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IT Support Specialist

Job in Madison, Dane County, Wisconsin, 53774, USA
Listing for: Drivewyze by Fleetworthy
Full Time position
Listed on 2026-10-21
Job specializations:
  • IT/Tech
    HelpDesk/Support, IT Support
Salary/Wage Range or Industry Benchmark: 38000 - 48000 USD Yearly USD 38000.00 48000.00 YEAR
Job Description & How to Apply Below

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 d opera te 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  .

Role Overview

We'rehiring 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 theIT 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 ina timelyand 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.
Equipment & Setup
  • Assistin 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 helpmaintainIT 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 tonew technologies.
  • Ability to stay calm and professional under pressure.
  • Associate'sdegree, certificate program in IT/Computer Science, ordemonstratedequivalent experience or self-study.
Preferred
  • Familiarity with Microsoft Active Directory,EntraIDAzure, M365 Suite
  • Any experience with a ticketing system such as Jira Service Management, Service Now, 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. Youdon'tneed to have all the answers — you need thedriveto find them. You take ownership of the tickets you touch, communicate proactively, and leave every interaction better…

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