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DataAnnotation

Cybersecurity Engineer - AI Trainer

DataAnnotation
Cambridge, MA Remote $50 - $100/hr Contract Posted 22m ago
Ai Content Evaluation Ai Security Training Cybersecurity Information Security InfoSec Security Security Testing
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Job Description

DataAnnotation is seeking a Cybersecurity Engineer - AI Trainer to support the training of AI chatbots focused on real-world cybersecurity. In this fully remote contract role, you will review AI-generated security material, help design security-oriented technical tasks, and provide feedback that influences how AI models reason about threats and defenses.

Based in Cambridge, MA (remote), this position is paid hourly and offers a flexible schedule. Your work will be carried out on your own computer, with the goal of improving the accuracy and usefulness of AI systems used in cybersecurity contexts.

What you’ll do

  • 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 that are used to train AI systems.
  • Write clear technical explanations and security-relevant code.
  • Provide feedback that directly shapes 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 adjacent fields, including government or military cyber operations.
  • Some coding experience is required, with comfort navigating and patching a codebase.
  • Fluency in English (native or bilingual level) with strong writing skills.
  • Bachelor’s degree preferred.
  • Cybersecurity certifications are a plus, for example OSCP, CRTO, GREM, GCFA, CEH, or similar.

Compensation and contract details

  • Job type: contract
  • Pay rate: $50 to $100 USD per hour
  • Payment method: paid via PayPal
  • Experience level: minimum 2 years

Remote schedule and location

  • 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.
  • Work setup: use your own computer from home.

Additional notes

  • Bonus opportunities: higher bonus rates may be available for certain projects.
  • Impact: help shape AI technologies built for cybersecurity.
  • Security note: DataAnnotation will never ask for any money from you.
  • Eligibility: this role is only available to candidates in the US, Canada, UK, Ireland, Australia, and New Zealand.

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