Director of Engineering

This is a fully remote position, open to applicants in Canada, +1 more country.

📋 Description

• Oversee, mentor, and nurture engineers through regular one-on-one meetings, clear expectations, and ongoing feedback.

• Evaluate team strengths and weaknesses, recommending hiring strategies, development opportunities, and organizational structure.

• Recruit and onboard engineers while fostering a culture of ownership, accountability, and continuous improvement.

• Establish technical direction and lead architectural decisions for the next-generation ERP, including finalizing the Java-based technology stack.

• Perform code reviews, design, prototype, and directly contribute to key components.

• Balance modernization efforts with support for existing product lines and customers while proactively managing technical debt.

• Control the software development lifecycle, managing sprint cadence, daily standups, retrospectives, and release schedules.

• Enhance automated testing, CI/CD processes, and engineering accountability for release quality.

• Set benchmarks for code reviews, testing, and observability practices.

• Promote the use of AI-assisted development tools such as Claude Code, Cursor, and Copilot.

• Provide technical feasibility assessments and sizing estimates during epic kickoffs and discovery phases.

• Manage quarterly and sprint engineering capacity planning.

• Communicate trade-offs, risks, and progress to Product, Support, and leadership teams.

• Supervise IT/Infrastructure and Site Reliability Engineering in conjunction with software engineering.

• Handle production incidents and the on-call model, serving as the escalation point for outages and critical issues.

• Take ownership of the PCI compliance process, overseeing controls, audits, and remediation efforts.

• Optimize Azure costs by monitoring spending and ensuring environments are appropriately sized.

• Maintain the stability and security of the legacy Linux, Perl, Spring Boot, Oracle, and SQL platforms.

⛳️ Requirements

• A minimum of 8 years in software development, with at least 3 years of experience managing engineering teams.

• Extensive hands-on Java expertise in back-end and enterprise applications.

• Proven experience in building or modernizing an ERP system or complex transactional B2B systems.

• Demonstrated success in implementing agile methodologies, CI/CD processes, and test automation.

• Strong skills in relational database design and performance optimization.

• Ability to evaluate talent, provide direct feedback, and make difficult personnel decisions.

• Practical experience with Azure, including managing and optimizing cloud expenditures; AWS or GCP experience is also acceptable.

• Experience in establishing or leading a QA function and developing a test automation strategy.

• Experience in managing production operations, on-call rotations, incident management, and Site Reliability Engineering practices.

• Familiarity with PCI DSS compliance or a similar security and compliance framework within a production environment.

• Comfort in supporting and modernizing legacy systems including Linux, Perl, Spring Boot, Oracle, and SQL.

• Active, hands-on engagement with AI-assisted development tools.

• Exceptional communication skills with the ability to convey technical issues in terms of business impact.

• Experience in distribution or supply chain software or the print and promotional products industry is highly preferred.

• Background in an acquisitive, growth-stage vertical software business is strongly preferred.

• Experience managing teams located across Canada and the U.S. is highly preferred.

🏝️ Benefits

• AI-powered tools, such as transcription and automated note-taking, utilized during parts of the interview process.

• Alternative interview process accommodations available upon request.

• Commitment to building diverse, equitable, and inclusive teams.