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

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