Tier 2 Technical Support Specialist- Freelance, Remote

About the Client

Our client is an IT services and cybersecurity company that helps businesses manage their technology environments, protect their systems, and maintain secure day-to-day operations. Its services span managed IT support, cloud administration, cybersecurity, compliance, and automation. The team values reliable technical support that resolves user issues efficiently while recognizing and addressing potential security risks.

Why does this role exist?

The business needs an experienced Tier 2 Technical Support Specialist who can independently manage routine technical issues while applying a security-first mindset to every ticket. You will support users across Windows, macOS, Microsoft 365, Google Workspace, and related systems, ensuring issues are properly documented, resolved, or escalated. This role is ideal for someone who combines hands-on troubleshooting with sound security judgment and clear communication.

Tier 2 Helpdesk & Technical Troubleshooting

• Serve as a frontline contact for client IT issues received through phone, email, Freshservice, and Slack.
• Log, prioritize, troubleshoot, and resolve support tickets using documented procedures and knowledge-base articles
• Diagnose Windows and macOS issues involving software, peripherals, Wi-Fi, VPNs, and network connectivity.
• Support users with Microsoft 365 and Google Workspace.
• Maintain accurate ticket notes, follow established workflows, and meet service-level agreement (SLA) expectations.
• Escalate unresolved, complex, or non-standard issues to Level 3 (L3) with clear troubleshooting steps and supporting documentation.

Identity & Access Administration

• Support user onboarding, role changes, and offboarding across JumpCloud, Microsoft 365, and Google Workspace.
• Verify user identity before performing account-related actions.
• Assist with multi-factor authentication (MFA), Cisco Duo, conditional access, and device-compliance remediation.
• Apply least-privilege principles and follow approved access-management procedures.

Security-Aware Support & Incident Triage

• Recognize and triage phishing reports, suspicious emails, and other potential security concerns.
• Review and respond to endpoint protection and endpoint detection and response (EDR) alerts according to documented procedures.
• Assist with patch management and vulnerability remediation.
• Identify when a routine support request may involve a security risk and escalate it through the appropriate process.
• Coach users on basic security hygiene and safe technology practices.

Documentation & Continuous Improvement

• Maintain accurate technical records, security documentation, and compliance evidence.
• Improve knowledge-base articles based on recurring issues and resolved tickets.
• Flag gaps in troubleshooting guidance, access controls, and security procedures.
• Communicate technical findings clearly to users and teammates.

Required

• 2–4 years of Service Desk, Helpdesk, or IT Support experience with hands-on Tier 2 troubleshooting.
• Strong practical troubleshooting skills across Windows and macOS environments.
• Experience supporting Microsoft 365 and Google Workspace users.
• Working knowledge of MFA, least privilege, phishing indicators, identity and access management, endpoint security, and basic incident response.
• Strong ticket documentation, prioritization, escalation, and user communication skills.

Your superpowers are...

• Technical troubleshooting: You investigate issues methodically and work toward reliable resolutions rather than relying on guesswork.
• Security-first thinking: You recognize when access requests, suspicious messages, or endpoint alerts may require additional scrutiny.
• Sound judgment: You know when to follow a documented procedure, verify a user's identity, or escalate.
• Clear communication: You explain technical issues and next steps in a professional, easy-to-understand way.
• Ownership and organization: You manage tickets carefully, keep documentation current, and follow through on open issues.

WFH Set-Up:

• Computer with at least 8GB RAM, an Intel i5 core processor/AMD Ryzen 5 Processor and up.
• Internet speed of at least 40MBPS
• Headset with an extended mic that has noise cancellation and a webcam
• Back-up computer and internet connection
• Quiet, dedicated workspace at home

You should apply if...

• You have hands-on Tier 2 support experience and can troubleshoot independently.
• You understand that security is part of everyday IT support, not a separate afterthought.
• You are comfortable supporting users across different operating systems and cloud productivity platforms.
• You follow procedures carefully, document your work, and recognize the limits of your access or expertise.
• You enjoy helping users while contributing to a more reliable and secure IT environment.

What to expect...

Work Setup:

• Remote position
• Must have a reliable internet connection and a quiet workspace
• Required to provide own computer with Intel Core i5 or something similar or higher operating system

Working Hours:

• 40 hours per week
• Friday - Tuesday, 8AM - 5PM Manila Time

Compensation:

• $7 per hour
• No benefits package included