Name: Succession Spotlight: How to Be a Universal Operator and Transcend Industries
Uploaded: 2026-06-02
Duration: 14 min 4 s

Dennis Woodside has held senior operational roles at Google, Motorola Mobility, Dropbox, Impossible Foods, and now Freshworks, where he is CEO. His breadth of experience raises a pointed question: What actually transfers when the industry, business model, and mission change completely?  In this conversation, Woodside will share which fundamental operational skills proved universal, which demanded fresh thinking, and how the COO role prepared him for the top job. 

Dennis Woodside, Chief Executive Officer and President, Freshworks
Interviewer: Diane Brady, Executive Editorial Director, Fortune; Co-Chair, Fortune COO Summit 

Succession Spotlight: How to Be a Universal Operator and Transcend Industries

Conferences

Dennis does a fabulous haiku. We'll see if you come up with someone on the spot, but let's start. So let's start with FreshWorks. You've had obviously this great background, but you are in the middle of a very interesting area with software right now. So you're doing well. What are you doing right? Well, so FreshWorks, we're a software company. We provide software primarily to two teams customer support and IT. And as such we're right in the middle of the AI revolution for better and for worseification of everything, so changing your cost model and changing every business here. So if you think about customer support, many organizations here probably have hundreds of people in support or IT. You have hundreds of people manning a help desk in the next. Years you might have 1/10 the number of people and most of those kinds of operations questions are going to be handled by AI and that's the software that my company builds at the same time we're that's not 10th the income for you, no. So and that's the challenge is that we come from a seat-based model where we price based on the number of agents that you have. What happens if you have no agents and we have customers that literally have gone to support teams of zero and everything is being handled by AI, so your pricing model changes, your products have to change. There's completely new competition from startups as well as huge companies like Anthropic and OpenAI. Many customers here, if you want, you can go to those organizations and build your own software. You couldn't do that a year ago. Uh, so it's a tremendous time of change. At the same time we have the right to win because we've got 75,000 customers. They trust us. We provide software today that actually solves their problems for them. They want governance. They want security. They want control over those outcomes, and that's what we do. OK, so let me, you have been you were a CEO, you're a president really. You're in an operating role and you've been a COO to CEO before. I was talking to another guy this morning who talked about the vision when you're in that COO role and you know that you're going to be in charge, which you did. Did you, um, did you have a vision? Were you going to change things from day one, or was there sort of a tacit understanding that, you know, they were going to start your process once you came on board? Yes, I think it's really interesting, you know, the COO role means different things in different organizations. I was, I was the CEO of Motorola Mobility. We sold it, which meant. I sold it, which meant I sold myself out of a job, and I went to, uh, Dropbox, helped take that public as the COO. Uh, my role there was very much about complementing a very strong founder who, who cared a lot about product and engineering, so I focused on everything else coming into FreshWorks. Girish Mahatra Bin is the founder and CEO for 12 years of the company, also a really strong product visionary and product leader. He wanted to spend all his time on product and engineering. He didn't wanna deal with go to market and sales and finance. And so we just had a clear understanding. I'm gonna focus on the areas that he doesn't wanna, that those happen to be the areas I know the best, and I'm gonna learn from him on the product and engineering side. And if things go well, potentially someday I could become the CEO. But it was a long, you know, there's a lot to do. I had to earn the trust of the board and of. Garish in order to win that job. Well, I think the yin yang of the rule is very interesting, and one of the things I don't think we've actually surveyed who wants to be a CEO here? It's hard to raise your, OK, there's, so there's, OK, and then who's not raising their hand, who's not raising modest and being modest, but you, when you want to be the CEO, what have you learned from your prior experience? that maybe made you better prepared this time around. Well, I think it's important. It's interesting that not many people raise their hands. I think if you have the title target on your back, maybe, maybe I want your job, but if you have the title of COO, you have it for a reason. 