Penetration Tester (Ethical Hacker) - AI Trainer

DataAnnotation offers a remote, flexible environment for cybersecurity professionals to shape AI security while tackling real world challenges. This contract role, based in Iowa with remote options, invites a Penetration Tester (Ethical Hacker) - AI Trainer to help train AI models by evaluating AI generated cybersecurity content and solving authentic security problems.

Benefits

• Fully remote: work from anywhere in the United States, Canada, United Kingdom, Ireland, Australia, or New Zealand.
• Flexible schedule: choose projects and set your own hours, using your own computer from home.
• Competitive pay: hourly compensation with potential higher bonus rates on select projects.
• Impact: help shape AI technologies built for cybersecurity and influence future security models.

Responsibilities

• 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 used to train AI systems.
• Write clear technical explanations and security relevant code.
• Provide feedback that directly informs the next generation of 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 fields, including government or military cyber operations.
• Some coding experience required; comfort navigating and patching a codebase is key.
• Fluency in English (native or bilingual level) with strong writing skills.

Notes

Payment is made via PayPal. We will never ask for money. This contract is available to candidates in the United States, Canada, United Kingdom, Ireland, Australia, and New Zealand.