IT Support Level 2

Freelance Latin America; Porlamar; Remote; VES 57,269,000 - 79,295,000; Full time

Benefits offered by this job

Fully remote

Stable collaboration

Structured workflows

Training & onboarding

International teams

Career growth

Job summary

Freelance Latin America is seeking a skilled IT Support Specialist - Level 2 to deliver advanced technical support for a U.S.-based organization. You will troubleshoot complex issues across Windows, macOS, Linux, and server environments while maintaining documentation and proactive customer service.

This role is fully remote, with a Monday–Friday EST schedule. You will work with diverse international teams, manage tickets, and escalate when needed, using ConnectWise, Proxmox, and cloud tools to

Qualifications

• Mid-senior IT support with Level 2 troubleshooting capabilities.
• Strong troubleshooting across Windows, macOS, and Linux environments.
• Experience administering Windows Server and Linux servers (Debian/Proxmox).
• Proficiency with Microsoft 365 and Google Workspace administration.

Responsibilities

• Provide Level 2 technical support for hardware, software, systems, and network issues.
• Troubleshoot Windows, macOS, Linux, and server environments and document results.
• Administer and support Microsoft 365 and Google Workspace environments.
• Perform remote software install/configuration/maintenance.
• Manage network connectivity issues and IP addressing.

Skills

IT Support

Level 2 Troubleshooting

Customer Service

Ticketing Systems

Remote Support

Tools

Windows OS

macOS

Linux (Debian, Proxmox)

Windows Server

Microsoft 365

Google Workspace

Proxmox

Hyper-V

ConnectWise

RustDesk

Job description

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.

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

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.