Security Adversarial Evaluation Cybersecurity 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 Engineer

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Job Description

The Cybersecurity Engineer - AI Trainer role supports the training of AI models by reviewing AI-generated cybersecurity material and addressing technical security challenges. This contract position is fully remote, with a flexible schedule and paid hourly work following a short assessment.

Key Responsibilities

Review and evaluate AI-generated cybersecurity content for real-world accuracy and validity, including threat analysis, vulnerability assessments, and offensive security techniques.
Create and solve security-focused technical problems that are used to train AI systems.
Produce clear technical explanations along with security-relevant code as part of the training process.
Deliver feedback that directly informs the next iteration of AI security models.

Required Qualifications

2+ years of practical 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.
Coding experience required, with comfort navigating and patching a codebase.
English fluency at native or bilingual level, with strong writing skills.
Bachelor’s degree preferred.
Cybersecurity certifications are a plus, including OSCP, CRTO, GREM, GCFA, CEH, and similar credentials.

Contract Details

Job type: Contract
Location: Chicago, IL (remote)
Compensation: USD 50 to 100 per hour (paid hourly)

Benefits and Working Model

Fully remote: opportunity to work from anywhere in the US, Canada, UK, Ireland, Australia, and New Zealand.
Flexible schedule: select projects and determine when you work, using your own computer.
Competitive pay: projects are paid hourly at $50 to $100 USD per hour, with potential for higher bonus rates on certain projects.
Impact: contribute to improving AI technologies developed for cybersecurity use cases.

Payment and Eligibility Notes

Payment is made via PayPal.
DataAnnotation will never ask candidates for money.
This role is available only to candidates located in the US, Canada, UK, Ireland, Australia, and New Zealand.

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