Lead Penetration Tester (Remote)

Primary responsibilities:
Direct testing methodology and safety controls; conduct assumed-breach testing from up to three network locations; assess privilege escalation, lateral movement, and segmentation; lead authenticated vulnerability scanning and wireless configuration review; assess Microsoft 365, Entra ID, and Azure configurations; evaluate MFA and timeout settings; validate findings and recommend remediation.

Reporting responsibilities:
Own technical accuracy, risk prioritization, NIST SP 800-53 Rev. 5/CSF 2.0 mappings, and remediation recommendations; prepare the internal/configuration report and contribute to the final report and briefing.

Required technical knowledge:
AD and Entra ID attack paths; network protocols and segmentation; vulnerability assessment; Wi-Fi controller configuration; Microsoft 365/Azure security; conditional access, MFA, PIM, Defender, and logging; CIS benchmarks and NIST frameworks.

Recommended experience:
5+ years in penetration testing/security assessment, with demonstrated AD, Entra ID, and Microsoft 365 experience and hands-on Azure configuration review capability.

Recommended certifications:
OSCP, OSEP, GPEN, or equivalent; relevant Microsoft security credentials such as SC-100 or SC-300 desirable.

Key deliverables:
Validated internal/cloud findings; vulnerability and configuration assessment results; authentication/timeout recommendations; internal technical/executive report; prioritized remediation roadmap.