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 podcasts including New CISO and CISO Tradecraft.

00:00 Welcome and Introductions 00:36 Dale’s Career Snapshot 02:08 Life as a CSO 03:06 Leaving the Military 05:00 Certs Resumes and Value 07:31 First Civilian Break 08:51 Networking as a Superpower 10:05 How Promotions Happen 13:20 Building Business Awareness 17:03 Speaking Board Level Risk 17:40 Books and Daily Routines 18:26 AI Needs Human Communication 19:51 Phone Calls and Real Talk 21:18 Using AI Responsibly 22:15 AI Resumes and Hiring Reality 23:29 Culture Fit and Honesty 25:06 Never Stop Learning 27:11 Learning Resources and Creativity 30:26 AI Accelerates Skill Gaps 32:22 Leadership Lessons and Quotes 33:21 Books Podcasts and Wrap Up