Evolving Security Practices with Ben Wilcox

Evolving Security Practices with Ben Wilcox

Author: PM Power Consulting December 14, 2025 Duration: 52:05


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




Behind every line of code, there's a person with a story. Software People Stories, from PM Power Consulting, moves beyond abstract theory and polished case studies to explore the real, human experience of building technology. This isn't about hypotheticals; it's a collection of candid conversations with the practitioners themselves-developers, designers, product managers, and architects-who share firsthand accounts from the trenches. They talk about the paths that led to success and, just as importantly, the unexpected detours and failures that provided the most valuable lessons. Each episode delves into the nuanced journey of discovering what users need, designing elegant systems, navigating complex development, and ultimately delivering solutions that matter. By focusing on these personal narratives, the podcast reveals the core of software creation: a blend of technical skill, creative problem-solving, and team dynamics. Listeners gain practical wisdom and relatable perspectives on the challenges and triumphs inherent in the tech industry. Tune in for an honest look at the craft, where the stories of people are just as crucial as the software they build. You'll find this podcast a refreshing source of insight for anyone involved in or curious about the technology and business landscapes, offering career lessons learned the hard way.
Author: Language: English Episodes: 50

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