Remote AI IT Support Engineer – Tier 2 Automation

Helpware Inc; Taguig; Hybrid; PHP 420,000 - 660,000; Full time

Job summary

Helpware Inc. is seeking a Technical Support Specialist L2 to serve as the Tier 2 escalation point, working closely with the Helpdesk Technician I and the Network & Security Analyst. The role leverages scripts and automation to improve helpdesk efficiency and user experience, with a strong emphasis on AI-assisted development.

This position is remote-friendly and part of a collaborative IT team, supporting users in the Philippines from Manila or Cebu and beyond.

Qualifications

• 2–4 years of experience in IT support, with demonstrated Tier 2 or escalated support experience.
• Proficiency with Windows and/or macOS environments.
• Hands-on scripting experience in PowerShell, Python, or Bash.
• Familiarity with Active Directory, Microsoft 365, and common enterprise applications.
• Basic understanding of networking concepts (TCP/IP, DNS, DHCP, VPN).
• Working knowledge of AI tools applied to scripting or automation (e.g., prompt engineering, AI-assisted code generation, API integrations).
• Strong analytical and troubleshooting skills.
• Clear written and verbal communication skills.

Responsibilities

• Tier 2 escalation: receive and resolve escalated tickets beyond Tier 1 scope.
• Diagnose and troubleshoot complex hardware, software, OS, and application issues remotely.
• Manage user accounts, permissions, and access provisioning via Active Directory or equivalent.
• Document resolutions and contribute to the IT knowledge base to reduce repeat escalations.
• Collaborate with Network & Security Analyst on connectivity, access controls, or security incidents.
• Coordinate remote onboarding/offboarding processes including system access provisioning and remote configuration guidance.
• AI-Driven Automation & Scripting: write and maintain scripts (PowerShell, Python, Bash) with AI tools to accelerate delivery and accuracy.
• Identify and build automation workflows for tasks like patch management, reporting, account provisioning, and system monitoring.

Skills

Analytical and troubleshooting

Clear written and verbal communication

Self-motivated

AI tooling curiosity

Collaborative with async communication

Education

CompTIA A+ or Network+ (preferred)

Tools

PowerShell

Python

Bash

Active Directory

Microsoft 365

ServiceNow

Jira

Zendesk

Job description

Helpware Inc. is seeking a Technical Support Specialist L2 to serve as the Tier 2 escalation point, working closely with the Helpdesk Technician I and the Network & Security Analyst. The role leverages scripts and automation to improve helpdesk efficiency and user experience, with a strong emphasis on AI-assisted development.

This position is remote-friendly and part of a collaborative IT team, supporting users in the Philippines from Manila or Cebu and beyond.