About The Position

The Tier 2 Technical Support Specialist independently manages routine technical issues while applying a security-first mindset. The role supports users across Windows, macOS, Microsoft 365, Google Workspace, and related systems, ensuring issues are documented, resolved, or escalated appropriately. The position serves as a frontline contact for client IT issues and handles troubleshooting, identity and access support, security triage, and documentation. This is a freelance, remote role working 40 hours per week, Friday through Tuesday, 8 AM–5 PM Manila Time. Compensation is $7 per hour, and no benefits package is included. The specialist troubleshoots Windows and macOS software, peripheral, Wi-Fi, VPN, and network connectivity issues; supports Microsoft 365 and Google Workspace; and administers onboarding, role changes, and offboarding across JumpCloud and cloud productivity platforms. The role also involves recognizing and triaging potential security concerns, responding to endpoint protection and EDR alerts under documented procedures, assisting with patching and vulnerability remediation, and escalating appropriate issues. The specialist maintains accurate ticket notes, technical records, security documentation, and compliance evidence; improves knowledge-base articles; identifies procedural gaps; and communicates technical findings clearly to users and teammates. The worker must provide their own computer and internet connection, along with the other listed work-from-home equipment and a quiet, dedicated workspace.

Requirements

  • 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.
  • Computer with at least 8GB RAM and an Intel i5 or AMD Ryzen 5 processor or higher.
  • Internet speed of at least 40 Mbps.
  • Headset with an extended, noise-canceling microphone and a webcam.
  • Backup computer and internet connection.
  • Quiet, dedicated workspace at home.
  • Reliable internet connection.
  • Ability to work 40 hours per week, Friday through Tuesday, 8 AM–5 PM Manila Time.

Responsibilities

  • 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 SLA expectations.
  • Escalate unresolved, complex, or non-standard issues to Level 3 with troubleshooting steps and supporting documentation.
  • Support user onboarding, role changes, and offboarding across JumpCloud, Microsoft 365, and Google Workspace.
  • Verify user identity before performing account-related actions.
  • Assist with MFA, Cisco Duo, conditional access, and device-compliance remediation.
  • Apply least-privilege principles and follow approved access-management procedures.
  • Recognize and triage phishing reports, suspicious emails, and other potential security concerns.
  • Review and respond to endpoint protection and EDR alerts according to documented procedures.
  • Assist with patch management and vulnerability remediation.
  • Identify potential security risks in routine support requests and escalate them through the appropriate process.
  • Coach users on basic security hygiene and safe technology practices.
  • 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.
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