Penetration Tester (Ethical Hacker) - AI Trainer

DataAnnotation offers a fully remote contract role for a Penetration Tester (Ethical Hacker) - AI Trainer. In this position you will train AI cybersecurity models by evaluating AI generated content, solving security problems, and providing feedback to shape how AI systems reason about threats and defenses. The role is remote and based in Virginia.

Benefits

• Fully remote: 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 from home.
• Competitive pay: hourly compensation, with possibilities for higher bonus rates on select projects.
• Impact: contribute to shaping the next generation of AI technologies built for cybersecurity.

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 shapes 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) with strong writing skills.
• A bachelor’s degree is preferred.
• Cybersecurity certifications are a plus (for example OSCP, CRTO, GREM, GCFA, CEH, and similar).

Note: Payment is made via PayPal. We will never ask for money from you. This job is only available to those in the US, Canada, UK, Ireland, Australia, and New Zealand.