Help Desk Support/Technical Support - Remote

Job Description Job Description

Help Desk Technician (AI-Enabled Support)

Department: Information Technology

Reports To: IT Manager / Systems Administrator

Employment Type: Full-Time

Location: [On-site / Hybrid / Remote]

Position Summary We are seeking a Help Desk Technician who combines strong traditional troubleshooting skills with hands-on experience using AI tools to accelerate issue resolution, automate repetitive tasks, and improve the end-user support experience. This role is ideal for someone comfortable working directly with end users while also using AI-assisted platforms (chatbots, ticket triage automation, scripting copilots, knowledge-base generation) to work faster and smarter.

Key Responsibilities Provide Tier 1/Tier 2 technical support for hardware, software, network connectivity, and account access issues via phone, email, chat, and ticketing system

Diagnose and resolve issues involving Windows OS, Microsoft 365, Active Directory/Entra ID, VPN, printers, and common business applications

Use AI-powered tools (e.g., Copilot, ChatGPT, Claude, or internal AI assistants) to draft troubleshooting steps, summarize tickets, generate scripts, and speed up root-cause analysis

Maintain and improve a knowledge base, using AI tools to help draft, organize, and update articles

Identify opportunities to automate repetitive helpdesk tasks (password resets, account provisioning, routine diagnostics) using scripting (PowerShell) and AI-assisted automation

Escalate complex issues to Tier 3/systems administrators with clear documentation

Support onboarding/offboarding processes, including account creation and device setup

Monitor and respond to tickets in a timely manner

Educate end users on new AI tools and features rolled out across the organization

Document recurring issues and recommend process improvements

Required Qualifications 1–3 years of experience in a help desk, desktop support, or IT support role

Working knowledge of Windows 10/11, Microsoft 365 (Outlook, Teams, SharePoint), and Active Directory

Hands‑on experience using AI chat tools (ChatGPT, Copilot, Claude, Gemini, etc.) for real work tasks — not just casual use

Comfortable writing or adapting basic scripts (PowerShell, batch) with AI assistance

Strong written and verbal communication skills; able to explain technical issues to non‑technical users

Ability to prioritize and manage multiple tickets simultaneously

Customer‑service mindset with patience and professionalism

Preferred Qualifications Experience with ticketing systems (ConnectWise, ServiceNow, Freshdesk, Zendesk)

Familiarity with AI‑assisted IT automation platforms or AI‑driven ticket triage/routing tools

Basic understanding of networking concepts (DNS, DHCP, VPN)

Exposure to Exchange Online/Hybrid environments

Experience prompting AI tools to generate documentation, SOPs, or training material

Associate's degree or certification (CompTIA A+, Network+, or similar)

AI Competency Expectations Candidates should be able to speak to specific examples of:

Using AI tools to troubleshoot an unfamiliar error or issue

Writing effective prompts to get accurate, actionable technical answers

Using AI to summarize long threads/tickets into concise action items

Generating or debugging a script with AI assistance

Evaluating AI output critically rather than applying it blindly

Physical/Work Requirements Ability to lift up to 25 lbs (workstation/equipment moves)

Extended periods at a computer workstation

On-call or after‑hours availability may be required for critical outages

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