[Remote] Penetration Testing Engineer - AI Trainer

Note: The job is a remote job and is open to candidates in USA. DataAnnotation is a company focused on developing cutting-edge AI systems, and they are seeking experienced cybersecurity professionals to contribute to AI development. The role involves evaluating AI-generated security content, solving technical security problems, and providing feedback to shape AI security models.ResponsibilitiesEvaluate AI-generated cybersecurity content — including threat analysis, vulnerability assessments, and offensive security techniques — for real-world accuracy and validityDesign and solve security-focused technical problems used to train AI systemsWrite clear technical explanations and security-relevant codeProvide feedback that directly shapes the next generation of AI security modelsSkills2+ 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 operationsSome coding experience required; comfort navigating and patching a codebase is keyFluency in English (native or bilingual level) with strong writing skillsA bachelor's degree is preferredCybersecurity certifications are a plus (e.g., OSCP, CRTO, GREM, GCFA, CEH, and similar)BenefitsBonus rates available on some projectsYou'll be able to choose which projects you want to work on and whenYou work on your own schedule, on your own computer, from the comfort of your own homeCompany OverviewWelcome to DataAnnotation! We pay smart folks to train AI. It was founded in undefined, and is headquartered in New York, New York, USA, with a workforce of 5001-10000 employees. Its website is https://dataannotation.tech.