Remote IT Support Specialist: Expert Troubleshooter

Recruitment Room; United States; Remote; USD 86,000 - 154,000; Full time

Benefits offered by this job

Job summary

Appsierra Group is seeking an IT Support Specialist Expert for a fully remote, contract engagement. The role focuses on authoring and evaluating realistic troubleshooting scenarios used to test AI systems handling professional IT support.

You will draw on hands-on enterprise IT experience across AD, M365, and MDM to assess, document, and improve diagnostic reasoning. You will also craft reference answers, evaluate AI responses for technical accuracy and safety, and identify incorrect or

Qualifications

• 2+ years of professional IT support, help desk, or sysadmin work.
• Experience in enterprise IT environments with AD, M365, and MDM.
• Strong troubleshooting skills and clear documentation of reasoning.

Responsibilities

• Author realistic IT support scenarios covering full troubleshooting from first contact to resolution.
• Create reference answers that explain the diagnostic reasoning behind each step.
• Evaluate AI-generated support responses for accuracy, practicality, and safety.
• Identify incorrect steps, flawed assumptions, and potentially harmful recommendations.
• Assess issues across hardware, software, OS, apps, and networks.
• Apply enterprise IT experience to realistic support and system administration scenarios.
• Document technical findings clearly and justify chosen diagnostic/resolution approaches.

Skills

IT Support

Troubleshooting

Documentation

Root Cause Analysis

Enterprise IT

Active Directory

Microsoft 365

MDM

English Writing

Tools

PowerShell

Bash

Job description

Appsierra Group is seeking an IT Support Specialist Expert for a fully remote, contract engagement. The role focuses on authoring and evaluating realistic troubleshooting scenarios used to test AI systems handling professional IT support.

You will draw on hands-on enterprise IT experience across AD, M365, and MDM to assess, document, and improve diagnostic reasoning. You will also craft reference answers, evaluate AI responses for technical accuracy and safety, and identify incorrect or