Senior Penetration Tester: Red Team, ICS/OT, Cloud

Jobtailor; Washington (District of Columbia); On-site; USD 120,000 - 180,000; Full time

Job summary

Jobtailor in Washington, DC seeks an experienced Penetration Tester to execute complex assessments of networks, systems, and web applications. You will follow formal rules of engagement, document exploitation paths, and contribute to test plans for upcoming engagements.

The role requires 5+ years of hands-on pentesting, strong tool proficiency, and security testing across ICS/OT, cloud, and wireless environments.

Qualifications

• Bachelor's degree in cybersecurity, CS, IT, engineering, math or physics.
• 5+ years hands-on penetration testing across networks, systems, and web apps.
• At least 2 years of recent hands-on testing (last 3 years).
• Proficiency with Metasploit, Burp Suite, Nmap and related frameworks.
• Experience with formal Rules of Engagement and producing structured PTRs.
• Understanding of network protocols, routing, switching, firewalls and misconfigurations.
• Experience with OWASP testing methodology for web apps.
• Ability to obtain and maintain a Public Trust.
• One Red Teaming certification (OSCP/OSCE/OSWP/OSWE/CEH/ECSA etc.).
• Blue Team certifications accepted (CND/CNDA/GCIH/GCIA/GDAT/GCED/GCFA). OSCP or GPEN preferred.
• Experience testing ICS/OT environments or critical infrastructure.
• Experience with wireless security testing or satellite comms.
• Experience with cloud pen testing (AWS, Azure).
• Familiarity with aircraft systems, avionics or aviation protocols.
• Prior red team experience in government/military contexts.
• C2 frameworks for adversary simulation beyond Metasploit.
• BloodHound and Impacket for AD attack paths.
• Nuclei for automated vulnerability detection at scale.
• Cloud tools (Pacu, AzureHound) for cloud-hosted environments.
• SDR/HackRF tools for wireless/RF testing.
• AI-assisted fuzzing tools for exploit discovery.

Responsibilities

• Execute penetration tests against NAS and Mission Support systems, networks, and applications following approved Rules of Engagement and test plans.
• Identify and exploit vulnerabilities in network infrastructure, OS, web apps, and databases.
• Participate in red team and blue team exercises in simulated environments.
• Execute attack scenarios and document findings in PTRs.
• Perform regression penetration tests to validate remediation of vulnerabilities.
• Support aircraft cyber testing activities including avionics and flight system security assessments.
• Support edge devices, firewalls, load balancers, and other network components testing.
• Assess and document potential for lateral movement when access is gained.
• Report high-risk findings immediately.
• Maintain and update penetration testing tools and lab environments; FAA-approved tools only.
• Assist Penetration Testing Lead in developing Rules of Engagement and test plans for upcoming engagements.

Skills

Penetration testing

Red Team experience

Blue Team experience

Report writing

Education

Bachelor's degree in Cybersecurity, Computer Science, Information Technology, Engineering, Mathematics, or Physics

Tools

Metasploit

Burp Suite

Nmap

C2 frameworks (Cobalt Strike, Sliver, Mythic)

BloodHound/Impacket

Job description

Jobtailor in Washington, DC seeks an experienced Penetration Tester to execute complex assessments of networks, systems, and web applications. You will follow formal rules of engagement, document exploitation paths, and contribute to test plans for upcoming engagements.

The role requires 5+ years of hands-on pentesting, strong tool proficiency, and security testing across ICS/OT, cloud, and wireless environments.