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.
• **S...