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Job Description

DataAnnotation is seeking a Cybersecurity Manager - AI Trainer to support the training of AI chatbots focused on cybersecurity. In this remote contract role, you will review AI-generated cybersecurity content, assess whether it is accurate and actionable, and provide feedback that helps strengthen AI security models over time.

What you’ll do

  • Evaluate AI-generated cybersecurity content, including threat analysis, vulnerability assessments, and offensive security techniques, with an emphasis on 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 influences the next generation of AI security models.

What you’ll 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 adjacent work, including government or military cyber operations.
  • Some coding experience, with comfort navigating and patching a codebase.
  • English fluency at native or bilingual level, along with strong writing skills.
  • Bachelor’s degree preferred.
  • Certifications are a plus, such as OSCP, CRTO, GREM, GCFA, CEH, or similar.

Contract details and compensation

This position is a remote contract based in Rockville, MD with hourly pay of USD $50 to $100 per hour. Work is available through a remote contracting platform, and you can take projects that match your schedule.

  • Fully remote: available to candidates 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.
  • Competitive hourly rates: $50 to $100 USD per hour.
  • Higher bonus rates may be available for certain projects.
  • Impact: contribute to shaping AI technologies built for cybersecurity.

Payment and important notes

  • Payment method: PayPal.
  • No fees: the role does not require you to pay anything.
  • Eligibility: this opportunity is limited to those in the US, Canada, UK, Ireland, Australia, and New Zealand.

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