Senior Penetration Tester: Red Team & Cloud Security

Jobtailor; Seattle (WA); On-site; USD 140,000 - 210,000; Full time

Job summary

Jobtailor is seeking a senior security professional to lead penetration testing engagements across enterprise networks, web applications, and APIs in Seattle. You will run internal and external assessments, conduct Red Team operations, and simulate adversaries aligned to MITRE ATT&CK frameworks.

You will test Active Directory, Entra ID, Azure, and Microsoft 365 environments, validate VPN and SSO/MFA controls, and produce clear reports with prioritized remediation for clients.

Qualifications

• Hands-on penetration testing across network, web, and API targets.
• Experience with enterprise internal and external assessments.
• Strong ability to present findings to technical and non-technical stakeholders.
• Active offensive security certifications preferred.

Responsibilities

• Conduct enterprise internal and external penetration tests against network, web application, and API targets
• Execute Red Team and adversary simulation engagements aligned to MITRE ATT&CK and industry frameworks
• Perform Active Directory and Entra ID security testing, including privilege escalation and lateral movement techniques
• Assess Azure and Microsoft 365 environments for security vulnerabilities and misconfigurations
• Test VPN, SSO/MFA, and remote-access solutions for exploitable weaknesses
• Validate, exploit, and conduct post-exploitation activities in authorized, controlled engagements
• Produce clear, actionable technical reports with prioritized remediation recommendations
• Present findings and risk summaries to technical and non-technical stakeholders

Skills

Penetration Testing

Red Team Engagements

Active Directory Security Testing

Azure Security Assessments

Vulnerability Validation

Privilege Escalation Techniques

Lateral Movement Techniques

Post-Exploitation Activities

Technical Writing

Presentation Skills

Tools

MITRE ATT&CK

NIST SP 800-115

OWASP Methodologies

Job description

Jobtailor is seeking a senior security professional to lead penetration testing engagements across enterprise networks, web applications, and APIs in Seattle. You will run internal and external assessments, conduct Red Team operations, and simulate adversaries aligned to MITRE ATT&CK frameworks.

You will test Active Directory, Entra ID, Azure, and Microsoft 365 environments, validate VPN and SSO/MFA controls, and produce clear reports with prioritized remediation for clients.