CEO of TaskRabbit

Sheryl [Sandberg] saw the potential for leadership, so pulled me into her group to run a 200-person team. I went from managing 14 to 200 people overnight. That was a big step up in not just how I led but how I talked to people, how I communicated. I went from managing direct reports to managing managers, and becoming more responsible as a leader. And then I went to India, and went from managing 200 people to 1,000 people.