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DataAnnotation

Penetration Tester (Ethical Hacker) - AI Trainer

DataAnnotation
Delaware Remote $50 - $100/hr Contract Posted 5h ago
Adversarial Ai Security Ai Training Ethical Hacking Information Security InfoSec Offensive Security Penetration Testing Security Security Testing
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Job Description

DataAnnotation is looking for an existing Penetration Tester (Ethical Hacker) - AI Trainer to support the training of AI models focused on cybersecurity. In this contract role (remote in Delaware), you will review and test AI-generated security material, work through security-oriented technical challenges, and provide feedback that helps improve how AI reasons about real-world threats and defenses.

You will apply hands-on penetration testing and security knowledge to ensure training outputs are accurate and meaningful, while also contributing clear technical explanations and security-relevant code that supports model improvement.

Responsibilities

  • Evaluate AI-generated cybersecurity content, including threat analysis, 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 along with security-relevant code.
  • Provide feedback that shapes AI security models by influencing the next generation of AI reasoning about threats and defenses.

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 related work, including government or military cyber operations.
  • Some coding experience, with comfort navigating and patching a codebase.
  • Fluency in English (native or bilingual level) with strong writing skills.
  • Bachelor’s degree preferred.
  • Certifications are a plus (examples: OSCP, CRTO, GREM, GCFA, CEH, and similar).

Benefits

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

Contracting Details

  • Payment method: paid via PayPal.
  • No fees: DataAnnotation will never ask for money from you.
  • Eligibility: this role is available only to candidates in the US, Canada, UK, Ireland, Australia, and New Zealand.

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