Lead Red Team Penetration Tester

Job Summary

Leading a team of cybersecurity professionals, the full-time Lead Red Team Penetration Tester will execute comprehensive Red Team simulations, develop Command and Control infrastructure, and leverage AI tooling to enhance offensive security efforts in a hybrid onsite environment based in Chicago, IL or Dallas, TX.

Key responsibilities

• Execute Red Team simulations, including network and application penetration testing, cloud security, and social engineering
• Develop and deploy Command and Control infrastructure using evasion techniques to test Cyber Defense capabilities
• Conduct threat modeling and security risk assessments, providing actionable remediation recommendations to stakeholders

Required qualifications

• 7+ years of experience in penetration testing
• Strong proficiency in network, web application, cloud, and mobile device security testing
• Experience with AI/LLM tooling for offensive research and exploit development
• Demonstrated knowledge of EDR detection capabilities and defense evasion techniques
• Strong experience with common penetration testing tools and custom scripting (Python, PowerShell, Bash)