Bailey’s career reflects progression from hands-on offensive security work to leadership in large-scale security operations. He began consulting roles at organizations such as Accenture, FishNet Security, and HP, conducting penetration testing and vulnerability assessments. He later moved into enterprise security leadership roles at SunGard, HSBC, Discover Financial Services, and Zynga, where he led incident response and cyber operations teams. As Director of Incident Handling at Red Canary, he oversaw detection and response programs at scale, shaping how organizations operationalize threat detection. These experiences directly inform the labs, where students simulate adversary behavior and learn how to execute and defend against attacks in enterprise environments.
He holds the Offensive Security Certified Professional (OSCP) certification and earned a Master of Science in Computer, Information, and Network Security from DePaul University, along with a Bachelor of Arts in English from Colorado State University. In addition to his instructional role, Bailey has contributed to the security community through incident response leadership, red team program development, and public speaking engagements focused on improving detection and response capabilities. Greg is also a faculty member of the SANS Technology Institute, which has been designated an NSA Center of Academic Excellence in Cyber Defense and is a multi-year winner of the National Cyber League competition.
In the classroom, Bailey is known for translating complex attacker techniques into practical, actionable skills. His teaching emphasizes hands-on learning, encouraging students to think like both attackers and defenders while working through realistic scenarios. Students leave the course with the ability to plan and execute penetration tests, emulate adversaries, and communicate findings effectively. Outside of cybersecurity, Greg enjoys his role as a father and mentor and supports local community services. He enjoys going outdoors with his son, playing board games, and traveling.
Qualifications Summary
- SANS Principal Instructor; Manager, Security Operations Center, Huntress
- Certification: Offensive Security Certified Professional (OSCP)
- Master of Science in Computer, Information, and Network Security, DePaul University
- Bachelor of Arts in English, Colorado State University
- Former Director of Incident Handling, Red Canary; Security leadership roles at Zynga, Discover Financial Services, and HSBC
