Penetration Tester (Ethical Hacker) - AI Trainer

DataAnnotation is seeking an experienced Penetration Tester (Ethical Hacker) to support AI model training through cybersecurity validation and technical feedback. This contract role is fully remote, with flexible scheduling and paid assessments/projects available after completing an initial assessment.

What you will do

• Review AI-generated cybersecurity outputs, including threat analysis, vulnerability assessments, and offensive security techniques, with an eye toward real-world accuracy and validity.
• Create and work through security-focused technical problems that are used to train AI systems.
• Produce clear technical write-ups and security-relevant code to support training materials.
• Provide feedback that directly informs and improves 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 work, including government or military cyber operations.
• Coding experience, with the ability to navigate and patch a codebase comfortably.
• English fluency (native or bilingual) paired with strong writing skills.
• Bachelor’s degree preferred.
• Certifications are a plus (examples include OSCP, CRTO, GREM, GCFA, CEH, and similar).

Contract details

• Location: Kansas (remote)
• Job type: Contract
• Pay: USD 50 to 100 per hour
• Schedule: flexible, with the ability to choose projects and timing

Remote work and compensation

• Fully remote: available for applicants in the US, Canada, UK, Ireland, Australia, and New Zealand.
• Flexible schedule: work from your own computer from home and select which projects you take on.
• Competitive hourly rates: projects are paid hourly at $50 to $100 USD per hour.
• Potential bonus increases: higher bonus rates may be available for certain projects.
• Payment method: PayPal.

Impact

Contribute to the training and validation of cybersecurity-focused AI technologies by assessing technical outputs and shaping feedback that improves model performance.

Important notes: We will never ask you for money. This role is available only to candidates located in the US, Canada, UK, Ireland, Australia, and New Zealand.