Lessons from the Frontlines

CHAPTER 5Change Management

Change isn’t an occasional disruption in security leadership—it’s the fundamental nature of the job. Threats evolve constantly. Technologies shift rapidly. Organizations restructure regularly. Regulations change frequently. The leaders who thrive are those who don’t just tolerate change but leverage it as a competitive advantage.

I learned this lesson the hard way during my first year at PayPal, when I had four or five managers. I don’t even remember the exact number anymore—that’s how chaotic it felt at the time.

By the end of that first year, I was struggling emotionally with the organizational turbulence. I felt fear—am I going to be next? I felt confused about who I was supposed to report to and what my priorities should be. Most concerning, I felt like I might not belong in an environment where everything seemed to be in constant flux.

Finally, I went to one of the senior leaders and basically asked, “What the hell is going on here? Why can’t we maintain stable management structures?”

His response changed how I think about change in leadership: “This is how we operate. Either you get comfortable with change or you burn out. But keep this in mind—change is opportunity.”

That conversation was a turning point, though not immediately. His words initially felt dismissive—almost threatening, as if he was saying “adapt or leave.” But over the following weeks, as I watched how the organization actually functioned, it clicked: the constant changes weren’t ...