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SkyePoint Decisions logo

Penetration Testing Team Lead

SkyePoint Decisions
Posted May 28, 2026, 1:15 AM UTC
🇺🇸United States🏠Remote📁Engineering & Development
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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 Testing Team Lead 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 is a remote position. Responsibilities: Plans, coordinates and leads red team and penetration testing engagements across FSA systems. Oversees test planning, execution, and reporting. Maintain tools (patches and upgrades), their environment and inventory used in pen testing/Red Team exercises. Ensures alignment with NIST SP 800-115, MITRE ATT&CK, and DHS RVA standards. Mentors junior testers and evaluates new testing tools. Required Qualifications: Bachelor's degree and 12+ years of experience in offensive security. At least an active Secret level clearance. At least one of these certifications: OSCP, OSCE, GXPN, CEH. Experience with network, application, AWS cloud, and API testing in complex environments. Must be a U.S Citizen. Compensation: Salary Range: $100,000-$120,000 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. CCPA Disclosure Notice Here

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