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; establish and maintain high hiring standards.

• Standardize AI-assisted development, testing, review, and operations throughout the organization.

• Ensure AI adoption is verified through actual behaviors instead of just dashboards, and guide leaders and skeptical senior engineers through the transition.

• Conduct engineering experiments with established baselines and clear scale, adjusting or halting decisions as necessary.

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

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

• Plan and execute the roadmap in collaboration with Product, address trade-offs early, and drive customer escalations to identify root causes alongside Customer Success.

• Lead the engineering and SaaS operations organization end to end, reporting directly to the CTO.

• Influence how the organization develops and operates software with AI, while measuring quality, reliability, cycle time, predictability, and customer impact.

⛳️ Requirements

• Bachelor’s degree in Computer Science or a related field, or equivalent practical experience.

• Over 12 years of experience in software engineering, which includes more than 5 years in engineering leadership and at least 2 years in a managerial capacity.

• Proven experience in leading a multi-team engineering organization through managers across various products with distinct codebases, including legacy modernization.

• Demonstrated experience in leading engineering for a B2B SaaS product and managing production operations through a team, including reliability, on-call duties, incident response, security operations, and cloud expenses.

• Actively uses AI coding assistants and agents in current production work and has successfully led their adoption across multiple teams with measurable outcomes.

• Experienced in designing and conducting engineering experiments with established baselines, success metrics, and clear criteria for decision-making.

• Practical experience with flow-based delivery methods (such as Kanban), CI/CD, automated testing, and release management on a large scale.

• Proficient in reading code and reviewing architectural designs.

• Familiarity with the following technology stack is advantageous: .NET, C#, JavaScript/TypeScript, Angular, SQL, MAUI, and Azure PaaS.

• Experience leading a remote, distributed engineering organization.

• Proficient in professional English.

• Available for regular overlap with North American business hours.

• Preferred qualifications include a background as a Software Architect or Staff/Principal Engineer, experience in logistics, routing, dispatch, courier, or healthcare operations software, knowledge of Azure managed services, infrastructure as code, SRE, SOC 2, or FinOps, as well as experience with acquisition integration or multi-business-unit engineering, and AI-enabled product features such as embedded agents, MCP connectors, or AI vision.

🏝️ Benefits

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

• Fully remote work environment available globally.

• Flexible working hours and the option for asynchronous work.

• A structured growth trajectory with regular, meaningful feedback and support towards achieving career aspirations.

• Access to top-tier tools, playbooks, and technologies within the Ionic portfolio.

• An engaging community featuring coffee chats, happy hours, cooking classes, book clubs, and more.

• Engagement as an independent contractor.