Freshworks Refresh 2025 | Dennis Woodside, Freshworks

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Dennis Woodside

CEO

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Dennis Woodside, Freshworks

Dennis Woodside

CEO Freshworks

In this interview from Refresh North America 2025 at Oracle Park in San Francisco, Dennis Woodside, president and chief executive officer at Freshworks, joins theCUBE’s Bob Laliberte to unpack how Freshworks is “uncomplicating service” with tightly embedded, people-first AI across customer and employee experience. Woodside shares why he joined what he first saw as a “hidden gem,” how the company has grown to serve over 75,000 customers and how Freshdesk and Freshservice are weaving AI directly into service workflows so agents can focus on higher-value work. H... Read more

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How is AI currently impacting the service industry and the roles of employees within that sector? add

What was the initial status of AI adoption among customers a year ago compared to the current situation? add

What significant changes occurred in the support operations of a major aviation software company in response to their leadership's goals regarding AI integration? add

What is the significance of AI in your platform's approach to future growth, particularly in relation to IT service management and employee service management? add

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Dennis Woodside, Freshworks

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Bob Laliberte

>> Hello and welcome back. We're here at Freshworks Refresh at Oracle Park in San Francisco for a great day. And I'm pleased to say that I'm joined by Dennis Woodside, president and CEO of Freshworks. Welcome, Dennis.

Dennis Woodside

>> Thanks for having me. And I'm sorry we didn't get a sunnier day. We could have been out in the ball field right now.

Bob Laliberte

>> That would've been great, but you know what? This is pretty good.

Dennis Woodside

>> Yeah, it's pretty good.

Bob Laliberte

>> It's pretty special being here at Oracle Park. Let's start with your role as CEO at Freshworks. I know when you came here, you probably had lots of opportunities. Someone of your background. Why did you choose to come to Freshworks? What opportunity did you see and what are the things you're most proud of accomplished being here for the last couple of years?

Dennis Woodside

>> Yeah, so I was introduced to Girish Mathrubootham, who is the founder and was the CEO of Freshworks a couple of years ago. And I was just really impressed by what he had accomplished. He had built a company from Chennai, India, taking it public on NASDAQ. When I met him, we already were at about half a billion in revenue scale, already had, I think 50,000 customers at the time. So really was getting some real traction. At the same time. I've been in the valley for a long time. I had not heard of the company, so here's a hidden gem, so to speak. A company that has great product, has a great customer base, is off to the races. Needs some help to get to multi-billion dollar scale, and that's what I've done in the past. I did that at Dropbox. I helped Google do that. And I just really like Girish. So he said, "Hey, I might not want to be the CEO forever. Why don't you come in, learn the business, and maybe someday you get to be the CEO?" And that happened.

Bob Laliberte

>> Yeah, I think that's great. The one thing that's been clear today in all the conversations we're having is the growth and momentum that the company's had. So clearly you're doing something right. Over the last couple of years, we continue to hear about the expanded product line, the continued growth. I think, what did you say this morning, over 75,000 customers now?

Dennis Woodside

>> That's right.

Bob Laliberte

>> So really amazing growth over just a couple of years, so congratulations on that. One of the things I wanted to talk to you about as well, in your keynote, you talked about AI and the need for it to be tightly integrated into the products and not bolted on. So I'm wondering if you could share with everyone more about your vision for AI as it relates to Freshworks and then maybe also where you see it for the industry as a whole.

Dennis Woodside

>> Yeah, so first of all, AI is going to affect every profession, every job in the world. And it's affecting right now the service industry, whether you're providing service to employees or service to customers. And we provide products to both the IT department and the customer support department. So it's imperative for us to lead when it comes to embedding AI in those products. Our customers want their employees who are in service roles to be doing higher value work. They don't want them answering the same question or taking the same actions. "How do I return my order? How do I reset my password?" That's not interesting work for the agent. It's actions that the AI naturally can take on their behalf and actually get to better results for the customer. So that's what we've built into our products both on CX and our EX set of products. And today we announced a slew of AI innovation that enables our customers to get more out of their service teams, more out of their support teams, be able to elevate them. So you heard stories of customers who have transformed cost centers, service centers into revenue centers because of AI. AI has taken that rote work off the table for the humans and enabled the humans to do more interesting things. So we think that's a massive revolution and we're leading our customers and helping them make their way through that revolution and deliver better outcomes.

