This course introduces students how to improve an enterprise cybersecurity architecture from a managerial perspective. The course introduces methodologies to analyze and identify threats, vulnerabilities, and mitigations in an enterprise network. Students will utilize penetration testing, business, and managerial knowledge to initiate a penetration testing project. Students will then evaluate the mitigations and resources needed to address vulnerabilities found from the penetration testing projects. Upon successful course completion, students will be able to scope a penetration test project, understand the legal and ethical obligation of a business, defend and prioritize mitigations to obtain needed resources to address weaknesses in an enterprise cybersecurity architecture. This course prepares students to become more knowledgeable in cybersecurity management.