The Virtual CISO Moment · 2026-06-23 · 33 min
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.
S8E25 - From Help Desk to Enterprise Security with Travis Stein47 / 100S8E23 - Bruno Lecoq on AI, CMMC, and SMB SecurityS8E22- Alan Clinard Discusses Building Security Programs That Actually WorkS8E21 - Cy Sturdivant on Community Banking, Risk, and Cyber LeadershipS8E20 - Becky MacDonald on Building Security Beyond Compliance