible for defining commercial models and negotiating contracts resulting in longstanding win-win partnerships independently.
- Successfully navigate, identify, evaluate and prioritize risk to minimize negative impacts to the business.
- Manage partnerships in alignment with contracts.
- Relationship Management: Ensure healthy partner relationships that both position the partnership for success in achieving objectives, and are aligned with League's core values.
- Develop and nurture relationships at all levels (including senior executives) and across all applicable functions within the partner organization. Identify and collaborate with key decision-makers and influencers.
- Coordinate governance (e.g. QBRs) with key stakeholders to drive partnerships forward.
- Manage partnerships such that teams that are responsive, execute, make decisions, ideate well together, and trust each other. If one of these tenants falls, you ensure that it is promptly addressed.
- Security-related responsibilities:
- Compliance with Information Security Policies
- Responsibility and accountability for executing League's policies and procedures
- Notification of HR, Legal, Compliance & Security of any incidents, breaches or policy violations
We're looking for:
- 5+ Years of partner or channel development/management, co-selling, and/or experience working with ISVs, Global System Integrators (e.g. Deloitte, Accenture - experience in digital transformation a bonus) and/or with a Cloud Provider (e.g. Google, Microsoft, AWS)
- 5+ years of partner management experience with revenue-generating KPIs
- Experience building partner evaluation frameworks, building and onboarding new partners, and ongoing execution of the partnership post-launch.
- 7+ years of experience in healthcare/digital health
- AI and agentic platform literacy
- Nice-to-have:
- Consulting, investment banking, corporate development experience and/or MBA
- AI-native platform experience
- Entrepreneurial experience or experience building net new partner revenue lines at a hyper-growth organization
- Strong understanding of the payor market
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
- 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
- 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
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.
CANADA APPLICANTS ONLY: The Canada-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 Canadian 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.
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 recruitinginfo@league.com.
- 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.
- Learn about our platform, leadership team and partners
- Highmark Health, Google Cloud, League: new digital front door to seamless care
- Former Providence President and Workday EVP of Corporate Strategy join League Board of Directors
- League raises $95 million USD in Series C to build world’s leading healthcare CX platform
- Forbes x League: The Platformization Of Healthcare Is Here
- Fast Company x League: If we want better innovations in healthtech, we need more competition
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.
Recognize and Avoid Employment scams. Practice safe job searching.
Scammers are getting craftier and leveraging fake job postings to get personal information. Know the warning signs and protect yourself from scammers. Learn more here.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.
Ready to apply?
Apply to League Inc.
Director, Sales and Account Management
Share this job
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:
League’s PaaS business, Powered by League, is rapidly scaling. Building on the proven success among our market-leading customers and partners including Medibank, Highmark Health, Google, Accenture, Manulife, and Shoppers Drug Mart - our Go-to-Market team is expanding and seeking a Director, Sales & Account Management to help us achieve this next phase of growth.
As a Director, Sales & Account Management, you will be a core part of the Go-to-Market team working across priority segments including Private Health Insurers, Private Healthcare Providers, Public Sector Health Agencies, Retail Pharmacies, and Digital Health Innovators. You will be responsible for leading complex enterprise-scale business development and sales initiatives with prospects and carry a quota for Powered by League platform sales. In addition, responsible for nurturing and growing existing client relationships, identifying new opportunities within these accounts, and ensuring the long-term success and satisfaction of League’s customers in Australasia.
Working in collaboration with other parts of the Go-to-Market team (including Solution Engineering, Partnerships and Product Marketing) as well as our Delivery & Product Management functions, you will identify, design, plan and deliver impactful customer partnerships that power the transformation of their digital consumer, member or patient experiences.
In this role you will:
- Be the first Growth & Customer employee on the ground in Australia, representing League in this important new growth market, and supporting our flagship customers (one each in Australia & New Zealand)
- Support League’s international growth - working closely with our Growth Organisation including: Account Management and Sales Leadership.
- Lead and own the end-to-end sales process for target platform strategic accounts, including formulating sales strategy, driving revenue growth and developing new customer relationships.
