Penetration Tester

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 serious 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

$75 to $125+/hr depending on task difficulty and specialization. Many contributors add $10k to $100k+ a year; some make it their full-time income.

About DataAnnotation

DataAnnotation is where 100k+ experts train the world’s leading AI models. $150M+ paid to contributors to date, and the average contributor stays 5+ years. Flexible, remote, and always project-available.

Terms

• Engagement: Independent contractor
• Hours: Flexible hours
• Location: Remote
• Payouts: Weekly