From Government CISO to AI-Native Security Founder (Robert Wood)

We Built It Because We Had To - Tech Founder Backstories · Jul 30, 2026 · 41m

His hardest problem wasn't hackers — it was a 500-person security organization whose specialist teams couldn't speak the same language.

In this episode of We Built It Because We Had To, host Jonathan W. Buckley sits down with Robert Wood, founder and CEO of Sidekick Security, an AI-native cybersecurity consulting firm. Robert started out doing offensive red team work, then ran security programs at several tech companies before becoming the enterprise CISO at the Centers for Medicare and Medicaid Services, leading a team of nearly 500 across five divisions. That job exposed the problem that…