- Develop and execute comprehensive account plans for League’s Australiasian customer base, outlining clear objectives, strategies, and tactics to drive revenue growth.
- Leverage your own relationships to build pipeline (both net new and up-sell / cross-sell of new solutions to existing customers), and work in partnership with the Business Development and Marketing teams to run account-based marketing campaigns that lead to closed revenue and quota attainment.
- Successfully achieve and exceed budgeted sales objectives, and maintain sales forecast in an accurate and thorough manner.
- Negotiate complex software and professional services agreements from initial stages through to completion; and execute contract amendments and renewals
- Create demand by leveraging healthcare industry expertise and what the priorities from C-level executives are, uncovering business problems for prospects and customers and matching them to our solution.
- Work collaboratively with League Executives and Go-to-Market leaders to build the story and tailored materials for meetings with prospective accounts.
- Work with the Go-to-Market leadership team to create and improve sales processes and buyer journeys, especially in new industry verticals.
- Serve as the voice of the Australiasian customer base ensuring their needs and priorities are understood and addressed and proactively identify and communicate product needs of Powered by League prospects and industry verticals to executive and product leadership.
- Cultivate and maintain strong, trusted advisor relationships with key stakeholders within League’s customer base and establish and monitor key performance indicators (KPIs) for customer health, providing regular reporting and actionable insights to internal stakeholders.
- Work with the Value Realization function to measure impact and ensure customers are consistently achieving their desired business outcomes and realizing the full value of League's platform and services.
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
About you:
- 10 years of experience in ‘Platform as a Service’ (PaaS) or ‘Software as a Service’ (SaaS) sales and account management experience
- 5 years of healthcare industry experience in digital transformation and/or consumer & patient engagement sales required
- Strong knowledge of the Australian healthcare industry (Providers, Pharmacy Retailers) and/or health benefits industry
- A history of successful quota attainment in a complex sales environment
- Exceptional relationship-building and interpersonal skills, with the ability to establish rapport, build trust and win the support of key C-suite executives in large corporations
- Demonstrated ability to develop and execute strategic account plans that drive measurable results
- Excellent analytical and problem-solving skills, with the ability to interpret data and develop actionable insights
- Proficiency with Salesforce and sales acceleration tools
- Experience developing exceptional documentation for client presentations and webinars
- Bachelor's degree in Business or equivalent experience
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
- 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
- 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
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 recruitinginfo@league.com.
- 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.
- Learn about our platform, leadership team and partners
- Highmark Health, Google Cloud, League: new digital front door to seamless care
- Former Providence President and Workday EVP of Corporate Strategy join League Board of Directors
- League raises $95 million USD in Series C to build world’s leading healthcare CX platform
- Forbes x League: The Platformization Of Healthcare Is Here
- Fast Company x League: If we want better innovations in healthtech, we need more competition
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.
Recognize and Avoid Employment scams. Practice safe job searching.
Scammers are getting craftier and leveraging fake job postings to get personal information. Know the warning signs and protect yourself from scammers. Learn more here.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.
Ready to apply?
Apply to League Inc.
Director, Platform Sales - Canada
Share this job
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:
League’s footprint is strategically scaling. Building on the proven success among our market-leading customers and partners in Canada and the US, our Go-to-Market team is expanding and seeking a Director, Platform Sales to help us achieve this next phase of growth.
As a Director, Platform Sales, you will be a core part of the Go-to-Market team working across priority segments including public sector, healthcare providers, insurers, pharmacy retailers and digital health innovators. You will be responsible for leading complex enterprise-scale business development and sales initiatives with prospects and carry a quota for our consumer experience platform sales.
Working in collaboration with other parts of the Go-to-Market team (including Solution Engineering, Partnerships, Product Marketing), you will strategize, scope and design impactful customer partnerships that power the digital transformation of their consumer, member or patient experience.
In this role you will:
- Focus on expanding League’s footprint in Canada and building on the success of existing customer relationships.
