Penetration Tester (Ethical Hacker) - AI Trainer

DataAnnotation is building and training AI systems that support cybersecurity use cases, and it needs experienced penetration testers to validate AI-generated security content and solve technical problems that reflect real-world threats. This fully remote contract role is based in Ohio, with work completed from your own computer and focused on improving how AI systems reason about security risks and defenses.

You will review AI outputs for accuracy, develop and address security-focused training challenges, and deliver clear technical explanations and code that help guide future model behavior. Your feedback will be used to shape the next generation of AI security models.

Key Responsibilities

• Assess AI-generated cybersecurity content, including threat analysis, vulnerability assessments, and offensive security techniques, to confirm real-world validity.
• Design and solve security-focused technical problems used to train AI systems.
• Produce clear technical explanations and security-relevant code.
• Provide feedback that directly influences how AI models learn and respond to real-world threats and defensive needs.

Requirements

• 2+ 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 areas, including government or military cyber operations.
• Coding experience required; comfort navigating and patching a codebase is important.
• Fluency in English (native or bilingual level) with strong writing skills.
• A bachelor’s degree is preferred.
• Certifications are a plus (for example: OSCP, CRTO, GREM, GCFA, CEH, and similar).

Contract Details

• Location: Ohio (remote)
• Job type: contract
• Pay: USD $50 to $100 per hour (hourly)

Benefits

• Fully remote: work from anywhere in the US, Canada, UK, Ireland, Australia, and New Zealand.
• Flexible schedule: select projects and work timing; perform work on your own computer.
• Competitive pay: projects paid hourly at $50 to $100 USD per hour.
• Higher bonus rates may be available for certain projects.
• Impact: contribute to the development of AI technologies in the cybersecurity space.

Notes

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