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DataAnnotation

Penetration Tester

RemoteRemoteAlways hiring

Pay not listed

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.

  • 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.

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