Stories of what worked and sometimes what did not, in the course of discovering, designing, developing and delivering software based solutions – as shared by practitioners who went through these situations.
Stories of what worked and sometimes what did not, in the course of discovering, designing, developing and delivering software based solutions – as shared by practitioners who went through these situations.
In this episode of the Software People Stories, my guest Ben Wilcox is the Chief Technology Officer and Chief Information Security Officer at ProArch.
Ben shares his fascinating journey from building a web hosting business as a teenager to his current role as CTO and CISO at ProArch. Ben discusses the evolution of his career, his involvement in various projects, and the ever-changing landscape of security, especially with the advent of AI. He also provides valuable insights into how enterprises should approach security, the complexities of data localization, and the importance of a continuous security model. The conversation also delves into career advice for aspiring IT and security professionals.
00:00 Introduction and Guest Welcome
00:42 Early Career and Web Hosting Business
02:49 Transition to Software Development
03:51 Joining Advisor Group and Pro
05:06 Challenges of Running a Business as a Teenager
07:55 Learning and Growth in a Larger Company
09:14 Becoming a CISO and Security Focus
12:21 Evolving Security Landscape and AI
15:01 Data Security and Insider Risk Management
20:51 Zero Trust Environments and Legacy Systems
23:58 Sleepless Nights and Security Concerns
25:50 Balancing Innovation and Security
26:11 Finding Joy in Leadership
26:54 Navigating the CTO and CISO Roles
28:55 Keeping Up with Technology Trends
31:27 Hyper-Personalization and Security Risks
36:02 The Role of Open Source in Security
41:03 Career Advice for Aspiring Security Professionals
45:35 The Impact of AI on Security Jobs
49:11 Conclusion and Contact Information
The timestamps are approximate, and after the intro that is about 90 seconds.
For more closer timestamps, add 90 seconds to the labels above
Ben Wilcox is the Chief Technology Officer and Chief Information Security Officer at ProArch, where he leads the company’s cloud, security, and AI enablement strategy. With more than 20 years of experience spanning software engineering, cybersecurity, and enterprise architecture, Ben helps organizations modernize their technology foundations while navigating the evolving threat landscape.
Ben’s career began in hands-on development and infrastructure work, giving him a deep technical grounding that informs his leadership today. He has built and led high-performing engineering teams, guided complex cloud migrations, and designed modern security programs that balance innovation with risk management. At ProArch, he works closely with clients to architect AI-ready, scalable systems that drive business transformation.
Connect with Ben: https://www.linkedin.com/in/ben-wilcox