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Job Title


Principal Software Engineer


Company : Bestpass - Fleetworthy


Location : Toronto, Ontario


Created : 2026-03-26


Job Type : Full Time


Job Description

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 AIenabled, 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 nextgen compliance platform. This is a handson leadership role you will own technical direction, mentor and lead a team of 34 developers, and contribute meaningfully at the individual contributor level. The ideal candidate brings 1015+ years of fullstack experience, thrives in fastpaced and sometimes ambiguous environments, and has a track record of leading distributed, multitimezone teams. You will be expected to think beyond your immediate team. As a member of our Team Leads Team, you will collaborate crossfunctionally 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 lowlatency, highavailability, 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 teams domains. Drive adoption of microservice and micro frontend 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 34 developers, providing technical direction, code review, and career guidance. Navigate ambiguity and fastchanging 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 relationshipbuilding, 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 crossteam leadership forum where engineering leads share learnings, align on practices, and collectively influence engineering culture beyond their own teams. Bring insights from your teams 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. 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 remotefirst practices. Ability to operate and deliver in fastpaced, ambiguous environments without loss of quality or team morale. Experience facilitating crossteam engineering forums, communities of practice, or similar leadership collaboration. Front End Development Vue.js 2 or 3 / Vuetify / Vuex / Webpack Testing Jest / Vitest Tooling VS Code Back End Development .NET Framework / .NET Core / .NET 78 / C# REST API design and implementation Entity Framework (code first and database first) MSSQL / SQL Profiler / Query Tuning Testing nUnit / Moq / Autofixture Tooling Visual Studio / Rider DevOps Github Other Tooling Sentry Voluntary SelfIdentification For government reporting purposes, we ask candidates to respond to the below selfidentification survey. Completion of the form is entirely voluntary. Whatever your decision, it will not be considered in the hiring process or thereafter. Any information that you do provide will be recorded and maintained in a confidential file. As set forth in Fleetworthys Equal Employment Opportunity policy, we do not discriminate on the basis of any protected group status under any applicable law. If you believe you belong to any of the categories of protected veterans listed below, please indicate by making the appropriate selection. As a government contractor subject to the Vietnam Era Veterans Readjustment Assistance Act (VEVRAA), we request this information in order to measure the effectiveness of the outreach and positive recruitment efforts we undertake pursuant to VEVRAA. Classification of protected categories is as follows: A disabled veteran is one of the following: a veteran of the U.S. military, ground, naval or air service who is entitled to compensation (or who but for the receipt of military retired pay would be entitled to compensation) under laws administered by the Secretary of Veterans Affairs; or a person who was discharged or released from active duty because of a serviceconnected disability. A recently separated veteran means any veteran during the threeyear period beginning on the date of such veterans discharge or release from active duty in the U.S. military, ground, naval, or air service. An active duty wartime or campaign badge veteran means a veteran who served on active duty in the U.S. military, ground, naval, or air service during a war, or in a campaign or expedition for which a campaign badge has been authorized under the laws administered by the Department of Defense. An Armed forces service medal veteran means a veteran who, while serving on active duty in the U.S. military, ground, naval or air service, participated in a United States military operation for which an Armed Forces service medal was awarded pursuant to Executive Order 12985. Voluntary SelfIdentification of Disability We are a federal contractor or subcontractor. The law requires us to provide equal employment opportunity to qualified people with disabilities. We have a goal of having at least 7% of our workers as people with disabilities. The law says we must measure our progress towards this goal. To do this, we must ask applicants and employees if they have a disability or have ever had one. People can become disabled, so we need to ask this question at least every five years. Completing this form is voluntary, and we hope that you will choose to do so. Your answer is confidential. No one who makes hiring decisions will see it. Your decision to complete the form and your answer will not harm you in any way. If you want to learn more about the law or this form, visit the U.S. Department of Labors Office of Federal Contract Compliance Programs (OFCCP) website at www.dol.gov/ofccp. How do you know if you have a disability? A disability is a condition that substantially limits one or more of your major life activities. If you have or have ever had such a condition, you are a person with a disability. Disabilities include, but are not limited to: Alcohol or other substance use disorder (not currently using drugs illegally) Autoimmune disorder, for example, lupus, fibromyalgia, rheumatoid arthritis, HIV/AIDS Blind or low vision Cancer (past or present) Cardiovascular or heart disease Celiac disease Cerebral palsy Deaf or serious difficulty hearing Diabetes Disfigurement, for example, disfigurement caused by burns, wounds, accidents, or congenital disorders Epilepsy or other seizure disorder Gastrointestinal disorders, for example, Crohns Disease, irritable bowel syndrome Intellectual or developmental disability Mental health conditions, for example, depression, bipolar disorder, anxiety disorder, schizophrenia, PTSD Missing limbs or partially missing limbs Mobility impairment, benefiting from the use of a wheelchair, scooter, walker, leg brace(s) and/or other supports Nervous system condition, for example, migraine headaches, Parkinsons disease, multiple sclerosis (MS) Neurodivergence, for example, attentiondeficit/hyperactivity disorder (ADHD), autism spectrum disorder, dyslexia, dyspraxia, other learning disabilities Partial or complete paralysis (any cause) Pulmonary or respiratory conditions, for example, tuberculosis, asthma, emphysema Short stature (dwarfism) Traumatic brain injury We are 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. #J-18808-Ljbffr