Assistant Vice President of Engineering, League
Applications & Solutions
CA$210.2-262k
+ Bonus + Equity
React
GCP
iOS
Go
Android
Expert level
Remote from Canada
More information about location
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$210.2-262k
+ Bonus + Equity
React
GCP
iOS
Go
Android
Expert level
Remote from Canada
More information about location
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
- League is seeking an AVP, Engineering to join the Apps & Solutions engineering organization — a leader who brings deep technical credibility, strong delivery instincts, and the people leadership skills to build and sustain high-performing teams
- 12+ years of progressive software engineering experience, including 5+ years in engineering leadership roles managing teams and engineering managers
- Proven track record owning end-to-end delivery of complex, enterprise-grade SaaS products in a B2B or B2B2C environment
- Deep experience building and shipping member-facing or consumer-facing applications — you understand this domain and have strong instincts for what quality looks like at scale
- Health tech or enterprise healthcare SaaS experience strongly preferred; experience working within HIPAA, PIPEDA, or equivalent regulated data environments is an asset
- Strong architectural fluency in cloud-native systems (GCP preferred), microservices, and full-stack development (Go, React, mobile — Android and/or iOS
- Actively uses AI tools in engineering and leadership workflows
- Strong executive presence; you communicate with confidence and clarity in client escalations, executive reviews, and cross-functional forums
- Clear communicator who translates technical complexity into business language for non-technical stakeholders
- Experience managing delivery partners, offshore QA or development teams, or hybrid internal/external engineering models
- Familiarity with HIPAA, PIPEDA, or equivalent regulated data environments; understanding of what compliant engineering practice looks like in a healthcare SaaS context
- 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
What the job involves
- Reporting directly to the VP, Engineering (Apps & Solutions), this role is the connective tissue between technical execution and enterprise delivery: you own the architecture and quality of member-facing applications, drive implementation excellence across your squads, and show up as a trusted engineering partner to League's most strategic clients
- This is not a platform role. You will be building and leading teams that deliver directly to end members; consumer health experiences that are fast, reliable, personalized, and clinically meaningful. You bring hands-on architectural judgment, a genuine bias for delivery, and the ability to represent engineering with conviction in executive and client-facing settings
- AI fluency is a core expectation of this role, not a bonus. You lead by example; integrating AI into your own engineering workflow, driving adoption across your teams, and building the culture and practices that make AI-native delivery a daily operational reality
- League is at an inflection point — executing a delivery transformation while scaling our most strategic enterprise accounts. This AVP role is a critical hire: you'll own the engineering execution that makes our delivery commitments real
- Direct reports: 3–5 Engineering Managers. Indirect reports: 25–35 engineers across web, mobile, and integration squads
- Own the technical direction for member-facing applications — define and enforce architectural standards, patterns, and guardrails across your squads; make trade-off calls with speed, quality, and scalability in mind
- Drive architectural reviews and decisions — lead design reviews for major features and platform integrations; ensure technical choices align with League’s roadmap, client commitments, and long-term platform health
- Maintain hands-on technical credibility — engage directly with engineers on architecture, code quality, and system design; you don’t need to be in the code daily, but you must be credible when you are
- Own end-to-end delivery accountability for your squads — from project scoping and estimation through to production release and post-launch stability; delivery commitments you make are commitments you keep
- Drive delivery predictability — implement the planning, tracking, and escalation practices that give the VP and CDO clear, real-time visibility into delivery health across your portfolio
- Build and maintain delivery metrics — track PR throughput, defect rates, test automation coverage, and incident resolution SLAs; use data to drive continuous improvement, not just reporting
- Serve as a senior engineering point of contact for strategic enterprise clients — represent engineering in client escalations, technical reviews, and delivery status conversations with the credibility and presence that builds lasting trust
- Translate complex technical realities into clear client communication — own the narrative on delivery timelines, architectural decisions, and quality trade-offs in language that resonates with non-technical executive stakeholders
- Lead engineering delivery for consumer health experiences — own the quality, performance, and reliability of member-facing applications across web and mobile; you understand what ‘good’ looks like from a member’s perspective, not just an engineer’s
- Partner closely with Product Management and Design to translate roadmap commitments into realistic engineering plans; own the technical scoping and estimation that makes delivery promises credible
- Serve as the engineering point of contact within League's CDO delivery governance model; surface risks early and resolve cross-functional blockers before they become customer issues
- Own performance management with rigor — set clear expectations for every EM, deliver candid feedback on a consistent cadence, and hold yourself accountable for developing the next tier of engineering leadership at League
- Lead the hiring process for your squads — partner with Talent on sourcing strategy, conduct calibrated interviews, and make hiring decisions that raise the bar
- Run structured calibration and career pathing — quarterly calibrations across your EM cohort; every engineer has a clear growth path and knows where they stand
- Build inclusive, high-trust team culture — track engagement signals and act before attrition becomes a problem
- Build the practices that make AI-native delivery real — micro-sprint methodologies, AI-informed delivery decisions, and AI-assisted defect classification are things your teams actually do
- Maintain strong ownership and judgment over AI-generated outputs — your teams use AI confidently and responsibly; you set the standard for what that looks like in a regulated healthcare environment
- Stay ahead of AI tooling evolution — continuously evaluate new capabilities and bring the right ones to your teams with a clear point of view on adoption
- Desired Outcomes:
- Delivery predictability: sprint commitments met at 85%+ with real-time visibility into delivery health
- PR throughput per developer at or above industry p75; trajectory toward p90 within 12 months
- Defect rate below p75 benchmark; high/critical incident rate below 10/month; incident SLA attainment at 100%
- Test automation coverage at 80%+ within 6 months of hire
- AI-assisted delivery decisions at 30%+ within 12 months
- Every EM has a current development plan; no unmanaged performance gaps older than 60 days
- 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
- 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
- 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
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
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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