Senior Penetration Tester: Red Team & Cloud Security

Jobtailor; Seattle (WA); On-site; USD 120,000 - 150,000; Full time

Job summary

Jobtailor in Seattle is seeking an experienced penetration tester to conduct hands-on assessments, internal and external testing, and adversary simulations across enterprise environments.

You will test Active Directory, Entra ID, Azure and Microsoft 365 security, network, web apps, and APIs, and deliver remediation recommendations and client presentations. This role emphasizes adhering to established methodologies and communicating findings clearly.

Qualifications

• 3+ years of hands-on penetration testing/offensive security experience
• 5+ years of enterprise internal and external penetration testing experience
• Experience with Red Team/adversary simulation
• Active Directory and Entra ID security testing
• Azure and Microsoft 365 security assessments
• Network, web application, and API penetration testing
• VPN, SSO/MFA, and remote-access security testing
• Privilege escalation and lateral movement
• Vulnerability validation, exploitation, and post-exploitation
• Strong reporting and client presentation skills
• Preferred certifications: OSCP, OSEP, OSWE, GPEN, GXPN, GWAPT, CEH or equivalent offensive-security certifications
• Visa eligibility: GC & USC

Responsibilities

• Conduct hands-on penetration testing and offensive security assessments
• Perform enterprise internal and external penetration testing
• Execute Red Team and adversary simulation engagements
• Test Active Directory and Entra ID security
• Assess Azure and Microsoft 365 security
• Conduct network, web application, and API penetration testing
• Test VPN, SSO/MFA, and remote-access security
• Perform privilege escalation, lateral movement, vulnerability validation, exploitation, and post-exploitation
• Follow NIST SP 800-115, MITRE ATT&CK, and OWASP methodologies
• Produce technical reports and remediation recommendations
• Present findings to clients

Skills

Penetration Testing

Offensive Security

Vulnerability Validation

Exploitation

Post-Exploitation

Privilege Escalation

Lateral Movement

Network Security Testing

Web Application Testing

API Testing

Tools

NIST SP 800-115

MITRE ATT&CK

OWASP

Job description

Jobtailor in Seattle is seeking an experienced penetration tester to conduct hands-on assessments, internal and external testing, and adversary simulations across enterprise environments.

You will test Active Directory, Entra ID, Azure and Microsoft 365 security, network, web apps, and APIs, and deliver remediation recommendations and client presentations. This role emphasizes adhering to established methodologies and communicating findings clearly.