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Job Description

DataAnnotation is building and training AI systems with a focus on cybersecurity, and they need an experienced professional to evaluate AI-generated security content and help solve training problems. This fully remote contract role is available with flexible scheduling and paid hourly work after a short assessment.

Role

In this Cybersecurity Engineer - AI Trainer position, you will review cybersecurity outputs produced by AI models for accuracy and realism, then contribute security-focused technical solutions that support the next iteration of AI security training.

Responsibilities

  • Evaluate AI-generated cybersecurity content, including threat analysis, vulnerability assessments, and offensive security techniques, to ensure real-world accuracy and validity.
  • Design and solve security-focused technical problems that are used to train AI systems.
  • Write clear technical explanations and security-relevant code.
  • Provide feedback that directly influences the development of future 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 related areas, including government or military cyber operations.
  • Some coding experience is required, including comfort navigating and patching a codebase.
  • English fluency (native or bilingual level) with strong writing skills.
  • A bachelor’s degree is preferred.
  • Cybersecurity certifications are a plus, such as OSCP, CRTO, GREM, GCFA, CEH, and similar.

Contract Details

  • Location: Chicago, IL (remote)
  • Job type: contract
  • Pay: projects paid hourly at $50 to $100 USD per hour
  • Schedule: flexible, with selection of projects and work times

Benefits

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

Additional Notes

  • Payment is made via PayPal.
  • DataAnnotation will never ask for any money from you.
  • This job is only available to applicants in the US, Canada, UK, Ireland, Australia, and New Zealand.

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