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Lead Penetration Tester

Labelbox

San Francisco Remote permanent

Posted: December 9, 2025

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Job Description

Role Overview
The Lead Penetration Tester evaluates system security through offensive testing, vulnerability identification, and exploitation workflows. This role focuses on replicating adversary behavior, documenting findings clearly, and validating mitigation strategies.
What You’ll Do
- Conduct penetration tests across applications, networks, and cloud systems
- Identify vulnerabilities and validate exploitability
- Perform post-exploitation analysis and summarize impact
- Document findings with clear severity assessments and remediation guidance
- Validate defensive assumptions and detection logic
- Support recurring red-team and purple-team engagements
What You Bring
Must-Have:
- Strong background in offensive security or pentesting
- Experience with common exploitation frameworks, tools, and methodologies
- Ability to write clear, structured technical reports
Nice-to-Have:
- Certifications (OSCP, OSWE, OSEP, etc.) welcome but not required

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