IT Support Specialist

Fleetworthy; Madison (WI); Hybrid; USD 40,000 - 52,000; Full time

Job summary

Fleetworthy is hiring an entry-level IT Support Specialist to join the Help Desk team. You will be on the front lines supporting team members across the organization, solving everyday technical problems, building relationships, and delivering excellent service.

As part of the IT Support team, you will assist in setup and provisioning, document common issues, and contribute to knowledge base resources while learning and growing in a fast-paced technology environment.

Qualifications

• 0–1 year of IT support or help desk experience (internships welcome).
• Basic understanding of Windows and/or Apple operating systems.

Responsibilities

• Serve as the first point of contact for employees with technical issues via phone, email, chat, or in person.
• Provide friendly, patient, and professional customer service to end-users.
• Log, track, and resolve help desk tickets promptly and thoroughly.
• Diagnose and resolve basic hardware, software, and connectivity issues.
• Escalate complex issues to senior IT staff with documented steps.

Skills

IT support basics

Windows/macOS

Customer service

Learning mindset

Communication

Calm under pressure

Education

Associate's degree or IT certificate

Tools

Jira Service Management

ServiceNow

Ticketing systems

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, 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 fleetworthy.com .

Role Overview

We'rehiring an enthusiastic and customer-focused IT Support Specialistto 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 Supportteam, 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 resolvecommon supportrequests.

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, 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. 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 than you found it.You'recomfortable asking questions, learning on the fly, andgrowingwith a team that will invest in your development.

Application Note

This role will include routine help desk responsibilities and otherdutiesassigned 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.

Voluntary Self-Identification

For government reporting purposes, we ask candidates to respond to the below self-identification survey.Completion of the form is entirely voluntary. Whatever your decision, it will not be considered in the hiringprocess or thereafter. Any information that you do provide will be recorded and maintained in aconfidential file.

As set forth in Fleetworthy ’s 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 measurethe effectiveness of the outreach and positive recruitment efforts we undertake pursuant to VEVRAA. Classification of protected categoriesis 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 service-connected disability.

A "recently separated veteran" means any veteran during the three-year period beginning on the date of such veteran's 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.