Senior Penetration Tester

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 behavior to defensive telemetry, identifying detection gaps, and recommending improvements to SIEM, EDR, and incident response processes. - Analyze logs, endpoint artifacts, and network telemetry during exercises or assessments to help validate whether adversary behaviors are detected and escalated appropriately. - Write and present clear, evidence-based reports that document findings, affected assets, exploitability, business or mission impact, and prioritized remediation recommendations. - Deliver technical and executive out-briefs to client stakeholders, including system owners, security operations teams, engineering teams, and senior leaders. - Stay current on emerging attack techniques, offensive tooling, detection approaches, and federal cybersecurity requirements, and apply that knowledge to strengthen client security posture. Required Qualifications: - Bachelor’s degree in Cybersecurity, Information Technology, Computer Science, Information Systems, or a related field; additional relevant experience may be considered in lieu of degree. - Minimum of FIVE (5) or more years of demonstrated hands-on experience in penetration testing, red team operations, adversary emulation, vulnerability assessment, application security testing, cyber operations, or related offensive security work. - An ACTIVE and MAINTAINED SECRET Federal or DoD security clearance. - Experience performing internal and external network penetration testing, including reconnaissance, enumeration, exploitation, privilege escalation, lateral movement, and documentation of attack paths. - Experience performing web application penetration testing using manual and automated techniques. - Experience assessing Active Directory environments, Windows and Linux systems, and common enterprise network services. - Experience using common penetration testing tools such as Burp Suite, Metasploit, Nmap, Nessus, Kali Linux, Wireshark, BloodHound, Impacket, Responder, Hashcat, John the Ripper, Cobalt Strike, Sliver, or similar tools. - Experience developing test plans, documenting Rules of Engagement, tracking assessment activities, and producing formal penetration test reports. - Ability to explain technical findings, attack paths, business impact, and remediation options to both technical and non-technical stakeholders. - Strong written and verbal communication skills, including the ability to develop client-ready deliverables and executive-ready summaries. - Ability to work independently, manage multiple priorities, and collaborate across multidisciplinary teams in complex federal environments. Preferred Qualifications: - An ACTIVE and MAINTAINED TOP SECRET Federal or DoD security clearance. - Experience supporting HVA cybersecurity assessments or federal enterprise penetration testing programs. - One or more relevant offensive security certifications such as OSCP, GPEN, GWAPT, GXPN, GRTP, PenTest+, CEH, GCIH, or similar certification. - Experience with adversary emulation, purple team operations, detection engineering support, or validation of SIEM and EDR detection coverage. - Experience with Cobalt Strike, Sliver, custom payload development, or command-and control simulation in approved assessment environments. - Experience with cloud security testing or assessment activities across AWS, Azure, or other cloud environments. - Experience supporting incident response, threat hunting, or post-incident analysis. - Experience creating proof-of-concept exploit examples for reports or live demonstrations in controlled, authorized environments. - Experience mentoring junior penetration testers or leading small offensive security workstreams. - Excellent oral and written communication and presentation skills. Compensation: Salary Range: TBD The SkyePoint Decisions salary range for this position is a general guideline only. It represents an estimated range for this position and is just one piece of our total compensation package. Salary at SkyePoint is determined by various factors, including but not limited to location, work schedule, the candidate’s combination of education, knowledge, skills, competencies, and experience, as well as contract-specific affordability, market data and business considerations. In addition to a competitive salary, SkyePoint offers benefits including a certification incentive program, PTO, floating federal holiday options, several insurance options including HMO and High Deductible plans with Health Savings Accounts [HSAs], Flex Spending Accounts [FSAs], Full Dental Plans, Vision, ST/LT Disability, Life Insurance, and 401k matched. What We Can Offer You: - At SkyePoint, we go B.I.G. (beginning in GRATITUDE) by recognizing all we have and giving back to our employees, families, and communities. It instills a positive mindset that permeates all we do. By beginning in gratitude, SkyePoint can continue to spread living in gratitude each day. - Great Benefits: Several insurance options including HMO and High Deductible plans with Health Savings Accounts [HSAs], Flex Spending Accounts [FSAs], Full Dental Plans, ST/LT Disability, Life Insurance, floating federal holiday options, and 401k matched - Certificate Incentive Program: To promote professional development, we recognize and reward employees who obtain new certifications aligned with business needs. - Flexible Work Environment SkyePoint Decisions is an established ISO 9001:2015 and ISO/IEC 27001:2013 certified small business and appraised at CMMI Level 3 for Services and Development. We possess a common vision of excellence and foster a collaborative team culture built upon individual performance and accountability. We invest in our people and systems to create value for our clients. It is the SkyePoint Way. We are grateful for the opportunity to work with exceptional people and give back to the communities we serve. Our employees value the flexibility at SkyePoint that allows them to balance quality work and their personal lives. SkyePoint Decisions is a participating E-Verify Employer. U.S. Citizenship is required for most positions. Equal Opportunity Employer/Veterans/Disabled. CCPA Disclosure Notice Here