Dennis Woodside at the Fortune COO Summit
Freshworks’ CEO made the case that AI transformation starts with a business problem, not a technology decision
The stages at Fortune conferences have seen everyone from Nvidia’s Jensen Huang to GM’s Mary Barra open up about their companies and their personal experiences. On June 2, 2026, Freshworks CEO Dennis Woodside sat down with Diane Brady at Fortune COO Summit to discuss AI transformation, the COO-to-CEO path, and what separates companies that win with AI from those that fall behind.
Highlights below, and watch the full interview here:
AI transformation hinges on executive ownership
“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, that's vague and unanswered.”
The current AI moment is larger than the internet and mobile
“It's important to start acting now in a way that makes business sense. There's a lot of hype—I guarantee you a lot of companies are going to go completely under. You don't want to partner with them; you want to find trusted partners that are going to be around for 10 years, that have strong business models, that understand your business and what you're trying to accomplish, and can drive real business outcomes.”
Trust, built over time with real customers, is the differentiator
“We have the right to win, because we've got 75,000 customers and they trust us. We provide software today that actually solves their problems. They want governance, they want security, they want control over those outcomes, and that's what we do.”
A fresh perspective from the COO seat
“AI is disrupting us, but every business here is going through some disruption of a different making, and you need to understand that and think about how [to do] things better. So when the time comes that maybe you do become the CEO, you are ready to go.”
Watch the full interview at Fortune
Image courtesy of Fortune