- Lead and own the end-to-end sales process for target platform strategic accounts including formulating sales strategy, driving revenue growth and developing new customer relationships.
- Leverage your own relationships to build pipeline, and work in partnership with the Business Development and Marketing teams to run account-based marketing campaigns that lead to closed revenue and quota attainment.
- Successfully achieve and exceed budgeted sales objectives, and maintain sales forecast in an accurate and thorough manner.
- Negotiate complex software and professional services agreements from initial stages through to completion.
- Create demand by leveraging healthcare industry expertise and what the priorities from C-level executives are, uncovering business problems and matching them to our solution.
- Work collaboratively with League Executives and Go-to-Market leaders to build the story and tailored materials for meetings with prospective accounts.
- Work with the Go-to-Market leadership team to create and improve sales processes and buyer journeys, especially in new industry verticals.
- Proactively identify and communicate product needs of Powered by League prospects and industry verticals to executive and product leadership.
- Ensure and monitor successful handoffs of accounts from the sales process and into customer strategy and delivery.
About you:
- 8+ years of experience in ‘Platform as a Service’ (PaaS) or ‘Software as a Service’ (SaaS), digital transformation and/or consumer & patient engagement sales required
- Previous experience in a consulting role focusing on digital health and consumer experience is a significant asset
- Knowledge of the healthcare industry, especially public healthcare services and provincial/territorial health plans
- A history of successful quota attainment in a complex sales environment
- Ability to win the support of key C-Suite stakeholders in large corporations
- Proficiency with Salesforce and sales acceleration tools
- Experience developing exceptional documentation for client presentations and webinars
- Bachelor's degree in Business or equivalent experience
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
- 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
- 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
- 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
CANADA APPLICANTS ONLY: The Canada-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 Canadian 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.
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 recruitinginfo@league.com.
- 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.
- Learn about our platform, leadership team and partners
- Highmark Health, Google Cloud, League: new digital front door to seamless care
- Former Providence President and Workday EVP of Corporate Strategy join League Board of Directors
- League raises $95 million USD in Series C to build world’s leading healthcare CX platform
- Forbes x League: The Platformization Of Healthcare Is Here
- Fast Company x League: If we want better innovations in healthtech, we need more competition
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.
Recognize and Avoid Employment scams. Practice safe job searching.
Scammers are getting craftier and leveraging fake job postings to get personal information. Know the warning signs and protect yourself from scammers. Learn more here.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.
Ready to apply?
Apply to League Inc.
Director, Platform Sales
Share this job
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:
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 SalesForce and sales acceleration tools
- Experience developing exceptional documentation for client presentations, webinars
- Bachelor's degree in Business or equivalent experience
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
- 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
- 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
- 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.
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 recruitinginfo@league.com.
- 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.
- Learn about our platform, leadership team and partners
- Highmark Health, Google Cloud, League: new digital front door to seamless care
- Former Providence President and Workday EVP of Corporate Strategy join League Board of Directors
- League raises $95 million USD in Series C to build world’s leading healthcare CX platform
- Forbes x League: The Platformization Of Healthcare Is Here
- Fast Company x League: If we want better innovations in healthtech, we need more competition
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.
Recognize and Avoid Employment scams. Practice safe job searching.
Scammers are getting craftier and leveraging fake job postings to get personal information. Know the warning signs and protect yourself from scammers. Learn more here.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.
Ready to apply?
Apply to League Inc.
Director, Platform Sales
Share this job
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:
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 SalesForce and sales acceleration tools
- Experience developing exceptional documentation for client presentations, webinars
- Bachelor's degree in Business or equivalent experience
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
- 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
- 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
- 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.
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 recruitinginfo@league.com.
- 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.
- Learn about our platform, leadership team and partners
- Highmark Health, Google Cloud, League: new digital front door to seamless care
- Former Providence President and Workday EVP of Corporate Strategy join League Board of Directors
- League raises $95 million USD in Series C to build world’s leading healthcare CX platform
- Forbes x League: The Platformization Of Healthcare Is Here
- Fast Company x League: If we want better innovations in healthtech, we need more competition
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.
