Wiley Bayes on Red Teaming, Networking Fundamentals, and Breaking into Cybersecurity

Thomas hosts Wiley Bayes on the Cybersecurity Recruiter Podcast to discuss Wiley’s career path from early Linux curiosity and the US Navy into networking, systems/cloud engineering, penetration testing, and his current role as Senior Principal Red Team Operator at Dark Wolf Solutions.

Wiley explains day-to-day red teaming on DoD contracts, emphasizing long preparation cycles, payload testing against major security tools, patience, and tailoring phishing to the audience. He advises career changers to keep learning, focus on fundamentals (especially networking), troubleshooting, and scripting/programming, and to break into IT first rather than fixating on a dream cybersecurity role unless you’re exceptionally advanced.

They discuss Dark Wolf’s custom CTF-based hiring, communication skills gained from executive briefings, concerns about shortcuts and AI, and Wiley recommends OpenBSD and Peter N.M. Hansteen’s book “The Book of PF,” plus home lab tinkering.

00:00 Welcome and Golf Talk

01:27 Career Journey Intro

02:26 Early Curiosity and Navy Roots

03:17 Why Networking Matters

04:04 Red Team Day to Day

06:35 Phishing and Security Hygiene

08:09 Transitioning to Civilian Life

09:50 Hiring with Custom CTFs

11:31 Breaking In Is Harder Now

14:45 Finding Your Path in Security

17:55 Staying Relevant and Next Steps

20:39 Pentest To Architect Shift

21:25 Communication Under Pressure

23:17 Fundamentals And Hiring Quality

25:43 Stop Chasing Dream Roles

27:57 Learning Resources And Practice

28:57 Troubleshooting War Story

32:31 AI Shortcuts Vs Real Skills

34:36 Code And Scripting Matters

36:04 Books And Home Labbing

38:37 Wrap Up And Thanks