AI-Native VP of Software Engineering, Canada-based (CAD $260,000/year)

Role overview

Lead engineering and SaaS operations across multiple products, with responsibility for the teams, architecture, delivery practices, and production outcomes. A central part of the role is making AI-assisted development, testing, review, and operations part of everyday engineering work, then measuring its effects on quality, reliability, delivery speed, and customer outcomes.

Responsibilities

- Lead, hire, and develop directors, architects, and engineering teams, maintaining clear expectations for hiring and performance. - Guide organization-wide adoption of AI coding tools and agents, coaching leaders and engineers and assessing adoption through observed work. - Run engineering experiments with baselines, success measures, and explicit decisions about whether to expand, adjust, or stop. - Own release quality and production reliability, including uptime, service commitments, on-call, incident response, security operations, and cloud spending. - Set architecture direction across products, including legacy modernization and standards for AI-generated code. - Coordinate roadmap delivery with Product and work with customer-facing teams to resolve escalations at their root cause.

Requirements

- A computer science or related degree, or equivalent experience. - 12 or more years in software engineering, including at least five years leading engineering and two years managing managers. - Experience leading multiple teams through managers across several products and codebases, including modernization of legacy systems. - Leadership of a B2B SaaS engineering organization with team ownership of production operations. - Current production use of AI coding assistants or agents, plus experience leading measured adoption across multiple teams. - Experience designing engineering experiments and using flow-based delivery at scale, with CI/CD, automated testing, and release management. - Experience leading a remote, distributed engineering organization; ability to review code and architecture.

Nice to have

- Background as a software architect or Staff/Principal engineer. - Experience with logistics, routing, dispatch, courier, or healthcare operations software; Azure, infrastructure as code, SRE, SOC 2, or FinOps. - Experience integrating acquired teams, leading across business units, or building AI-enabled product features.

Benefits and work setup

- Fully remote, global independent-contractor engagement with flexible, asynchronous hours; the listing states this arrangement is not eligible for employer-sponsored benefits. - Access to AI engineering tools and a mandate to shape their use, plus professional growth support, shared tools and playbooks, and virtual community activities.