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 manner * Manage user accounts (email, DMS, CRMs, etc.), including onboarding/offboarding and permission updates * Maintain and troubleshoot workstations, printers, phones, and related IT hardware * Monitor network connectivity and escalate more complex issues to our part-time consultant or third-party vendor, as needed * Perform basic system updates and ensure antivirus and security tools are up-to-date * Coordinate with managers to support dealership-specific tools such as DMS, scheduling platforms, and marketing applications * Maintain documentation of IT assets, warranties, software licenses, and support procedures * Provide onsite support across multiple Milwaukee-area locations as needed (mileage reimbursed) * Train employees on best practices for device usage, email security, and password hygiene Qualifications: * 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 environment * Proficiency with Microsoft 365, Windows 10/11, basic networking, and common office equipment * Experience with Active Directory or similar user management tools * Familiarity with VoIP phone systems, Google Workspace, or DMS platforms (Reynolds & Reynolds, CDK, etc.) a plus * Strong communication skills and a friendly, service-oriented attitude * Must be able to travel between stores locally with reliable transportation What We Offer: * Competitive salary with benefits (health, dental, vision, PTO) * A collaborative and stable work environment * Mileage reimbursement for inter-store travel * Opportunity to build internal IT systems and processes from the ground up * Flexible hours with occasional remote troubleshooting capability
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