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Remote Cybersecurity Penetration Tester Jobs (NOW HIRING)

Penetration Tester - AI Trainer

Kent, WA ยท Remote

$50 - $100/hr

... of remote work and setting your own schedule. We are looking for existing cybersecurity ... as penetration testing, red teaming, incident response, detection engineering, DFIR, malware ...

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Remote Cybersecurity Penetration Tester information

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$22.5K

$119.9K

$168.5K

How much do remote cybersecurity penetration tester jobs pay per year?

As of Jul 14, 2026, the average yearly pay for remote cybersecurity penetration tester in the United States is $119,895.00, according to ZipRecruiter salary data. Most workers in this role earn between $96,000.00 and $141,000.00 per year, depending on experience, location, and employer.

What is the difference between Remote Cybersecurity Penetration Tester vs Remote Security Analyst?

AspectRemote Cybersecurity Penetration TesterRemote Security Analyst
CertificationsOSCP, CEH, GPENCISSP, Security+
Primary FocusIdentifying vulnerabilities through simulated attacksMonitoring, analyzing security events
Work EnvironmentProject-based, testing environmentsContinuous monitoring, security operations centers
Industry UsageIT, cybersecurity firms, consultingCorporate, government, financial sectors

While both roles focus on cybersecurity, a Remote Cybersecurity Penetration Tester actively seeks vulnerabilities through simulated attacks, whereas a Remote Security Analyst monitors and responds to security threats in real-time. The penetration tester's work is more offensive and project-based, while the security analyst's role is ongoing and defensive.

More about Remote Cybersecurity Penetration Tester jobs
What cities are hiring for Remote Cybersecurity Penetration Tester jobs? Cities with the most Remote Cybersecurity Penetration Tester job openings:
What are the most commonly searched types of Cybersecurity Penetration Tester jobs? The most popular types of Cybersecurity Penetration Tester jobs are:
What states have the most Remote Cybersecurity Penetration Tester jobs? States with the most job openings for Remote Cybersecurity Penetration Tester jobs include:
Infographic showing various Remote Cybersecurity Penetration Tester job openings in the United States as of July 2026, with employment types broken down into 1% Locum Tenens, 91% Full Time, 5% Part Time, and 3% Contract. Highlights an 79% Physical, 5% Hybrid, and 16% Remote job distribution, with an average salary of $119,895 per year, or $57.6 per hour.
Penetration Tester - AI Trainer

Penetration Tester - AI Trainer

DataAnnotation

Kenosha, WI โ€ข Remote

$50 - $100/hr

Contractor

This job post hasย expired today.ย Applications are no longer accepted.


Job description

About the job:

Contribute to developing cutting-edge AI systems, while enjoying the flexibility of remote work and setting your own schedule.

We are looking for existing cybersecurity professionals to help advance AI development. Cybersecurity platforms are increasingly powered by AI โ€” but these systems still need practitioners with real-world experience to validate whether the outputs actually hold up in practice. That's where you come in.

You'll work closely with state-of-the-art AI models on tasks like evaluating AI-generated security content, solving technical security problems, and providing feedback that directly shapes how these systems reason about real-world threats and defenses.

To get started, once you sign up for an account, you'll take a short assessment (this serves as our version of an interview). If you pass, you'll receive an email confirmation, and paid work will become available to you through our platform.

Advantages of contracting with us:

  • 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.
  • You work on your own schedule, on your own computer, from the comfort of your own home
  • Projects are paid hourly starting at $50-100+/hr, with bonus rates available on some projects
  • Impact: help shape the future of AI technologies built for cybersecurity.

Responsibilities:

  • Evaluate AI-generated cybersecurity content โ€” including threat analysis, vulnerability assessments, and offensive security techniques โ€” 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.

Qualifications:

  • 2+ years of hands-on experience in a cybersecurity role โ€” such as penetration testing, red teaming, incident response, detection engineering, DFIR, malware analysis, threat intelligence, or adjacent fields, including government or military cyber operations.
  • Some coding experience required; comfort navigating and patching a codebase is key.
  • Fluency in English (native or bilingual level) with strong writing skills.
  • A bachelor's degree is preferred.
  • Cybersecurity certifications are a plus (e.g., OSCP, CRTO, GREM, GCFA, CEH, and similar).

Note: Payment is made via PayPal. We will never ask for any money from you. This job is only available to those in the US, Canada, UK, Ireland, Australia, and New Zealand. This is an independent contractor position.

#cybersecurity