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

The 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

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