The Cybersecurity Recruiter talks to Dale Hoak, Chief Information Security Officer, RegScale

In this Cybersecurity Recruiter podcast episode, Thomas chats with Dale Hoak, a former US Navy veteran who transitioned to the commercial sector and progressed from to senior director and now Chief Security Officer/CISO at RegScale.Dale explains that leaving the military is difficult because individuals must take ownership of healthcare, career planning, compensation negotiation, and resume-building, recommending an exit strategy starting two years before separation and seeking early help (including AI tools) while understanding one’s individual value.He credits his advancement to strong networks and mentors, hard work, and learning to understand business value and communicate cyber risk in non-technical terms to leaders and boards, using approaches like threat modeling and risk scoring. He discusses AI as a helpful but fallible tool requiring fact-checking, emphasizes continuous learning.Dale recommends as a starting point "The 7 Habits of Highly Effective People" and then progressing on to 2 series of books by Gary Hayslip. He listens to lots of podcastsincluding New CISO and CISO Tradecraft.00:00 Welcome and Introductions00:36 Dale’s Career Snapshot02:08 Life as a CSO03:06 Leaving the Military05:00 Certs Resumes and Value07:31 First Civilian Break08:51 Networking as a Superpower10:05 How Promotions Happen13:20 Building Business Awareness17:03 Speaking Board Level Risk17:40 Books and Daily Routines18:26 AI Needs Human Communication19:51 Phone Calls and Real Talk21:18 Using AI Responsibly22:15 AI Resumes and Hiring Reality23:29 Culture Fit and Honesty25:06 Never Stop Learning27:11 Learning Resources and Creativity30:26 AI Accelerates Skill Gaps32:22 Leadership Lessons and Quotes33:21 Books Podcasts and Wrap Up