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Winnipeg, Manitoba, Canada
Remote only
Are you an engineering leader who has scaled a SaaS organization through managers and turned AI-assisted development into measurable results?
CXT Software provides the technology backbone for courier, route delivery, and healthcare logistics companies. Our customers run their daily physical operations on our software, so reliability, predictable delivery, and strong regression control are not optional.
We are looking for an AI-Native VP of Software Engineering to lead our engineering and SaaS operations organization end to end and to define how it builds and runs software in the AI era. You will own people, architecture, quality, delivery, production reliability, and customer outcomes. Our stack is .NET, C#, JavaScript/TypeScript, Angular, SQL, MAUI, and Azure PaaS.
Reporting to the CTO, you will shape how we build and run software with AI, verify adoption through real behavior rather than dashboards, and shape its evolution with evidence. You will be measured on quality, reliability, cycle time, predictability, and customer impact.
If you want to lead a serious engineering organization and define how it works with AI, we would love to hear from you.
Responsibilties
*Lead, hire, and develop Directors, architects, and their teams; set and hold the hiring bar.
*Make AI-assisted development, testing, review, and operations the way the organization works; verify adoption through real behavior, not dashboards; and coach leaders and skeptical senior engineers through the change.
*Run engineering experiments with baselines and clear scale, modify, or stop decisions.
*Own quality, releases, and production reliability: uptime and SLAs, on-call, incidents, security operations, and cloud cost.
*Own architecture across our products, including legacy modernization and standards for AI-generated code.
*Plan and deliver the roadmap with Product, raise trade-offs early, and drive customer escalations to root cause with Customer Success.
Requirements
*Degree in Computer Science or a related field, or equivalent experience
*12+ years in software engineering, including 5+ years in engineering leadership and 2+ years managing managers.
*Led a multi-team engineering organization through managers, across several products with separate codebases, including legacy modernization.
*Led engineering for a B2B SaaS product and owned its production operations through a team: reliability, on-call, incidents, security operations, and cloud cost.
*Uses AI coding assistants and agents in production work today, and has led their adoption across multiple teams with measured results.
*Designed and run engineering experiments with baselines, success metrics, and clear decision criteria.
*Hands-on experience running flow-based delivery (Kanban or similar) at scale, with CI/CD, automated testing, and release management.
*Still reads code and reviews architecture; experience in our stack is a plus.
*Led a remote, distributed engineering organization.
Nice to have
*Software architect or Staff/Principal engineer background.
*Logistics, routing, dispatch, courier, or healthcare operations software.
*Azure managed services, infrastructure as code, SRE, SOC 2, or FinOps.
*Integrating teams that join through acquisition, or running engineering across multiple business units.
*Building AI-enabled product features such as embedded agents, MCP connectors, or AI vision.
Benefits
More than just perks, they're part of what makes working at CXT Software great.
*Access to leading AI engineering tools and platforms, and a real mandate to shape how they are used across the organization.
*100% remote and global: live your best life wherever that may be, and never lose out on career opportunities because of it.
*Flexible work hours: we work asynchronously and care about results and customer satisfaction, not when you're online.
*Dedicated growth path: consistent, meaningful feedback and support toward your career goals.
*Access to leading tools, playbooks, and technology across the Ionic portfolio.
*Engaging community: coffee chats, happy hours, cooking classes, book clubs, and more.
