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DataAnnotation

Penetration Tester (Ethical Hacker) - AI Trainer

DataAnnotation
Louisville, KY Remote $50 - $100/hr Contract Posted 6h ago
Ai Trainer Ai Training Artificial Intelligence Information Security Infosec Penetration Testing Security Security Testing
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Job Description

DataAnnotation seeks a Penetration Tester (Ethical Hacker) to serve as an AI Trainer in a contract capacity. You will evaluate AI-generated security content and solve security problems to train AI models, with remote, flexible scheduling from Kentucky. The role can be pursued alongside another job or as your primary focus, with compensation ranging from USD 50 to 100 per hour.

Responsibilities

  • Assess AI-produced cybersecurity content, such as threat analyses, vulnerability evaluations, and offensive security techniques, for real-world accuracy and relevance.
  • Develop and resolve security-centric technical challenges used to train AI systems.
  • Produce clear technical explanations and security-focused code.
  • Provide actionable feedback that informs the next generation of AI security models.

Requirements

  • Minimum of 2 years of hands-on experience in a cybersecurity role, including penetration testing, red teaming, incident response, detection engineering, DFIR, malware analysis, threat intelligence, or related fields, including government or military cyber operations.
  • Some coding experience is required; you should be comfortable navigating and patching a codebase.
  • English fluency at native or bilingual level with strong writing skills.
  • A bachelor's degree is preferred.
  • Cybersecurity certifications are a plus (for example 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 you take on and when you work, on your own computer, from home.
  • Competitive pay: projects are paid hourly, up to $60 USD per hour. Opportunities for higher bonus rates available for certain projects.
  • Impact: help shape the future of AI technologies built for cybersecurity.

Note

Payments are issued via PayPal. We will never ask for any money from you. This job is only available to individuals located in the United States, Canada, United Kingdom, Ireland, Australia, and New Zealand.

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