SkyePoint Decisions, Inc. Logo

SkyePoint Decisions, Inc.

Penetration Testing Team Lead

Posted 4 Days Ago
Be an Early Applicant
Remote
Hiring Remotely in USA
130K-160K Annually
Expert/Leader
Remote
Hiring Remotely in USA
130K-160K Annually
Expert/Leader
Leads red team and penetration testing engagements across Federal Student Aid systems, overseeing planning, execution, reporting, tool maintenance, and testing environments. Ensures compliance with NIST SP 800-115, MITRE ATT&CK, and DHS RVA standards. Mentors junior testers, evaluates testing tools, and supports network, application, AWS cloud, and API testing in complex environments.
The summary above was generated by AI

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: $130,000-$160,000

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 

Similar Jobs

30 Minutes Ago
Easy Apply
Remote or Hybrid
Easy Apply
140K-175K Annually
Senior level
140K-175K Annually
Senior level
Cloud • Information Technology • Security • Software • Cybersecurity
Build and operate multi-cloud platform automation across AWS, GCP, and Azure. Develop Terraform modules, CI/CD components, Python automation, infrastructure provisioning, lifecycle management, drift detection, dependency scanning, and remediation workflows. Integrate AI-assisted and agentic tooling into operational processes while establishing security guardrails. Collaborate with Security, IAM, Network, and FinOps teams on identity, secrets management, least-privilege controls, and cloud governance.
Top Skills: Amazon BedrockAmazon SagemakerArgocdAWSAws Control TowerAws OrganizationsAzureBashDependabotGCPGemini EnterpriseGitlab Ci/CdGitopsKubeflowKubernetesMlflowPythonRenovateResource Control Policies (Rcps)Service Control Policies (Scps)TerraformVertex Ai
39 Minutes Ago
Remote
USA
175K-200K Annually
Senior level
175K-200K Annually
Senior level
Artificial Intelligence • Cloud • Software • Infrastructure as a Service (IaaS)
Design and maintain automated testing frameworks for cloud-scale distributed systems. Build performance, load, stress, integration, API, end-to-end, chaos, security, and infrastructure tests. Integrate continuous testing into CI/CD pipelines, analyze observability data, validate Kubernetes and microservices environments, and collaborate with Engineering and SRE teams to improve reliability. The role also participates in on-call rotations and helps establish QA strategy and standards across GPU infrastructure, serverless endpoints, storage, billing, and event-driven systems.
Top Skills: AWSAzureChaos MeshCi/CdDatadogGCPGoGrafanaGraphQLGremlinInfrastructure As Code (Iac)JmeterK6KafkaKubernetesLitmuschaosLocustOpentelemetryPrometheusPythonRabbitMQRedisTypescript
39 Minutes Ago
Remote
USA
42K-52K Annually
Junior
42K-52K Annually
Junior
Artificial Intelligence • Cloud • Software • Infrastructure as a Service (IaaS)
Provide first-line technical and non-technical support through email, phone, chat, and video. Manage and resolve L1 tickets, troubleshoot system behavior and configurations, document solutions, explain technical issues clearly, and escalate complex problems to L2 or engineering teams. The role requires shell scripting, Python, SQL, REST APIs, GraphQL, and customer support experience, with possible weekend and allocated-shift availability.
Top Skills: Crm/Ticketing ToolsDockerGoogle MeetGraphQLLinuxObservability ToolsPythonRest ApisShell ScriptingSQLSshTerminal CommandsZendeskZoom

What you need to know about the Charlotte Tech Scene

Ranked among the hottest tech cities in 2024 by CompTIA, Charlotte is quickly cementing its place as a major U.S. tech hub. Home to more than 90,000 tech workers, the city’s ecosystem is primed for continued growth, fueled by billions in annual funding from heavyweights like Microsoft and RevTech Labs, which has created thousands of fintech jobs and made the city a go-to for tech pros looking for their next big opportunity.

Key Facts About Charlotte Tech

  • Number of Tech Workers: 90,859; 6.5% of overall workforce (2024 CompTIA survey)
  • Major Tech Employers: Lowe’s, Bank of America, TIAA, Microsoft, Honeywell
  • Key Industries: Fintech, artificial intelligence, cybersecurity, cloud computing, e-commerce
  • Funding Landscape: $3.1 billion in venture capital funding in 2024 (CED)
  • Notable Investors: Microsoft, Google, Falfurrias Management Partners, RevTech Labs Foundation
  • Research Centers and Universities: University of North Carolina at Charlotte, Northeastern University, North Carolina Research Campus

Sign up now Access later

Create Free Account

Please log in or sign up to report this job.

Create Free Account