Manager, Software Engineering at Fleetworthy in Canada

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. We are looking for a technically strong and people-oriented Software Development Manager to lead the Smart Roadside team. This is a hands-on leadership role — while coaching and growing a team of talented engineers. You will be the bridge between strategic product direction and engineering execution, moving with urgency and a ship-and-iterate mindset to ensure the team delivers robust, scalable, and secure solutions across the Fleetworthy ecosystems. Key Responsibilities Lead and mentor a team of software developers, supporting their career growth and performance. Manage team performance using engineering management metrics and software engineering best practices to drive continuous improvement and accountability. Manage a portfolio of internal business applications, ensuring ongoing stability, performance, and scalability. Oversee the full Software Development Life Cycle (SDLC) including design, planning, implementation, deployment, and support. Collaborate with business stakeholders to gather requirements, define scope, and deliver practical, scalable software solutions. Coordinate priorities and development schedules across multiple initiatives and applications. Contribute to high-level system architecture and application design, ensuring alignment with business objectives and technical best practices. Be part of the team’s troubleshooting and problem solving sessions including implementing, testing, and deploying proposed solutions. Ensure adherence to coding standards, version control, testing practices, and release procedures. Contribute to cross-team engineering culture and helping identify and resolve systemic issues across teams. What You Bring Required Skills & Experience Post-secondary education in Computer Science, Computer Engineering, Electrical Engineering, or equivalent practical experience. 9+ years of hands-on software development experience, including back-end services, APIs, and databases. Experience in a leadership role managing software teams or projects — including 1–2 years of direct people management. Strong Problem-Solving Skills: Architect mindset — thinks beyond the code to design systems that solve real problems creatively and scalably. Strong technical knowledge of C# and ASP.NET with the ability to design, review, and contribute to production-quality code. Proficiency in Microsoft SQL Server, including schema design, performance tuning, and complex query development. Self-Starter: Doesn't wait for direction; proactively identifies work, removes blockers, and pushes initiatives forward. Documentation & Organization: Communicates clearly, documents decisions and code thoroughly, and brings structure to ambiguous situations. Monitoring Mindset: Understands observability — logs, metrics, and alerting — and knows how to troubleshoot and resolve production issues confidently. Quality Assurance Mindset: Treats quality as a shared responsibility, not a handoff — champions testing at every stage of the SDLC, from unit and integration tests through to end-to-end validation. Understands the value of test coverage, code reviews, and regression safety nets in maintaining a healthy, production-ready codebase. Ambiguity navigation: Thrive in fast-paced, evolving environments — comfortable making decisions with incomplete information. Remote Experience: Comfortable working in distributed teams with async communication and a high degree of self-management. Hands-on balance: Maintain the right mix of direct technical contribution and team leadership depending on the needs of the team. AI Tools: Comfortable leveraging AI coding tools to accelerate development understanding AI limitations and security implication. Critically evaluating output for bias, errors, and correctness. Open to learning and adopting new AI tools and workflows as the landscape evolves. Nice to Have Familiarity with cloud-native architecture (microservices, containerization, cloud platforms). Experience modernizing legacy .NET Framework or WebForms applications. Exposure to Linux-based server environments, Elixir, or Erlang. Experience with electrical systems or embedded systems development. Experience in fleet management, transportation technology, or safety/compliance domains 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.