A leading healthcare technology company seeks a Technical Delivery Project Manager in Toronto. The role involves coordinating technical projects, managing customer-facing data products, and ensuring effective communication among teams. Candidates should have 3+ years of experience in technical coordination, proficiency in Jira, and knowledge of data platforms. The compensation range is CAD 94,900 - 115,900. This position offers comprehensive health benefits, a bonus program, and unlimited paid time off. #J-18808-Ljbffr
About League
Founded in 2014 , League is the leading healthcare consumer experience (CX) platform, powered by artificial intelligence (AI), reaching more than 63 million people around the world and delivering the highest level of personalization in the industry. Payers, providers, and consumer health partners build on League’s platform to deliver high-engagement healthcare solutions proven to improve health outcomes. League has raised over $285 million in venture capital funding to date, powering the digital experiences for some of healthcare’s most trusted brands, including Highmark Health, Manulife, Medibank, and Shoppers Drug Mart.
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.
In This Role, You Are Expected To
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:
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
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.
Compensation range for Canada applicants only
$94,900—$115,900 CAD
Our employees come from different backgrounds, and we celebrate those differences. We are looking for the best candidates for our open roles, but do not expect applicants to meet every qualification in order to be considered. If you are excited about what you could accomplish at League and believe you can add value to our team, we would love to hear from you.
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.
Our Application Process
Applying to a role you love can be exhausting, and understanding the next steps can feel vague and uncertain. You have done the hard part of submitting your application; let's do ours by sharing potential next steps
You should receive a confirmation email after submitting your application.
A recruiter (not a computer) reviews all applications at League.
If we see alignment with League's needs, a recruiter will reach out to learn more about your goals. The recruiter will also share the team-specific interview process depending on the roles you are exploring.
The final step is an offer, which we hope you will accept!
Prior to joining us, we conduct reference and background checks. Additional checks could be required for US Candidates, depending on the role you are exploring.
Additional Resources
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.
Use of AI Notice
We are committed to ensuring fairness and transparency throughout our hiring process. League may use Artificial Intelligence (AI) tools to assist in the screening of applicants for this position. Please check out our stance on using AI in recruitment here.
Privacy Policy
Review our Privacy Policy for information on how League is protecting personal data.
#J-18808-Ljbffr
About League
Founded in 2014, League is the leading healthcare consumer experience (CX) platform, powered by artificial intelligence (AI), reaching more than 63 million people around the world and delivering the highest level of personalization in the industry. Payers, providers, and consumer health partners build on League’s platform to deliver high‑engagement healthcare solutions proven to improve health outcomes. League has raised over $285 million in venture capital funding to date, powering the digital experiences for some of healthcare’s most trusted brands, including Highmark Health, Manulife, Medibank, and Shoppers Drug Mart.
Position Summary
The Quality Assurance Analyst plays a critical role in ensuring product excellence by leading testing strategy and execution across functional, integration, and end‑to‑end systems. This individual serves as the primary QA partner on implementation initiatives, driving comprehensive test coverage, strengthening automation frameworks, and preventing critical defects from reaching customers. Through strong collaboration with Engineering and project teams, the Senior QA Analyst safeguards release quality and ensures on‑time, high‑confidence deployments.
What You’ll Be Doing
Serve as primary tester on implementation projects.
Develop and maintain test plans and test cases based on project and technical requirements.
Creates and executes functional, integration / E2E test cases to validate business systems.
Ensures our products meet high quality standards. Conduct peer reviews of test cases to ensure depth and breadth of test coverage.
Reviews automated test case execution results; analyzing results to identify potential issues.
Adds functionality to test cases using an automated test framework/suite.
Identify, document and prioritize defects using Jira; collaborate with engineers and project team to understand requirements.
Execute automated test scripts and analyze results to identify defects and report issues.
Work closely with the Engineering team; track development progress and identify risks and issues related to quality deliverables.
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
What We’re Looking For
Bachelor’s degree in Computer Science, Engineering, or a related field.
5+ years experience in Quality Assurance. Ability to write test plans, test cases and follow processes.
Expertise in manual testing including functional, integration, E2E and regression testing.
Experience running test automation and reviewing results. Ability to understand business requirements and develop comprehensive test scenarios that include positive and negative testing.
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.
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. 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.
Compensation range for Canada applicants only
$75,000—$90,000 CAD
Our employees come from different backgrounds, and we celebrate those differences. We are looking for the best candidates for our open roles, but do not expect applicants to meet every qualification in order to be considered. If you are excited about what you could accomplish at League and believe you can add value to our team, we would love to hear from you.
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.
Our Application Process
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.
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.
Use of AI Notice
We are committed to ensuring fairness and transparency throughout our hiring process. League may use Artificial Intelligence (AI) tools to assist in the screening of applicants for this position. Please check out our stance on using AI in recruitment here.
Privacy Policy
Review our Privacy Policy for information on how League is protecting personal data.
