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.

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)
• 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:
• 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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