#158 | From Teenage Entrepreneur to the CTO: Building Teams That Win in the AI Era w/ Ben Wilcox @ProArch

Episode notes

▶︎ #158 | From Teenage Entrepreneur to the CTO: Building Teams That Win in the AI Era w/ Ben Wilcox @ProArch In this episode of the Leman Tech Leadership Podcast, Alex welcomes Ben Wilcox: a CTO and CISO of ProArch, for a wide-ranging conversation about what it actually takes to lead technology teams in the age of AI. Ben's story is anything but conventional: he started monetising the internet as a 15-year-old, built and sold a web hosting business before most people his age had a bank account, and has spent the last 19 years growing from an individual contributor to holding two C-suite roles simultaneously. Ben brings a rare perspective: one that sits at the intersection of deep technical expertise, security leadership, and people development. He started his career in Microsoft infrastructure and consulting, got into cloud migrations as early as 2008, and found his way into leadership not because he was chasing a title, but because he needed to "reproduce himself" at scale. That origin story shapes everything about how he leads today.

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