SkyePoint Decisions is a leading Cybersecurity Architecture and Engineering, Critical Infrastructure and Operations, and Applications Development and Maintenance IT service provider headquartered in Dulles, Virginia with operations across the U.S. We provide innovative enterprise-wide solutions as well as targeted services addressing the complex challenges faced by our federal government clients. Our focus is on enabling our clients to deliver their mission most efficiently and effectively – anytime, anywhere, securely. We combine technical expertise, mission awareness, and an empowered workforce to produce meaningful results.
This is a contingent position based upon customer approval.
SkyePoint Decisions is seeking a Senior Pen Tester/Pentest Operator to support a Department of State program. The Pentest Operator will support and lead pen testing engagements on High Value Asset (HVA) systems and enterprise security assessments, helping clients understand real-world attack paths, validate defensive controls, and prioritize remediation activities based on mission risk. The role includes internal and external network testing, web application testing, Active Directory assessment, adversary emulation, red team and purple team activities, vulnerability validation and reporting, and developing and presenting executive-level out-briefs. The ideal candidate brings hands-on offensive security experience, strong client-facing communication skills, and the ability to translate technical findings into risk-based recommendations for system owners, security teams, and senior leaders. The candidate should be comfortable working in commercial and federal environments and collaborating with technical operators, analysts, engineers, and government stakeholders as required.
This position is located in Beltsville, MD and will be onsite 5 days a week. No hybrid/telework allowed.
Responsibilities:
Performing penetration testing activities across internal networks, external networks, web applications, enterprise systems, cloud-connected systems, and mission environments.
Supporting High Value Asset (HVA) cybersecurity assessments by identifying and communicating exploitable vulnerabilities, validating security control effectiveness, and determining risk to critical systems and data.
Conducting network mapping, reconnaissance, vulnerability validation, exploitation, post exploitation analysis, and documentation of attack paths within approved Rules of Engagement.
Draft and/or provide input into Rules of Engagement, test plans and objectives, scope input and documentation, and revising and updating assessment procedures required to obtain management and stakeholder approval.
Conduct external testing to evaluate what an outside attacker may be able to access, exploit, or exfiltrate within the approved scope.
Conduct internal testing to evaluate risk posed by users or systems with different access levels, including privilege escalation, lateral movement, persistence, and Active Directory attack paths.
Support red team and adversary emulation activities that simulate realistic threat behavior, including targeted access objectives, command-and-control simulation, crafted test artifacts, and controlled social engineering when authorized.
Conduct web application testing for common vulnerability classes, including broken access control, authentication and authorization weaknesses, injection flaws, cross-site scripting, insecure configuration, and other OWASP Top 10 risks.
Use offensive security tools and frameworks such as Kali Linux, Burp Suite, Metasploit, Nmap, Nessus, Wireshark, BloodHound, Impacket, Responder, Hashcat, John the Ripper, CrackMapExec, Cobalt Strike, Sliver, and similar tools within approved engagement boundaries.
Drive vulnerability analysis and validation using manual techniques, automated tools, and custom scripts or proof-of-concept code where appropriate.
Support purple team and detection validation activities by mapping attacker…