Manager, Software Engineering at Bestpass by Fleetworthy

<div class="content-intro"><p><span style="font-family: arial, helvetica, sans-serif; font-size: 12pt;"><span class="TextRun SCXW248234814 BCX0" lang="EN-CA" data-contrast="auto"><span class="NormalTextRun SCXW248234814 BCX0">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, an</span><span class="NormalTextRun SCXW248234814 BCX0">d&nbsp;</span><span class="NormalTextRun SCXW248234814 BCX0">opera</span><span class="NormalTextRun SCXW248234814 BCX0">te</span><span class="NormalTextRun SCXW248234814 BCX0">&nbsp;with confidence.</span></span><span class="LineBreakBlob BlobObject DragDrop SCXW248234814 BCX0"><span class="SCXW248234814 BCX0">&nbsp;</span><br class="SCXW248234814 BCX0"></span><span class="LineBreakBlob BlobObject DragDrop SCXW248234814 BCX0"><span class="SCXW248234814 BCX0">&nbsp;</span><br class="SCXW248234814 BCX0"></span><span class="TextRun SCXW248234814 BCX0" lang="EN-CA" data-contrast="auto"><span class="NormalTextRun SCXW248234814 BCX0">Trusted by 75% of the top fleets in North America,&nbsp;</span><span class="NormalTextRun SpellingErrorV2Themed SCXW248234814 BCX0">Fleetworthy</span><span class="NormalTextRun SCXW248234814 BCX0">&nbsp;offers the most adopted toll management solution and largest weigh station bypass network. Going beyond regulatory requirements, our&nbsp;</span><span class="NormalTextRun SCXW248234814 BCX0">safety and&nbsp;</span><span class="NormalTextRun SCXW248234814 BCX0">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.</span></span><span class="LineBreakBlob BlobObject DragDrop SCXW248234814 BCX0"><span class="SCXW248234814 BCX0">&nbsp;</span><br class="SCXW248234814 BCX0"></span><span class="LineBreakBlob BlobObject DragDrop SCXW248234814 BCX0"><span class="SCXW248234814 BCX0">&nbsp;</span><br class="SCXW248234814 BCX0"></span><span class="TextRun SCXW248234814 BCX0" lang="EN-CA" data-contrast="auto"><span class="NormalTextRun SCXW248234814 BCX0">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&nbsp;</span></span><a class="Hyperlink SCXW248234814 BCX0" href="http://fleetworthy.com/" target="_blank"><span class="TextRun Underlined SCXW248234814 BCX0" lang="EN-CA" data-contrast="none"><span class="NormalTextRun SCXW248234814 BCX0" data-ccp-charstyle="Hyperlink">fleetworthy.com</span></span></a><span class="TextRun SCXW248234814 BCX0" lang="EN-CA" data-contrast="auto"><span class="NormalTextRun SCXW248234814 BCX0">.</span></span></span></p></div><p><span style="font-family: arial, helvetica, sans-serif; font-size: 12pt;">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.</span></p> <h2><span style="font-family: arial, helvetica, sans-serif; font-size: 12pt;">Key Responsibilities</span></h2> <ul> <li style="font-family: arial, helvetica, sans-serif; font-size: 12pt;"><span style="font-family: arial, helvetica, sans-serif; font-size: 12pt;">Lead and mentor a team of software developers, supporting their career growth and performance.</span></li> <li style="font-family: arial, helvetica, sans-serif; font-size: 12pt;"><span style="font-family: arial, helvetica, sans-serif; font-size: 12pt;">Manage team performance using engineering management metrics and software engineering best practices to drive continuous improvement and accountability.</span></li> <li style="font-family: arial, helvetica, sans-serif; font-size: 12pt;"><span style="font-family: arial, helvetica, sans-serif; font-size: 12pt;">Manage a portfolio of internal business applications, ensuring ongoing stability, performance, and scalability.</span></li> <li style="font-family: arial, helvetica, sans-serif; font-size: 12pt;"><span style="font-family: arial, helvetica, sans-serif; font-size: 12pt;">Oversee the full Software Development Life Cycle (SDLC) including design, planning, implementation, deployment, and support.</span></li> <li style="font-family: arial, helvetica, sans-serif; font-size: 12pt;"><span style="font-family: arial, helvetica, sans-serif; font-size: 12pt;">Collaborate with business stakeholders to gather requirements, define scope, and deliver practical, scalable software solutions.