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

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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 eventually pushed him to found Sidekick: specialist security teams that all report to the same leader still can't speak the same language, so he built an internal Snowflake-based "security data lake" to force the data together. They talk about why AI governance has become Sidekick's fastest-growing line of work as boards push AI adoption faster than security teams can keep up, how deepfakes and voice cloning are making old-school phishing dramatically more effective, and zerodayclock.com, the site Robert points to that tracks how the time between a vulnerability being discovered and weaponized has shrunk from years to minutes. Robert also breaks down why Sidekick made a hard pivot away from generic federal cyber contracting, how they built the business almost entirely on trust-based referrals instead of a sales team, and VSEC, their virtual CISO offering that blends senior human judgment with AI tooling they originally built just for themselves. He closes with advice for founders three months into building a services firm: don't rush to extract yourself from the work, and be ready to sit in the uncomfortable middle for longer than social media tells you to.

Connect with Robert Wood: https://www.linkedin.com/in/holycyberbatman/
Zero Day Clock (mentioned in the episode): https://zerodayclock.com

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