This CEO has had 6 major jobs in Silicon Valley: How Dennis Woodside built a career on saying yes to hard problems

Dennis Woodside has one of the most eclectic résumés in Silicon Valley — a former M&A lawyer turned Mc Kinsey 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. ‘I sold myself out of a job’ When Woodside became CEO of Motorola Mobility in 2012, following Google’s acquisition of the company, he inherited a $ 1 billion hardware operation in the middle of a brutal smartphone war. He launched the Moto X and Moto G — products that revitalized the brand — but when Google moved to sell Motorola Mobility to Lenovo in early 2014, Woodside engineered the deal. “I was the CEO of Motorola Mobility,” he told the audience in Arizona. “We sold it — which meant I sold it — which meant I sold myself out of a job.