</span></li> <li style="font-family: arial, helvetica, sans-serif; font-size: 12pt;"><span style="font-family: arial, helvetica, sans-serif; font-size: 12pt;">Coordinate priorities and development schedules across multiple initiatives and applications.</span></li> <li style="font-family: arial, helvetica, sans-serif; font-size: 12pt;"><span style="font-family: arial, helvetica, sans-serif; font-size: 12pt;">Contribute to high-level system architecture and application design, ensuring alignment with business objectives and technical best practices.</span></li> <li style="font-family: arial, helvetica, sans-serif; font-size: 12pt;"><span style="font-family: arial, helvetica, sans-serif; font-size: 12pt;">Be part of the team’s troubleshooting and problem solving sessions including implementing, testing, and deploying proposed solutions.</span></li> <li style="font-family: arial, helvetica, sans-serif; font-size: 12pt;"><span style="font-family: arial, helvetica, sans-serif; font-size: 12pt;">Ensure adherence to coding standards, version control, testing practices, and release procedures.</span></li> <li style="font-family: arial, helvetica, sans-serif; font-size: 12pt;"><span style="font-family: arial, helvetica, sans-serif; font-size: 12pt;">Contribute to cross-team engineering culture and helping identify and resolve systemic issues across teams.</span></li> </ul> <h2><span style="font-family: arial, helvetica, sans-serif; font-size: 12pt;">What You Bring</span></h2> <p><span style="font-family: arial, helvetica, sans-serif; font-size: 12pt;"><strong>Required Skills &amp; Experience</strong></span></p> <ul> <li style="font-family: arial, helvetica, sans-serif; font-size: 12pt;"><span style="font-family: arial, helvetica, sans-serif; font-size: 12pt;">Post-secondary education in Computer Science, Computer Engineering, Electrical Engineering, or equivalent practical experience.</span></li> <li style="font-family: arial, helvetica, sans-serif; font-size: 12pt;"><span style="font-family: arial, helvetica, sans-serif; font-size: 12pt;">9+ years of hands-on software development experience, including back-end services, APIs, and databases.</span></li> <li style="font-family: arial, helvetica, sans-serif; font-size: 12pt;"><span style="font-family: arial, helvetica, sans-serif; font-size: 12pt;">Experience in a leadership role managing software teams or projects — including 1–2 years of direct people management.</span></li> <li style="font-family: arial, helvetica, sans-serif; font-size: 12pt;"><span style="font-family: arial, helvetica, sans-serif; font-size: 12pt;"><strong>Strong Problem-Solving Skills: </strong>Architect mindset — thinks beyond the code to design systems that solve real problems creatively and scalably.</span> <ul> <li style="font-family: arial, helvetica, sans-serif; font-size: 12pt;"><span style="font-family: arial, helvetica, sans-serif; font-size: 12pt;">Strong technical knowledge of C# and ASP.NET with the ability to design, review, and contribute to production-quality code.</span></li> <li style="font-family: arial, helvetica, sans-serif; font-size: 12pt;"><span style="font-family: arial, helvetica, sans-serif; font-size: 12pt;">Proficiency in Microsoft SQL Server, including schema design, performance tuning, and complex query development.</span></li> </ul> </li> <li style="font-family: arial, helvetica, sans-serif; font-size: 12pt;"><span style="font-family: arial, helvetica, sans-serif; font-size: 12pt;"><strong>Self-Starter: </strong>Doesn't wait for direction; proactively identifies work, removes blockers, and pushes initiatives forward.</span></li> <li style="font-family: arial, helvetica, sans-serif; font-size: 12pt;"><span style="font-family: arial, helvetica, sans-serif; font-size: 12pt;"><strong>Documentation &amp; Organization: </strong>Communicates clearly, documents decisions and code thoroughly, and brings structure to ambiguous situations.