VP Engineering (Apps & Solutions) (Healthcare AI)

TL;DR

VP Engineering (Apps & Solutions): Lead AI-native engineering transformation for healthcare CX platform with an accent on micro-sprint methodologies, agentic capacity management, and AI-informed delivery decisions. Focus on scaling 50+ engineer organization, defining cloud-native architecture, and owning executive relationships with strategic enterprise clients.

Location: Canada applicants only; remote-eligible anywhere in Canada

Salary: $239,400–$299,200 CAD

Company

Leading AI-powered healthcare consumer experience platform reaching 63M+ people globally for payers, providers, and partners.

What you will do

• Lead AI-native transformation driving 40%+ AI-informed decisions via micro-sprints, agentic tooling, and automated workflows.
• Build and scale 50+ engineer organization through Directors and Managers, developing leadership bench.
• Set technical vision for Apps & Solutions including GCP cloud-native, microservices, CI/CD, and test automation.
• Own executive relationships and delivery for strategic enterprise accounts, managing escalations and P&L accountability.
• Partner with CTO, CPO, CDO on strategy, architecture, and cross-functional alignment.

Requirements

• 15+ years software engineering, 8+ years senior leadership managing multiple teams and leaders-of-leaders
• Demonstrated AI conviction with hands-on deployment of AI workflows (capacity management, PR review, defect classification)
• Track record scaling 50+ engineers for enterprise SaaS in B2B/B2C, preferably health tech
• Deep fluency in cloud-native (GCP), microservices, full-stack (Go, React, mobile)
• Experience in HIPAA, PIPEDA or equivalent regulated environments required
• Executive presence for C-suite and customer relationships; managed delivery partners/offshore teams

Nice to have

• Health tech or enterprise healthcare SaaS experience

Culture & Benefits

• AI-native organization expecting all to leverage AI daily with judgment and responsibility
• Remote-eligible in Canada with flexible remote days; Toronto office collaboration Mon-Thu for locals
• Full-time with bonus, equity, benefits; equal opportunity employer

Hiring process

• Application review by recruiter (human), initial goals discussion, team-specific interviews
• Reference and background checks prior to offer