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
