VP of Software Engineering – AI-Native

This is a fully remote position, open to applicants in Canada.

📋 Description

• Lead, recruit, and nurture Directors, architects, and their teams while establishing and maintaining high hiring standards.

• Integrate AI-assisted development, testing, review, and operations as the standard practice within the organization.

• Confirm AI adoption through actual behaviors instead of dashboards, coaching leaders and hesitant senior engineers through the transition.

• Conduct engineering experiments with established baselines and clear scaling parameters, making adjustments or halting decisions as needed.

• Take ownership of quality, releases, and production reliability, which includes uptime, SLAs, on-call duties, incident management, security operations, and cloud costs.

• Oversee architecture across products, addressing legacy modernization and setting standards for AI-generated code.

• Strategize and execute the roadmap in collaboration with Product, proactively addressing trade-offs, and driving customer escalations to root causes alongside Customer Success.

• Lead the engineering and SaaS operations organization comprehensively, taking responsibility for personnel, architecture, quality, delivery, production reliability, and customer outcomes.

• Report directly to the CTO, influencing how software is constructed and operated with AI.

⛳️ Requirements

• A degree in Computer Science or a related discipline, or equivalent professional experience.

• A minimum of 12 years in software engineering, including over 5 years in an engineering leadership role and at least 2 years managing other managers.

• Experience leading a multi-team engineering organization through managers, across various products with distinct codebases, including those undergoing legacy modernization.

• Experience managing engineering for a B2B SaaS product and overseeing its production operations via a team: reliability, on-call duties, incident management, security operations, and cloud costs.

• Proficient in using AI coding assistants and agents in current production work, along with a track record of leading their adoption across multiple teams with measurable outcomes.

• Designed and executed engineering experiments with established baselines, success metrics, and clear decision-making criteria.

• Hands-on experience with flow-based delivery methods (Kanban or similar) at scale, including CI/CD, automated testing, and release management.

• Familiarity with reviewing code and architecture; experience with .NET, C#, JavaScript/TypeScript, Angular, SQL, MAUI, and Azure PaaS is advantageous.

• Experience leading a remote, distributed engineering organization.

• Background as a software architect or Staff/Principal engineer is a plus.

• Familiarity with logistics, routing, dispatch, courier, or healthcare operations software is beneficial.

• Experience with Azure managed services, infrastructure as code, SRE, SOC 2, or FinOps is a plus.

• Experience in integrating teams through acquisitions or managing engineering across multiple business units is desirable.

• Experience in developing AI-enabled product features such as embedded agents, MCP connectors, or AI vision is a plus.

🏝️ Benefits

• Access to cutting-edge AI engineering tools and platforms, along with a genuine mandate to influence their application across the organization.

• 100% remote and global: live your best life wherever you choose, without sacrificing career opportunities.

• Flexible work hours: we prioritize asynchronous work and focus on results and customer satisfaction, rather than your online presence.

• Dedicated growth path: receive consistent, meaningful feedback and support tailored to your career aspirations.

• Access to premier tools, playbooks, and technology throughout the Ionic portfolio.

• Engaging community: participate in coffee chats, happy hours, cooking classes, book clubs, and more.

• Independent contractor engagement.

• Not eligible for company-sponsored employee benefit programs.