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 thoughtfu...