Product Security Engineer - AI Trainer

DataAnnotation seeks a remote, contract Product Security Engineer - AI Trainer based in Wisconsin. The role centers on evaluating AI-generated cybersecurity content, crafting security-focused training challenges, and delivering actionable feedback to refine AI security models. The position carries an hourly rate between USD 50 and 100, with payment via PayPal. This opportunity is available to applicants in the US, Canada, UK, Ireland, Australia, and New Zealand.

Responsibilities

• Assess AI-generated cybersecurity content for real-world accuracy, including threat analysis, vulnerability assessments, and offensive security techniques.
• Design and solve security-centric technical problems used to train AI systems.
• Produce clear technical explanations and security-relevant code.
• Provide feedback that informs the next generation of AI security models.

Requirements

• Minimum 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 is required; comfort navigating and patching a codebase is essential.
• Fluent in English with strong writing skills (native or bilingual level).
• Bachelor's degree is preferred.
• Cybersecurity certifications are a plus (for example OSCP, CRTO, GREM, GCFA, CEH, and similar).

Benefits

• Fully remote work from the US, Canada, UK, Ireland, Australia, or New Zealand.
• Flexible schedule: select projects and work times, using your own computer from home.
• Competitive pay: hourly compensation listed as USD 50 - 100 per hour; some projects offer higher bonus rates.
• Impact: contribute to shaping AI technologies designed for cybersecurity.