“Can Defense Keep Up?” Is the Wrong Question

How defense keeps up with AI, cyber threats, and private-sector innovation. In this episode of The Watchtower, Ash Hunt sits down with Jimmy Harrington, retired Air Force colonel and former Deputy CIO at U.S. Special Operations Command, for a conversation about cyber resilience, defense innovation, and what large organizations often misunderstand about speed. From NATO and the Pentagon to AI-enabled defense systems and private-sector collaboration, Jimmy shares what defense can teach enterprise security leaders about resilience, leadership, mentorship, and building organizations that can operate through uncertainty. Highlights - Why “keeping up” may be the wrong question - How zero trust changes the goal from prevention to resilience - Why defense innovation can become “innovation theater” - What it takes for new technology to actually scale - What CISOs can learn from military leadership and mentorship Chapters 0:00 Can organizations keep up with innovation? 1:14 Jimmy Harrington Deputy CIO 5:36 The pace problem inside defense institutions 6:50 Reframing cyber success: stop trying to stop everything 8:49 Run fast, trip less - operating under uncertainty 12:12 Threat-agnostic vs threat-specific cyber defense 14:09 Defense tech: from leading edge to catching up 15:14 Innovation theater: the $5B that never scaled 18:55 Slow is smooth, smooth is fast 21:16 Palantir, Anduril, and selling belief to the DoD 24:33 Building the plane while it's flying 27:23 Why CISOs and defense leaders don't collaborate enough 31:34 The military's leadership DNA corporate lacks 35:49 Mentorship and the replacement-first model 41:24 How leaders are actually built 43:10 The hardest part of leaving the military 46:28 What corporate underestimates about veterans