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/