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 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 schedule Type Independent contractor Payouts Weekly Apply now