IT Support Specialist I

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., * 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.

• 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.

Pulled from the full job description

• Tuition reimbursement
• 401(k)
• Health insurance
• 401(k) matching
• Paid time off
• Vision insurance
• Health savings account, * 401(k)
• 401(k) matching
• Dental insurance
• Health insurance
• Health savings account
• Life insurance
• Paid time off
• Tuition reimbursement
• Vision insurance