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DataAnnotation

Penetration Tester (Ethical Hacker) - AI Trainer

DataAnnotation
Indianapolis, IN Remote $50 - $100/hr Contract Posted 2h ago
Ai Security Ai Security Training Ethical Hacking Information Security InfoSec Security Security Testing
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Job Description

DataAnnotation is seeking a Penetration Tester (Ethical Hacker) - AI Trainer to support the evaluation and improvement of AI chatbots and models used for cybersecurity. This contract role blends hands-on security expertise with the ability to assess AI-generated content and help solve security problems that strengthen real-world guidance.

Based in Indiana (remote), work can be performed from your own computer with a flexible schedule. Projects are compensated on an hourly basis, supporting meaningful impact in how AI security technologies are trained and validated.

Key Responsibilities

  • Evaluate AI-generated cybersecurity content, including threat analysis, vulnerability assessments, and offensive security techniques, with an eye toward real-world accuracy and validity.
  • Design and solve security-focused technical problems that are used to train AI systems.
  • Write clear technical explanations and security-relevant code.
  • Provide feedback that directly informs improvements to upcoming generations 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 work, including government or military cyber operations.
  • Some coding experience is required, with comfort navigating and patching a codebase.
  • English fluency (native or bilingual level) with strong writing skills.
  • Bachelor’s degree preferred.
  • Certifications are a plus (examples include OSCP, CRTO, GREM, GCFA, CEH, and similar).

Contract Details

  • Job type: contract
  • Location: Indiana (remote)
  • Schedule: flexible; choose which projects to take on and when to work
  • Pay: $50 to $100 USD per hour
  • Bonuses: opportunities for higher bonus rates for certain projects

Benefits

  • Fully remote: available to work from anywhere in the US, Canada, UK, Ireland, Australia, and New Zealand.
  • Flexible schedule: complete work on your own computer from home.
  • Competitive hourly pay: $50 to $100 USD per hour for projects.
  • Impact: contribute to shaping AI technologies built for cybersecurity.

How to Get Started

After you sign up for an account, you’ll take a short assessment that serves as a version of an interview. If you pass, you’ll receive an email confirmation, and paid work becomes available to you through the platform.

  • Payment method: PayPal
  • Cost to apply: we will never ask you for any money
  • Eligibility: this role is only available to candidates in the US, Canada, UK, Ireland, Australia, and New Zealand

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