Penetration Tester

Summary

DataAnnotation is looking for experienced cybersecurity professionals to join their team to help train AI models. In this role, you will evaluate AI-generated security content, solve technical cybersecurity problems, and provide feedback to improve AI systems' understanding of real-world threats and defenses.

Responsibilities

• Evaluate AI-generated cybersecurity content, including threat analysis, vulnerability assessments, and offensive security techniques
• Design and solve security-focused technical problems used to train AI systems
• Write clear technical explanations and security-relevant code
• Provide feedback that directly shapes the next generation of AI security models

Skills

• 2+ years of hands-on experience in cybersecurity (e.g., penetration testing, red teaming, incident response, detection engineering, DFIR, malware analysis, threat intelligence, or similar)
• Some coding experience required
• Fluency in English (native or bilingual level)
• Strong writing and analytical skills
• A bachelor's degree is preferred
• Cybersecurity certifications are a plus (e.g., OSCP, CRTO, GREM, GCFA, CEH)

Qualifications

Must Haves

• 2+ years of hands-on experience in cybersecurity (e.g., penetration testing, red teaming, incident response, detection engineering, DFIR, malware analysis, threat intelligence, or similar)
• Some coding experience required
• Fluency in English (native or bilingual level)
• Strong writing and analytical skills

Nice to Haves

• A bachelor's degree is preferred
• Cybersecurity certifications are a plus (e.g., OSCP, CRTO, GREM, GCFA, CEH)

Benefits

• You’ll be able to choose which projects you want to work on
• You can work on your own schedule
• Work from anywhere in the US, Canada, UK, Ireland, Australia, and New Zealand