Penetration Tester (Ethical Hacker) - AI Trainer

DataAnnotation is seeking a Penetration Tester (Ethical Hacker) - AI Trainer to help train AI models by evaluating AI generated security content and solving security problems. This fully remote role offers flexible scheduling and the chance to influence AI security outcomes from Illinois-based work.

Benefits

• Fully remote work from locations across the United States, Canada, the United Kingdom, Ireland, Australia, and New Zealand.
• Flexible schedule that lets you choose projects and working hours from your own setup.
• Competitive hourly compensation, with rates between $50 and $100 per hour, plus opportunities for higher bonuses on select projects.
• Impactful work that helps shape the future of AI technologies used in cybersecurity.

Responsibilities

• Evaluate AI generated cybersecurity content for real world accuracy, covering threat analysis, vulnerability assessments, and offensive security techniques.
• Design and solve security focused technical challenges used to train AI systems.
• Write clear technical explanations and security related code.
• Provide feedback that informs 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 required; comfortable navigating and patching a codebase.
• Fluency in English (native or bilingual) with strong writing skills.
• A bachelor's degree is preferred.
• Cybersecurity certifications are a plus (for example OSCP, CRTO, GREM, GCFA, CEH, and similar).

Notes

Payment is made via PayPal. We will never ask for money from you. This position is available to residents of the United States, Canada, the United Kingdom, Ireland, Australia, and New Zealand.