Penetration Tester (Ethical Hacker) - AI Trainer

DataAnnotation is seeking a Penetration Tester (Ethical Hacker) to help train AI systems by evaluating AI-generated security content, solving security challenges, and delivering actionable feedback that shapes the next generation of AI security models. The role is fully remote with flexible scheduling, anchored in North Dakota, and offers a competitive hourly rate for hands-on cybersecurity work.

Responsibilities

• Review AI-produced cybersecurity material such as threat analyses, vulnerability assessments, and offensive techniques for real world accuracy and applicability.
• Develop and solve security-centric technical problems used to train AI systems.
• Produce clear technical rationale and security-focused code explanations.
• Provide feedback that directly informs the evolution of AI security models.

Requirements

• 2+ years of hands-on cybersecurity experience in roles like 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 (examples include 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 to choose projects and working hours, using your own computer from home.
• Competitive hourly pay of $50 to $100 USD, with opportunities for higher bonus rates on certain projects.
• Opportunity to influence AI technologies built for cybersecurity and improve security models for real-world use.

Note

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