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Remote Penetration Testing Jobs (NOW HIRING)

DataAnnotation

Penetration Tester

Boston, 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 ...

DataAnnotation

Penetration Tester

New York, 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

Mcallen, 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

Columbus, OH · 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

Suffolk, VA · 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

Salt Lake City, UT · 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

Cincinnati, OH · 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

San Antonio, 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

Anchorage, AK · 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

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

Pomona, 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

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

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

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

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

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

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

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

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 ...

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 ...

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Remote Penetration Testing information

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$22.5K

$119.9K

$168.5K

How much do remote penetration testing jobs pay per year?

As of May 29, 2026, the average yearly pay for remote penetration testing 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, and why are they important?

To thrive as a Remote Penetration Tester, you need a solid understanding of computer networks, cybersecurity principles, and common vulnerabilities, often supported by a degree in computer science or related certifications like OSCP or CEH. Familiarity with penetration testing tools such as Metasploit, Burp Suite, Nmap, and various operating systems is essential. Strong analytical thinking, attention to detail, and clear written communication skills help you effectively discover, document, and explain security findings to clients. These competencies are crucial for accurately identifying risks and helping organizations strengthen their security posture.

What are some common challenges faced by remote penetration testers, and how can they be addressed?

Remote penetration testers often encounter challenges such as limited access to physical infrastructure, varying levels of client preparedness, and potential communication barriers with on-site teams. To address these issues, it's important to establish clear communication channels, use secure remote access tools, and maintain detailed documentation of testing activities. Building strong relationships with client IT staff and staying up-to-date with remote testing best practices can also help ensure effective and successful engagements.

What is remote penetration testing?

Remote penetration testing is a security assessment process where cybersecurity professionals, also known as ethical hackers, attempt to find and exploit vulnerabilities in an organization’s systems, networks, or applications from an offsite location. This simulates a real-world cyberattack to help organizations identify and fix security weaknesses before malicious actors can exploit them. Remote penetration testing is often conducted over the internet, making it a flexible and efficient option for businesses to assess their security posture without requiring onsite visits.

What is the difference between Remote Penetration Testing vs Vulnerability Assessment Specialist?

AspectRemote Penetration TestingVulnerability Assessment Specialist
CertificationsOSCP, CEH, GPENOSCP, CEH, CISSP
Work EnvironmentHands-on testing, simulated attacksScanning, identifying vulnerabilities
Industry UsageCybersecurity firms, IT departmentsSecurity teams, consulting firms

Remote Penetration Testing involves actively exploiting vulnerabilities to assess security defenses, while Vulnerability Assessment Specialists focus on identifying and prioritizing security weaknesses without exploiting them. Both roles require similar certifications and often work in overlapping environments, but penetration testers perform more in-depth, simulated attack scenarios to evaluate security robustness.

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Remote Penetration Testing jobs near you
Penetration Tester

Penetration Tester

DataAnnotation

Boston, MA • 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.

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