Senior Penetration Tester

SkyePoint Decisions is seeking a Senior Penetration Tester / PenTest Operator to support a Department of State program focused on High Value Asset (HVA) security assessments.

Responsibilities

• Lead penetration testing across internal networks, external networks, web applications, enterprise systems, cloud-connected systems, and mission environments.
• Support HVA cybersecurity assessments by identifying and communicating exploitable vulnerabilities, validating security control effectiveness, and determining risk to critical systems and data.
• Perform network mapping, reconnaissance, vulnerability validation, exploitation, post exploitation analysis, and document attack paths in accordance with approved Rules of Engagement.
• Contribute to Rules of Engagement, test plans and objectives, scope inputs and assessment documentation, and update assessment procedures for management and stakeholder approval.
• Conduct external testing to determine what an outside attacker may access, exploit, or exfiltrate within approved scope.
• Conduct internal testing to evaluate risk from 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, including realistic threat behavior, targeted access objectives, command-and-control simulation, crafted test artifacts, and controlled social engineering when authorized.
• Execute web application testing aligned to 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 within approved engagement boundaries (e.g., Kali Linux, Burp Suite, Metasploit, Nmap, Nessus, Wireshark, BloodHound, Impacket, Responder, Hashcat, John the Ripper, Cobalt Strike, Sliver).
• 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 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 validate detection and escalation of adversary behaviors.
• Produce clear, evidence-based reports covering 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 to strengthen client security posture.

Requirements

• 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 hands-on experience in penetration testing, red team operations, adversary emulation, vulnerability assessment, application security testing, cyber operations, or related offensive security work.
• 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 with tools including 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 technical and non-technical stakeholders.
• Strong written and verbal communication skills, including client-ready deliverables and executive-ready summaries.
• Ability to work independently, manage multiple priorities, and collaborate across multidisciplinary teams in complex federal environments.

Technologies

• Kali Linux
• Burp Suite
• Metasploit
• Nmap
• Nessus
• Wireshark
• BloodHound
• Impacket
• Responder
• Hashcat
• John the Ripper
• CrackMapExec
• Cobalt Strike
• Sliver
• Active Directory
• OWASP Top 10
• SIEM
• EDR

Preferred Qualifications

• 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 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.

Benefits

• Certification incentive program
• PTO
• Floating federal holiday options
• 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
• 401k matched

Compensation

• Salary Range: TBD
• Salary is determined by location, work schedule, education, knowledge, skills, competencies, experience, contract-specific affordability, market data, and business considerations.

What We Can Offer You

• Great benefits including multiple insurance options, HSAs, FSAs, full dental, ST/LT disability, life insurance, floating federal holiday options, and 401k matched
• Certificate incentive program to reward certifications aligned with business needs
• Flexible work environment

• Location: Beltsville, MD (onsite)
• Job type: contract
• Experience: 5+ years