Penetration Tester

GuidePoint Security provides trusted cybersecurity expertise, solutions and services that help organizations make better decisions and minimize risk. By taking a three-tiered, holistic approach for evaluating security posture and ecosystems, GuidePoint enables some of the nation's top organizations, such as Fortune 500 companies and U.S. government agencies, to identify threats, optimize resources and integrate best-fit solutions that mitigate risk.

About GuidePoint Security

GuidePoint Security is a leading cybersecurity solutions and services firm enabling federal government organizations to make smarter security decisions that minimize risk. With more than 800 vetted technology vendor partnerships and deep practitioner expertise across every major cybersecurity domain, GuidePoint serves more than half of the U.S. Government's cabinet-level agencies across Civilian, DoD, and Intelligence Community segments, as well as Federal System Integrators and major defense prime contractors. We are growing our federal engineering team and looking for technically exceptional engineers who thrive at the intersection of federal mission and cybersecurity technology.

The Pen Tester role will be responsible for performing comprehensive Risk and Vulnerability Analysis (RVA) assessments, functioning as penetration and purple team assessments. The role will be in response to performing penetration testing engagements using major frameworks like OWASP and NIST, against a range of technologies such as web applications, servers, operating systems, cloud services, AI workflows, and network devices.

Onsite requirement (Candidates must reside within the Washington, D.C. metropolitan area) - This role supports a federal customer in Alexandria, VA.

What You'll Get To Do:

• Perform analysis of submitted findings and vulnerabilities and provide a written report covering risk, likelihood of exploitation, and recommendations for remediation.
• Handle vetting of multiple vulnerabilities simultaneously, demonstrating efficiency and organization, to ensure all vulnerabilities are addressed in a timely manner.
• Swiftly confirm or deny the legitimacy of submitted vulnerabilities, ensuring rapid response times while maintaining the integrity of the vulnerability disclosure process.
• Provide insightful guidance and support to system owners regarding the agency's patching processes and timelines, helping them navigate and comply with these procedures.
• Ensure all findings and analyses are reported in a timely and efficient manner, maintaining a consistent flow of information and updates.
• Provide comprehensive start-to-finish RVA assessments, encompassing initial customer outreach, meticulous planning, thorough execution, and detailed reporting.
• Utilize expertise in assessing both current and emerging technology platforms and architectures, ensuring assessments are relevant and comprehensive.
• Conduct expert-level assessments using major frameworks like OWASP and NIST, covering a range of technologies such as web applications, servers, operating systems, cloud services, AI workflows, and network devices.
• Perform in-depth insider threat analysis, integrating it as a crucial part of the assessment process to identify potential internal security risks.
• Research and simulate emerging zero-day threats, creating mock-up scenarios to demonstrate the feasibility of exploitation and assess system vulnerabilities.
• Develop custom scripts for specialized exploitation scenarios, tailoring attack strategies to effectively test specific system vulnerabilities.
• Demonstrate hands-on experience with popular penetration testing software such as Meterpreter Pro, Nessus, and Cobalt Strike, using these tools to conduct thorough assessments.
• Analyze vulnerability scans and perform follow-on testing of systems to verify exploitability, ensuring comprehensive identification of security weaknesses.
• Conduct trend analysis across assessments to identify common vulnerabilities among disparate systems, aiding in the development of targeted security strategies.
• Develop SOPs and best practices for penetration testing and vulnerability assessment, documenting these in corporate knowledge repositories for enterprise-wide distribution.
• Communicate technical issues effectively to non-technical management, translating complex cybersecurity concepts into understandable terms.
• Work within corporate issue and knowledge tracking systems, providing continuous status updates on projects and ensuring seamless integration with existing workflows.
• Test and document new tools, techniques, tactics, and scripts for usability security acceptance testing.

Requirements

• Ability to obtain and maintain a Public Trust clearance.
• Bachelor's degree in computer science, Cybersecurity, Information Systems, Engineering, or a related technical field, or equivalent experience.
• 5 years of experience leading penetrating testing
• OSCP OR CEH Certification
• Experience developing custom scripts for certain exploit scenarios and tailoring attack scenarios to test specific system vulnerabilities.
• Embraces emerging technologies, including AI tools, to work smarter, solve problems, and drive better business outcomes

Preferred Qualifications

• Experience performing red-team or penetration testing engagements in a federal environment.
• Penetration testing on HVA assets in a federal environment.
• Hands-on experience with Meterpreter Pro, Nessus, and Cobalt Strike.
• US Government Clearance preferred

"Applicants selected will be subject to a security investigation and must meet eligibility requirements for access to classified information."

We use Greenhouse Software as our applicant tracking system and Zoom Scheduler for HR screen request scheduling. At times, your email may block our communication with you. Please be sure to check your SPAM folder so that you don't miss updates on your application.

Why GuidePoint? GuidePoint Security is a rapidly growing, profitable, privately-held value added reseller that focuses exclusively on Information Security. Since its inception in 2011, GuidePoint has grown to over 1,300 employees, established strategic partnerships with leading security vendors, and serves as a trusted advisor to more than 6,200 customers.

Firmly-defined core values drive all aspects of the business, which have been paramount to the company's success and establishment of an enjoyable workplace atmosphere. At GuidePoint, your colleagues are knowledgeable, skilled, and experienced and will seek to collaborate and provide mentorship and guidance at every opportunity.


This is a unique and rare opportunity to grow your career along with one of the fastest growing companies in the nation.

Some added perks....

• Remote workforce primarily (U.S. based only, some travel may be required for certain positions, working on-site may be required for Federal positions)
• Group Medical Insurance options: Zero Deductible PPO Plan (GuidePoint pays 90% of the premium for employees and 70% for family plans (spouse/children/family) or High Deductible Health Plan with HSA (GuidePoint pays 100% of the employees premiums and 75% for family plans (spouse/children/family). If you choose the High Deductible / HSA plan, GPS will contribute in 4 equal quarterly installments: ($850 per EE annually / $1750 per family annually (includes spouse/children/family options)
• Group Dental Insurance: GuidePoint pays 100% of the premium for employees and 75% of family plans
• 12 corporate holidays and a Flexible Time Off (FTO) program
• Healthy mobile phone and home internet allowance
• Eligibility for retirement plan after 2 months at open enrollment
• Pet Benefit Option