Hiring.fm
Bestpass

Principal Software Engineer

Canada (Remote or Hybrid) Full Time

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. Learn more at fleetworthy.com.

Road Map  

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 lead a team of 3–4 developers, and contribute meaningfully at the individual contributor level. The ideal candidate brings 10–15+ years of full-stack experience, thrives in fast-paced and sometimes ambiguous environments, and has a track record of leading distributed, multi-timezone teams. 

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. 

What Your Ride Will Look Like  

Technical Leadership 

  • Architect, write, and maintain reusable, testable, and efficient code (Clean Code / SOLID principles). 
  • 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. 
  • Share in DevOps responsibilities and champion observability tooling and practices. 
  • Participate in and often facilitate agile (Scrum/Kanban) ceremonies for your team. 

Team Leadership & People Development 

  • Lead, mentor, and grow a team of 3–4 developers, providing technical direction, code review, and career guidance. 
  • Navigate ambiguity and fast-changing priorities — helping your team stay focused and effective when requirements shift. 
  • 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 connection and accountability. 

Organizational Influence 

  • Team Leads Team — participate actively in this cross-team leadership forum where engineering leads share learnings, align on practices, and collectively influence engineering culture beyond their own teams. 
  • Bring insights from your team’s work and challenges to the broader group, and apply lessons from peers back to your team. 
  • Help identify and resolve systemic issues — tooling gaps, process bottlenecks, knowledge silos — that affect multiple teams. 

Show Off What You Have  

10+ years of experience required; 15+ years strongly preferred. Experience must span both technical depth and team leadership.  

Leadership & Collaboration (Required) 

  • Proven experience leading a team of developers in a remote or hybrid environment 
  • Experience managing or collaborating across multiple time zones 
  • Strong async communication skills — comfortable with written documentation, structured async workflows, and remote-first practices 
  • 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