
In this episode of Destination Cyber Season 2, Chahat Bagla speaks with Jason Menar, former FBI cybercrime leader and current CISO, about the human, operational, and leadership realities behind cybersecurity.
Jason reflects on his path from wanting to help underserved communities to investigating early cyber-enabled harm, and later advising organisations through ransomware, legacy risk, and board-level security decisions. The conversation examines how trust works in both systems and people, why influence often matters more than formal authority, and how security leaders can avoid becoming “the island of no”.
The episode also explores the emotional weight of high-stakes cyber work. Jason discusses burnout, risk acceptance, crisis decision-making, and the need for transparency between CISOs, executive teams, and boards. For students and early-career professionals, he offers practical advice on stepping outside narrow role definitions, building communication skills, using AI thoughtfully, and learning how to work in teams before the pressure arrives.
At its core, this is a discussion about calm leadership in volatile environments, and why cybersecurity careers are shaped as much by judgement, empathy, and communication as by technical skill.
Chapters
- (00:00:03) - 12 Cyberpaths
- (00:00:52) - Destination Cyber: CISO Jason Menar
- (00:01:58) - CISO on Standing Between Harm and Other People
- (00:05:12) - The Need for Trust in Security
- (00:07:16) - In the Cybersecurity World, Power Has Changed
- (00:10:27) - How to Build Influence in the Dev Lab
- (00:12:47) - Are CISOs Too Preoccupied With Cybersecurity?
- (00:17:57) - CISO: The Board's cybersecurity oversight
- (00:23:47) - WSJDLive: Deciding Between Paying the Ransomware
- (00:27:46) - The Secret to Mental Health in Cybersecurity
- (00:37:04) - What matters most in cyber security? The role of AI in the
- (00:41:15) - The New CIS University Curriculum
- (00:47:59) - Microsoft's Cybersecurity Center
- (00:49:43) - One leadership habit that you've consciously unlearn
- (00:51:36) - Slow Down: How to Make a Decisive Decision
- (00:54:00) - Destination Cyber: Where Did You Come From?
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