--- title: 'IT Support Specialist at Fleetworthy' canonical: 'https://feeny.ai/job/it-support-specialist-fleetworthy-edmonton-wsg853r1ta30' type: 'job' last_seen: '2026-09-15' --- # IT Support Specialist at Fleetworthy - **Company:** Fleetworthy - **Location:** Edmonton, Canada - **Work type:** hybrid - **Posted:** 2026-08-26 - **Last confirmed live:** 2026-09-15 - **Apply:** https://job-boards.greenhouse.io/bestpass/jobs/4708299006 ## 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 AI-enabled, connected fleet technology that keeps drivers safe, fleets compliant, and operations running at peak efficiency. Learn more at [fleetworthy.com](http://fleetworthy.com/). ## Role Overview We're hiring an enthusiastic and customer-focused IT Support Specialist to join our Help Desk team. This is an entry-level role that is perfect for someone beginning their IT career who is eager to learn and grow in a fast-paced technology environment. As part of the IT Support team, you will be on the front lines supporting team members across the organization — solving everyday technical problems, building relationships, and delivering excellent service. Core Responsibilities End-User Support & Customer Service - Serve as the first point of contact for employees experiencing technical difficulties via phone, email, chat, or in person. - Provide friendly, patient, and professional customer service to end-users at all levels of the organization. - Log, track, and resolve incoming help desk tickets in a timely and thorough manner. Troubleshooting & Issue Resolution - Diagnose and resolve basic hardware, software, and connectivity issues for end-users across multiple locations. - Escalate complex or unresolved issues to senior IT staff with detailed documentation of steps already taken. - Follow established procedures and knowledge base articles to resolve common support requests. Equipment & Setup - Assist in the setup, configuration, and deployment of laptops, desktops, peripherals, and mobile devices for new employees. - Support basic account provisioning and access requests under the guidance of senior IT staff. Documentation & Knowledge - Document common issues, resolutions, and how-to guides to help build out Help Desk knowledge base resources. - Follow and help maintain IT procedures and standard operating documentation. Other - Assist the IT team with day-to-day operational tasks and project support as needed. - Execute other duties typical of an entry-level IT support role as assigned. ## Skills & Qualifications Required - 0–1 year of IT support, help desk, or customer service experience (internships, co-ops, and volunteer experience welcome). - Basic understanding of Windows and/or Apple operating systems. - Strong interpersonal and communication skills — able to explain technical concepts clearly to non-technical users. - Eagerness to learn, troubleshoot, and adapt to new technologies. - Ability to stay calm and professional under pressure. - Associate's degree, certificate program in IT/Computer Science, or demonstrated equivalent experience or self-study. ## Preferred - Familiarity with Microsoft Active Directory, EntraID Azure, M365 Suite - Any experience with a ticketing system such as Jira Service Management, ServiceNow, or similar. - CompTIA A+ certification or currently pursuing. - Interest in pursuing a long-term career in IT, cybersecurity, or infrastructure. Ideal Candidate A curious, people-oriented individual who genuinely enjoys helping others and solving problems. You don't need to have all the answers — you need the drive to find them. You take ownership of the tickets you touch, communicate proactively, and leave every interaction better than you found it. You're comfortable asking questions, learning on the fly, and growing with a team that will invest in your development. Application Note This role will include routine help desk responsibilities and other duties assigned consistent with entry-level IT support. We encourage candidates from all backgrounds to apply — if you are passionate about technology and helping people, we want to hear from you. 