Vice President of Engineering, League
Apps & Solutions
CA$239.4-299.2k
Exclusive of bonus and equity
React
GCP
Go
Expert level
Remote from Canada
Consumer experience platform for healthcare
Be an early applicant
Consumer experience platform for healthcare
501-1000 employees
HealthcareB2BPersonal healthSaaSData Analysis
Be an early applicant
CA$239.4-299.2k
Exclusive of bonus and equity
React
GCP
Go
Expert level
Remote from Canada
501-1000 employees
HealthcareB2BPersonal healthSaaSData Analysis
Company mission
To power next-generation healthcare experiences with a platform built to enable CX transformation.
Role
Who you are
- 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
- 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
- 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
What the job involves
- 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
- 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
- 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
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
Our take
Health benefits are a top requirement for anyone seeking a new job in the US today, but classic one-size-fits-all plans are no longer regarded fit for service. League's platform - for payers, providers, consumer health businesses, and employees - connects all benefits in one HIPAA-compliant place, to enable all bodies involved with health benefits to provide better customer healthcare experiences.
League is already one of the bigger players in the employee wellness space, having capitalised on the recently accepted correlation between employee health and productivity to secure huge clients like Uber, Shopify and Unilever. The company has seen significant investment, which will support the scaling of its platform-as-a-service offering. With more than 63 million contracted users, it is securing its position as the leading digital infrastructure for an integrated health ecosystem.
Freddie
Company Specialist at Welcome to the Jungle
Insights
Top investors
-4% employee growth in 12 months
Company
Funding (last 2 of 4 rounds)
Feb 2022
$95m
SERIES C
Jul 2018
$47.1m
SERIES B
Total funding: $171.1m
Company benefits
- Flexible medical and dental plans
- 401(k) and RRSP matching programs
- Health, lifestyle, learning and family spending accounts
- Employee stock option program (ESOP)
- Generous leaves (including parental and sabbatical)
- Flexible time off
Company HQ
Entertainment District, Toronto, ON
Leadership
Michael Serbinis
(Founder & CEO)Founder of DocSpace and Kobo. Experience as CEO for Three Angels Capital and Board Director for Vector Insitute, among other prominent business leadership roles.
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