IT Support Specialist Naperville, IL; on-site

IT Support Specialist | Full-Time On-Site

Location: Naperville, IL (on-site)

Employment Type: Full-Time

Reports to: Director of IT

Founded in 1995, Five-Star Audio Visual, Inc. is an independent boutique audiovisual company serving the luxury hospitality market nationwide. We partner with premier hotels, resorts, and event venues across the U.S., delivering high-touch service and seamless experiences.

• Technology is central to our work, and we prioritize professionals who are skilled, dependable, security-minded, and collaborative
• Candidates may be asked to participate in a technical assessment as part of the hiring process

Reporting to the Director of IT, the IT Support Specialist will support corporate and field technology operations with a focus on device deployment, system reliability, security, and end-user support. This role is ideal for someone who:

• Enjoys solving problems
• Values organization, documentation, and security best practices
• Takes pride in maintaining secure, efficient IT systems

• Configure, image, and deploy Windows 11 Pro and Apple devices
• Administer Microsoft 365, Entra  (Azure AD), and related cloud services
• Manage Apple Business Manager enrollment and device oversight
• Maintain system updates, security standards, and performance optimization
• Monitor and enforce security policies and IT best practices across systems
• Track IT assets, user accounts, and system documentation
• Provide on-site support in Naperville and remote support across locations
• Troubleshoot hardware, software, and network issues
• Collaborate with internal teams to maintain consistent IT and security standards

• 2–5 years of IT support experience, corporate or multi-site preferred
• CompTIA A+, Network+, or equivalent hands‑on experience
• Strong experience with Microsoft 365, Entra  (Azure AD), and Azure environments (AZ-900 preferred)
• Experience supporting Windows 11 Pro systems
• Familiarity with Apple device management and Apple Business Manager
• Knowledge of IT security principles and best practices
• Strong organizational, documentation, and troubleshooting skills
• Excellent communication skills across phone, Teams, email, and in person
• Must be local to the Naperville area and available on site
• Must be authorized to work in the U.S.
• Occasional travel may be required

• Intune or other MDM/device management tools
• Networking fundamentals (firewalls, switches, Wi‑Fi)
• Experience with ticketing systems and remote support platforms

• 401(k) and Roth 401(k) with company match
• Medical, dental, and vision insurance
• Health savings account
• Life insurance
• Paid vacation, sick time, and company holidays