Principal Software Engineer

Principal Software Engineer

Canada (Remote or Hybrid)

Fleetworthy offers the only complete technology suite for fleet readiness, uniting safety and compliance, toll management, and weigh station bypass solutions. We help fleets streamline operations, control costs, and operate with confidence. Trusted by 75% of the top fleets in North America, Fleetworthy offers the most adopted toll management solution and largest weigh station bypass network. Going beyond regulatory requirements, our safety and compliance capabilities strengthen safety programs and enable proactive audit readiness. We support millions of vehicles and drivers and are recognized across the industry for innovation and leadership. Fleetworthy is shaping the future of fleet readiness with AI-enabled, connected fleet technology that keeps drivers safe, fleets compliant, and operations running at peak efficiency.

The Principal Software Engineer is a senior technical leader embedded in our agile development organization, driving the architecture and delivery of our next-gen compliance platform. This is a hands-on leadership role. You will own technical direction, mentor and elevate a team of developers, and contribute meaningfully at the individual contributor level. The ideal candidate brings over 10 years of full-stack experience, leads with vision rather than command-and-control, and has a track record of guiding distributed, multi-time zone teams to ship high-quality software.

You will be expected to think beyond your immediate team. As a member of our Team Leads Team, you will collaborate cross-functionally with other engineering leaders, share learnings, and help shape engineering culture and practice across the broader organization. You will also work hand in hand with your Product Manager to shape, sequence, and deliver priorities. You will translate product strategy into technical execution and bring engineering insight back into roadmap decisions.

Technical Leadership

• Set the technical vision for your team's domain and continuously raise the bar on code quality, maintainability, and performance across the codebase.
• Architect, write, and review reusable, testable, and efficient code (Clean Code / SOLID principles), and coach the team to do the same.
• Design and implement low-latency, high-availability, and performant applications across the full stack.
• Lead front-end (Vue/Vuex) and back-end (.NET) development, setting patterns and standards for the team.
• Own SQL database architecture and query performance across your team's domains.
• Drive adoption of microservice and micro front-end architecture best practices.
• Identify and pay down technical debt strategically, knowing when to refactor, when to rewrite, and when to leave well enough alone.
• Share in DevOps responsibilities and champion observability tooling and practices.
• Participate in and often facilitate agile (Scrum/Kanban) ceremonies for your team.

Team Leadership

• Lead a team of developers, providing technical direction, mentorship, and thoughtful code review.
• Delegate effectively. Match work to the right people, create stretch opportunities, and resist the urge to do everything yourself.
• Communicate with clarity. Write and speak in a way that aligns engineers, product partners, and stakeholders. Make the complex understandable and make trade-offs explicit.
• Navigate ambiguity and shifting priorities, helping your team stay focused and effective when requirements change.
• Manage and coordinate across multiple time zones, ensuring remote team members are included, unblocked, and aligned.
• Build and sustain a strong remote team culture through intentional relationship-building, async communication practices, and virtual team rituals.
• Organize and run effective remote ceremonies (standups, retros, and planning sessions) that create genuine connections and accountability.

Product Partnership

• Partner closely with your Product Manager as a true counterpart, jointly shaping priorities, scoping work, and balancing customer needs against technical realities.
• Translate product goals into a clear technical plan, and surface engineering constraints, risks, and opportunities early, so the roadmap reflects what's buildable.
• Advocate for investment in platform health, developer experience, and quality alongside feature work.
• Help refine requirements, break down epics, and ensure the team has the context to make good day-to-day decisions without constant escalation.

Leadership & Collaboration (Required)

• Proven experience leading a team of developers in a remote or hybrid environment, with a clear philosophy on how to improve a codebase over time.
• Demonstrated ability to delegate, push decisions and ownership down to the team rather than centralizing them on yourself.
• Strong written and verbal communication skills, with comfort in documentation, structured async workflows, technical writing, and remote-first practices.
• Track record of partnering with product management to shape priorities, negotiate scope, and deliver business outcomes.
• Experience managing or collaborating across multiple time zones.
• Ability to operate and deliver in fast-paced, ambiguous environments without loss of quality or team morale.
• Experience facilitating cross-team engineering forums, communities of practice, or similar leadership collaboration.

Front End Development

• Vue.js 2 or 3 / Vuetify / Vuex / Webpack

Testing

• Jest / Vitest

Back End Development

• .NET Framework /.NET Core /.NET 7–8 / C#
• REST API design and implementation
• MSSQL / SQL Profiler / Query Tuning

Testing

• nUnit / Moq / Autofixture

DevOps

• Azure DevOps CI/CD (required)
• Azure / Windows IIS / Linux Nginx

Fleetworthy is committed to fostering a diverse and inclusive culture that is respectful and welcoming of individual differences. We are proud to be an equal opportunity employer and all qualified applicants will receive consideration for employment without regard to race, color, religion or belief (or lack thereof), sex, nationality, national or ethnic origin, civil status, age, citizenship status, sexual orientation, disability, genetic information, familial status, marital or registered civil partnership status, pregnancy or maternity status, gender identity, gender reassignment, military or veteran status, or any other protected characteristic in accordance with applicable laws and regulations.