VP, Engineering (Apps & Solutions) - Toronto, ON

Role Overview

Role type: Full-time, direct hire

Salary: $239,400 - $288,000 CAD/year

Location: Onsite (Toronto, ON)

About the Role This organization is a platform technology company powering next-generation consumer health experiences. Established in 2014, the platform delivers highly personalized experiences that help people get more out of their health benefits while helping employers and organizations achieve better outcomes. Millions of people use products built on the platform to access, navigate, and pay for care.

Position Summary We are looking for a seasoned and highly capable Vice President, Engineering to lead our Apps & Solutions engineering organization. This is a senior leadership role that sits at the intersection of technical excellence, strategic delivery, and customer partnership.

The ideal candidate brings deep external client-facing experience, a strong foundation in technical engineering, and a proven ability to lead and scale high-performing engineering teams. You are as comfortable in a boardroom managing client escalations as you are in a technical design review - and you bring clarity and confidence to both.

Essential Duties & Responsibilities

Technical Leadership

• Own the overall client solution architecture and set the technical direction for the Apps & Solutions team
• Maintain and uphold a high bar for technical excellence across all engineering output
• Actively guide, mentor, and support engineering leaders and individual contributors

Engineering Excellence

• Implement and continuously refine team processes, rituals, and delivery frameworks
• Establish robust systems for visibility, including engineering KPIs and performance metrics
• Champion a culture of quality, accountability, and efficient delivery

People Leadership

• Build, manage, and develop a high-performing, multi-layered engineering organization
• Hire and empower leaders to drive day-to-day execution while maintaining strong organizational awareness
• Coach and develop talent at all levels with thoughtfulness and intentionality

Cross-Functional Collaboration

• Serve as the primary engineering partner for Product and Customer teams
• Confidently negotiate on scope, timelines, and technical requirements to protect delivery integrity
• Build trusted, collaborative relationships with peers across the organization

Client Services & Delivery Management

• Manage direct client relationships with professionalism, managing expectations and navigating escalations effectively
• Oversee project delivery within budget, ensuring accurate estimation and disciplined scope management
• Represent engineering in client-facing conversations with clarity and credibility

Operational Complexity

• Thrive in a fast-paced, high-volume environment with multiple parallel initiatives
• Demonstrate high information-processing capability and sound prioritization judgment

Required Qualifications

• Strong technical background with a proven track record of architecting and delivering complex solutions
• Exceptional engineering leadership experience, including driving team processes focused on quality and delivery
• Demonstrated success building and developing high-performing engineering teams
• Extensive client services experience: relationship management, escalation handling, and project delivery ownership
• High capacity for managing complex, parallel workstreams with composure and precision

Nice to Have

• Experience in the health tech/software dev industry
• Proven track record of scaling engineering organizations in high-growth, fast-paced environments

Key Competencies & Attributes

• Genuinely aligned with League's mission to improve health outcomes through technology
• Strategic mindset - able to focus self and team on the highest-impact priorities
• Clear and effective communicator across diverse technical and non-technical audiences
• Resilient and adaptable in dynamic, ambiguous environments
• Results-driven with a high-performance orientation
• Intellectually curious with a commitment to continuous learning and improvement