Penetration Tester (Ethical Hacker) - AI Trainer

DataAnnotation seeks a remote Penetration Tester (Ethical Hacker) to serve as an AI Trainer. The role centers on evaluating AI-generated cybersecurity content and solving security challenges to inform the next generation of AI security models. This contract position is fully remote and based in Alaska, offering flexible scheduling.

Responsibilities

• Assess AI-generated cybersecurity content, including threat analyses, vulnerability assessments, and offensive security techniques, for accuracy and real-world relevance.
• Design and solve security-focused technical challenges used to train AI systems.
• Produce clear technical explanations and write security-relevant code.
• Provide actionable feedback that shapes the development of future AI security models.

Requirements

• Minimum of two years of hands-on experience in cybersecurity roles 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 is required; comfort navigating and patching a codebase is essential.
• Fluent English with strong writing skills, native or bilingual.
• A bachelor’s degree is preferred.
• Cybersecurity certifications are advantageous, such as OSCP, CRTO, GREM, GCFA, CEH, and similar.

Benefits

• Fully remote work from locations including the US, Canada, UK, Ireland, Australia, and New Zealand.
• Flexible schedule enabling project selection and work from your own device and home.
• Competitive hourly pay at USD 50 - 100 per hour, with opportunities for higher bonus rates on select projects.
• Impactful work contributing to the future of AI technologies built for cybersecurity.

Note

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