League Inc.

Lead the strategy and execution for a high-scale healthcare platform focusing on member experience and AI integration. | 6+ years in product management within US healthcare, experience with complex platforms, and leadership in agile environments. | 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: As a Principal Product Manager, you are the strategic architect of a sophisticated, high-scale platform for our Member Portal Solution for payer customers. You are directly responsible for accelerating our 2026 growth trajectory and long-term AI-native vision. While we operate a robust digital infrastructure, we are at a pivotal moment of evolution—leveraging our high-scale foundations to drive an AI-native experience that is proactive, personalized, and dynamic. Your mission is to drive the successful hardening of our core digital product capabilities while leading this strategic shift. This role requires a high degree of fluency in the US Payer landscape, claims data, and benefits orchestration. You will leverage the voice of the customer and deep healthcare market insights to inform our data-backed roadmap that prioritizes long-term margin expansion, TAM growth, and member experience quality. You will provide the strategic leverage required to de-risk delivery, mitigate architectural gaps before they become fires, and influence the Executive team with high-quality logic and roadmap rigor. In this role, you will: Serve as the subject matter expert for US Healthcare integrations, with a primary focus on helping members navigate the complexities of the healthcare system—specifically demystifying EOBs, claims status, accumulators, and complex benefits. Drive the product strategy for administrative self-service, ensuring members can easily take care of necessary actions and understand their financial and health data without friction. Synthesize complex member needs and market dynamics into a solidified, roadmap focused on new revenue generation and efficiency. Create buy-in for the product strategy with the Product Leadership Team through high-quality logic and rigorous business-case storytelling. Define and execute a roadmap to increase the utilization of key features, proving that users can successfully complete their intended tasks and derive tangible value from the portal. Ensures cross-functional alignment across the 'Triangle' (Product, Engineering, Design) to eliminate silos to the Essential Duties. Define goals & measure success for the portfolio. Represent our platform and infrastructure externally with clients and prospects. Establish and deliver a high-integrity roadmap built to ensure predictable, high-scale execution, characterized by vetted trade-offs and binary commitments. Significantly expand member reach and engagement. Accelerate program enrollment, feature adoption, and task completion rates through optimized member journeys, delivering measurable ROI for payer customers. Drive industry-leading utilization and accuracy across core member domains including coverage, cost, claims, and accumulators, ensuring seamless member access to their financial and health data. Optimize the home screen and overall information architecture (IA) of the Member Portal to ensure the experience is optimized for discoverability, findability, self service, and ease of use. Successfully transition AI prototypes into production-grade experiences that redefine the member experience and achieve market readiness. About You: 6+ years in Product Management with a minimum of 3 years specifically in the US Payer or Health Insurance space. Bachelor’s degree (or equivalent), preferred Proven work experience in product management creating successful products Proven ability to move an organization through architecting rather than individual output. Experience working at a platform company or leading the implementation of complex platforms. You have deep experience in agile methodologies—leading agile release planning and demonstrating an iterative, incremental, and value-driven delivery. 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 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 Compliance with Information Security Policies 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. Compensation range for USA applicants only $169,900—$207,700 USD 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. Here are some additional resources to learn more about League: 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.

The Principal AI Engineer will design, build, and maintain a scalable platform for AI/ML workloads while leading the MLOps strategy. This role involves collaborating with teams to implement AI solutions and ensuring platform excellence in performance and security. | Candidates should have extensive experience in software engineering and a strong understanding of the machine learning lifecycle. Proficiency in cloud platforms, programming languages, and MLOps tools is essential. | 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 We're looking for an exceptional Principal AI Engineer to join our Software Platform Engineering team. This role is a unique opportunity to shape the future of digital health by designing, building, and scaling the core platform that enables our AI-driven products. You will act as a technical leader, architecting the foundational systems and tools that empower data scientists and engineers to efficiently build, deploy, and manage machine learning models at scale. You will have a direct impact on our mission to help users lead healthier, happier lives by ensuring our AI platform is robust, secure, and performant. Your work will not only involve hands-on system development but also mentoring others and setting the technical vision for how we operationalize AI across League What you will do: Architect and Develop AI Infrastructure: Design, build, and maintain a highly scalable and reliable platform for AI/ML workloads, including model training, serving, and monitoring Lead MLOps Strategy: Champion and implement best practices for Machine Learning Operations (MLOps) to automate and streamline the entire model lifecycle, from experimentation to production deployment and maintenance Collaborate and Mentor: Work closely with data scientists, data engineers, and product teams to translate business needs into technical requirements and guide the implementation of AI solutions. You will be a key mentor, providing technical guidance and raising the engineering bar for the entire team Ensure Platform Excellence: Establish standards and best practices for performance, security, data governance, and reliability within the AI platform Evaluate and Innovate: Continuously evaluate new technologies, tools, and frameworks to improve the efficiency, speed, and capabilities of our AI platform What you bring: Deep Technical Expertise: Extensive hands-on experience in software engineering and a strong understanding of the entire machine learning lifecycle Platform-Level Thinking: Proven ability to design and build scalable, distributed systems, ideally for machine learning or data-intensive applications MLOps Mastery: Demonstrated experience with MLOps tools and practices, including CI/CD for machine learning, model versioning, and feature stores Cloud Proficiency: Expertise with public cloud platforms (e.g., AWS, GCP, Azure) and a solid understanding of containerization and orchestration technologies like Docker and Kubernetes Data Fluency: A strong grasp of data engineering concepts, including data pipelines, data warehousing, and distributed data processing frameworks Exceptional Leadership: The ability to lead technical conversations, influence decisions, and effectively mentor junior and senior engineers Required Tech Stack: Cloud Platforms: Extensive experience with AWS and/or GCP, including core compute, storage, and networking services Programming Languages: Expert-level proficiency in Python and familiarity with Go for backend services Data & AI Frameworks: Experience with big data processing platforms like Apache Spark, Apache Beam, Hadoop, etc Familiarity with modern machine learning frameworks such as TensorFlow, PyTorch, and scikit-learn MLOps & Orchestration: Deep understanding of MLOps principles and experience with tools like Kubeflow, MLflow, or AWS SageMaker Experience with workflow orchestration tools like Airflow or a similar platform DevOps & Infrastructure:Expertise in containerization and orchestration using Docker and Kubernetes Hands-on experience with Infrastructure as Code (IaC) tools like Terraform Data Systems: Experience with both relational and NoSQL databases, and familiarity with data warehousing and streaming technologies Security-related Responsibilities 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 Compliance with Information Security Policies 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. Compensation range for USA applicants only $214,800—$268,500 USD 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. Here are some additional resources to learn more about League: 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 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.