About 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 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. 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.

Why This Role, Why Now?

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.

In this role you will:

Team Scope

Direct reports: 3–5 Engineering Managers. Indirect reports: 25–35 engineers across web, mobile, and integration squads.

Technical & Architectural Leadership

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

Implementation & Project Delivery

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

Client-Facing Engineering Leadership

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

Member-Facing Application Ownership

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

Cross-functional Collaboration

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

People Leadership & Team Development

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

AI-Native Engineering Leadership

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

About you:

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

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

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

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

US APPLICANTS ONLY: The US-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 US 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.

Compensation range for USA applicants only

$239,300—$299,100 USD

Our employees come from different backgrounds, and we celebrate those differences. 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.

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.

Our 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.

Here are some additional resources to learn more about League:

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.

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Use of AI Notice
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.

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