Level 2 Help Desk Technician – Windows & Mac Expert

Milestone Technologies, Inc.; Jacksonville (FL); On-site; USD 42,000 - 62,000; Full time

Job summary

Milestone Technologies, Inc. is seeking a Help Desk Technician to join a dynamic team supporting primarily PC environments, with Mac support as well.

The role focuses on diagnosing and resolving complex technical issues across multiple channels (chat, ticket, phone) to deliver the best IT Help Desk experience. The environment is fast-paced, collaborative, and requires strong communication and technical aptitude.

Qualifications

• 2+ years of experience in a helpdesk role or similar.
• Strong interpersonal communication with empathy is a must.
• Experience with Microsoft Outlook client (Windows & Mac) and Outlook Web Access.
• Experience supporting PCs and Windows OS in a commercial or enterprise environment is preferred.
• Experience with Microsoft Exchange and AD administration is helpful.

Responsibilities

• Apply critical thinking to complex user requests and provide context to deliver solutions quickly.
• Troubleshoot client-side network connectivity issues, including authentication and remote access.
• Support user requests and perform remote installations as needed.
• Assist remote users with access problems including password resets and network access failures.
• Support messaging & calendar services and content collaboration.
• Support issues with mobile devices and collaboration tools.
• Lead in ticket processes and coach others when workflow deficiencies are identified.
• Participate in weekly team syncs and drive actionable discussions.

Skills

Empathy

Excellent communication

Problem solving

Team collaboration

Education

HS Diploma or GED

Tools

Microsoft Outlook (Windows & Mac)

Outlook Web Access

Microsoft Exchange

Active Directory

Remote support tools

Zoom / WebEx / video conferencing

Job description

Milestone Technologies, Inc. is seeking a Help Desk Technician to join a dynamic team supporting primarily PC environments, with Mac support as well.

The role focuses on diagnosing and resolving complex technical issues across multiple channels (chat, ticket, phone) to deliver the best IT Help Desk experience. The environment is fast-paced, collaborative, and requires strong communication and technical aptitude.