IT Support Specialist Expert

Contract · Remote

Annual Compensation Equivalent: $86,400–$153,600/year
Hourly Rate: $45–$80/hr

The annual compensation equivalent is calculated at 40 hours/week across 48 workable weeks/year and represents a full-time equivalent, not guaranteed earnings. The engagement requires a minimum of 10 hours per week, with no stated maximum.

About the Role

We’re looking for experienced IT Support Specialists to author and evaluate realistic troubleshooting scenarios used to assess how AI systems handle professional IT support.

You’ll draw on hands-on experience to create support scenarios that reflect real incidents, from initial user contact through diagnosis and resolution. You’ll also develop reference answers, evaluate AI-generated troubleshooting guidance, and identify recommendations that are technically incorrect, unsafe, or likely to make an issue worse.

This role is suited to IT professionals who combine strong troubleshooting skills with the ability to clearly explain their diagnostic reasoning.

What You’ll Do

• Author realistic IT support scenarios covering the full troubleshooting process from first contact through resolution.

• Create reference answers that explain the diagnostic reasoning behind each troubleshooting step.

• Evaluate AI-generated support responses for technical accuracy, practicality, and user safety.

• Identify incorrect troubleshooting steps, flawed assumptions, and potentially harmful recommendations.

• Assess issues across hardware, software, operating systems, applications, and networks.

• Apply enterprise IT experience to realistic support and system administration scenarios.

• Clearly document technical findings and explain why a particular diagnostic or resolution approach is appropriate.

What We’re Looking For

• At least 2 years of professional experience in IT support, help desk, or system administration.

• Hands-on experience working with enterprise IT environments.

• Experience with technologies such as:

  • Active Directory

  • Microsoft 365

  • Mobile Device Management (MDM) tools

• Strong troubleshooting experience across hardware, software, and networking issues.

• Ability to diagnose problems systematically and identify root causes.

• Strong written English and the ability to document technical reasoning clearly.

• Ability to commit at least 10 hours per week.

Preferred Experience

• CompTIA A+, Network+, Microsoft, or similar IT certifications.

• PowerShell or Bash scripting experience.

• Tier 2 or Tier 3 technical support experience.

• Experience handling escalations involving complex hardware, software, network, or enterprise-system issues.

Engagement & Compensation

• Fully remote

• Independent contractor engagement

• Fully asynchronous

• $45–$80/hr

• Paid weekly

• Minimum 10 hours per week

• No stated maximum weekly hours

• Flexible schedule with the ability to adjust workload from week to week

• Ongoing project work rather than a one-time engagement

• No screen recording, keystroke monitoring, or idle-time monitoring

The annual compensation figure is a full-time equivalent based on 40 hours per week and 48 workable weeks per year. It is provided for comparison purposes and is not a guaranteed annual salary.

Selection & Onboarding

The engagement process may include:

1. Application and structured screening questions

2. Resume review against role requirements

3. Written technical assessment, where applicable

4. Contractor onboarding and payment setup

5. Matching to relevant project work based on your technical specialization

You’ll be matched to work that aligns with your IT support and troubleshooting experience.