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
Skills Required
- 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
- Strong analytical and troubleshooting skills
- Clear written and verbal communication skills
What We Do
Founded in 2015, Helpware is a company taking a modern approach to the outsourcing industry. We created the company to change perceptions of what outsourcing is and can be, and we did that by building amazing cultures in each of our locations, and by simply treating our employees better. With Helpware, we are all a team and family, and you'll see that true difference when partnering with us. Helpware builds customized teams in Customer Service and Back Office for industry-leading startups and modern companies. With offices in California, Colorado, Kentucky, Ukraine, Philippines, Germany, and Mexico, we have the global scale to tailor custom teams and processes for success to our many powerhouse clients. Helpware has grown over the years, initially catering to startup client partners, and has now evolved into creating client partnerships with large enterprises as well.
