Executive Intelligence podcast - Freshworks CEO Dennis Woodside on AI adoption, simplifying IT complexity, and taking on legacy tech providers

AI adoption is a topic of conversation that dominates every tech agenda in 2025, with views ranging from evangelical fervor through to the ‘Robots are coming to steal your job’ armageddon pedling. For Freshworks CEO Dennis Woodside, there’s a pragmatic way of looking at the issue. In diginomica’s latest Executive Intelligence podcast, he tells me:

People have a way of working that's very specific, and you have to encourage them to try new methods and try new products that are going to make them more productive over time. I think that that is a real cultural change, even for a technology company, that we've had to make. We’ve had to encourage teams to explore AI.  We've had to get our own security team comfortable with that. We have an entire process for reviewing new AI applications. And I think that that's a really interesting place, where you're going to see more and more companies encouraging their workforce to make AI a part of their job, because it's going to make every every person who works in the organization much more effective over time.

He goes on:

Like with any any new technology, people who embrace the technology soon so as to understand how it can augment what they do, are going to be the ones that are more successful over time. So, we encourage our teams to think about, how can they become more creative if they're in design by using AI functionality? Or how can they free up their own time to do things that are more rewarding for themselves if they're in our customer support team? 

What we've done, as we've rolled out our own AI internally, we we have had less need for that frontline Customer Support Worker. But they are very valuable because they understand the product, they understand how to relate to people because they've been dealing with customers all their lives, all their career. We've put them into a new team that's focused on premium support, and that's focused on how do we drive adoption of our existing products, so more education of our customers, less reactive support. So there's always roles for highly productive, creative, motivated team members, but they all need to embrace AI because that's going to make them better at their jobs.

It’s also going to help address macro-economic pressures facing every company, he notes:

I haven't met an IT director that has a project list that's shorter than their resources. The project list always exceeds the resources, so if we can free up time - and we have customers that have freed up 30%, 40% of their IT teams time to work on higher order problems, higher order projects in the organization - that’s hugely valuable. So I would bring AI back to customer value, employee value, and then taking the humans in your environment and putting them on higher value activity.

AI adoption is just one subject covered in a wide-ranging discussion with Woodside. Check out the entire session by clicking on the link above.