About Us
Helpware is a technology-driven company with offices in the USA, Ukraine, Mexico, and the Philippines which provides Customer Experience & Operational Support for modern companies. Our team of professionals is driven by the purpose of providing best-in-class value-adding services to our partners by leveraging our empowered teams, innovative solutions, and technologies.
Position Summary:
The Technical Support Specialist L2 serves as the Tier 2 escalation point for technical support within the organization, working closely with the Helpdesk Technician I and the Network & Security Analyst. This role goes beyond traditional support by leveraging scripts and automation workflows that improve helpdesk efficiency, reduce manual workload, and enhance the overall end-user experience. The identification and implementation of improvements is encouraged. This position is remote-friendly and operates within a collaborative, digitally connected IT team.
Key Responsibilities:
Tier 2 Support
- Receive and resolve escalated tickets from the Helpdesk Technician I that exceed 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 the Network & Security Analyst on Issues involving 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, or similar) developed with the assistance of AI tools to accelerate delivery and improve accuracy.
- Identify and build automation workflows for tasks such as patch management, reporting, account provisioning, and system monitoring – using AI to enhance scope and effectiveness.
- Use AI platforms and tools to generate, test, refine, and document scripts and automations
- Partner with the Network & Security Analyst to automate security checks and compliance reporting.
- Continuously evaluate IT processes for automation opportunities, applying AI-assisted development practices to deliver solutions faster.
- Stay current with AI tools and techniques relevant to scripting, automation, and IT operations
Required 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
- Must be able to work full time, 40 hrs per week
Preferred Qualifications
- CompTIA A+, Network+, or equivalent certification
- Experience with ITSM platforms (ServiceNow, Jira, Zendesk, etc.)
- Familiarity with cloud environments (Azure, AWS, or Google Workspace)
- Experience with AI-assisted development tools (e.g., GitHub Copilot, Microsoft Copilot, OpenAI API, Power Automate)
- Exposure to security practices and tools in collaboration with a security-focused team member
Soft Skills
- Self-motivated with an ability to work independently and manage competing priorities
- Curious and proactive about emerging technology, particularly AI-driven tooling
- Patient and clear when communicating technical concepts to non-technical users
- Collaborative team player who supports peers across skill levels
- Comfortable working remotely with strong async communication habits
Location: Philippines – Open to applicants residing in Cebu or Manila.
