Episode 376 Deep Dive: Anna Wheeler | Synthetic Confidence - When the Board Believes the Machine

In this episode, Anna Wheeler, CEO of SSAW LLC, joins KB as she explains why so many cyber teams are stuck in event-driven strategy while calling it the real thing, why the doers can’t climb out of it because their KPIs won’t let them, and why visionary CEOs keep getting ousted when the board can’t see what they see. Along the way: the CEOs quietly burning more AI tokens than anyone else in their company, vendors winning unicorn exits on marketing rather than technology, adversaries stealing encrypted data as a long game, and what happens when boards start making decisions on synthetic confidence. Her closing advice for leaders: get very comfortable with being uncomfortable, and go looking for the sources you’d normally avoid. About Anna: Anna Wheeler is a cybersecurity strategist and former Army Blackhawk crew chief who has spent the last two decades helping government and industry modernize how they secure missions, data, and critical infrastructure. She has led federal modernization and cyber campaigns across DHS and the wider national security community, shaping multi‑billion‑dollar technology portfolios and advancing cloud, Zero Trust, and AI‑driven approaches to resilience. As CEO of SSAW LLC and a trusted advisor to C‑suites, boards, and policymakers, Anna is known for turning buzzword-heavy innovation into pragmatic, mission‑aligned change. She serves on multiple advisory boards, mentors rising cyber leaders, and speaks frequently on moving from “FOMO to focus” in cybersecurity innovation. Keywords: AI strategy, CISO, board of directors, CEO, cybersecurity leadership, event-driven strategy, strategic thinking, synthetic confidence, AI bias, go-to-market, vendor marketing, Symantec, SBOM, harvest now decrypt later, cybersecurity podcast