<div class="datj"><header class="topbar"><div class="topbar-in"><a class="back" href="/"><span class="back-arrow">←</span>All roles</a><nav class="topbar-actions"><a class="link-quiet" href="https://app.dataannotation.tech/users/sign_in">Sign in</a><a class="btn btn-primary" href="https://app.dataannotation.tech/worker_signup?worker_src=ai_jobs&utm_source=webflow_jobby&utm_medium=web&utm_campaign=ai_training_jobs&utm_content=role_topbar_penetration-tester&utm_role=penetration-tester&projects=PROG_SA">Apply now</a></nav></div></header><main class="wrap"><div class="rd-layout"><article><div class="rd-title"><h1>Penetration Tester</h1></div><section class="rd-section"><h2>Overview</h2><p>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.</p><p>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.</p></section><section class="rd-section"><h2>What you’ll actually do</h2><ul><li><b>Test offensive reasoning</b> across recon, exploitation, privilege escalation, and lateral movement, and see where the model bluffs.</li><li><b>Break the exploit chains</b> that don't hold up: filtered payloads, impossible preconditions, and steps that skip the hard part.</li><li><b>Write the attack path</b> that actually works when the model falls short, with the tradecraft a real operator would use.</li></ul></section><section class="rd-section"><h2>Roles this fits</h2><p>Common backgrounds: Penetration Tester, Red Team Operator, Offensive Security Engineer.</p></section><section class="rd-section"><h2>What we look for</h2><ul><li>Hands-on offensive security experience: penetration testing, red-teaming, or CTF at a serious level.</li><li>Fluency with the attacker's toolkit and how real exploit chains come together.</li><li>Clear written English: your explanations are the training signal.</li><li>No degree required. We care about what you can do, not where you learned it.</li></ul></section><section class="rd-section"><h2>How it works</h2><div class="rd-steps"><div class="rd-step"><span class="rd-step-n"></span><h3>Apply</h3></div><div class="rd-step"><span class="rd-step-n"></span><h3>Qualify</h3></div><div class="rd-step"><span class="rd-step-n"></span><h3>Work & get paid</h3></div></div></section><section class="rd-section"><h2>Compensation</h2><p>$75 – $125+/hr depending on task difficulty and specialization. Many contributors add $10k–$100k+ a year; some make it their full-time income.</p></section><section class="rd-section"><h2>About DataAnnotation</h2><p>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.</p></section></article><aside class="rail"><span class="rail-label">Hourly rate</span><span class="rate rail-rate">$75 – $125+ <small>/ hour</small></span><div class="rail-meta"><div class="rail-row"><span>Location</span><span>Remote</span></div><div class="rail-row"><span>Commitment</span><span>Flexible hours</span></div><div class="rail-row"><span>Type</span><span>Independent contractor</span></div><div class="rail-row"><span>Payouts</span><span>Weekly</span></div></div><a class="btn btn-primary btn-lg rail-btn" href="https://app.dataannotation.tech/worker_signup?worker_src=ai_jobs&utm_source=webflow_jobby&utm_medium=web&utm_campaign=ai_training_jobs&utm_content=role_rail_penetration-tester&utm_role=penetration-tester&projects=PROG_SA">Apply now</a></aside></div><section class="similar"><div class="proof-head"><h2>Similar roles</h2><a class="see-all" href="/">View all roles →</a></div><div class="grid"><a class="card" href="/job-board/cybersecurity-expert"><h2>Cybersecurity Expert</h2><div class="card-foot"><span class="rate">$75 – $125+ <small>/ hr</small></span><span class="hired">41 hired recently</span></div></a><a class="card" href="/job-board/incident-responder"><h2>Incident Responder</h2><div class="card-foot"><span class="rate">$75 – $125+ <small>/ hr</small></span><span class="hired">27 hired recently</span></div></a><a class="card" href="/job-board/application-security-engineer"><h2>Application Security Engineer</h2><div class="card-foot"><span class="rate">$75 – $125+ <small>/ hr</small></span><span class="hired">24 hired recently</span></div></a></div></section></main><footer class="footer"><div class="footer-in"><p>© DataAnnotation</p><div class="footer-links"><a href="https://www.dataannotation.tech/">dataannotation.tech</a><a href="https://www.dataannotation.tech/faqs">FAQs</a><a href="https://www.dataannotation.tech/trust-safety">Trust & Safety</a></div></div></footer></div>