Penetration Tester (Ethical Hacker) - AI Trainer

This contract role invites a Penetration Tester, also known as an Ethical Hacker, to join DataAnnotation as an AI Trainer. The core objective is to assess AI-generated cybersecurity content for real-world accuracy and to contribute to training AI security models. The position offers remote, flexible scheduling and is anchored to Wisconsin as the designated work location, with remote engagement possible from various environments.

Responsibilities

• Assess AI-produced cybersecurity content, including threat analyses, vulnerability assessments, and offensive security techniques, for accuracy and real-world relevance.
• Develop and resolve security-centric technical challenges used to train AI systems.
• Produce clear technical explanations and write security-relevant code.
• Deliver actionable feedback that informs the next generation of AI security models.

Requirements

• Minimum of 2+ years in hands-on cybersecurity roles 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; the ability to navigate and patch a codebase is essential.
• Fluency in English with strong written communication skills (native or bilingual level).
• A bachelor’s degree is preferred.
• Cybersecurity certifications are a plus (eg, OSCP, CRTO, GREM, GCFA, CEH, and similar).

Benefits

• Fully remote work: operate from anywhere in the US, Canada, the UK, Ireland, Australia, and New Zealand.
• Flexible schedule: decide which projects to take and when to work, using your own computer from home.
• Competitive compensation: hourly pay ranges from USD 50 to 100 per hour, with potential higher bonuses on select projects.
• Impactful work: contribute to shaping AI technologies designed for cybersecurity applications.