Position Summary:We are seeking a proactive, hands-on IT Support Specialist to manage the day-to-day technology needs of our dealership group. This role will serve as the primary point of contact for staff tech issues, ensuring seamless operation of desktops, phones, printers, network systems, and user access across multiple rooftops. The ideal candidate is resourceful, responsive, and comfortable supporting both tech-savvy and non-technical users in a fast-paced retail environment.Key Responsibilities:Serve as the first line of support for all help desk tickets, resolving hardware, software, and access issues in a timely mannerManage user accounts (email, DMS, CRMs, etc.), including onboarding/offboarding and permission updatesMaintain and troubleshoot workstations, printers, phones, and related IT hardwareMonitor network connectivity and escalate more complex issues to our part-time consultant or third-party vendor, as neededPerform basic system updates and ensure antivirus and security tools are up-to-dateCoordinate with managers to support dealership-specific tools such as DMS, scheduling platforms, and marketing applicationsMaintain documentation of IT assets, warranties, software licenses, and support proceduresProvide onsite support across multiple Milwaukee-area locations as needed (mileage reimbursed)Train employees on best practices for device usage, email security, and password hygieneQualifications:Associate’s or Bachelor’s degree in Information Technology, Computer Science, or related field (or equivalent work experience)2+ years of hands-on IT support experience, preferably in a multi-location or retail environmentProficiency with Microsoft 365, Windows 10/11, basic networking, and common office equipmentExperience with Active Directory or similar user management toolsFamiliarity with VoIP phone systems, Google Workspace, or DMS platforms (Reynolds & Reynolds, CDK, etc.) a plusStrong communication skills and a friendly, service-oriented attitudeMust be able to travel between stores locally with reliable transportationWhat We Offer:Competitive salary with benefits (health, dental, vision, PTO)A collaborative and stable work environmentMileage reimbursement for inter-store travelOpportunity to build internal IT systems and processes from the ground upFlexible hours with occasional remote troubleshooting capability