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.
“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 think the yin-yang of the role is very interesting,” he said, about his adventure going from CEO of a major Google subsidiary to COO of a major Silicon Valley firm. Woodside turned to the crowd and asked, “Who wants to be a CEO here?” Not many hands went up, and he called that “interesting.”
“If you have the title of COO, you have it for a reason,” he said, urging the crowd to think deeply about the question: “The board and your CEO decided that you are on a path to being ready potentially to be the CEO. Maybe they didn’t say that to you, but that’s what the title implies, and I think it’s important to recognize for yourself: Do you aspire to be the CEO or not? Some people don’t, and that’s fine, but if you do, you have to act a little bit differently.”
His prescription: make the ambition explicit, and make it early. “You have to have that conversation — ‘I want to be the CEO someday, help me get there.’ The board needs to understand that.” And before you can have that conversation credibly, he added, you have to be excellent at what you’re doing today. “You can’t just talk about what you want to do tomorrow.”
For all the success on his résumé, Woodside is unusually candid about the ceiling on his own abilities. When asked what draws him to big, hard problems — including his time at Impossible Foods, where founder Pat Brown’s mission was nothing less than replacing all animal meat with plant-based alternatives — Woodside didn’t reach for the standard Silicon Valley bravado.
That AI pivot is now the central challenge of Woodside’s tenure. Freshworks sits in a peculiar position: it sells software to customer support and IT teams, the exact functions most exposed to AI-driven automation. Some of its customers have already moved to support teams of zero.
His advice to business leaders navigating the chaos: get hands-on and stay ruthlessly focused on real problems. “The ones that are seeing real value have a business leader who’s deeply engaged — who says, ‘We have a business problem. Let’s see if the technology can solve it.’” The ones that fail, he said, aren’t clear in their thinking.
