League Inc.
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Technical Delivery Project Manager (Talent Pool Building)
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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.
The Role
As a Technical Delivery Project Manager, you support the successful execution of internal technical workstreams required for customer delivery. You serve as the day-to-day liaison between internal technical teams (e.g., Data Engineering, Data Science, Integrations, R&D) and the customer-facing delivery team. You coordinate technical requirements, gather inputs from customers, help translate requirements into internal technical tasks, manage supporting documentation, and ensure technical deliverables are completed on time.
In this role, you work closely with the Delivery Lead and functional technical leads to ensure alignment, visibility, and smooth execution of technical dependencies. You apply strong working knowledge of tools like Jira and foundational technical literacy to understand and communicate risks, issues, and timelines. You operate with growing independence while receiving guidance for complex or ambiguous matters.
One specific area of responsibility is to manage League’s customer-facing data product called Analytics Objects (AOs), which is a recurring data export of complex KPIs configured to meet a wide range of customer requirements. Your responsibilities include:
In this role, you are expected to:
Technical Workstream Coordination
- Coordinate technical tasks and dependencies across Data, Engineering, R&D, and other internal technical teams.
- Translate customer requirements into clear Jira tickets or internal work items.
- Maintain visibility into task progress, blockers, and timelines.
Manage Data Products
- Coordinate launch of Analytics Objects (AOs) and other data products to customers.
- Manage the configuration of AOs and other data products to suit customer use cases.
- Manage customization requests and recommend existing solutions to customers as needed. Coordinate with product managers on custom solutions.
Customer Engagement & Requirements Gathering
- Attend customer-facing technical requirement meetings as a supporting point of contact.
- Document technical requirements and ensure internal technical teams understand expected outcomes.
- Communicate updates, risks, and next steps back to customer-facing stakeholders.
Jira & Tooling Ownership
- Support maintaining Jira boards, grooming tasks, updating statuses, and ensuring accurate workflow progression for tasks related to customer delivery.
- Support reporting on technical delivery progress and timelines.
Risk & Issue Management
- Identify and flag risks or blockers related to technical workstreams.
- Escalate issues to the Delivery Lead or technical leads as needed.
Technical Delivery Support
- Support internal test cycles, data validation activities, and technical documentation requirements.
- Understand and articulate the impact of deviations from standard practices.
Process & Documentation
- Maintain technical requirement documentation, task tracking, and workstream-level artifacts.
- Contribute feedback to help improve technical delivery processes and tooling.
About You:
- 3+ years in SaaS technical coordination, technical support, or data operations.
- Working knowledge of data platforms (Airflow, BigQuery, Looker, or similar).
- Strong proficiency with Jira for workflow tracking and ticket management.
- Foundational understanding of SaaS architectures, APIs, data pipelines, or ETL.
- Experience collaborating with Data teams, R&D, or technical SMEs.
- Experience managing projects with complex technical dependencies.
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
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
Please note: We’re always excited to connect with exceptional talent. This posting is part of our proactive talent community efforts. While there may not be an immediate opening, we review applications on an ongoing basis and reach out as opportunities arise.
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
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 - Canada
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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:
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.