IT Support Specialist Expert

$45–80/hrrate as listed

Author realistic IT support scenarios — first contact through resolution — and grade AI model responses for technical accuracy and user safety. AfterQuery lists $45–80/hr for this work, remote, fully async, with a 10 hour per week minimum.

Summary, eligibility guidance and screening preparation are prepared by Sidequest from the platform's posting. Check the source listing before applying.

What the work involves

You write troubleshooting scenarios the way they actually arrive: a vague user report, incomplete information, a half-remembered error message. Then you write the reference resolution — not just the fix, but the diagnostic reasoning that gets there, including the branches you ruled out and why. A scenario about a user locked out after a password change should make clear whether you're checking cached credentials, a stale Kerberos ticket, a conditional access policy, or an MDM compliance flag, and how you'd distinguish them.

The second half of the job is grading. You read model output against your reference and score it for technical accuracy and, critically, for user safety. Frontier models are fluent enough to produce advice that sounds like it came from a senior admin and would still destroy a user's profile, break a domain trust, or send someone into regedit with no rollback. Flagging that gap — plausible-sounding, actively harmful — is the highest-value thing you do here.

What the platform screens for

AfterQuery's screen is AI-led and follow-up heavy. Expect it to take a claim like "Active Directory experience" and push on specifics: replication behaviour, GPO precedence, what you actually saw in an environment rather than what the documentation says. Breadth across hardware, software and networking matters more than depth in one vendor stack, because the scenarios span all three. Writing quality is assessed directly from your answers — if your reasoning doesn't survive being written down, it won't survive being used as a reference answer.

Logistics

Fully remote, fully async — no scheduled shifts, no live calls with users
Minimum commitment of 10 hours per week; you choose when
Paid weekly via Stripe at the listed band
Ongoing project work rather than a fixed-length contract, with volume varying by task queue

What they look for

2+ years professional IT support, help desk, or system administration
Hands-on enterprise experience with Active Directory, Microsoft 365, or MDM tooling
Cross-domain troubleshooting across hardware, software, and networking
Clear written English for documenting diagnostic reasoning
CompTIA A+/Network+ or Microsoft certifications (preferred)
PowerShell or Bash scripting; tier 2/3 escalation background (preferred)

Included with this listing

Interview prep — 10 questions

Matched to what this platform's screening actually measures. Answer each out loud in 60–90 seconds: claim → concrete example → implication.

What it tests: Whether your enterprise exposure is real operational ownership or a line on a résumé, and what tier of problem actually reached you.
A strong answer: Concrete numbers (seat count, number of sites, domain structure), the specific stack — AD on-prem vs Entra ID, Intune vs Jamf vs Workspace ONE, M365 tenant configuration — and an honest statement of what you escalated upward versus what stopped with you.
Where people lose it: Naming tools without describing what you did in them. 'We used Active Directory and Intune' invites a follow-up you can't answer; 'I owned the GPO baseline and rebuilt our Intune compliance policies after a co-management migration' does not.