IT Support Specialist

Fleetworthy•Madison, WI

About The Position

Fleetworthy is hiring an enthusiastic, customer-focused, entry-level IT Support Specialist for its Help Desk team. The role provides frontline technical support to employees across the organization, resolving everyday issues, building relationships, and delivering excellent service in a fast-paced technology environment. It is suited to someone beginning an IT career who is eager to learn and grow. The specialist serves as an initial contact for employee technical difficulties, manages help desk tickets, troubleshoots basic hardware, software, and connectivity issues, and escalates complex matters to senior IT staff. The role also assists with device setup and deployment, basic account provisioning, documentation, knowledge-base development, and general IT operations and project support. Fleetworthy describes itself as a provider of fleet-readiness technology, including safety and compliance, toll management, and weigh station bypass solutions. The company states that it supports millions of vehicles and drivers and is committed to a diverse and inclusive culture and equal opportunity employment.

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.
Associate's degree, certificate program in IT/Computer Science, or demonstrated equivalent experience or self-study.

Nice To Haves

Familiarity with Microsoft Active Directory, EntraID Azure, and M365 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.

Responsibilities

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.
Diagnose and resolve basic hardware, software, and connectivity issues for end-users across multiple locations.
Escalate complex or unresolved issues to senior IT staff, documenting the steps already taken.
Follow established procedures and knowledge-base articles to resolve common support requests.
Assist in setting up, configuring, and deploying 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.
Perform other duties typical of an entry-level IT support role as assigned.