Lead Penetration Tester

This is a fully remote position, open to applicants in United States.

📋 Description

• Establish and oversee the team's testing methodology, playbooks, and quality standards for evidence.

• Lead the most intricate penetration tests (web applications, APIs, cloud environments, Active Directory/Entra ID, AI/LLM applications) with complete autonomy.

• Operate and enhance the team's agentic AI offensive tools.

• Conduct adversarial evaluations of AI/LLM applications, including prompt injection (both direct and indirect), jailbreaks, and adversarial techniques.

• Identify deficiencies in testing coverage and organizational controls, and propose innovative assessment strategies for emerging threats.

• Convert technical findings into business risks for both technical and executive stakeholders.

• Assist with PCI-DSS and other compliance-related testing requirements.

⛳️ Requirements

• Over 7 years of experience in penetration testing, ethical hacking, or offensive security operations, including approximately 2 years of leading complex testing programs or technical workstreams.

• Comprehensive understanding of the modern attack surface, including web applications, APIs, cloud platforms (AWS/Azure/GCP), and Active Directory/Entra ID, with a proven history of independently leading the most complex assessments.

• Practical experience in testing AI/LLM-driven applications (prompt injection, jailbreaks, adversarial techniques) or a demonstrated capability to secure emerging AI systems.

• Experience with or a willingness to utilize agentic AI tools.

• Proficient in translating intricate technical findings into clear business risks for executive-level stakeholders.

• Certifications are advantageous, such as OSCP, OSWE, OSCE3, CPTS, CWEE, or other equivalent advanced credentials.

🏝️ Benefits

• Medical, dental, and vision coverage.

• 401(k) retirement savings plan.

• Paid time off, including company holidays, personal holidays, and paid parental and caregiver leave.

• Short-term and long-term disability coverage.

• Life insurance and a variety of additional opportunities.