VP of Software Engineering

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

📋 Description

• Lead, recruit, and nurture Directors, architects, and their teams; establish and maintain the hiring standards.

• Integrate AI-assisted development, testing, review, and operations into the organization's workflow; ensure adoption through actual behavior and guide leaders and skeptical senior engineers through the transition.

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

• Take charge of quality, releases, and production reliability, encompassing uptime and SLAs, on-call duties, incidents, security operations, and cloud costs.

• Oversee architecture across products, including modernization of legacy systems and standards for AI-generated code.

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

• Lead the engineering and SaaS operations organization from start to finish, with accountability for personnel, architecture, quality, delivery, production reliability, and customer outcomes.

• Report directly to the CTO and influence how the organization builds and operates software with AI.

⛳️ Requirements

• Bachelor's degree in Computer Science or a related discipline, or equivalent practical experience.

• Over 12 years of experience in software engineering, including more than 5 years in engineering leadership and at least 2 years managing managers.

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

• Managed engineering for a B2B SaaS product and oversaw its production operations through a team, focusing on reliability, on-call duties, incident management, security operations, and cloud costs.

• Proficient in utilizing AI coding assistants and agents in production work currently, and has successfully led their adoption across multiple teams with quantifiable results.

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

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

• Continuously engages with code and reviews architecture; familiarity with our technology stack is advantageous.

• Led a remote, distributed engineering organization.

• Background as a software architect or Staff/Principal engineer is preferred (nice to have).

• Experience in logistics, routing, dispatch, courier, or healthcare operations software is a plus (nice to have).

• Familiarity with Azure managed services, infrastructure as code, SRE, SOC 2, or FinOps is beneficial (nice to have).

• Experience integrating teams post-acquisition or managing engineering across multiple business units is an asset (nice to have).

• Background in developing AI-enabled product features such as embedded agents, MCP connectors, or AI vision is a plus (nice to have).

🏝️ Benefits

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

• Fully remote and global: enjoy your best life wherever that may be, without missing out on career opportunities.

• Flexible working hours: we operate asynchronously and prioritize results and customer satisfaction over your online presence.

• Clear growth trajectory: receive consistent, constructive feedback and support aimed at your career objectives.

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

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

• This position is an independent contractor engagement and does not qualify for company-sponsored employee benefit programs.