Senior Penetration Tester

Role Overview

The Senior Penetration Tester will serve as the Red Team technical lead for Offensive Security. They will be responsible for Red Team Engagements, Application Penetration Tests, and Purple Team Engagement activities. This role requires deep technical expertise, strategic vision, and leadership in guiding the team toward proactive risk management.

The Senior Penetration Tester will lead penetration testing of network and application infrastructures, using both automated and manual testing techniques. They will identify vulnerabilities, evaluate potential risks, and document findings thoroughly. They will also lead and execute end-to-end adversarial Red Team engagements, including scoping and rules-of-engagement development, threat-informed attack planning, and deployment of secure command-and-control infrastructure.

The ideal candidate will have deep knowledge of Active Directory and Microsoft Entra , authentication, authorization, privilege escalation paths, security controls, and cross-environment attack paths. They will also have expertise in designing, building, and maintaining secure cloud-based command-and-control infrastructure, and experience in developing and safely operating custom offensive capabilities for authorized adversary emulation.

• Bachelor's degree in Information Security, Computer Science, or a related field
• 6-8+ years of experience in penetration testing, red teaming, or a related field
• Deep knowledge of Active Directory and Microsoft Entra
• Fluency in designing, building, and maintaining secure cloud-based command-and-control infrastructure
• Expert-level experience developing and safely operating custom offensive capabilities
• Advanced scripting and programming skills in languages like Python, C, or Power Shell
• Proficiency in using ITSM tools like Service Now and Jira
• Expertise in a wide range of penetration testing tools and custom exploitation techniques
• Extensive knowledge of compliance requirements, ethical best practices, and regulations impacting penetration testing

• Competitive salary
• Equity
• Health insurance
• Paid time off
• Retirement plan
• Learning budget
• Parental leave
• Wellness program
• Visa/relocation assistance
• Remote flexibility
• Stipends
• Bonus/commission
• Paid holidays