Technical Support Specialist Tier 2 at Helpware

Job 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

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