Red Team Operator/Penetration Tester

Company Overview

 

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.

 

Join the SkyePoint team and become part of a highly skilled, professional workforce dedicated to delivering mission-critical solutions. Our exceptional technical experts provide innovative services and solutions to federal agencies, making a meaningful impact every day. At SkyePoint, we value top talent and foster an environment where your ideas and contributions truly matter. Be part of a team that values excellence and rewards innovation—your future starts here!

 

This is a contingent position based upon customer approval and funding. 

 

Position Details and Responsibilities

SkyePoint Decisions is seeking a Red Team Operator/Penetration Tester for our customer. The Red Team Operator executes sophisticated adversary emulation exercises designed to test the customer's security controls, processes, and personnel against real-world attack scenarios. This highly technical role requires expertise across multiple offensive security disciplines to simulate the tactics, techniques, and procedures of nation-state actors and advanced threat groups targeting diplomatic infrastructure. Working under the Red Team Lead's direction, the Red Team Operator conducts objective-based attack simulations that provide realistic assessment of defensive capabilities while supporting the broader Purple Team framework for continuous security improvement. 

 

This position is onsite in Beltsville, MD.

 

Responsibilities:

 

Technical Offensive Operations: 

• Execute multi-phase attack simulations following MITRE ATT&CK framework methodology 
• Perform comprehensive penetration testing across network infrastructure, web applications, and endpoints 
• Conduct privilege escalation, lateral movement, and persistence activities within approved scope 
• Emulate specific threat actor TTPs based on intelligence provided by CTI Cell 
• Maintain detailed logs of all actions taken during engagements for post-exercise analysis 

Specialized Attack Techniques: 

• Develop and deploy custom exploits and tools for unique infrastructure 
• Conduct wireless network assessments and attacks against  facilities 
• Perform physical security assessments including badge cloning, lock picking, and facility infiltration 
• Execute advanced evasion techniques to test security tool effectiveness 
• Research and implement zero-day and emerging attack methodologies 

Purple Team Collaboration: 

• Participate in collaborative Purple Team debriefs with SOC Blue Team analysts 
• Provide technical expertise on attack techniques and detection opportunities 
• Support development of new detection rules based on engagement findings 
• Assist in tuning security tools to improve detection accuracy and reduce false positives 
• Contribute to SOAR playbook development for automated response to identified attack techniques 

Documentation & Knowledge Sharing: 

• Maintain comprehensive technical documentation of exploitation techniques and tools 
• Contribute to Red Team playbooks, procedures, and methodology documentation 
• Share threat intelligence and attack technique research with broader CIC team 
• Support training and mentoring of junior team members 
• Participate in knowledge sharing sessions with SOC and other security teams 

 

Qualifications

Required Qualifications:

• High School diploma with 6 years of penetration testing and red teaming experience OR Bachelor's degree with 4 years of experience OR 2 years with a Master's degree
• Hands-on experience with penetration testing tools and methodologies 
• Understanding of network protocols, system architectures, and security controls 
• Knowledge of exploit development, privilege escalation, and post-exploitation techniques 
• Familiarity with Windows, Linux, and network infrastructure security assessment 
• Ability to work within strict Rules of Engagement and maintain operational security 
• Must be a U.S. citizen
• Must have a current, active Secret clearance with the ability to obtain Top Secret 

Preferred Qualifications:

• Offensive security certifications (OSCP, GPEN, CEH, or equivalent) 
• Experience with custom tool development and exploit modification 
• Knowledge of nation-state threat actor TTPs and advanced persistent threats 
• Understanding of social engineering principles and techniques 
• Federal government or cleared contractor experience preferred 

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

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.

 

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.

Please be aware of recruiting scams and people claiming to be from SkyePoint Decisions. For more information, please see the Welcome Page of our Careers site.

Skyepoint Decisions is a participating E-Verify Employer. 

U.S. Citizenship is required for most positions.

Equal Opportunity Employer/Veterans/Disabled.

Client-provided location(s): Greenbelt, MD

Job ID: 35192998

Employment Type: OTHER

Posted: 2025-09-11T19:18:00