Full-Time

IT Support Specialist

Updated on 9/4/2026

Bestpass

Bestpass

51-200 employees

Toll management for commercial fleets

No salary listed

Edmonton, AB, Canada

Hybrid

Associate's, Certification

Category
IT Operations (1)
Required Skills
Microsoft Azure
ServiceNow
Microsoft Windows
Cybersecurity
Customer Service

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Requirements
  • 0–1 year of IT support, help desk, or customer service experience; internships, co-ops, and volunteer experience are welcome.
  • Basic understanding of Windows and/or Apple operating systems.
  • Strong interpersonal and communication skills, including the ability 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.
  • An Associate's degree, a certificate program in IT or Computer Science, or demonstrated equivalent experience or self-study.
Responsibilities
  • Serve as the first point of contact for employees experiencing technical difficulties via phone, email, chat, or in person.
  • Provide 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.
  • 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.
  • 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.
  • Document common issues, resolutions, and how-to guides to help build Help Desk knowledge base resources.
  • Follow and help maintain IT procedures and standard operating documentation.
  • 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.
Desired Qualifications
  • Familiarity with Microsoft Active Directory, Entra ID, Azure, and the Microsoft 365 suite.
  • Experience with a ticketing system such as Jira Service Management, ServiceNow, or similar.
  • CompTIA A+ certification or currently pursuing it.
  • Interest in pursuing a long-term career in IT, cybersecurity, or infrastructure.

Bestpass provides toll management services for commercial fleets in the United States. It uses vehicle transponders to automatically pay tolls, then consolidates charges into a single invoice with online reporting to assign costs to specific vehicles. The company differentiates itself with nationwide coverage on major U.S. toll roads and strategic tolling partnerships that streamline payments for fleets. Its goal is to reduce administrative work and toll costs so fleet operators can focus on their core logistics.

Company Size

51-200

Company Stage

Growth Equity (Venture Capital)

Total Funding

$19.1M

Headquarters

Town of Colonie, New York

Founded

2001

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Simplify Jobs

Simplify's Take

What believers are saying

  • May 20, 2026 unified logins and centralized vehicle management reduced multi-product friction.
  • February 4, 2026 Toll360 added AI-driven real-time toll forecasting and automated recovery.
  • Bestpass still advertises coverage across 100% of major U.S. toll roads.

What critics are saying

  • New York Thruway sued Bestpass on August 11, 2026 over the 1% fee fight.
  • The February 2026 rebrand exposes customers to portal churn and integration failures.
  • PrePass and toll authorities can disintermediate Bestpass, crushing the toll-management moat quickly.

What makes Bestpass unique

  • Fleetworthy folded Bestpass into a single fleet-readiness suite on February 23, 2026.
  • Toll360 predicts, reconciles, and disputes tolls directly inside the payment workflow.
  • Geotab integration lets fleets compare GPS, ELD, and toll data in one interface.

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Benefits

Flexible Work Hours

Paid Vacation

401(k) Retirement Plan

401(k) Company Match

Wellness Program

Employee Referral Bonus

Company News

PR Newswire
Aug 7th, 2024
Bestpass-Fleetworthy Solutions Acquires Drivewyze to Create Industry's Only Suite for Safety, Compliance, and Efficiency

/PRNewswire/ -- Bestpass-Fleetworthy Solutions, the leader in toll management, safety, and compliance solutions, today announced it has acquired Drivewyze, the...

PR Newswire
Mar 26th, 2024
Bestpass Adds Innovation And Growth Executives

ALBANY, N.Y., March 26, 2024 /PRNewswire/ -- Bestpass, Inc., the leader in toll management solutions and major innovator in safety and compliance solutions for commercial fleets, today announced two key additions to its leadership team. Bestpass is pleased to welcome Shay Demmons as Chief Product Officer and Scott Chao, as Chief Marketing Officer. These strategic hires will aid in Bestpass' commitment to scale its service offerings and network integrations for commercial fleets and owner operators."We're thrilled to have Shay and Scott join the team at Bestpass," said Tom Fogarty, CEO of Bestpass. "We set out to build out our Innovation and Growth teams by attracting accomplished leaders as our first C-Level executives in Product and Marketing. Scott and Shay bring extensive and dynamic work experience, both in and outside the transportation industry. As we continue to grow the Bestpass brand and bring forth new solutions for our customers, I am confident that their leadership will play a pivotal role in driving our success."Chao joins Bestpass as CMO with deep experience in growing companies through strategy and transformational improvements

FreightWaves
Feb 7th, 2024
Bestpass, Geotab collaborate on toll-telematic integration

Toll management solutions provider Bestpass is working with telematics creator Geotab to help commercial fleets better manage and monitor tolls to reduce expenses.

Yahoo Finance
Feb 7th, 2024
Bestpass Announces New Integration With Geotab

Geotab customers using Bestpass can now access new toll activity data and reporting features through a single interfaceALBANY, N.Y., Feb. 7, 2024 /PRNewswire/ -- Bestpass, Inc., a comprehensive payment platform provider and the leader in toll management solutions for commercial fleets, today announced a new integrated offering within the Geotab ecosystem that will enable Bestpass customers access to first-of-its-kind toll data and reporting tools in their Geotab account. Geotab, a global leader in connected transportation solutions, provides telematics – vehicle and asset tracking – capabilities to over 50,000 customers in 160 countries. The integration will allow fleets and owner operators the ability to gain new insight into toll activity to more effectively manage tolls and identify opportunities to reduce toll expenses.Bestpass LogoAccording to David Long, Head of Product at Bestpass, the company developed its Toll Genius data reporting system to integrate with telematics providers, such as Geotab, to enable Bestpass to synchronize and share toll and telematics data through a single interface.With this integration, Bestpass customers can leverage accurate vehicle data and GPS location through Geotab and match that information with toll charges received from their Bestpass account via the MyGeotab interface. If there's a discrepancy between vehicle GPS location and the toll a vehicle received, it's reported. This feature makes it easier for customers to identify and investigate the issue, dispute an inaccurate toll charge or violation, and reduces the risk of disputes over toll charges with drivers and customers.The integration also has a new toll activity reporting feature that shows a high-level heat map that allows fleets to identify hot spots for toll spend

PR Newswire
Nov 28th, 2023
Bestpass Acquires Fleetworthy Solutions

/PRNewswire/ -- Bestpass, the leading toll management and payment platform for commercial vehicles, announced today that it has acquired Fleetworthy Solutions,...