Senior Penetration Tester - HVA & Red Team Lead

SkyePoint Decisions; Laurel (MD); On-site; USD 140,000 - 200,000; Full time

Benefits offered by this job

Certification incentive program

Paid time off (PTO)

Floating federal holiday options

Health insurance options including HMO

Job summary

SkyePoint Decisions is seeking a Senior Pen Tester/Pentest Operator to support a DoS program and lead pentesting engagements on HVA systems. This onsite, Beltsville, MD role requires five+ years of offensive security experience and active Secret clearance.

You will conduct internal and external testing, web app assessments, AD reviews, and adversary emulation, delivering executive-ready reports and risk-based recommendations.

Qualifications

• Bachelor’s degree in Cybersecurity, IT, CS, IS, or related field; additional relevant experience may be considered in lieu of degree.
• 5+ 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.
• An ACTIVE and MAINTAINED SECRET Federal or DoD security clearance.
• Experience performing internal and external network penetration testing, including recon, 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.

Responsibilities

• Perform penetration testing across internal and external networks, web applications, enterprise systems, cloud-connected systems, and mission environments.
• Support HVA cybersecurity assessments by identifying vulnerabilities, validating security controls, and determining risk to critical systems and data.
• Conduct network mapping, reconnaissance, vulnerability validation, exploitation, and post-exploitation analysis with approved Rules of Engagement.
• Draft and input into Rules of Engagement, test plans, scope input, and assessment procedures for approvals.
• Conduct external testing to evaluate what an outside attacker could access within the approved scope.
• Conduct internal testing to evaluate risk from users or systems with varying access levels, including privilege escalation and lateral movement.
• Support red team and adversary emulation activities; simulate threat behavior and conduct C2 simulations when authorized.
• Perform web application testing for OWASP Top 10 risks and common vulnerability classes.
• Utilize offensive security tools (e.g., Kali, Burp Suite, Metasploit, Nmap, Nessus, Cobalt Strike, Sliver) within approved engagements.
• Drive vulnerability analysis with manual techniques, automated tools, and custom scripts.
• Support purple team and detection validation by mapping attacker behavior to telemetry and recommending improvements to SIEM/EDR.
• Analyze logs and network telemetry to validate detections and escalation of adversary behaviors.
• Write and present evidence-based reports detailing findings, impact, and remediation recommendations.
• Deliver technical and executive out-briefs to client stakeholders.
• Stay current on emerging attack techniques and federal cybersecurity requirements to strengthen client security posture.

Skills

Penetration testing

Red team operations

Adversary emulation

Vulnerability assessment

Web application testing

Active Directory assessment

Communication skills

Education

Bachelor’s degree in Cybersecurity, IT, CS, IS

Tools

Burp Suite

Metasploit

Nmap

Nessus

Kali Linux

Wireshark

BloodHound

Impacket

Responder

Hashcat

John the Ripper

Cobalt Strike

Sliver

Job description

SkyePoint Decisions is seeking a Senior Pen Tester/Pentest Operator to support a DoS program and lead pentesting engagements on HVA systems. This onsite, Beltsville, MD role requires five+ years of offensive security experience and active Secret clearance.

You will conduct internal and external testing, web app assessments, AD reviews, and adversary emulation, delivering executive-ready reports and risk-based recommendations.