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Remote Penetration Testing Jobs in Virginia (NOW HIRING)

Endyna

Penetration Testing - SME

Mclean, VA · Remote

Remote / Hybrid / Travel as Required Security Requirement: Must be eligible to obtain and maintain ... Lead penetration testing engagements * Develop attack strategies * Review Rules of Engagement

SixGen, Inc.

Senior Red Team Operator

Sterling, VA · On-site +1

Apply penetration testing, network analysis, and adversary emulation techniques to identify ... Flexible and remote work policies for most positions * Flexible PTO and holiday schedule For more ...

Maximus

Senior Director - Cyber Security & Innovation

VA · On-site +1

$111K - $150K/yr

... assessment, penetration testing, and threat mitigation techniques. - Expertise in cloud ... Remote EEO Statement Maximus is an equal opportunity employer. We evaluate qualified applicants ...

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Remote Penetration Testing information

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.

Is there a demand for penetration testing?

There is strong demand for penetration testers, including those in remote roles, as organizations prioritize cybersecurity and vulnerability assessments. Skilled professionals with knowledge of tools like Kali Linux, Metasploit, and certifications such as OSCP are especially sought after in the industry.

Will pentesters be replaced by AI?

Remote penetration testers perform manual and creative security assessments that AI currently cannot fully replicate. While AI tools can assist with vulnerability scanning and data analysis, human expertise is essential for identifying complex threats, interpreting results, and developing effective security strategies. The role of pentesters is expected to evolve with technology, but not be entirely replaced by AI.

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.

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.

How much do remote penetration testers make?

Remote penetration testers typically earn between $70,000 and $130,000 annually, depending on experience, certifications, and the complexity of the projects. Senior professionals with advanced skills and certifications like OSCP or CISSP can earn higher salaries, especially when working for specialized firms or as freelancers.

Do penetration testers work remotely?

Many penetration testers work remotely, especially those in freelance or consulting roles, utilizing tools like VPNs, remote access software, and security testing platforms. Remote work allows flexibility, but some employers may require on-site presence for certain assessments or client interactions.

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.
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Remote Penetration Testing jobs near you
Infographic showing various Remote Penetration Testing job openings in Virginia as of June 2026, with employment types broken down into 72% Full Time, 17% Part Time, and 11% Contract. Highlights an 100% Remote job distribution.
Penetration Testing - SME

Penetration Testing - SME

Endyna

Mclean, VA • Remote

Contractor

Posted 4 days ago

Job description

Location: Remote / Hybrid / Travel as Required

Security Requirement:
Must be eligible to obtain and maintain an HHS Tier 4 High Risk Public Trust.

Position Summary

EnDyna is seeking a highly experienced Penetration Testing Subject Matter Expert (SME) to provide technical leadership supporting the HHS Office of Inspector General Cyber Assessment Team.

The SME will lead complex penetration testing engagements, provide technical consulting to Federal auditors, develop testing methodologies, mentor penetration testers, deliver cybersecurity training, and serve as a trusted advisor to Government leadership.

Primary Responsibilities

Technical Leadership

  • Lead penetration testing engagements
  • Develop attack strategies
  • Review Rules of Engagement
  • Provide technical oversight
  • Review testing methodologies
  • Ensure technical quality
  • Mentor penetration testers
  • Validate technical findings

Advanced Penetration Testing

Lead and perform:

  • Red Team operations
  • Advanced exploitation
  • Cloud security testing
  • AI security testing
  • Active Directory attacks
  • Wireless testing
  • Mobile security
  • Web application assessments
  • Social engineering assessments
  • Container security testing
  • Internal network assessments
  • External network assessments

Technical Consulting

Serve as cybersecurity advisor to OIG auditors by:

  • Providing technical guidance
  • Supporting complex audits
  • Evaluating security architectures
  • Reviewing vulnerability data
  • Advising on remediation strategies
  • Supporting Cyber Range activities

Reporting

Lead development of:

  • Executive briefings
  • OARS findings
  • Penetration test reports
  • Conclusions memoranda
  • Attack confirmation lists
  • Risk analyses
  • Technical recommendations

Training

Develop and deliver:

  • 4-5 day penetration testing courses
  • Hands-on laboratories
  • Live exploit demonstrations
  • Capstone exercises
  • Instructor coaching
  • Training materials
  • Student guides
  • Presentation slides

Technical Expertise

Demonstrated expertise in:

  • Offensive Security
  • Threat emulation
  • Adversary tactics
  • Cloud security
  • Active Directory
  • Application security
  • Network security
  • Secure development
  • Risk management
  • Federal cybersecurity

Minimum Qualifications

  • Bachelor's degree
  • Master's preferred
  • 10+ years of penetration testing experience
  • 5+ years leading technical teams
  • Experience supporting Federal agencies
  • Extensive report writing experience
  • Strong presentation skills

Highly Desired Certifications

One or more advanced certifications:

  • OSCE3
  • OSEP
  • OSEE
  • GXPN
  • GPEN
  • CISSP
  • GREM
  • CRTO
  • CARTP
  • CARTC

Preferred Experience

Experience with:

  • HHS
  • OIG
  • DHS
  • Federal Inspector General organizations
  • NIST SP 800-115
  • Federal auditing
  • Cyber Range environments
  • Offensive security consulting

Apply