Money Maze Podcast

195: From Battlefield to Boardroom: Assessing the Cyber War Frontlines - Jen Easterly on the New Era of Cyber Risk

Mar 5, 2026
Jen Easterly, former U.S. cybersecurity leader and Army colonel now leading RSAC, traces a path from West Point and Oxford to building the nation’s cyber defenses. She discusses commanding the Army’s first cyber battalion, standing up CISA, private sector responsibility for critical infrastructure, AI’s dual role in security and threat amplification, and why boards must treat cyber as an existential business risk.
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INSIGHT

Cybersecurity Is A Software Quality Problem

  • Cybersecurity is primarily a software quality problem because insecure code creates the aftermarket of fixes.
  • Easterly launched a secure-by-design campaign to push vendors to design, test and deliver more resilient software.
ADVICE

Use AI To Fix Legacy Code At Scale

  • Use AI to find and refactor insecure legacy code at scale to reduce vulnerability estate.
  • Easterly points to bespoke AI tools rewriting COBOL and millions of lines of old code to save manpower and harden systems.
ADVICE

Assume Disruption And Build For Resilience

  • Assume disruption and build resilience across systems and supply chains rather than aiming for perfect prevention.
  • Easterly urges exercises, worst-case planning and redesigning for recovery using lessons from finance fusion resilience centres.
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