Leadership in Cyber: Lessons from the Frontlines
Real stories and practical frameworks for building resilient security teams, communicating with clarity, and leading with impact.

"I had prepared for weeks. In front of PayPal's CEO and executive team, I was ready to demonstrate the seriousness of our security challenges. For 15 minutes, I cataloged everything that was wrong. Following what I thought was security best practice, I was making sure the CEO 'understood how bad things were.' Then Dan Schulman interrupted me. Visibly annoyed. 'I don't need you to tell me that things are bad. I know they are. What are you doing about it?' After the meeting, Dan taught me a framework that transformed my leadership: 'State Reality, Inspire Hope.'"

— Chapter 8: Communication

"I sat on the message for three days before hitting send. During the pandemic, one of my leaders told me an employee was struggling with PTSD, afraid for their job because they needed medication to control stress. I'd been dealing with PTSD from my military service for years. Only my wife and kids knew. But someone needed to hear they weren't alone. So I went to a public Slack channel and wrote: 'I am dealing with this.' That message went out before my parents knew about my PTSD. The response was overwhelming—and supportive. But more importantly, it shifted something fundamental in our team culture."

— Chapter 10: Self-Help Strategies

"The room went silent. Then the pushback started. At a CISO roundtable, we were discussing how to measure security leadership success. Others mentioned budgets, compliance scores, and frameworks. I said: 'We are measured by the stock price and the success of the business.' Security is fundamentally a business function. We protect AND enable. We ensure customers and employees are protected while the business thrives. When security enables business success, everyone wins."

— Chapter 6: Business and Finance Acumen

"Multiple advisors said this when I left my role as CTO of a 50+ person team to join PayPal as Head of Global Incident Response—managing just 4 people initially. They were measuring the wrong thing. Career progression isn't based on the size of your team but the level of experiences you bring to the table. That 'step backward' led to rebuilding PayPal's global SOC across three continents, achieving 80% automation of security operations, and eventually becoming a CISO who could operate at any scale."

— Chapter 12: Leading from the Front