Penetration Tester Team Lead

Leidos•Ashburn, VA

1d•Hybrid

About The Position

The U.S. Department of Homeland Security (DHS), Customs and Border Protection (CBP) Security Operations Center (SOC) is a U.S. Government program responsible for preventing, identifying, containing, and eradicating cyber threats to CBP networks. This involves monitoring, intrusion detection, and protective security services for CBP information systems. The CBP SOC is responsible for the overall security of CBP Enterprise-wide information systems and investigates and reports any suspected and confirmed security violations. This role is for a highly skilled and experienced Penetration Testing Team Lead to join the team supporting CBP. As the leader of this highly technical Penetration Testing Team supporting CBP, you will manage the day-to-day operations of the team, coordinate team efforts, lead by example, and conduct comprehensive security assessments of CBP FISMA systems to identify vulnerabilities and provide actionable recommendations to enhance the security posture of CBP's critical systems and networks. This role requires a deep understanding of offensive cybersecurity techniques, strong analytical capabilities, detailed report writing skills, and the ability to lead a team of skilled penetration testers.

Requirements

T5: Minimum of a Bachelor's and twelve (12) years of professional experience in penetration testing, red teaming, or offensive security experience, with a minimum of four (4) years of experience directly leading a Penetration Testing Team. Additional years of experience can be accepted in lieu of degree.
T6: Minimum of a Bachelor's and fifteen (15) years of professional experience in penetration testing, red teaming, or offensive security experience, with a minimum of four (4) years of experience directly leading a Penetration Testing Team. Additional years of experience can be accepted in lieu of degree.
Must have an active TS/SCI.
Demonstrated expertise in multi-layer exploitation, with the ability to identify, chain, and execute attacks across network infrastructure, operating systems (Windows/Linux), web applications, APIs, and cloud platforms; proven capability to move from initial access through full domain or environment compromise.
Proficiency with offensive security tooling and frameworks, including Cobalt Strike, Mythic, Sliver, Metasploit, Burp Suite Pro, BloodHound, Nmap, and similar tools with specific experience modifying and extending tools to evade controls.
Strong understanding of enterprise networking and protocols with the ability to enumerate, pivot, and exploit across complex, segmented network environments.
Hands-on experience with cloud and modern infrastructure security, familiarity with IAM abuse, privilege escalation, token theft, insecure configurations, and lateral movement within cloud-native services and hybrid environments.
In-depth knowledge of operating systems and security controls, including Windows/Linux internals, endpoint protections, logging mechanisms, and common defensive controls with a demonstrated ability to bypass or evade these protections during engagements.
Proven leadership and team management experience, including leading technical teams through complex engagements, mentoring junior and mid-level testers, conducting quality assurance on deliverables, and managing multiple concurrent assessments without sacrificing technical depth.
Strong communication skills, with the ability to clearly articulate complex technical findings, attack paths, and risk implications to both technical stakeholders and executive leadership through written reports and verbal briefings.
Must be a US Citizen.
Must be able to travel to the Ashburn VA office location up to 5 days per week.
At least one certification from the below list: OSCP, OSCE, OSWP, OSEE, GPEN, GISF, GXPN, GWAPT.
All CBP SOC employees are required to favorably pass a 5-year Background Investigation (BI).
The candidate must currently possess a Top Secret Clearance with the ability to obtain a Top Secret/SCI Clearance.

Nice To Haves

Experience conducting full-scope red team operations and adversary emulation campaigns.
Familiarity with MITRE ATT&CK framework and threat-informed testing methodologies.
Knowledge of container and Kubernetes security testing.
Prior experience supporting federal or regulated environments.

Responsibilities

Managing the team of Penetration Testers and penetration tests.
Scheduling and coordinating pentests.
Leading and executing advanced penetration testing, purple team engagements, and red team engagements across complex enterprise environments, including internal/external network infrastructure, Active Directory domains, APIs, hybrid cloud architectures, and on-prem systems.
Developing, coordinating, and enforcing Rules of Engagement (ROE) for penetration tests.
Leading stakeholder planning sessions to define scope and constraints of upcoming pentests.
Delivering clear, actionable outbriefings on findings, impact, and remediation to technical and executive audiences.
Developing, modifying, and deploying custom exploits, payloads, and tooling, including scripting in Python, Ruby, PowerShell, Bash, and other languages to bypass security controls, automate attack paths, and enhance tradecraft.
Conducting penetration testing activities aligned with CBP and industry best practices.
Providing real-time technical mentorship during engagements, including paired testing, whiteboarding attack paths, and guiding junior testers through exploitation chains and industry best practices.
Maintaining accountability for engagement quality and technical depth, reviewing findings, validating exploit paths, and ensuring reports accurately reflect risk, attack feasibility, potential impacts, and recommended remediations.
Conducting technical oversight and quality assurance across all engagements, reviewing testing approaches, validating exploit chains, and ensuring consistency in methodology, depth, and reporting standards across the team and engagements.
Leading purple team collaboration efforts from the pentest perspective, working directly with the CBP SOC, detection engineering team, and Cyber Threat Hunt team to execute actions designed to validate detections, tune SIEM use cases, and improve defensive posture.
Mentoring and developing team members through structured and ad hoc technical coaching, raising the overall capability of the team while maintaining individual technical skillsets and experience.
Utilizing the MITRE ATT&CK framework to understand and emulate TTPs of adversaries, threat actors, APTs, and threats targeting CBP and map operations to ATT&CK techniques and sub-techniques.
Creating detailed reports listing vulnerabilities identified during pentests, with actionable mitigation recommendations following completion of pentest engagements.
Staying actively engaged in emerging vulnerability research, exploit techniques, and adversary methodologies, rapidly integrating new capabilities into both personal and team operations.
Fostering a high-performance, technically rigorous team culture, driving continuous learning through labs, internal exercises, and knowledge-sharing sessions while nurturing cutting-edge offensive skillsets.