Penetration Tester (Ethical Hacker) - AI Trainer

DataAnnotation is seeking a contract Penetration Tester (Ethical Hacker) focused on AI training. The role involves evaluating AI-generated security content and solving security challenges to help train AI security models. This is a remote position with a Maryland base and flexible scheduling.

Responsibilities

• Assess AI-produced cybersecurity material, including threat analyses, vulnerability assessments, and offensive security techniques, for real-world accuracy and relevance.
• Design and resolve security-centric technical problems used to train AI systems.
• Produce clear technical explanations and write security-related code as needed.
• Deliver actionable feedback that informs the next iterations 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 is required; comfort navigating and patching a codebase is essential.
• Fluency in English with strong writing skills (native or bilingual level).
• Bachelor's degree is preferred.
• Cybersecurity certifications are a plus (examples include OSCP, CRTO, GREM, GCFA, CEH, and similar credentials).

Benefits

• Fully remote work from anywhere in the US, Canada, the UK, Ireland, Australia, and New Zealand.
• Flexible scheduling to choose projects and working times, using your own computer from home.
• Competitive hourly pay ranging from USD 50 to 100, with opportunities for higher bonus rates on certain projects.
• Opportunity to influence the development of AI technologies designed for cybersecurity.

Advantages of Contracting with Us

• Fully remote work from the US, Canada, the UK, Ireland, Australia, and New Zealand.
• Flexible scheduling to select projects and working times, on your own device and at home.
• Competitive pay at hourly rates of USD 50 to 100, with potential boosts for select projects.
• Meaningful impact on the future of AI security technologies.

Note

Payment is made via PayPal. We will never request funds from you. This opportunity is available to residents of the United States, Canada, the United Kingdom, Ireland, Australia, and New Zealand.