Senior Penetration Tester

The role

The Senior Pen Tester will lead and support penetration testing engagements on High Value Asset systems and enterprise security assessments. This role involves internal and external network testing, web application testing, adversary emulation, and reporting findings to stakeholders.

What you will do

• Performing penetration testing across internal and external networks, web applications, and cloud-connected systems.
• Supporting High Value Asset cybersecurity assessments.
• Conducting network mapping, reconnaissance, exploitation, and documentation of attack paths.
• Drafting Rules of Engagement, test plans, and assessment procedures.
• Conducting external and internal testing to evaluate attacker access and risk.
• Supporting red team and adversary emulation activities.
• Conducting web application testing for OWASP Top 10 risks.
• Using offensive security tools and frameworks.
• Driving vulnerability analysis using manual techniques and automated tools.
• Supporting purple team and detection validation activities.

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 op
• An ACTIVE and MAINTAINED SECRET Federal or DoD security clearance.
• Experience performing internal and external network penetration testing.
• 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,
• 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.
• Ability to work independently, manage multiple priorities, and collaborate across multidisciplinary teams in complex federal environments.

Nice to have

• 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.
• 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.
• 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
• 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

Before you apply

• This is a contingent position based upon customer approval.
• U.S. Citizenship is required for most positions.

About the company

SkyePoint Decisions is a Cybersecurity Architecture and Engineering, Critical Infrastructure and Operations, and Applications Development and Maintenance IT service provider. They provide solutions addressing complex challenges faced by federal government clients.