#J-18808-Ljbffr
A leading healthcare technology company is seeking a Senior Product Manager to manage client relationships and product roadmaps. The ideal candidate has over 5 years of experience in product management, particularly in healthcare, with strong client-management skills. Responsibilities include managing product discovery and engaging with both internal stakeholders and clients to ensure successful implementation of solutions. This position allows for a mix of in-office and remote work based in Canada. #J-18808-Ljbffr
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. League has raised over $285 million in venture capital funding to date, powering the digital experiences for some of healthcare’s most trusted brands.
The role
League’s platform enables our customers to offer highly engaging and personalized health experiences to their users. The Appsixels & Solutions Senior Product Manager is a customer‑facing role that is instrumental in helping define the long‑term strategy and roadmaps for some of the most complex applications powered by League.
In this role you will build unab maintain strong relationships with client leaders and fellow PMs, ensuring a deep understanding of their priorities, smooth implementations and delivery of features, expert product solutioning, professional and timely client communication, and execute strong product judgment.
Manage the roadmap for various A&S customers, identifying opportunities to create new capabilities or optimize existing ones.
Develop the client relationship via offering, educating and delivering League solutions, and promoting the client’s vision and needs within League.
Run product discovery, compile product requirements, and solicit engineering feedback to create solution definitions that are strategic and compelling.
Serve as a subject‑matter expert on League platform capabilities, evangelizing the value of the League platform to stakeholders.
Proactively manage and prioritize the backlog of enhancements.
Monitor engagement with the applications you are managing and identify opportunities to create value and exceed our goals.
Communicate effectively and clearly articulate trade‑offs to internal and external leadership.
Define requirements and value proposition of custom features and complex capability deployments.
Monitor application performance and identify opportunities to create more value and exceed our goals.
Partner with Account Management to be the primary Product Management point of contact with our customer.
About You
5+ years of Product Management experience.
Digital healthcare experience; experience with the payer market is preferred.
Exceptional client‑management skills, ensuring requirements are accurately captured, communication is clear, and relationships are developed.
Expert at balancing client requests with organizational goals.
Expert‑level feature solutioning that includes soliciting internal stakeholder feedback.
Experience working with large engineering teams of various types, including SI’s.
Experience working at a platform company or on the implementation of platforms.
Strong desire to tighten every feedback loop regarding the product.
Experience with large corporate clients and communication with corporate leaders.
Excellent communication, presentation, interpersonal and analytical skills.
Demonstrated problem‑solving skills and business acumen.
Ability to learn quickly and gain proficiency in areas with limited experience.
Passionate about Generative AI and its potential to accelerate product workflows and improve customer experience.
Thrives in a fast‑paced environment where priorities shift rapidly and needs compete.
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.
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.
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 the US. Each job posting will indicate the role’s location. Toronto‑area Leaguers collaborate in‑office Monday through Thursday.By distance to the office, you’ll enjoy 10 or 20 flexible remoteесу each quarter.
#J-18808-Ljbffr
A leading healthcare technology company in Toronto seeks a Director of Growth Enablement to architect enablement strategy, curate training programs, and leverage AI for sales enablement. Candidates should have 8+ years of product marketing experience, particularly in B2B SaaS, and a strong understanding of healthcare technology. The role requires excellent communication and organizational skills, as well as a data-driven approach to measuring impact. #J-18808-Ljbffr
A leading healthcare technology company is seeking a Senior AI Engineer to join their AI & Data Group. The role involves designing and building production-grade AI systems, including RAG pipelines and distributed software engineering tasks. The ideal candidate should have extensive experience in software engineering, MLOps mastery, and a strong understanding of cloud platforms. The position is primarily based in Toronto, Canada, but offers flexibility for remote work. #J-18808-Ljbffr
A leading healthcare technology company is seeking a Quality Assurance Analyst based in Toronto, Ontario. This role is crucial for ensuring product excellence by managing the testing strategy and execution across various systems. The ideal candidate will have at least 5 years of experience in Quality Assurance, proficient in manual testing and automation tools, particularly Jira. Competitive salary ranging from CAD 75,000 to CAD 90,000 is offered, reflecting job-related skills and experience. Apply now to be part of a dynamic team! #J-18808-Ljbffr
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:
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.
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.
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.
Qualifications
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.
Benefits
Comprehensive Health Benefits: complete medical, dental, and vision coverage.
Bonus Program: performance‑based bonus program.
Employee Stock Option Program: share in our success through stock options.
Unlimited Paid Time Off.
Spending Accounts: tax‑advantaged accounts for healthcare and dependent care expenses.
Wellness Days: dedicated wellness days throughout the year.
Growth Opportunities: professional development and advancement.
Mentorship Program: guidance and support from experienced leaders.
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.
Compensation Range (Canada Only)
$94,900 - $115,900 CAD
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 .
Application Process
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.
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.
#J-18808-Ljbffr
A leading healthcare technology firm in Toronto seeks a Technical Delivery Project Manager to coordinate technical deliverables and manage customer-facing data products. This role involves maintaining the technical workflow through Jira, translating customer requirements, and ensuring timely delivery of complex KPIs. Ideal candidates have over 3 years in SaaS technical coordination and strong proficiency with data platforms. Competitive salary of $94,900 to $115,900 CAD offered, along with comprehensive health benefits and a bonus program. #J-18808-Ljbffr