Bob Laliberte

>> Yeah. I was definitely super impressed with your use of AI and agentic AI. It's still fairly early. It was only about nine months ago-

Dennis Woodside

>> That's right....

Bob Laliberte

>> when people were first starting to talk about MCP servers, things like that, and it's really accelerated. I think one of the things I was really impressed with was the vertical agents as well. I've heard people talking about it, but this is the first time I've seen it executed against. And really being able to help specialize in deliver value to those, right, not generic, but specialize service for certain organizations.

Dennis Woodside

>> Yeah. So I think that illustrates a difference of approach that we have. So our core customer is from a 5,000 employee to a 20,000 employee company. So think of New Balance, think of Fabletics, think of A&E Networks. These are sophisticated organizations. They typically have global operations, a lot of security needs. So you can't be an unsophisticated solution for them. You have to be able to operate in that enterprise environment. At the same time, they don't have the resources of a JP Morgan or a Home Depot, so they need solutions that out of the box are going to work for them. What the vertical AI agents do for industries like e-commerce and travel and logistics out of the box, they come with integrations to systems of record that are relevant for those industries. And if I'm a customer, I can get up and running in a matter of hours. It's not a huge lift for me to get value. If I want to go from there and get much more sophisticated, much more integrated, I can use the AI agent platform to build my own agent on top of what we built. But if I just want something out of the box that works, that's what you get. And that's our value, and that's very different than a lot of the other vendors out there.

Bob Laliberte

>> Yeah, I think that makes a lot of sense in that ability to get those quick wins for AI. We've all seen the MIT report talking about people aren't getting value. Obviously, when you've got specialized solutions like this that are focused on a specific vertical and things like that, it's a lot easier for them to generate-

Dennis Woodside

>> That's right....

Bob Laliberte

>> some type of a return. One of the other questions, I know that you did have a number of announcements today over six, I think that at least a half a dozen that I saw.

Dennis Woodside

>> That's right.

Bob Laliberte

>> Maybe more. How important it's to you in this AI era where things are really accelerating, we're seeing innovation accelerate. I'm wondering if you could talk about how important is it for you at Freshworks and for Freshworks to continue that flywheel of innovation and to keep working with customers to accelerate new feature functionality that supports their outcomes?

Dennis Woodside

>> So it's super important. So a year ago we had our customer advisory board. Those are 40 customers that we talked to to learn and help build our products. And I asked the question, "How many of you have AI in production right now?" And I was in a subgroup of that. There were about 14 customers, three of the 14 had AI in production, and I was surprised it was that low. And there were concerns about security and legal stuff, all that. We asked the same question this week, everybody's got something in production. So every professional, whether you're a service professional or an IT professional, it's now a top-down imperative. Your CEO expects you to have AI. And what we can do is help you get there. So our customers are turning to us and they expect us to be able to help them understand the lingo, the terminology, what the capabilities of the products are, help them understand the potential business impact, which is super important. And then help them tell the story internally of how to get the most value out of the AI. And so that's our role. It's a lot more than just providing a product. It's helping educate the people who actually deliver the service. It's helping them be champions in their organization and ultimately be successful because most of our customers are not in the IT business.

Bob Laliberte

>> Correct.

Dennis Woodside

>> And the IT leader or the customer support leader is perceived as the AI leader now, whether they intend so or not. So if we can arm them with knowledge and information, then that becomes a way that we support them beyond just providing a product.

Bob Laliberte

>> Yeah, I think that's so important in this day and age right now. For a long time I've been talking about the time to comfort with AI because it needs to be validated, it needs to be tested and proven because these people's jobs are on the line who are using it.

Dennis Woodside

>> Totally.

