Penetration Tester (Ethical Hacker) - AI Trainer

DataAnnotation offers a remote, contract opportunity for a Penetration Tester (Ethical Hacker) to serve as an AI Trainer. You will help advance AI security by evaluating AI generated threat analyses and security content, solving security challenges, and contributing to the refinement of AI models, all with a flexible schedule that accommodates your life and commitments.

This role is remote from Oregon and open to applicants in the United States, Canada, the United Kingdom, Ireland, Australia, and New Zealand. Compensation is hourly, with a range of USD 50 - 100 per hour, and some projects may include higher bonus opportunities.

Responsibilities

• Assess AI generated cybersecurity content for real world accuracy and reliability, covering threat analysis, vulnerability assessments, and offensive security techniques.
• Design and solve security oriented technical problems that are used to train AI systems.
• Produce clear technical explanations and write security relevant code when needed.
• Provide feedback that directly informs the next generation of AI security models.

Requirements

• Minimum of 2 years 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. Experience in government or military cyber operations is a plus.
• Some coding experience is required; comfort navigating and patching a codebase is essential.
• Fluency in English with strong writing skills (native or bilingual level).
• A bachelor’s degree is preferred.
• Cybersecurity certifications are a plus (examples include OSCP, CRTO, GREM, GCFA, CEH and similar).

Benefits

• Fully remote work from the US, Canada, UK, Ireland, Australia, or New Zealand.
• Flexible schedule, allowing you to choose projects and when you work, using your own computer from home.
• Competitive hourly pay with opportunities for higher bonus rates on select projects.
• Opportunity to influence the future of AI technologies designed for cybersecurity.

Payment is processed via PayPal. We will not request money from you. This role is restricted to candidates located in the United States, Canada, the United Kingdom, Ireland, Australia, and New Zealand.