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Remote Penetration Tester Trainee Jobs (NOW HIRING)

DataAnnotation

Penetration Tester

Rochester, NY · Remote

$40 - $75/hr

Fully remote: work from anywhere in the US, Canada, UK, Ireland, Australia, and New Zealand ... as penetration testing, red teaming, incident response, detection engineering, DFIR, malware ...

DataAnnotation

Penetration Tester

Tallahassee, FL · Remote

$40 - $75/hr

Fully remote: work from anywhere in the US, Canada, UK, Ireland, Australia, and New Zealand ... as penetration testing, red teaming, incident response, detection engineering, DFIR, malware ...

DataAnnotation

Penetration Tester

Tampa, FL · Remote

$40 - $75/hr

Fully remote: work from anywhere in the US, Canada, UK, Ireland, Australia, and New Zealand ... as penetration testing, red teaming, incident response, detection engineering, DFIR, malware ...

DataAnnotation

Penetration Tester

Chicago, IL · Remote

$40 - $75/hr

Fully remote: work from anywhere in the US, Canada, UK, Ireland, Australia, and New Zealand ... as penetration testing, red teaming, incident response, detection engineering, DFIR, malware ...

DataAnnotation

Penetration Tester

Augusta, GA · Remote

$40 - $75/hr

Fully remote: work from anywhere in the US, Canada, UK, Ireland, Australia, and New Zealand ... as penetration testing, red teaming, incident response, detection engineering, DFIR, malware ...

DataAnnotation

Penetration Tester

Norman, OK · Remote

$40 - $75/hr

Fully remote: work from anywhere in the US, Canada, UK, Ireland, Australia, and New Zealand ... as penetration testing, red teaming, incident response, detection engineering, DFIR, malware ...

DataAnnotation

Penetration Tester

Henderson, NV · Remote

$40 - $75/hr

Fully remote: work from anywhere in the US, Canada, UK, Ireland, Australia, and New Zealand ... as penetration testing, red teaming, incident response, detection engineering, DFIR, malware ...

DataAnnotation

Penetration Tester

Everett, WA · Remote

$40 - $75/hr

Fully remote: work from anywhere in the US, Canada, UK, Ireland, Australia, and New Zealand ... as penetration testing, red teaming, incident response, detection engineering, DFIR, malware ...

DataAnnotation

Penetration Tester

Moreno Valley, CA · Remote

$40 - $75/hr

Fully remote: work from anywhere in the US, Canada, UK, Ireland, Australia, and New Zealand ... as penetration testing, red teaming, incident response, detection engineering, DFIR, malware ...

DataAnnotation

Penetration Tester

Buckeye, AZ · Remote

$40 - $75/hr

Fully remote: work from anywhere in the US, Canada, UK, Ireland, Australia, and New Zealand ... as penetration testing, red teaming, incident response, detection engineering, DFIR, malware ...

Aerstone

Penetration Tester

Springfield, VA · Remote

As a Penetration Tester, you will join our growing testing team and have the opportunity to support ... Experienced with virtual machine platforms and remote testing solutions * Experienced with cloud ...

DataAnnotation

Penetration Tester

Huntington Beach, CA · Remote

$40 - $75/hr

Fully remote: work from anywhere in the US, Canada, UK, Ireland, Australia, and New Zealand ... as penetration testing, red teaming, incident response, detection engineering, DFIR, malware ...

DataAnnotation

Penetration Tester

Murrieta, CA · Remote

$40 - $75/hr

Fully remote: work from anywhere in the US, Canada, UK, Ireland, Australia, and New Zealand ... as penetration testing, red teaming, incident response, detection engineering, DFIR, malware ...

DataAnnotation

Penetration Tester

Denton, TX · Remote

$40 - $75/hr

Fully remote: work from anywhere in the US, Canada, UK, Ireland, Australia, and New Zealand ... as penetration testing, red teaming, incident response, detection engineering, DFIR, malware ...

DataAnnotation

Penetration Tester

Charleston, SC · Remote

$40 - $75/hr

Fully remote: work from anywhere in the US, Canada, UK, Ireland, Australia, and New Zealand ... as penetration testing, red teaming, incident response, detection engineering, DFIR, malware ...

DataAnnotation

Penetration Tester

New Braunfels, TX · Remote

$40 - $75/hr

Fully remote: work from anywhere in the US, Canada, UK, Ireland, Australia, and New Zealand ... as penetration testing, red teaming, incident response, detection engineering, DFIR, malware ...

DataAnnotation

Penetration Tester

Spokane Valley, WA · Remote

$40 - $75/hr

Fully remote: work from anywhere in the US, Canada, UK, Ireland, Australia, and New Zealand ... as penetration testing, red teaming, incident response, detection engineering, DFIR, malware ...

