IT Support Specialist I

• This is a in-person office, non-remote position
• Position is based in our Collier County region (Naples, Marco Island). The ideal candidate will be able to travel to our offices in this region.

We are seeking a proactive and technically skilled IT Support Specialist I to join our Technology Team. This role provides comprehensive technology support to real estate professionals and staff in a BYOD (Bring Your Own Device) environment across multiple office locations in Southwest Florida. The ideal candidate will demonstrate expertise in both Windows and macOS environments and leverage AI-powered support tools to enhance efficiency, automate diagnostics, and improve end-user satisfaction. Reporting Relationship Reports directly to the Director of IT . Key Responsibilities End-User Support: Provide tier-one and tier-two technical support for both Windows and macOS devices, including system configuration, driver installation, email setup, and AI-assisted troubleshooting. AI-Powered Ticket Resolution: Utilize AI-enabled helpdesk systems (such as Atlassian, Freshservice, or Microsoft Copilot) to accelerate ticket triage, suggest resolutions, and optimize response time. Account & System Management: Administer user accounts through Active Directory , Microsoft 365 , and Exchange , including password resets and security configuration. Onboarding & Setup: Manage new hire setup, system provisioning, and user training — leveraging automation and AI-driven onboarding tools where applicable. Software & Network Support: Assist with access issues across browsers and cloud platforms; collaborate with network specialists to resolve connectivity and security issues (VPN, VLAN, VoIP, and firewall systems). AI-Augmented Training & Documentation: Create and maintain knowledge base articles and training materials using generative AI tools to ensure clear, consistent communication. System Monitoring & Automation: Use AI-based endpoint management and monitoring tools (e.g., Microsoft Intune, CrowdStrike Falcon Insight, or Atera) to detect, diagnose, and prevent issues proactively. Data & Security Compliance: Support the implementation of cybersecurity measures, including spam filtering, antivirus management, and data integrity checks using AI-enhanced threat detection systems. Cross-Team Collaboration: Serve as the regional point of contact for agents and staff, ensuring uninterrupted technology operations and a positive user experience. Travel: Travel to office locations within the assigned region at least two days per week and as required for on-site support or system rollout projects. Qualifications Proven experience supporting Windows and macOS environments in a BYOD setting. Strong problem-solving and analytical skills, with the ability to apply AI-driven insights for faster resolution. Experience with Active Directory , Microsoft 365 administration , and Exchange management . Familiarity with AI support tools , such as: Chatbots or virtual assistants (Microsoft Copilot, ChatGPT for ITSM) Predictive analytics for device monitoring Automated ticket classification and workflow tools Understanding of network infrastructure concepts (firewalls, VPNs, VLANs, and VoIP). Experience with Atlassian or similar ticketing systems enhanced by automation rules or AI plug-ins. Knowledge of cybersecurity tools that employ AI for anomaly detection and response. Experience supporting printers (Konica Minolta, HP) and print management systems (e.g., PaperCut). Excellent communication, organization, and documentation skills. Ability to work independently while maintaining strong collaboration across distributed teams. Knowledge of real estate technology systems and processes is a plus. Requirements Valid driver’s license and reliable transportation. Willingness to travel within the assigned region. Ability to lift up to 15 pounds. Commitment to professional appearance and customer service excellence. Job Type: Full-time Pay: $50,000.00 - $55,000.00 per year Benefits: 401(k) 401(k) matching Dental insurance Health insurance Health savings account Life insurance Paid time off Tuition reimbursement Vision insurance Willingness to travel: 25% (Preferred) Work Location: In person #J-18808-Ljbffr Socket.dev