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DataAnnotation

Penetration Tester (Ethical Hacker) - AI Trainer

DataAnnotation
San Francisco, CA Remote $50 - $100/hr Contract Posted 9h ago
Ai Security Ai Trainer Ai Training Artificial Intelligence Incident Response Information Security InfoSec Investigative Skills Penetration Testing Red Team Security Security Testing Threat Modeling
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Job Description

DataAnnotation is seeking a Penetration Tester (Ethical Hacker) to join as an AI Trainer on a remote contract basis. You will help train AI models by evaluating AI-generated security content and solving security problems to strengthen defense, detection, and response capabilities.

This fully remote opportunity lets you work from anywhere within the eligible regions, contributing to the next generation of cybersecurity tools built for AI. The role blends hands-on security work with AI training, allowing you to shape security outcomes from your own environment.

Benefits

  • Fully remote: work from anywhere in the US, Canada, UK, Ireland, Australia, and New Zealand.
  • Flexible schedule: choose which projects you take on and when you work, using your own computer from home.
  • Competitive pay: hourly rate of 50 to 100 USD, with potential for higher bonus rates on select projects.
  • Impact: contribute to the future of AI technologies designed for cybersecurity.

Responsibilities

  • Assess AI-generated cybersecurity content, including threat analyses, vulnerability assessments, and offensive security techniques, for real-world accuracy and validity.
  • Design and solve security-focused technical problems used to train AI systems.
  • Write clear technical explanations and security-relevant code.
  • Provide feedback that directly informs the next generation of AI security models.

Requirements

  • 2+ years of hands-on experience in a cybersecurity role such as penetration testing, red teaming, incident response, detection engineering, DFIR, malware analysis, threat intelligence, or adjacent fields, including government or military cyber operations.
  • Some coding experience; comfort navigating and patching a codebase is key.
  • Fluency in English (native or bilingual level) with strong writing skills.
  • Bachelor's degree is preferred.
  • Cybersecurity certifications are a plus (for example, OSCP, CRTO, GREM, GCFA, CEH, and similar).

Note: Payment is made via PayPal. We will never ask for money from you. This job is only available to residents of the US, Canada, UK, Ireland, Australia, and New Zealand.

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