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DataAnnotation

Penetration Tester (Ethical Hacker) - AI Trainer

DataAnnotation
Minneapolis, MN Remote $50 - $100/hr Contract Posted 12m ago
Ai Security Evaluation Ai Training Artificial Intelligence Ethical Hacking Information Security InfoSec Offensive Security Security Security Testing
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Job Description

Join DataAnnotation as a remote Penetration Tester (Ethical Hacker) - AI Trainer supporting the evaluation and training of AI models built for cybersecurity. This contract role focuses on hands-on technical work, clear security communication, and direct feedback that helps improve AI security reasoning. You can work from your own computer with scheduling flexibility while contributing to the future of AI technologies in the security domain.

What you’ll do

  • Assess AI-generated cybersecurity content for real-world accuracy, including threat analysis, vulnerability assessments, and offensive security techniques.
  • Develop and work through security-focused technical problems designed to train AI systems.
  • Create clear technical explanations and produce security-relevant code when needed.
  • Provide feedback intended to directly shape the next generation of AI security models.

What you bring

  • 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 closely related fields, including experience in government or military cyber operations.
  • Some coding experience and comfort navigating, working through, and patching a codebase.
  • English fluency (native or bilingual) with strong writing skills.
  • A bachelor’s degree is preferred.
  • Cybersecurity certifications are a plus, including OSCP, CRTO, GREM, GCFA, CEH, or similar.

Contracting 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.
  • Competitive hourly pay: $50 to $100 USD per hour.
  • Potential for higher bonus rates on certain projects.
  • Impact: contribute to AI systems that support cybersecurity use cases.

Additional details

Location: Minnesota (remote). Job type: contract.

Payment: paid via PayPal.

Important: DataAnnotation will never ask for any money from you.

Eligibility: this role is available only to applicants in the US, Canada, UK, Ireland, Australia, and New Zealand.

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