Recognize and Avoid Employment scams. Practice safe job searching.
Scammers are getting craftier and leveraging fake job postings to get personal information. Know the warning signs and protect yourself from scammers. Learn more here.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.
Ready to apply?
Apply to League Inc.
Director, Platform Sales
Share this job
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:
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 SalesForce and sales acceleration tools
- Experience developing exceptional documentation for client presentations, webinars
- Bachelor's degree in Business or equivalent experience
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
- 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
- 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
- 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.
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 recruitinginfo@league.com.
- 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.
- Learn about our platform, leadership team and partners
- Highmark Health, Google Cloud, League: new digital front door to seamless care
- Former Providence President and Workday EVP of Corporate Strategy join League Board of Directors
- League raises $95 million USD in Series C to build world’s leading healthcare CX platform
- Forbes x League: The Platformization Of Healthcare Is Here
- Fast Company x League: If we want better innovations in healthtech, we need more competition
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.
Recognize and Avoid Employment scams. Practice safe job searching.
Scammers are getting craftier and leveraging fake job postings to get personal information. Know the warning signs and protect yourself from scammers. Learn more here.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.
Ready to apply?
Apply to League Inc.
Director, Platform Sales
Share this job
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:
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 SalesForce and sales acceleration tools
- Experience developing exceptional documentation for client presentations, webinars
- Bachelor's degree in Business or equivalent experience
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
- 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
- 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
- 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.
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 recruitinginfo@league.com.
- 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.
- Learn about our platform, leadership team and partners
- Highmark Health, Google Cloud, League: new digital front door to seamless care
- Former Providence President and Workday EVP of Corporate Strategy join League Board of Directors
- League raises $95 million USD in Series C to build world’s leading healthcare CX platform
- Forbes x League: The Platformization Of Healthcare Is Here
- Fast Company x League: If we want better innovations in healthtech, we need more competition
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.
Recognize and Avoid Employment scams. Practice safe job searching.
Scammers are getting craftier and leveraging fake job postings to get personal information. Know the warning signs and protect yourself from scammers. Learn more here.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.
Ready to apply?
Apply to League Inc.
Director, Platform Sales
Share this job
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:
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 SalesForce and sales acceleration tools
- Experience developing exceptional documentation for client presentations, webinars
- Bachelor's degree in Business or equivalent experience
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
- 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
- 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
- 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.
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 recruitinginfo@league.com.
- 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.
- Learn about our platform, leadership team and partners
- Highmark Health, Google Cloud, League: new digital front door to seamless care
- Former Providence President and Workday EVP of Corporate Strategy join League Board of Directors
- League raises $95 million USD in Series C to build world’s leading healthcare CX platform
- Forbes x League: The Platformization Of Healthcare Is Here
- Fast Company x League: If we want better innovations in healthtech, we need more competition
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.
Recognize and Avoid Employment scams. Practice safe job searching.
Scammers are getting craftier and leveraging fake job postings to get personal information. Know the warning signs and protect yourself from scammers. Learn more here.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.
Ready to apply?
Apply to League Inc.
Director, Platform Sales
Share this job
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:
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 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 SalesForce and sales acceleration tools
- Experience developing exceptional documentation for client presentations, webinars
- Bachelor's degree in Business or equivalent experience
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
- 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
- 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
- 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.
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 recruitinginfo@league.com.
- 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.
- Learn about our platform, leadership team and partners
- Highmark Health, Google Cloud, League: new digital front door to seamless care
- Former Providence President and Workday EVP of Corporate Strategy join League Board of Directors
- League raises $95 million USD in Series C to build world’s leading healthcare CX platform
- Forbes x League: The Platformization Of Healthcare Is Here
- Fast Company x League: If we want better innovations in healthtech, we need more competition
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.
Recognize and Avoid Employment scams. Practice safe job searching.
Scammers are getting craftier and leveraging fake job postings to get personal information. Know the warning signs and protect yourself from scammers. Learn more here.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.
