Security Adversarial Evaluation Engineer Jobs

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Cybersecurity Engineer - AI Trainer

DataAnnotation Chicago, IL 🇺🇸 Remote

Chicago, IL

Today

$50 - $100/hr Contract Ai Content Evaluation Ai Security Information Security

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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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