Bob Laliberte

>> So that prescriptive approach that you're taking and being able to show them, "Here's how to use it, these are the specific use cases, this is where you get the value." I think that's really needed right now. And then as you said, once they get more comfortable with it, they have the ability to build out their own agents to take that to the next level.

Dennis Woodside

>> And we do events like this so that the customers learn from one another. So you notice there were a bunch of customers on stage sharing the impact that they've already seen with AI, talking about the challenges that they've had internally. What metrics, what business metrics they're changing, because all of them have to become AI forward within their organizations very quickly.

Bob Laliberte

>> Yeah. Especially if they want to compete. So one of the things that I wanted to talk about a little bit more is also this morning, you talked a lot about uncomplicate your software environment and so forth. How do you see yourselves from a differentiation standpoint versus your competitors, right? You said you're focusing on that mid-market, people that are of good size and growth, but maybe not 5,000 IT people-

Dennis Woodside

>> Correct. Correct....

Bob Laliberte

>> in departments and so forth. So talk a little bit about your differentiation and how taking away that complexity really helps you.

Dennis Woodside

>> Yeah, so our focus again is 5,000 employees to 20,000. So think mid-market, lower end of enterprise. These are, if you're in the IT department, it's a couple hundred people maybe. If you're in support, again, a couple hundred people, maybe 1,000. So you have the same problems as a much larger organization, but you have far fewer resources. So you're not looking for an unsophisticated solution, but you sure don't want something that's going to take a year to deploy and get value from. So we focus on a couple of pillars. Number one, you want a complete product that is truly end-to-end. So if you're buying an IT solution, it has to work for operations management, asset management. And if you want to take it outside of the IT department, it has to work for other departments as well. On the support side, it has to work in a conversational environment, in email and in voice. So that's super important that it's truly unified. You want AI to be built in, and that's critical. You want your AI to learn from all the knowledge that's already in the system. And as you learn more about your customers and your employees, the AI has to get smarter and you want fast time to value. So in a world where most of our customers, they don't want to commit to five year deals at all. They're saying, "Look, AI is changing so fast that I'm thinking out one year. And if I don't see value fast, I'm going to go somewhere else." So our products have to demonstrate value really quickly and really easily for our customer. And that's the differentiating factor that we have. No other vendor is providing that kind of sophistication, but lack of complexity, fast time to value and AI.

Bob Laliberte

>> Yeah. And that makes a lot of sense, that also you're cloud-based, so there's no long deployment times.

Dennis Woodside

>> Correct.

Bob Laliberte

>> Right. Customers are easily able to get your services, onboard them quickly, and then expand as needed.

Dennis Woodside

>> And we're true multi-tenant. So as we innovate, that innovation is delivered to the customer much more rapidly than some of our competitors who are not true multi-tenant as well.

Bob Laliberte

>> And that also enables your channel partners to deliver as-

Dennis Woodside

>> That's right....

Bob Laliberte

>> a service also. Yeah, that sounds great. So we talked a couple of times about the outcomes and the ROI being really required now. You mentioned a few ways in which your solution is delivering value to organizations. Wanted to give you an opportunity to maybe share some of your favorite customer examples of where they're getting value from your solution as well.

Dennis Woodside

>> So I talked yesterday to a very large player in the aviation space. It's a customer of ours. Now they provide software to their customers, which are Lufthansa and United Airlines. So very sophisticated customers. It's a software company. So the product is complicated, it's mission-critical. If the software goes down, it's a real problem. So they are relying on us for all of their interactions with their customers through our CX product, Freshdesk. And this past year, the leader of the support operation was challenged by their general manager, who like many of us has been seeing all this action in AI. He said, "Look, I want half of our inbound queries to be addressed by AI by October." And this was in May. And so he worked with our team and by October, well over half of their inbound queries, these are sophisticated questions. They're urgent, very time-sensitive, are multilingual, are being answered by AI. So he got there half... Now, what has he been able to do? The people who were previously answering those kinds of questions are working on harder problems, the things that take a lot of human interaction to actually resolve, the never-been-seen-before problems. And that has allowed them to elevate their service delivery overall, resulting in happier customers. So overall, that's just one example of many that we're seeing where it's a win for the customer, it's a win for the service leader, and the business winds up being more effective.

