Penetration Tester

Job Description

Job Description

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 contract win.

SkyePoint Decisions is seeking a Penetration Tester to join our team supporting the Department of Education's (DoED) Federal Student Aid (FSA) Cybersecurity and Privacy Support Services (CPSS) in Washington, DC. This person will support authorized red team, penetration testing, and adversarial security assessment activities across FSA systems and applications. Working under the guidance of senior team members, the tester helps identify exploitable vulnerabilities, validate security controls, document attack paths, and provide actionable findings that strengthen FSA's cybersecurity posture.

This is a remote position.

Responsibilities:

• Support authorized red team and penetration testing engagements across FSA systems, networks, applications, APIs, and cloud environments.
• Conduct vulnerability validation and exploitation activities under established rules of engagement.
• Assist with reconnaissance, enumeration, attack-path analysis, exploitation, and post-exploitation activities.
• Perform web application, network, API, and infrastructure security testing.
• Support testing scenarios based on real-world adversary tactics, techniques, and procedures (TTPs).
• Apply the MITRE ATT&CK framework to categorize and document adversary techniques.
• Assist with testing security controls and identifying weaknesses that could lead to unauthorized access or privilege escalation.
• Document testing procedures, evidence, vulnerabilities, attack paths, and results.
• Develop clear technical findings describing vulnerabilities, risk, evidence, and recommended remediation.
• Retest identified vulnerabilities following remediation.
• Maintain knowledge of emerging vulnerabilities, exploits, attack techniques, and defensive technologies.
• Follow FSA rules of engagement, security requirements, and testing procedures.

Required Qualifications:

• Bachelor's degree in Cybersecurity, Computer Science, Information Technology, Information Systems, Engineering, or related field, or equivalent relevant experience.
• 5+ years' experience in the subject area.
• Professional certification such as CEH, CompTIA PenTest+, or OSCP.
• Demonstrated experience conducting penetration testing, Red Team assessments, or offensive-security testing.
• Hands-on experience testing enterprise networks, applications, APIs, and/or cloud environments.
• Knowledge of common exploitation techniques and attack paths across Windows and Linux environments.
• Experience translating technical testing results into well-supported findings and remediation recommendations.
• Working knowledge of MITRE ATT&CK and penetration-testing methodologies.
• U.S. Citizenship required.
• Must be able to obtain High Risk Public Trust Security Clearance. 

Preferred Qualifications:

• Active Secret or Top Secret security clearance.
• Experience with tools such as Burp Suite, Nmap, Metasploit, Kali Linux, Wireshark, Nessus/Tenable, BloodHound, or comparable offensive security tools .
• Familiarity with Windows and Linux environments.
• Exposure to AWS cloud security testing.
• Familiarity with NIST SP 800-115.
• Scripting experience using Python, PowerShell, Bash, or similar technologies.

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.

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