Help Desk Technician (AI-Enabled Support)

Mid Suffolk company; New York (NY); On-site; USD 45,000 - 70,000; Full time

Job summary

Mid Suffolk company is seeking a Help Desk Technician (AI-Enabled Support) to provide Tier 1/2 IT help desk support on-site in New York. The role blends traditional troubleshooting with AI-assisted workflows to accelerate issue resolution and knowledge-base generation.

You will work with end users, draft scripts with PowerShell, and leverage AI copilots to triage tickets, automate routines, and improve service delivery.

Qualifications

• 1–3 years of experience in a help desk or IT support role.
• Hands-on experience using AI chat tools for real work tasks, not just casual use.
• Comfortable writing or adapting basic scripts (PowerShell, batch) with AI help.

Responsibilities

• Provide Tier 1/2 support for hardware, software, network, and account access.
• Diagnose issues with Windows, M365, AD/Entra ID, VPN, printers, and business apps.
• Use AI tools to draft steps, summarize tickets, and speed root-cause analysis.
• Maintain and improve a knowledge base with AI-assisted articles.
• Automate repetitive tasks using scripting and AI automation.
• Escalate complex issues to Tier 3 with clear documentation.
• Assist onboarding/offboarding and device setup.
• Monitor tickets and respond promptly.

Skills

Windows 10/11

Microsoft 365

Active Directory/Entra ID

AI chat tools

PowerShell scripting

Communication

Ticketing systems

Multi-ticket management

Education

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

Tools

ConnectWise

ServiceNow

Freshdesk

Zendesk

Job description

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