Cybersecurity Manager - AI Trainer

DataAnnotation is seeking a remote Cybersecurity Manager - AI Trainer to help train AI security models by evaluating AI-generated cybersecurity content, solving security-focused problems, and delivering feedback to improve how AI defenses reason about threats. This contract role offers flexible scheduling and is based remotely with Bethesda, MD listed as the location.

Responsibilities

• Assess AI-generated cybersecurity content, including threat analyses, vulnerability assessments, and offensive security techniques, for accuracy and real-world relevance.
• Design and solve security-focused technical problems used to train AI systems.
• Prepare clear technical explanations and security-relevant code.
• Provide feedback that directly 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 adjacent fields, including government or military cyber operations.
• Some coding experience is required; comfort navigating and patching a codebase is essential.
• Fluency in English at native or bilingual level with strong writing skills.
• A bachelor’s degree is preferred.
• Cybersecurity certifications are a plus, such as OSCP, CRTO, GREM, GCFA, CEH, and similar credentials.

Benefits

• Fully remote: work from anywhere in the United States, Canada, United Kingdom, Ireland, Australia, and New Zealand.
• Flexible schedule: select projects and set your own hours, using your own computer from home.
• Competitive pay: hourly rates of $50 to $100 USD, with potential higher bonus rates on certain projects.
• Impact: contribute to shaping AI technologies designed for cybersecurity.
• Payment: compensation issued via PayPal.

Notes

Eligibility for this remote contract is limited to residents of the United States, Canada, United Kingdom, Ireland, Australia, and New Zealand.