$40-125/hrAs published by the platform.
This role involves evaluating how AI models reason about offensive security concepts and identifying flaws in their exploit chain reasoning. Penetration testers with hands-on red team experience will test model outputs across reconnaissance, exploitation, privilege escalation, and lateral movement, then write accurate attack paths that reflect real-world tradecraft when models fall short.
$40-125/hr
Pay as published by the platform. It is not a guarantee of income or hours.
The platform has not published which countries are eligible for this job.
You apply on DataAnnotation: create an account, take the qualification assessment for your field, then pick up paid projects when you qualify.
Official posting: https://www.dataannotation.tech/job-board/penetration-tester
Last checked on October 8, 2026.
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