Job descriptionAbout 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 League is at an inflection point. We’re executing a delivery transformation — moving from reactive implementation to an AI‑native, industrialized delivery model — at the same time as we’re scaling our most strategic enterprise accounts and standing up new delivery capabilities. This VP role is a defining hire: you’ll shape how engineering operates at League for the next five years, not just manage what exists today.
You are a seasoned engineering leader who leads with AI conviction — someone who doesn’t just adopt AI practices but pulls the entire engineering organization forward through them. As VP Engineering, Apps & Solutions at League, you'll set the technical vision, own end‑to‑end delivery across a 50+ engineer organization, and drive an AI‑native engineering transformation that makes League's delivery faster, more reliable, and more predictable. You’ll own executive‑level relationships with League’s most strategic enterprise clients and be a defining voice in how League builds software for the next five years.
In This Role You Will
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.
About You
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; health tech or enterprise healthcare SaaS experience strongly preferred.
Deep technical fluency in cloud‑native architectures (GCP preferred), 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.
Desired Outcomes
Developer throughput and predictability: PR throughput per developer sustained at or above industry p75, with a clear trajectory toward p90.
Developer Experience Index (DXI): measurable quarter‑over‑quarter improvement, with named actions and owners.
Engineering quality: defect rate below p75 benchmark, high/critical incident rate below 10 per month, incident resolution SLA attainment at 100%.
Test automation coverage: 80%+ across the portfolio with quarterly delivery milestones.
AI‑informed delivery: 40%+ of engineering delivery decisions AI‑assisted within 12 months.
Customer satisfaction: NPS and CSAT scores for strategic enterprise accounts trending positive.
AI Fluency (Core Competency)
Lead the Apps & Solutions org through an AI‑native delivery transformation — micro‑sprints, agentic capacity management, AI‑informed PR review and defect classification are operational realities under your leadership, not future‑state aspirations.
Champion AI tooling adoption across engineering pods (Copilot, LLM‑assisted workflows, AI‑driven observability) and build a team culture where AI fluency is expected at every level of the engineering org.
Use AI actively in your own strategic work — synthesizing delivery data, accelerating architectural thinking, staying ahead of market and tooling evolution.
Define and own the org’s posture on responsible AI adoption at scale — what to build with, what to evaluate carefully, and where human judgment must remain primary.
Integrate AI into your daily workflow, not just occasional use.
Maintain strong ownership and judgment over AI‑generated outputs.
Security‑Related Responsibilities
Compliance with Information Security Policies.
Compliance with League's secure coding practice.
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.
AI Fluency & Ways of Working
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.
How This Scales By Level
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.
What We Look For
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.
Compensation Range for Canada Applicants Only $239,400 — $299,200 CAD
Equal Employment Opportunity Statement 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.
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.
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