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Labelbox

Lead Penetration Tester

Labelbox, San Francisco, California, United States, 94199

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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

$40 - $80 an hour

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