Principal Software Engineer

Fleetworthy

12d•Remote

About The Position

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.

Requirements

10+ years of experience required; 15+ years strongly preferred. Experience must span both technical depth and team leadership.
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
Vue.js 2 or 3 / Vuetify / Vuex / Webpack
Jest / Vitest
VS Code
.NET Framework / .NET Core / .NET 7–8 / C#
REST API design and implementation
Entity Framework (code first and database first)
MSSQL / SQL Profiler / Query Tuning
nUnit / Moq / Autofixture
Visual Studio / Rider
Azure DevOps CI/CD (required)
Github
Azure / Windows IIS / Linux Nginx
Sentry
Azure Cloud – App Services / VMs / Azure App Gateway
Data Dog / New Relic
Log Rocket

Responsibilities

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.
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.
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.