VP, Engineering (Apps & Solutions)

League is one of the fastest-growing technology companies in Canada and the leading healthcare experience platform. As the VP of Engineering for Apps & Solutions, you will shape the technical vision and lead a transformation towards AI-native engineering, overseeing a team of over 50 engineers and managing executive-level relationships with strategic enterprise clients.

Responsibilities:

• Lead the AI-native engineering transformation for Apps & Solutions — drive the adoption of micro-sprint methodologies, agentic capacity management, and AI-informed delivery decisions across all engineering pods; set a target of 40%+ AI-informed delivery decisions across the portfolio and build the operating model that makes it real, not aspirational
• Build and scale a world-class engineering organization — lead 50+ engineers through multiple Directors and Engineering Managers, manage through leaders of leaders, develop the EM cohort as a performance management discipline, and build the leadership bench that sustains delivery excellence through growth and change
• Set the technical vision and engineering standards — define the architecture direction for Apps & Solutions aligned with League's business objectives and product roadmap; champion CI/CD, observability, cloud-native engineering on GCP, and test automation practices that drive measurable quality improvement across all squads
• Own executive-level customer relationships — serve as the senior engineering sponsor for League's most strategic enterprise accounts; own escalation management, delivery confidence, and the executive relationships that determine whether clients stay, expand, or churn
• Partner at the company-wide level — work alongside the CTO, CPO, and CDO to shape technology strategy, architecture decisions, and go-to-market execution for enterprise customers; own P&L accountability for engineering delivery across the Apps & Solutions portfolio
• Drive cross-functional alignment at the leadership level — work closely with the CPO, CTO, and CDO to ensure engineering decisions are tightly coupled to product roadmap commitments and delivery capacity; own the relationship between engineering velocity and commercial feasibility before commitments leave the building

Requirements:

• 15+ years of progressive software engineering experience, including 8+ years in senior leadership roles managing multiple engineering teams and leaders of leaders
• Demonstrated AI conviction — you lead AI-native delivery in practice, not just in aspiration; you have hands-on experience deploying AI-assisted engineering workflows (capacity matching, automated defect classification, PR review, agentic tooling) and a track record of pulling engineering organizations forward on AI adoption
• Proven track record scaling engineering organizations of 50+ engineers and delivering complex, enterprise-grade SaaS products in a B2B or B2B2C environment
• Deep technical fluency in cloud-native architectures, microservices, and full-stack development (Go, React, mobile) — you engage credibly with engineers on architectural trade-offs without losing your strategic altitude
• Exceptional executive presence with a demonstrated ability to build trust with C-suite stakeholders and enterprise customers; track record of owning high-stakes customer relationships at the account level, not just in QBRs
• Experience working within HIPAA, PIPEDA, or equivalent regulated data environments is required at this level — you understand the compliance obligations that come with handling PHI and have built engineering practices that treat security and data governance as foundational, not afterthought
• Demonstrated experience managing delivery partners, offshore teams, or hybrid internal/external engineering models; comfort holding external teams to the same quality bar as internal engineers
• health tech or enterprise healthcare SaaS experience strongly preferred
• GCP preferred