Penetration Tester (Ethical Hacker) - AI Trainer

DataAnnotation seeks a remote Penetration Tester, functioning as an Ethical Hacker, to join as an AI Trainer. This role sits at the intersection of hands-on security and AI development, focusing on evaluating AI-generated security content and solving security problems to help train next-generation defenses. The position is a remote role based in Colorado, offering flexible scheduling and compensation through the platform after a short assessment.

Responsibilities

• Assess AI-generated cybersecurity content, including threat analyses, vulnerability assessments, and offensive security techniques, for real-world accuracy and validity.
• Design and solve security-focused technical challenges used to train AI systems.
• Produce 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 and comfort navigating and patching a codebase.
• Fluency in English with strong writing skills (native or bilingual level).
• A bachelor’s degree is preferred.
• Cybersecurity certifications are a plus (e.g., OSCP, CRTO, GREM, GCFA, CEH, and similar).

Benefits

• Fully remote: work from anywhere in the US, Canada, UK, Ireland, Australia, and New Zealand.
• Flexible schedule: choose projects and work on your own terms from your own machine.
• Competitive pay: projects are paid hourly at $50 to $100 USD per hour, with opportunities for higher bonus rates on certain projects.
• Impact: contribute to shaping AI technologies designed for cybersecurity.

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