Post by Greg Schaffer

In this episode of The Virtual CISO Moment, Greg Schaffer welcomes cybersecurity veteran, consultant, author, podcaster, and private pilot Andrew Kalat for a wide-ranging discussion spanning more than three decades in information security. Andrew shares his journey from the early days of bulletin board systems and managed security services to leadership roles at organizations including Check Point, U.S. Bank, and SalesLoft, along with the lessons learned from both successes and failures along the way. The conversation takes an unexpected and fascinating turn into aviation, as Greg and Andrew explore the many parallels between flying and cybersecurity. Together, they discuss risk management, incident response, checklists, decision-making under pressure, and what the cybersecurity profession can learn from aviation's mature safety culture. They also examine the realities of security leadership, the challenges of sharing lessons learned from breaches, the importance of preparation before a crisis occurs, and the ongoing struggle to maintain balance and avoid burnout in a demanding profession. Whether you're a security practitioner, consultant, aspiring CISO, or simply interested in leadership and risk, this episode offers practical insights and thoughtful perspectives from a seasoned industry leader who has spent decades helping organizations navigate cybersecurity challenges.

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