Bob Laliberte

>> Yeah, absolutely. And the happier the customers are, the more likely they are to buy more from.

Dennis Woodside

>> Exactly. Exactly.

Bob Laliberte

>> It's just a big flywheel that keeps going.

Dennis Woodside

>> Exactly.

Bob Laliberte

>> So that makes a lot of sense. And again, working on more of those strategic initiatives, those strategic problems and so forth for organizations adds more value. So that all makes a lot of sense. One of the other areas I wanted to touch upon today was the fact that we're seeing so many organizations, so many technology vendors moving to a platform approach and being able to drive some simplicity. What I might refer to as the principle of least astonishment. So when you go and you open it up, it's intuitively obvious as you work across the platform and so forth. Obviously AI is important. I'm wondering if you could talk a little bit about how your platform approach plays into what you see for your future growth and how AI plays into that as well.

Dennis Woodside

>> Yeah, and I'll talk specifically about the EX side of the business, for our service. So we've intentionally built fresh service to serve the principal needs of an IT department. So the idea is that you can power your IT department and get most of your work done in the environment. So IT service management sits right alongside IT operations management. Asset management, where we acquired a company recently that provides a much more sophisticated advanced version of asset management. We're integrating that into our cloud offering this year. And then employee service management. And then there are other modules that you can invest in too that go even deeper. So we need those experiences to be seamless. We need the information that's resident in one area of that system, one module to flow seamlessly across. We need integrations to work seamlessly in all of those environments. We have several hundred integrations for that system alone that are available in our marketplace. And that really becomes the source of the primary system of record that powers an IT department. So when we say "platform," that's what we mean.

Bob Laliberte

>> Got it. Got it. Yeah, no, I think that makes a lot of sense. So this has been a great conversation. We're getting towards the end. So I just want to, from a CEO's perspective, what are some of the other trends that you're following and what are you excited about right now in software?

Dennis Woodside

>> Well, I think if you're in our space, we are the ones ultimately that are delivering real value for business customers. All this investment that you read about every day is going into the ground, into hardware. And eventually that has to deliver value. So for that to deliver value, our customers need to see the benefit. We have 75,000 customers. What's great is 6,000 of them are paying for our AI capabilities, but 69,000 are not. So we're still really early in this migration and in this AI evolution and revolution. And I think the next couple of years it will definitely accelerate, but it's going to take more and more innovation and time for that 69,000 customers to come along. And so I'm excited about events like this where we get our customers learning from one another, hearing what the latest innovations are, and they'll go back. They'll tell their teams and things will just keep going. So I just think we're so early in this, it's easy to try to anticipate where we're going to be in five years. We got a lot of work to do ahead of us though.

Bob Laliberte

>> Yeah, absolutely. I completely understand that. I think you're in a great position though with all the examples you already have.

Dennis Woodside

>> Absolutely.

Bob Laliberte

>> People leveraging AI, how to maybe even turn that into blueprints for use. The way I always look at it is being able to accelerate those who aren't using it to get beyond the common hurdles that you find from your early adopters. So that next wave really picking up the pace and accelerating.

Dennis Woodside

>> Yeah. I think one of the things that I've taken away from this is we classically think of ourselves as a software development company, but the reality is what we are becoming and what we need to become is an insights company that can help our customers understand what to do with the software, as well as provide the software. At the end of the day, they're making decisions to partner with us as people because they believe they're going to learn something from us and deliver better outcomes. Not just because of the software, but because of what we know, because of the networks that we can bring to them and the learnings that we can bring.

Bob Laliberte

>> Yeah. You become that strategic partner that's integral to their success as well.

Dennis Woodside

>> Exactly.

Bob Laliberte

>> Yeah. Ask them. Well, that's been fantastic. Thank you for all your insights. It's all the time we have for now. Dennis, thank you so much. And I want to thank all of you for joining us. Make sure you stay tuned for more of theCUBE's coverage of Freshworks Refresh.