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DataAnnotation

Penetration Tester (Ethical Hacker) - AI Trainer

DataAnnotation
Connecticut Remote $50 - $100/hr Contract Posted 3h ago
Adversarial Ai Ai Trainer Ai Training Artificial Intelligence Information Security InfoSec Penetration Testing Red Team Security Security Testing
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Job Description

DataAnnotation offers a fully remote, contract opportunity designed for cybersecurity professionals who value flexibility, project-based work, and real-world impact. In this role you will train AI security models by evaluating AI-generated content, solving security problems, and delivering actionable feedback, all on a schedule that fits your life using your own equipment.

Location: Connecticut (remote). This remote role is open to residents in the United States, Canada, United Kingdom, Ireland, Australia, and New Zealand. Payments are processed via PayPal.

Benefits

  • Fully remote: work from anywhere in the US, Canada, UK, Ireland, Australia, and New Zealand.
  • Flexible schedule: choose which projects you take on and when you work, on your own computer from home.
  • Competitive pay: hourly rates range from $50 to $100 USD, with potential bonuses on select projects.
  • Meaningful impact: help shape the next generation of AI technologies built for cybersecurity.

Note: Payment is via PayPal. This role is limited to residents of the US, Canada, UK, Ireland, Australia, and New Zealand.

Responsibilities

  • Evaluate AI-generated cybersecurity content, including threat analysis, vulnerability assessments, and offensive security techniques, for real-world accuracy and validity.
  • 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.

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 related fields, including government or military cyber operations.
  • Coding experience is required; comfort navigating and patching a codebase is essential.
  • Fluent English with strong writing skills (native or bilingual level).
  • A bachelor’s degree is preferred.
  • Cybersecurity certifications are a plus (examples include OSCP, CRTO, GREM, GCFA, CEH, and related credentials).

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