Lead Adversary-Emulation Penetration Tester

Crest Security Assurance; Alexandria (VA); On-site; USD 120,000 - 180,000; Full time

Job summary

Crest Security Assurance is seeking a seasoned Penetration Tester to support a federal cybersecurity program. This role leads planning, coordination, execution, and reporting of enterprise penetration tests across agency systems, applications, and infrastructure.

The candidate will perform adversary emulation, red/purple team exercises, and breach simulations to identify vulnerabilities and strengthen defenses, with strong documentation and stakeholder coordination skills required.

Qualifications

• U.S. citizenship and the ability to satisfy personnel-security requirements for a Non-Sensitive/High-Risk position.
• Bachelor of Science in Computer Science, Information Technology, Information Security, Cybersecurity, or a related field.
• Minimum of five years of experience conducting, supporting, or leading penetration tests.
• Demonstrated experience assessing enterprise networks, systems, applications, and security controls.
• Strong knowledge of Windows and Linux operating systems, network architecture, and common networking protocols.
• Demonstrated ability to identify, validate, and safely exploit security vulnerabilities.
• Knowledge of web application technologies, common attack methods, and application-security testing practices.
• Proficiency with industry-standard penetration-testing, vulnerability-assessment, and exploitation tools.
• Proficiency with one or more scripting or programming languages used to automate testing, analyze results, or develop custom assessment capabilities.
• Experience conducting adversary emulation, red team, or purple team exercises using threat-informed tactics, techniques, and procedures.
• Experience developing Rules of Engagement, test plans, assessment documentation, and technical penetration-testing reports.
• Ability to translate complex technical findings into clear, risk-based recommendations for technical and nontechnical stakeholders.
• Strong analytical, problem-solving, technical writing, and verbal communication skills

Responsibilities

• Plan, coordinate, and execute adversarial-based internal, external, and web application penetration testing across enterprise networks, systems, applications, APIs, and cloud environments.
• Develop and maintain penetration testing CONOPS, SOPs, methodologies, test plans, Rules of Engagement (ROE), and supporting documentation aligned with NIST SP 800-115, MITRE ATT&CK, and OWASP standards.
• Coordinate with stakeholders to define assessment scope, objectives, target technologies, testing constraints, authorized TTPs, and success criteria.
• Conduct internal penetration testing using Nmap, Metasploit, Impacket, BloodHound, NetExec, and other tools to assess Active Directory, network segmentation, credential security, privilege escalation, and lateral movement.
• Perform external penetration testing using Nmap, Nessus, Nuclei, Metasploit, and reconnaissance techniques to identify exploitable vulnerabilities, exposed services, and potential attack paths.
• Execute web application and API penetration testing using Burp Suite, OWASP ZAP, SQLmap, and other tools to identify authentication, authorization, injection, session management, and OWASP Top 10 vulnerabilities.
• Conduct red team, blue team, and purple team exercises, adversary emulation, and breach-and-attack simulations using MITRE ATT&CK-aligned TTPs and tools such as MITRE CALDERA and Atomic Red Team.
• Execute authorized reconnaissance, enumeration, exploitation, credential attacks, privilege escalation, lateral movement, persistence simulation, and post-exploitation analysis to assess enterprise security resilience.
• Assess security controls, EDR, IDS/IPS, SIEM detection capabilities, SOC monitoring, and incident response effectiveness against simulated adversarial activity.
• Validate vulnerabilities through manual and automated testing, controlled exploitation, attack-path analysis, and proof-of-concept demonstrations.
• Document findings, technical evidence, exploitability, severity, mission impact, and recommended remediation; immediately escalation critical vulnerabilities.
• Conduct remediation verification, exploit retesting, patch validation, and post-engagement reviews to identify control gaps and improve defensive capabilities.
• Maintain penetration testing records, findings, remediation tracking, and deliverables while integrating results with vulnerability management, RMF, threat intelligence, and continuous monitoring.
• Prepare comprehensive technical and executive reports and present attack paths, risk implications, and corrective actions to Government stakeholders and leadership.

Skills

Analytical thinking

Technical writing

Verbal communication

Risk-based recommendations

Stakeholder coordination

Report writing

Adversary emulation

Education

Bachelor of Science in Computer Science, Information Technology, Information Security, Cybersecurity, or related field

Tools

Nmap

Metasploit

Impacket

BloodHound

Burp Suite

OWASP ZAP

Nessus

Nuclei

SQLmap

MITRE CALDERA

Atomic Red Team

Job description

Crest Security Assurance is seeking a seasoned Penetration Tester to support a federal cybersecurity program. This role leads planning, coordination, execution, and reporting of enterprise penetration tests across agency systems, applications, and infrastructure.

The candidate will perform adversary emulation, red/purple team exercises, and breach simulations to identify vulnerabilities and strengthen defenses, with strong documentation and stakeholder coordination skills required.