DataAnnotation

Penetration Tester

Cape Coral, FL · Remote

$40 - $75/hr

Fully remote: work from anywhere in the US, Canada, UK, Ireland, Australia, and New Zealand ... as penetration testing, red teaming, incident response, detection engineering, DFIR, malware ...

DataAnnotation

Penetration Tester

Pasadena, CA · Remote

$40 - $75/hr

Fully remote: work from anywhere in the US, Canada, UK, Ireland, Australia, and New Zealand ... as penetration testing, red teaming, incident response, detection engineering, DFIR, malware ...

DataAnnotation

Penetration Tester

Lynn, MA · Remote

$40 - $75/hr

Fully remote: work from anywhere in the US, Canada, UK, Ireland, Australia, and New Zealand ... as penetration testing, red teaming, incident response, detection engineering, DFIR, malware ...

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Remote Penetration Tester Trainee information

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$22.5K

$119.9K

$168.5K

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

As of May 29, 2026, the average yearly pay for remote penetration tester trainee 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 are the key skills and qualifications needed to thrive as a Remote Penetration Tester Trainee, and why are they important?

To thrive as a Remote Penetration Tester Trainee, you need foundational knowledge in networking, cybersecurity principles, and operating systems, often supported by coursework or entry-level certifications like CompTIA Security+. Familiarity with tools such as Kali Linux, Metasploit, Wireshark, and vulnerability scanners is typically required. Strong analytical thinking, problem-solving abilities, and effective written communication help you document findings and collaborate remotely with teams. These skills ensure you can identify and report security weaknesses efficiently, supporting organizational cybersecurity objectives in a remote environment.

What are some common challenges faced by remote penetration tester trainees, and how can they overcome them?

Remote penetration tester trainees often encounter challenges such as limited direct mentorship, communicating effectively with team members across different time zones, and maintaining focus in a home environment. To overcome these, it's helpful to proactively schedule regular check-ins with mentors, utilize collaborative tools for clear communication, and set up a dedicated workspace to stay productive. Engaging in online training communities and seeking feedback can also accelerate learning and help trainees feel more connected to their team.

What is a Remote Penetration Tester Trainee?

A Remote Penetration Tester Trainee is an entry-level cybersecurity professional who assists in testing computer systems, networks, and applications for vulnerabilities from a remote location. Trainees work under supervision, learning how to identify security weaknesses and suggest improvements. They use various tools and techniques to simulate cyberattacks, helping organizations strengthen their defenses against real threats. This role is ideal for those looking to start a career in ethical hacking or information security, offering hands-on experience and training in a remote work setting.

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

AspectRemote Penetration Tester TraineeRemote Security Analyst
CertificationsBasic cybersecurity certifications (e.g., CompTIA Security+)Security+ or equivalent; may include CISSP or CEH
Work EnvironmentHands-on testing in simulated or real environments, often under supervisionMonitoring, analyzing security systems, and incident response
Industry UsageEntry-level, training-focused role in cybersecurity firms or IT departmentsMid-level role in organizations managing security operations

While both roles focus on cybersecurity, a Remote Penetration Tester Trainee is primarily involved in learning and assisting with penetration tests, whereas a Remote Security Analyst monitors and analyzes security threats. The trainee role emphasizes skill development, while the analyst role involves ongoing security management.

More about Remote Penetration Tester Trainee jobs
What cities are hiring for Remote Penetration Tester Trainee jobs? Cities with the most Remote Penetration Tester Trainee job openings:
What states have the most Remote Penetration Tester Trainee jobs? States with the most job openings for Remote Penetration Tester Trainee jobs include:
What job categories do people searching Remote Penetration Tester Trainee jobs look for? The top searched job categories for Remote Penetration Tester Trainee jobs are:
Remote Penetration Tester Trainee jobs near you
Infographic showing various Remote Penetration Tester Trainee job openings in the United States as of May 2026, with employment types broken down into 94% Full Time, 2% Part Time, and 4% Contract. Highlights an 10% Physical, 5% Hybrid, and 85% Remote job distribution, with an average salary of $119,895 per year, or $57.6 per hour.
Penetration Tester

Penetration Tester

DataAnnotation

Rochester, NY • Remote

$40 - $75/hr

Part-time

Posted 5 days ago

Job description

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

We are looking for experienced cybersecurity professionals to help advance AI development. Cybersecurity platforms are increasingly powered by AI — 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.

As a member of DataAnnotation's team, 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. Some team members fit this work alongside a full-time role, while others treat it as their primary focus.

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.

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.
  • Projects are paid hourly starting at $50-75+/hr, with bonuses for high-quality and high-volume work
  • Impact: help shape the future of AI technologies built for cybersecurity.

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.

Qualifications:

  • 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 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.

#cybersecurity