Lessons from the Frontlines

CHAPTER 12Leading from the Front

When I left SenseCy after having vision disagreements with my co-founders, I made a decision that surprised many people in my network. I was leaving a CTO role where I managed 50+ people to join PayPal as Head of Global Incident Response—a significantly smaller scope in terms of team size and organizational authority.

“You’re taking a step backward,” several advisors told me. “Why would you reduce your scope like that?”

But I understood something that took me years to articulate clearly: career progression isn’t based on the size of your team but the level of experiences you bring to the table. I wanted to work at internet scale, to understand what global security leadership looked like at a company processing billions of transactions. Sometimes you have to step back to move forward.

What I didn’t realize at the time was that this decision would teach me the most important lesson of my leadership career: “leading from the front” means something completely different at every level of leadership. As a director, leading from the front meant being in the trenches during incidents. As a VP, it meant being first to articulate vision and make difficult strategic choices. As a CISO, it meant taking public responsibility for failures while inspiring confidence that challenges could be overcome.

I joined eBay/PayPal just a couple of months before the historic split that would separate PayPal into an independent company. Talk about jumping into the ...