Posted 1 month ago
VP, AI Engineering
AI Summary
Leads the design and delivery of League’s AI engineering and data platform, defining architecture, governance, and operational practices for AI-native healthcare solutions.
About this role
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 is seeking a VP, AI Engineering to lead the technical vision, architecture strategy, and operational execution of our next-generation AI and data ecosystem.
Reporting into senior technology leadership, this role sits at the intersection of AI engineering, healthcare intelligence, and enterprise architecture. You will be responsible for defining how League’s AI-native platform capabilities are architected, governed, scaled, and operationalized across our healthcare ecosystem.
This is a deeply strategic and highly technical leadership role. You will guide the evolution of League’s AI and data architecture strategy while partnering closely with Engineering, Product, Security, Data Science, Infrastructure, and Go-to-Market leadership to ensure scalable, secure, and high-performing systems that power consumer healthcare experiences for millions of members.
You will lead teams responsible for:
- AI and agentic systems architecture
- ML infrastructure and orchestration
- Data governance and interoperability
- AI-native engineering enablement
- Scalable analytics and operational intelligence systems
AI & Data Architecture Leadership
- Define and evolve League’s enterprise AI and data architecture strategy across platform, product, and operational systems.
- Lead architectural modernization initiatives focused on cloud-native AI systems, data orchestration, and scalable healthcare intelligence platforms.
- Establish architectural standards, governance frameworks, and engineering guardrails across AI and data ecosystems.
- Drive technical strategy for AI-native platform capabilities, including agentic workflows, orchestration systems, vectorized data systems, and intelligent automation frameworks.
- Partner closely with Engineering and Product leadership to ensure architectural decisions align with business priorities, customer commitments, and long-term platform scalability.
AI-Native Platform & Engineering Enablement
- Champion AI-native engineering practices across the organization, enabling teams to effectively leverage AI-assisted development, intelligent automation, and agentic tooling in day-to-day workflows.
- Build scalable frameworks for AI-enabled delivery, experimentation, evaluation, observability, and operational governance.
- Guide adoption of emerging AI technologies and establish standards for responsible, secure, and compliant AI implementation in healthcare environments.
- Partner with Engineering leadership to improve developer productivity, architectural consistency, and delivery velocity through AI-assisted engineering systems.
Enterprise Data & Platform Modernization
- Lead the modernization of League’s data ecosystem into scalable, cloud-native architectures supporting analytics, machine learning, operational intelligence, and member personalization.
- Define strategies for data interoperability, healthcare data exchange, identity resolution, event-driven architectures, and platform resiliency.
- Partner with Security, Compliance, and Infrastructure teams to ensure systems meet HIPAA, PIPEDA, SOC2, and enterprise healthcare compliance requirements.
- Drive architectural decisions balancing performance, scalability, reliability, security, and operational simplicity.
Operational Excellence & Delivery Leadership
- Build and operationalize engineering governance models for AI and data platform delivery.
- Establish KPIs and operational metrics around platform reliability, delivery predictability, AI model performance, system scalability, and engineering effectiveness.
- Lead prioritization and execution across highly cross-functional environments with competing priorities and organizational complexity.
- Navigate ambiguity and make pragmatic architectural trade-offs in rapidly evolving technical and business environments.
Executive & Cross-Functional Leadership
- Serve as a strategic advisor to executive leadership on AI transformation, platform scalability, and enterprise data strategy.
- Partner cross-functionally with Product, Engineering, Security, Compliance, Customer Delivery, and Go-to-Market leaders.
- Translate complex technical concepts into business-aligned recommendations for non-technical stakeholders and executive audiences.
- Mentor and develop senior engineering and architecture leaders across the organization.
About You
Experience
- 15+ years of progressive software engineering, data platform, or AI systems experience, including significant leadership experience in enterprise-scale environments.
- Proven track record leading large-scale AI, data, or platform modernization initiatives in complex SaaS or healthcare technology organizations.
- Deep experience architecting and operationalizing cloud-native AI and data systems at scale.
- Experience leading highly cross-functional technical organizations through periods of transformation, ambiguity, and rapid growth.
- Strong background in enterprise architecture, AI platform strategy, distributed systems, and operational engineering governance.
- Experience building or scaling AI-native engineering organizations and workflows.
- Healthcare, life sciences, payer/provider, or regulated enterprise platform experience strongly preferred.
- Experience operating in highly matrixed organizations with executive stakeholder management responsibilities.
- Strong operational leadership capability balancing delivery, platform stability, scalability, and organizational effectiveness.
Technical Expertise & Stack
AI & Data Systems
- AI-native architectures
- Agentic systems and orchestration frameworks
- ML platform architecture
- Vector databases and retrieval systems
- AI evaluation and observability systems
- Enterprise analytics and operational intelligence platforms
- Data governance and lineage systems
Cloud & Infrastructure
- AWS, GCP, and/or Azure
- Cloud-native platform architectures
- Distributed systems
- Event-driven systems
- Microservices
- Kubernetes and containerized infrastructure
- CI/CD and platform engineering practices
Engineering & Architecture
- Scalable SaaS platform architectures
- API ecosystems and interoperability
- Data-intensive systems
- Enterprise integration patterns
- System resiliency and reliability engineering
- Performance optimization and observability
AI-Native Engineering
- AI-assisted software development workflows
- Intelligent automation systems
- Developer enablement platforms
- Engineering productivity optimization
- AI governance and responsible AI practices
Education
- Bachelor’s degree in Computer Science, Engineering, Computational Science, Data Science, or related technical discipline required.
AI Fluency & Ways of Working
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
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
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.
