The Cyber Security Recruiter Podcast
Thomas Richard talks to Jeff Bailey, Director, IT and Information Security, Apptegy
Protecting Student Data, Leading Security Teams, and Keeping Up With AI: Jeff Bailey on Security Leadership Thomas chats with Jeff Bailey on the Cybersecurity Recruiter podcast about his career path from GameStop into security roles at Simmons Bank and now as Director of Security and IT at Apptegy, a K–12 communications platform focused on protecting sensitive student data across all 50 states’ regulations. They discuss how rapidly evolving AI models (including Fable and Opus) are changing security work, vendor risk/GRC reviews as SaaS apps add AI features, and how teams can build small internal tools instead of buying expensive products. Jeff shares leadership lessons on perception and trust: making security approachable (including his bright shirts), encouraging reporting, and empowering experts to challenge him, while managing workload to prevent burnout by aiming for 80% capacity. They also cover AI’s impact on learning, CTF competitions, and parenting in an AI-saturated world. Book recommendation: “Time Management for Mortals” by Oliver Burkeman; Jeff also recommends Adam Grant’s work. 00:00 Welcome and Catch Up 00:52 Jeff Bailey Career Intro 01:36 ADHD and Security Culture 03:27 Director Role at Apptegy 04:42 Fable vs Opus AI Talk 07:57 Kids Growing Up With AI 09:36 Token Costs and IPO Pricing 11:06 Purpose Protecting Student Data 13:54 Leadership and Approachability 18:32 Empowering Experts on Your Team 20:03 Avoiding Burnout at 80% 21:22 AI Like the Cloud Shift 22:28 New AI Security Reviews 23:06 Vendor Acronyms and Confusion 23:56 Adapt or Get Left Behind 25:50 AI Slop in Customer Touch 28:45 Using AI for Real Gains 31:30 CTFs and AI Cheating 33:07 Learning Still Needs Struggle 35:56 Book Picks and Wrap Up For Executive, GTM, Cybersecurity searches, contact Tom: https://www.linkedin.com/in/thomaspropen/
