Penetration Testing Team Lead (R-00251)

True Zero Technologies , a veteran-owned small business, was founded on the principle that the purposeful enablement of people and technology in an organization directly ties to the quality of its outcomes. True Zero recognizes that those outcomes begin and end with our people, and that is what we have built a community of like-minded, driven, and passionate individuals and innovators who are aligned in a common goal of delivering top-tier services to our customers. Our culture and commitment have been recognized through numerous accolades, including being named one of the Best Places to Work in 2023 in two categories (“Prosperous and Thriving” ($5MM–$50MM in gross revenue) and “Mid-Atlantic Region” (DC, DE, MD, NC, VA, WV)), and again in 2025 as a Best Places to Work honoree. In addition, True Zero earned coveted spots on the Inc. 5000 list of fastest-growing companies in America in 2022, 2023, and 2025 , a testament to our sustained growth driven by our people-first approach and unwavering dedication to excellence. Position Overview True Zero Technologies is seeking an experienced Penetration Testing Team Lead to oversee and execute advanced penetration testing and Red Team operations across federal systems and environments. This role is responsible for leading offensive security assessments, identifying exploitable vulnerabilities, evaluating security controls, and providing actionable recommendations to strengthen the organization's cybersecurity posture. The ideal candidate will possess extensive hands-on offensive security experience, strong technical leadership skills, and a deep understanding of penetration testing methodologies, adversary simulation, and federal cybersecurity standards. Job Responsibilities Key Responsibilities Penetration Testing & Red Team Leadership: Plan, coordinate, and lead comprehensive penetration testing and Red Team engagements across federal enterprise systems, networks, applications, cloud infrastructure, and APIs. Security Assessment Execution: Oversee all phases of penetration testing engagements, including scoping, reconnaissance, vulnerability identification, exploitation, post-exploitation analysis, and reporting while ensuring adherence to authorized testing parameters. Offensive Security Tools & Infrastructure: Manage, maintain, and optimize penetration testing tools, frameworks, infrastructure, and testing environments, including software patches, upgrades, inventory management, and evaluation of emerging technologies. Compliance & Testing Methodologies: Ensure testing activities align with NIST SP 800-115, MITRE ATT&CK, DHS Risk and Vulnerability Assessment (RVA) standards, and applicable federal cybersecurity policies and procedures. Vulnerability Analysis & Reporting: Develop detailed technical findings, risk assessments, executive summaries, and remediation recommendations. Collaborate with security engineering and operational teams to validate findings and prioritize corrective actions. Team Leadership & Mentorship: Provide technical direction, mentorship, and quality assurance for junior penetration testers while promoting consistent testing methodologies, knowledge sharing, and continuous skill development. Adversary Simulation & Security Improvement: Design and execute realistic attack scenarios to assess detection and response capabilities, identify security gaps, and recommend improvements to enterprise defensive controls. Job Requirements Required Qualifications Offensive Security Experience: Minimum of 12 years of progressive experience in offensive cybersecurity, penetration testing, vulnerability exploitation, Red Team operations, or related technical security disciplines, including experience leading complex security engagements. Professional Certifications: Must possess at least one of the following certifications: Offensive Security Certified Professional (OSCP), Offensive Security Certified Expert (OSCE), GIAC Exploit Researcher and Advanced Penetration Tester (GXPN), or Certified Ethical Hacker (CEH). Technical Penetration Testing Expertise: Demonstrated hands-on experience performing network, web application, API, and AWS cloud penetration testing within complex enterprise environments, including identifying, exploiting, and documenting security vulnerabilities. Federal Security Frameworks & Methodologies: Strong understanding of NIST SP 800-115, MITRE ATT&CK, DHS RVA methodologies, and security assessment processes, with the ability to apply standardized testing techniques in regulated or federal environments. Leadership, Communication & Reporting: Proven ability to lead technical testing teams, manage multiple assessment engagements, mentor junior personnel, and communicate complex security findings and actionable remediation strategies to both technical and executive stakeholders. Originally posted on Himalayas