</span></li> <li style="font-family: arial, helvetica, sans-serif; font-size: 12pt;"><span style="font-family: arial, helvetica, sans-serif; font-size: 12pt;"><strong>Monitoring Mindset: </strong>Understands observability — logs, metrics, and alerting — and knows how to troubleshoot and resolve production issues confidently.</span></li> <li style="font-family: arial, helvetica, sans-serif; font-size: 12pt;"><span style="font-family: arial, helvetica, sans-serif; font-size: 12pt;"><strong>Quality Assurance Mindset:</strong> 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.</span></li> <li style="font-family: arial, helvetica, sans-serif; font-size: 12pt;"><span style="font-family: arial, helvetica, sans-serif; font-size: 12pt;"><strong>Ambiguity navigation: </strong>Thrive in fast-paced, evolving environments — comfortable making decisions with incomplete information.</span></li> <li style="font-family: arial, helvetica, sans-serif; font-size: 12pt;"><span style="font-family: arial, helvetica, sans-serif; font-size: 12pt;"><strong>Remote Experience: </strong>Comfortable working in distributed teams with async communication and a high degree of self-management.</span></li> <li style="font-family: arial, helvetica, sans-serif; font-size: 12pt;"><span style="font-family: arial, helvetica, sans-serif; font-size: 12pt;"><strong>Hands-on balance: </strong>Maintain the right mix of direct technical contribution and team leadership depending on the needs of the team.</span></li> <li style="font-family: arial, helvetica, sans-serif; font-size: 12pt;"><span style="font-family: arial, helvetica, sans-serif; font-size: 12pt;"><strong>AI Tools:</strong></span> <ul> <li style="font-family: arial, helvetica, sans-serif; font-size: 12pt;"><span style="font-family: arial, helvetica, sans-serif; font-size: 12pt;">Comfortable leveraging AI coding tools to accelerate development understanding AI limitations and security implication.</span></li> <li style="font-family: arial, helvetica, sans-serif; font-size: 12pt;"><span style="font-family: arial, helvetica, sans-serif; font-size: 12pt;">Critically evaluating output for bias, errors, and correctness.</span></li> <li style="font-family: arial, helvetica, sans-serif; font-size: 12pt;"><span style="font-family: arial, helvetica, sans-serif; font-size: 12pt;">Open to learning and adopting new AI tools and workflows as the landscape evolves.</span></li> </ul> </li> </ul> <p><span style="font-family: arial, helvetica, sans-serif; font-size: 12pt;"><strong>Nice to Have</strong></span></p> <ul> <li style="font-family: arial, helvetica, sans-serif; font-size: 12pt;"><span style="font-family: arial, helvetica, sans-serif; font-size: 12pt;">Familiarity with cloud-native architecture (microservices, containerization, cloud platforms).</span></li> <li style="font-family: arial, helvetica, sans-serif; font-size: 12pt;"><span style="font-family: arial, helvetica, sans-serif; font-size: 12pt;">Experience modernizing legacy .NET Framework or WebForms applications.</span></li> <li style="font-family: arial, helvetica, sans-serif; font-size: 12pt;"><span style="font-family: arial, helvetica, sans-serif; font-size: 12pt;">Exposure to Linux-based server environments, Elixir, or Erlang.</span></li> <li style="font-family: arial, helvetica, sans-serif; font-size: 12pt;"><span style="font-family: arial, helvetica, sans-serif; font-size: 12pt;">Experience with electrical systems or embedded systems development.</span></li> <li style="font-family: arial, helvetica, sans-serif; font-size: 12pt;"><span style="font-family: arial, helvetica, sans-serif; font-size: 12pt;">Experience in fleet management, transportation technology, or safety/compliance domains</span></li> </ul><div class="content-conclusion"><p><span style="font-size: 12pt;"><em><span data-contrast="auto">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.</span></em></span></p></div>