Steve, the CEO of Tripadvisor, had gathered the company's top executives. As the newcomer—having joined just months earlier—I listened intently as he outlined “the most important initiative in Tripadvisor's history.”
For nearly a decade, travelers had to leave Tripadvisor to check hotel prices and complete bookings. This approach made sense when Tripadvisor operated as a subsidiary of Expedia (most of those travelers ended up at Expedia). Now, as an independent public company, we were embarking on a new strategy.
Steve explained how challenging it would be to transition a $700M-per-year business to a new model. It would require tight coordination across the entire company. He was putting a single person in charge of the initiative—someone everyone in the room would need to collaborate with closely and occasionally defer to.
Then, he pointed at me.
I was caught off guard. As the newest member of…
