Dennis Woodside has one of the most eclectic résumés in Silicon Valley — a former M&A lawyer turned McKinsey consultant turned Google sales chief turned Motorola Mobility CEO turned Dropbox COO turned Impossible Foods president. (Whew.)
Now the chief executive of Freshworks, a Nasdaq-listed software company with 75,000 customers, Woodside sat down with Fortune‘s Diane Brady at the Fortune COO Summit in Scottsdale, Arizona, to reflect on a career built less on a master plan than on a willingness to follow big challenges — even when those challenges came with no roadmap.
It’s a philosophy he applies off the clock, too. Woodside has completed 18 Ironman races and is doing four more races this summer — not, he says, for the bragging rights, but because physical endurance gives him the one thing a packed CEO calendar rarely does: uninterrupted time to think. “Some people meditate. Some people do yoga,” he told Brady. “I go ride a bike or I go for a run.” It’s also, it turns out, a pretty good metaphor for the rest of his career.
“I’ve always thought of my career as a little bit of an adventure,” Woodside has said previously. That spirit of adventure, it turns out, has also produced some sharply honest lessons — about failure, about the limits of individual genius, and about the things that nobody in Silicon Valley actually tells you out loud.
