The Cybersecurity Recruiter talks to Wylie Bayes, Director of Defensive Cyber, Dark Wolf

Wiley Bayes on Red Teaming, Networking Fundamentals, and Breaking into CybersecurityThomas 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 Talk01:27 Career Journey Intro02:26 Early Curiosity and Navy Roots03:17 Why Networking Matters04:04 Red Team Day to Day06:35 Phishing and Security Hygiene08:09 Transitioning to Civilian Life09:50 Hiring with Custom CTFs11:31 Breaking In Is Harder Now14:45 Finding Your Path in Security17:55 Staying Relevant and Next Steps20:39 Pentest To Architect Shift21:25 Communication Under Pressure23:17 Fundamentals And Hiring Quality25:43 Stop Chasing Dream Roles27:57 Learning Resources And Practice28:57 Troubleshooting War Story32:31 AI Shortcuts Vs Real Skills34:36 Code And Scripting Matters36:04 Books And Home Labbing38:37 Wrap Up And Thanks