Vice President of Software Engineering

Vice President, Software Engineering (Apps & Solutions)

Toronto or Chicago (hybrid).

$250-280k 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

To find out more please send up to date resume to conall.anderson@mparecruitment.ca