We are looking for a skilled and proactive IT Support Specialist – Level 2 (Mid-Senior) to provide advanced technical support, troubleshoot complex IT issues, and maintain reliable IT infrastructure for a U.S.-based organization.

The ideal candidate has strong technical expertise across operating systems, server administration, networking, and cloud services, combined with excellent customer service and problem-solving skills. This role is ideal for someone who enjoys resolving technical challenges, managing multiple support requests, and delivering efficient IT solutions.

Duties / Task to Perform

• Provide Level 2 technical support, resolving hardware, software, system, and network-related issues.
• Troubleshoot and maintain Windows, macOS, Linux (Debian and Proxmox), and Windows Server environments.
• Administer and support Microsoft 365 (Office 365) and Google Workspace environments.
• Perform remote software installations, configurations, updates, and maintenance.
• Troubleshoot network connectivity issues, manage IP addressing, and support local network administration.
• Configure and maintain antivirus, firewall, VPN, email filtering, and DNS security solutions.
• Support backup and virtualization environments, including Proxmox and Hyper-V.
• Manage remote access and troubleshooting tools such as ConnectWise and RustDesk.
• Monitor, update, prioritize, and resolve technical support tickets using ticketing systems.
• Create and maintain accurate technical documentation, troubleshooting procedures, and knowledge base articles.
• Communicate professionally with users, providing clear explanations and timely updates on technical issues.
• Escalate unresolved or highly complex incidents to higher-level technical teams when necessary.

Requirements

• Mid-senior-level experience in IT technical support, help desk operations, or systems administration, with strong Level 2 troubleshooting capabilities.
• Advanced troubleshooting skills across Windows, macOS, and Linux operating systems.
• Strong experience administering Windows Server and Linux server environments, including Debian and Proxmox.
• Advanced knowledge of Microsoft 365 and Google Workspace administration.
• Strong understanding of networking concepts, including TCP/IP, DNS, DHCP, IP addressing, and network troubleshooting.
• Experience managing firewalls, VPNs, and network security solutions such as pfSense, UniFi, and OPNsense.
• Experience administering antivirus solutions, email security, and DNS filtering.
• Familiarity with virtualization and backup technologies, particularly Proxmox and Hyper-V.
• Basic to intermediate scripting skills using PowerShell and Bash.
• Experience with remote support and connection tools such as ConnectWise and RustDesk.
• Proficiency in ticket management systems, including ConnectWise or similar platforms.
• Experience creating and maintaining IT documentation using IT Glue or similar knowledge management platforms.
• Strong analytical thinking, attention to detail, and problem-solving abilities.
• Excellent customer service and communication skills, with the ability to explain technical concepts clearly.
• Ability to prioritize multiple technical requests, work independently, and collaborate effectively with escalation teams.

Schedule: Monday through Friday, 8:30am to 5:30pm (EST)

Benefits

• Fully remote work environment
• Stable, long-term collaboration
• Clear scope of responsibilities and structured workflows
• Training and onboarding support
• Opportunity to work with international teams
• Exposure to modern tools and professional processes
• Supportive and collaborative work culture
• Opportunity for skill development and career growth

📌 Before You Apply, Please Read:

At Freelance Latin America, we’re excited to connect you with meaningful remote opportunities. However, we want to be clear:

⏰ These are professional roles with set schedules defined by the client.

Consistent availability is expected. You will have a set work schedule determined by the client, and you are expected to be present during those hours.

🤝 You will be part of the client’s team.

You’ll follow their company guidelines, communication practices, and workflows, ensuring seamless collaboration.

📈 KPIs and goals matter.

Your performance will be measured to ensure alignment with client expectations and project objectives.

🧑‍🏫 Training may be required.

You might need to complete training to fully understand your role, tools, and client processes.

🎯 Commitment and responsibility are essential.

We work with clients who rely on your dedication to deliver consistent, high-quality results. This is key to building trust and long-term partnerships.

🚀 Ready to grow your career with us?

Apply only if you are ready to commit, learn, and take ownership of your role.