Ready to apply?
Apply to League Inc.
Principal, Solution Engineering (Evergreen)
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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:
The solution consulting & sales engineering team is a critical part of League’s growth organization, focused on applying League’s platform capabilities to power new digital consumer experiences in healthcare.
Through collaborating with League’s market development, strategic sales, customer, partner, product & implementation teams, Solutions Engineering partners with the world’s leading healthcare organizations to design new digital business models, products, and experiences. League’s growth organization supports organizations across the Payer, Provider, Life Sciences, and Consumer Health markets (i.e., Pharmacy Retail).
As Principal, Solutions Engineering, you are a leader in League’s solution consulting & sales engineering team. You take a leadership role in having a deep understanding of the League platform, and are able to connect customer business priorities with League’s technology capabilities - while helping to chart League’s broader strategy for how our platform delivers a better digital health experience for consumers.
Note: this is an Evergreen role as we are always building our talent pipeline. This is a recurring role on our team and we are always excited to meet talent who may be a fit now or in the future.
In this role, you will:
- As a Principal, Solutions Engineering, you are a leader on the pre-sales team at League, partnering with Strategic Account Directors to showcase League’s platform capabilities, understand prospective customers’ business & digital requirements, visualize League’s platform capabilities, and collaborate with customers to align their needs with League’s market-leading capabilities and solutions.
- Design Digital Consumer Experiences - you will partner with prospective customers, and their business, product, digital & IT teams to design ‘what’s possible’ in redefining the role of digital in delivering healthcare and benefits for millions of consumers
- Align Platform Capabilities to Business Value - you will demonstrate a deep knowledge and understanding of League’s platform and technology capabilities with the ability to architect solutions and articulate how those solutions connect to the key business drivers for our prospective customers (e.g., business growth, service automation, experience transformation, high engagement care delivery, population health, etc.)
- Visualize Best-in-Class Health Experiences - bring to life League’s platform capabilities through presentations, mock-ups, and demonstrations by partnering with League’s product & design teams
- Partner for Success - you will work cross-functionally at League with our customer, implementation, product and engineering teams to turn strategy, solutions and requirements into concrete action plans to build, launch & scale our customers’ new digital health experiences
- Growth Team Alignment - you will work with Strategic Account Directors on RFP/RFIs, partner contracts and technical evaluations
- Security-related responsibilities:
- Compliance with Information Security Policies
- Compliance with League’s secure coding practice
- Responsibility and accountability for executing League's policies and procedures
- Notification of HR, Legal, Compliance & Security of any incidents, breaches or policy violations
What we're looking for:
- 8+ years Solutions Engineering / Pre-Sales / Solutions Consulting experience
- 10+ years total professional experience
- Deep healthcare (specifically Payer) industry experience in sales, business development and/or strategy consulting
- Experience in leading solution architecture and software demonstrations for healthcare IT, digital health and/or patient engagement solutions
- Platform-as-a-Service or Software-as-a-Service experience
- Excellent storytelling and communication skills, including presenting complex solutions, concepts & ideas to executive, technical and/or non-technical audiences
- Bachelor equivalent - minimum
Nice-to-Have
- Master equivalent
- Product Management experience
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.
CANADA APPLICANTS ONLY: The Canada-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 Canadian 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.
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 recruitinginfo@league.com.
- 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.
- Learn about our platform, leadership team and partners
- Highmark Health, Google Cloud, League: new digital front door to seamless care
- Former Providence President and Workday EVP of Corporate Strategy join League Board of Directors
- League raises $95 million USD in Series C to build world’s leading healthcare CX platform
- Forbes x League: The Platformization Of Healthcare Is Here
- Fast Company x League: If we want better innovations in healthtech, we need more competition
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.
Recognize and Avoid Employment scams. Practice safe job searching.
Scammers are getting craftier and leveraging fake job postings to get personal information. Know the warning signs and protect yourself from scammers. Learn more here.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.
Ready to apply?
Apply to League Inc.