Penetration Testing Engineer - AI Trainer

Role overview

Penetration Testing Engineer (AI Trainer) to help advance AI development by applying real-world cybersecurity expertise. You’ll evaluate and test AI-generated security outputs and contribute feedback that improves how AI systems reason about real-world threats and defenses.

Responsibilities

• Evaluate AI-generated cybersecurity content for real-world accuracy and validity (e.g., threat analysis, vulnerability assessments, 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 next-generation AI security models

Requirements

• 2+ years hands-on experience in a cybersecurity role (e.g., penetration testing, red teaming, incident response, detection engineering, DFIR, malware analysis, threat intelligence, or adjacent fields, including government/military cyber operations)
• Some coding experience; comfort navigating and patching a codebase
• English fluency (native or bilingual) with strong writing skills
• Bachelor’s degree preferred

Nice to have

• Cybersecurity certifications (e.g., OSCP, CRTO, GREM, GCFA, CEH, or similar)

Contracting & work style

• Independent contractor position
• Remote work with the ability to choose which projects and when you work
• Paid hourly starting at $50–$100+/hr, with possible bonus rates
• Payment via PayPal

Location eligibility

• Only available to candidates in the US (and also listed: Canada, UK, Ireland, Australia, New Zealand).