Bridging Military and Civilian Cybersecurity: Leadership, Skills, and Lifelong Learning with Christopher Ross

In this episode, host Aaron Crow sits down with cybersecurity leader and National Guard threat hunt team lead Christopher Ross, diving into the real-world experiences that shape careers in the intersecting worlds of IT and OT security. Chris shares his 18-year journey from joining the military with a passion for computers to leading critical infrastructure cybersecurity efforts - both in uniform and in the private sector. Together, Aaron and Chris break down myths about gatekeeping, discuss the unique challenges of military versus civilian roles, and highlight lessons learned along the way.

From imposter syndrome to servant leadership, the conversation unpacks how effective communication, continuous training, and the willingness to learn from failure fuel professional growth. Chris also reflects on how military training instills risk mitigation and teamwork, and how those skills can translate - and sometimes clash - with civilian cybersecurity cultures. They talk certifications, hands-on learning, the importance of meaningful tabletop exercises, and the evolving landscape as AI powers both attackers and defenders.

Whether you’re a veteran, a fresh analyst, or just passionate about cybersecurity, this honest and energetic exchange will leave you motivated to keep learning, keep growing, and keep protecting it all. So grab your energy drink and tune in for a conversation that proves everyone in cyber, no matter their path, has wisdom worth sharing.

 

Key Moments: 

05:30 Military Adventures Surpass Civilian Opportunities

07:28 Military vs. Civilian Leadership Dynamics

10:42 Clarifying Civilian vs Military Missions

12:22 Leadership: Addressing Miscommunication & Misalignment

15:45 Toxic Leadership and Military Transition

20:01 Reliance on Tools vs. Core Skills

22:29 "Forgotten Skills Fade Over Time"

25:13 Boosting Confidence in New Roles

29:42 Interactive Training and Environmental Protection

32:37 Purple Teaming Strategy Insights

36:15 Persistence in Skill Development

39:04 Soft Skills Matter for Career Growth

42:44 "Technical & Business Acumen Fusion"

44:41 Military: Career Value and Benefits

48:09 "Cyber Education for K-12"

Resources Mentioned : 

https://www.ransomware.live/

• comprehensive resource that tracks and monitors ransomware groups and their activities.

https://ransomwhe.re/

• tracks ransomware payments by collecting and analyzing cryptocurrency addresses associated with ransomware attacks. 

https://www.ransom-db.com/

• real-time ransomware tracking platform that collects, indexes, and centralizes information on ransomware groups and their victims. 

About the Gu...