Remote IT Support Specialist: Expert Troubleshooter

Appsierra Group

United States

On-site

USD 86,000 - 154,000

Full time

4 days ago

Be an early applicant

Application generator

Turn this role into an interview — a resume and cover letter built around what this employer wants.

Get past ATS filters

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.