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. ## About Fleetworthy ## Company Overview - **One-liner**: Fleetworthy provides a unified technology suite for fleet readiness, combining safety and compliance, toll management, and weigh station bypass solutions. - **Entity Type**: Private (subsidiary of Bestpass, Inc.; acquired in 2023) - **Headquarters**: Albany, New York, United States - **Founded**: Not publicly available (brand launched in 2024/2025 through a rebrand of Bestpass, Fleetworthy Solutions, ExpressTruckTax, and Drivewyze) - **Founders**: Not publicly available ## Core Business - Primary industry: Fleet management software for commercial trucking and logistics. - Target customers: B2B – fleet managers, owner-operators, human resources, and finance teams in transportation. - Mission or purpose: "Simplify road safety and fleet operations through integrated, innovative technology" – helping fleets stay compliant, efficient, and safe. ## Products & Services - **[Safety & Compliance]**: Digital tools for regulatory compliance, driver monitoring, and audit readiness. - **[Toll Management]**: Nationwide toll coverage (Complete Pass+) with a single device, reducing violations and administrative burden. - **[Weigh Station Bypass]**: Access to 925+ locations across 48 states and provinces, with expedited inspection capabilities. These are delivered as a **Connected Suite** that integrates all products under one platform. ## Market Standing - **Valuation/Market Cap**: Not disclosed. - **Key Metric**: Annual Revenue of $37.4M (estimated by LinkedIn) and Total Funding of $105.8M across multiple rounds. - **Notable Investors/Partners**: The Argentum Group (led early round), Susquehanna Growth Equity (talent source), and partnerships with 90% of the largest fleets in North America. - **Growth Signals**: Headcount grew 213.9% YoY to 225 employees; recent rebrand unified four legacy brands; active job postings increased 700% YoY; AI-enabled features being rolled out. ## Competitive Advantages - Only vendor offering a complete, integrated suite for safety, tolls, and bypass – reducing the need for multiple point solutions. - Largest weigh station bypass network in North America, with 925+ locations. - Trusted by 90% of the largest fleets (e.g., Faith Technology saw 90% reduction in toll violations; RWE saw 15%+ reduction in compliance costs). - Deep domain expertise from decades of combined experience (Bestpass founded in 1993, Drivewyze in 2009, etc.). ## Strategic Focus - Unified brand strategy under Fleetworthy to cross-sell and simplify customer experience. - Investment in AI-enabled, connected fleet technology to improve real-time decision-making and proactive compliance. - Continued expansion of product features and geographic coverage (presence in Canada and India). ## Why Work Here - **Culture**: Collaborative, innovative, and fun environment with employee-led committees (Thrive, Hype, Care). Emphasis on "People First, Trust, Every Trip Matters, Always Innovating, Mindset". - **Work Model**: Offers remote, hybrid, and in-office roles. Many engineering positions are remote or hybrid (Edmonton, AB or US remote). - **Perks**: Comprehensive health/dental plans, life and disability insurance, wellness programs, Employee Assistance Program, paid time off, casual dress code, company swag, events, and learning & development programs. - **Engineering Culture**: Opportunities to work on meaningful products that impact real-world safety; stack includes modern software engineering roles (Platform Engineer, Senior Software Engineer, Manager, Software Engineering) with a focus on innovation. ## Sources 1. [fleetworthy.com](https://fleetworthy.com/) 2. [linkedin.com](https://www.linkedin.com/company/fleetworthy) 3. [greenhouse.io](http://job-boards.greenhouse.io/bestpass) 4. [fleetworthy.com](https://fleetworthy.com/resources/blog/a-new-era-in-fleet-management) ## Other roles at Fleetworthy - [Internship - Finance](https://feeny.ai/job/internship-finance-fleetworthy-albany-zg519wjpx272) — Albany, NY - [Senior Software Engineer](https://feeny.ai/job/senior-software-engineer-fleetworthy-edmonton-ktacemy44kfm) — Edmonton, Canada - [Fleet Compliance Associate](https://feeny.ai/job/fleet-compliance-associate-fleetworthy-madison-wq6cbyrek9aq) — Madison, WI - [Business Analyst](https://feeny.ai/job/business-analyst-fleetworthy-edmonton-e85z33p0h65t) — Edmonton, Canada - [R&D Imaging Specialist](https://feeny.ai/job/r-d-imaging-specialist-fleetworthy-edmonton-0gz77gcct8a8) — Edmonton, Canada - [Platform Engineer](https://feeny.ai/job/platform-engineer-fleetworthy-edmonton-03dgkxgp5tm6) — Edmonton, Canada - [Billing Specialist](https://feeny.ai/job/billing-specialist-fleetworthy-edmonton-ec5exjbbfst9) — Edmonton, Canada - [Field Service Technician](https://feeny.ai/job/field-service-technician-fleetworthy-wisconsin-9xsq9ns3sqgk) — Wisconsin - [Field Service Technician](https://feeny.ai/job/field-service-technician-fleetworthy-new-york-fg5sbpm1vvsx) — New York, NY - [Field Service Technician](https://feeny.ai/job/field-service-technician-fleetworthy-georgia-kys7trmtx5e1) — Georgia