To enhance cybersecurity measures, the full-time Lead Penetration Tester will execute Red Team simulations, develop Command and Control infrastructure, and leverage AI tools while working remotely or onsite in Chicago, IL, or Dallas, TX. Key responsibilities: Execute comprehensive Red Team simulations including penetration testing across various environments Develop and deploy Command and Control (C2) infrastructure to enhance Cyber Defense detection capabilities Conduct threat modeling and security risk assessments, providing actionable remediation recommendations to stakeholders Required qualifications: 7+ years of experience in penetration testing and information assurance or cybersecurity environments Security-related certifications (OSCP, OSWE, OSCE, GPEN, etc.) are highly desired Strong proficiency in network, web application, cloud, and mobile device security testing Experience with custom scripting (Python, Powershell, Bash) and process automation Broad expertise in various penetration testing techniques and tools