Vice President, Software Engineering

Vice President, Software Engineering (Apps & Solutions) Toronto or Chicago (hybrid). $260-320k base + bonus + stock options. Digital health SaaS platform MPA Recruitment has been retained by one of the leading digital health companies in North America to recruit a Vice President of Software Engineering. This Vice President, Software Engineering will lead their Apps & Solutions (Services) organization, responsible for delivering high-quality, scalable, and AI-native member experiences across web and mobile platforms. This is not a traditional product engineering leadership role. This is a client-facing, delivery-oriented leadership role operating within a services model, where you will be accountable for building and delivering member-facing applications for payer clients while evolving how delivery happens at scale. You will own the transformation of our engineering organization into an AI-native delivery engine, where AI is not a tool layered onto workflows, but a primary actor in how work is executed. You will lead the redesign of delivery systems, quality practices, and team structures to enable faster, higher-quality, and more predictable outcomes. This role sits at the intersection of: • AI-native architecture and operating models • Client delivery and services execution • Member-facing application development (web + mobile) • Lean, high-performance engineering leadership What You’ll Own 1. AI-Native Delivery & Architecture (Core Mandate) • Redesign engineering workflows where AI is embedded as a primary actor, not an assistive tool • Build and operationalize AI-native delivery systems across the organization • Define architecture patterns that enable: • AI-assisted development • automated validation and quality checks • intelligent orchestration of delivery workflows • Move the organization beyond experimentation into production-grade AI adoption at scale 2. Client Delivery & Services Execution (Critical) • Own delivery of member-facing applications across web and mobile platforms for payer clients • Lead cross-functional Service Pods accountable for end-to-end client delivery • Manage: • client expectations • escalations • scope and delivery integrity • Operate effectively in a services delivery model, balancing: • client needs • platform scalability • delivery efficiency 3. Member-Facing Application Excellence • Ensure high-quality delivery of consumer-grade digital experiences for healthcare members • Drive engineering standards across: • mobile (iOS/Android) • web applications • backend services supporting member journeys • Maintain a strong focus on: • usability • performance • reliability at scale 4. Test-Driven Delivery & Quality Systems • Own and complete League’s test automation framework (currently ~65% complete) • Establish a test-first engineering culture, where: • quality criteria are defined before design begins • Implement systems to ensure: • predictable delivery • reduced defects • consistent release quality across teams 5. Offshore Engineering Strategy & Governance • Lead a globally distributed engineering organization with significant offshore presence • Differentiate between: • transactional vs high-skill offshore capabilities • Evolve offshore teams up the value chain: • from execution → ownership → strategic contribution • Build governance models that ensure: • quality • alignment • scalability 6. Lean Engineering Leadership • Lead a flatter, leaner organization with fewer management layers • Drive outcomes through: • clarity • accountability • strong individual contributors • Maintain high standards for: • quality • velocity • ownership What You Bring Core Experience • Proven experience leading engineering organizations in a client delivery / services model (required) • Strong track record delivering member-facing applications (web + mobile) at scale • Deep technical background with the ability to guide architecture and system design decisions • Experience managing complex, multi-client delivery environments with parallel workstreams • Demonstrated ability to build and scale high-performing engineering teams AI-Native Capability (Non-Negotiable) • Demonstrated experience building or operating AI-native systems or workflows • Has already transitioned from: • “using AI tools” → designing AI-driven operating models • Able to clearly articulate: • how AI changes delivery systems • how AI improves quality, speed, and scalability Delivery & Operational Excellence • Strong experience implementing: • delivery frameworks • engineering KPIs and metrics • quality systems • Proven ability to: • manage delivery within budget • maintain scope discipline • ensure predictable execution Leadership & Influence • Experience leading cross-functional teams (Engineering, Product, Design, Client teams) • Ability to: • influence executive stakeholders • negotiate scope and priorities • drive alignment across complex organizations Additional Considerations • Experience in health tech, payer systems, or regulated environments is a strong asset • Experience scaling organizations in high-growth, fast-paced environments preferred

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