Vice President, Software Engineering (Apps & Solutions) Toronto or Chicago (hybrid).
$250-280k base + bonus + stock options.
Digital health SaaS platform.
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
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: 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: escalations
scope and delivery integrity

Operate effectively in a services delivery model, balancing: client needs
delivery efficiency

Ensure high‑quality delivery of consumer‑grade digital experiences for healthcare members
Drive engineering standards across: 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: 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
Build governance models that ensure quality, alignment, and scalability
Lead a flatter, leaner organization with fewer management layers
Drive outcomes through clarity and accountability
Maintain high standards for quality, velocity, and ownership
What You Bring Core Experience Proven experience leading engineering organizations in a client delivery / services model (required)
Solid 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:
Able to clearly articulate how AI improves quality, speed, and scalability
Delivery & Operational Excellence Strong experience implementing delivery frameworks, engineering KPIs and metrics, and quality systems
Proven ability to manage delivery within budget
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

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📌 Vice President of Software Engineering (Ontario)
🏢 MPA Recruitment
📍 Ontario