Overview

Models can describe an exploit chain in confident detail and miss that step three never actually works, the payload gets filtered, or the whole path assumes a misconfiguration no real target would have. Someone has to know which attacks land and which just sound good, and that someone is you.

As a Penetration Tester you'll evaluate how models reason about offensive security, break the chains that don't hold, and write the attack paths a real operator would take.

What you’ll actually do

- Test offensive reasoning across recon, exploitation, privilege escalation, and lateral movement, and see where the model bluffs.
- Break the exploit chains that don't hold up: filtered payloads, impossible preconditions, and steps that skip the hard part.
- Write the attack path that actually works when the model falls short, with the tradecraft a real operator would use.

Roles this fits Common backgrounds: Penetration Tester, Red Team Operator, Offensive Security Engineer.

What we look for





- Hands-on offensive security experience: penetration testing, red-teaming, or CTF at a responsible level.
- Fluency with the attacker's toolkit and how real exploit chains come together.
- Clear written English: your explanations are the training signal.
- No degree required. We care about what you can do, not where you learned it.

Compensation Up to $125+/hr depending on task difficulty and specialization. Many contributors add $100k–$200k a year; some make it their full-time income.

About DataAnnotation

DataAnnotation is where 1M+ experts train the world’s leading AI models. Hundreds of millions paid to contributors to date, and the average contributor stays 5+ years. Flexible, remote, and always project-available.

Apply now

Hourly rate up to $125+ / hour

Commitment Flexible hours

Type Independent contractor

Payouts Weekly

Apply now

📌 Penetration Tester (AI Training) (Australia)
🏢 DataAnnotation
📍 Australia