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Open nowPosted 16 days agoWe saw it 64 min after it went up

IT Support Specialist

Fleetworthy12 open roles

Where
Madison, WI, USA (Hybrid)
Work mode
Hybrid
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Your applicationOpen nowIT Support SpecialistFleetworthy · Madison, WI, USA (Hybrid)

  1. YouYes, apply to this one.

  2. CV RocketCV written for this posting.

  3. 25 readersRecruiter, hiring manager, skeptic. Round after round.

  4. CV RocketApplied on Fleetworthy's own form.

The reply lands in your private mailbox

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The clock on this job

Early applications get read.

13.3% of postings close within 7 days. Measured by our own scanner across the market. Fleetworthy postings stay open a median of 24 days.

Share of postings closed within
  1. 2.1%1 day
  2. 4.6%3 days
  3. 13.3%7 days
  4. 21.3%14 days
  5. 35.7%30 days
  6. 59.1%60 days
This job: posted 16 days ago

Fleetworthy median: 24 days open

The posting

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.

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.

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