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, 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. I think it's important to have a very open conversation with your CEO. Again, based on the trust that you've established, you have to be excellent at what you're doing today. You can't just talk about what you want to do tomorrow, but I think you have to have that conversation. I wanna be the CEO someday. Help me get there. The board needs to understand that the board, the board's job is to make sure there is a succession plan, and the COO can be an important part of that succession plan. So I, I, I found when I was in that role. No one really told me that, uh, and you kind of had to figure it out yourself, but I think it's really important because if you establish that, hey, you know, at some point in time, I want to be ready, you start acting differently. You start thinking differently about your job, and it opens up a whole level of growth that you might not otherwise have. So when you became CEO, especially replacing a founder, was it clear to you what needed to be done differently? Yes, I think that's another thing that's really important as the COO. You know, you have a purview that's probably the largest in the company next to the CEO. I was with the Instacart head of operations. He said he has about half the company reporting in. So you probably know a lot about what's. Going well and what's not going well maybe you know you have a different perspective than the CEO. I think it's important to develop that independent view of where should the business go, have an open conversation with the CEO when there's differences, but also be ready to act so that if you are called into the role, you, you take the company in the direction that is uniquely yours and you're not just perpetuating what was happening before. Even in the best run businesses there are things that you can do differently and better. There are changes happening from the outside, you know, AI is disrupting us, but every business here is going through some disruption. Of different making and you need to understand that and think about well how can we do things better so when the time comes that maybe you do become the CEO you are ready to go. You're not like spending six months figuring out what to do and you don't feel anchored by what was in the past because you have an independent view and you've already talked about it with the CEO. The CEO already knows that maybe you have a different view as to where the company should go, so boom, you move and you take the company forward and that's when I came in as a CEO here. In the 1st 3 months we bought a company, we shut down a couple product lines, and we wound up doing a riff and refocusing the organization, and it's worked and the CEO exited the building, so you didn't have to have them there to help. Well, no, Garris was super supportive. He was on the board for a year and a half. He was the executive chair, which meant that he helped me literally build the next set of products. A lot of the AI roadmap that we have now is because. Girish, he was, he was building AI products six years ago when AI was not a thing yet and so I valued that a lot and I wanted him involved as long as possible. Now he's now focused on his own venture capital fund. He invests in Indian-based entrepreneurs. That's what he wants to do full time. But we're still friends. He literally bought a house down the street from me, and I think that relationship is really important. I know in other situations it's like the old goes out and there's no relationship with the new. I think that's probably suboptimal. So I do want to be aware if you have questions, raise your hand. One of the things I want to talk a little bit about the personal because you also do a lot of Ironman competitions. You've worked at a remarkably eclectic group of firms including Impossible Foods, very different. Give me a sense of how those experiences have shaped the playbook you have as a leader. Well, I think, I think it's important to just other than being fit, we all have to be fit. Yeah, I think it's I like, I like to challenge myself. I think it's important to surround yourself with people who like challenges and like big things. And the great thing about, you know, I've been very fortunate to work in Silicon Valley and The companies that come out of the valley, they typically have very big visions. Impossible Foods was one where Pat Brown, our founder, he, his vision was to completely replace animal meat with plant-based meat, and there's lots of good reasons why that's a good thing for the planet, um, but that's not a small mission, and you know that's not always going to work. It's going to be hard. In that case, food is really hard. It's hard to change consumer behavior. We're a long way from fulfilling that mission, but. But I think, I think people who are attracted to those big challenges, um, like you had Charles from the Navy on, like, you don't, you, you don't, you volunteer to go into a submarine. You do that because you're, you're, you're deciding I want a big challenge for myself and I want to surround myself with people who like those challenges. So I've just always liked to do that. And I've been fortunate that these ideas keep popping up in the valley that keep interesting me, and I'm good at scaling stuff. I could never invent a company myself, but I can help these, and I know you're you're skipping over the Ironman part, but I am curious because I'd say one of the differences in my career in covering CEOs is it is very much now seen as an athletic pursuit in a way that it wasn't. 1520 years ago, I mean, I do want to do that correlation of personal health. How do you think about that? How do you conserve your energy because everybody wants a piece of you? Well, I think there's a couple of things. So I've done, I've done the Ironman 18 times. I usually finish close to the top of my age group. I'm doing 4 races this summer, not a full, but 3 halves in a short race, and And I think it's good to have something outside. It's a lot easier now that my kids are older. When the kids were younger, I couldn't do any of this. But now that the kids are older and out of the house, I think it's good to have something that pushes back against work, like something that where you can think. It's, you know, some people meditate, some people do yoga. I go ride a bike or I go for a run, and that's what I think about things. And I think even if you're not thinking consciously, I think you're probably subconsciously processing what can I do better. I'm going to speak at this event. What do I want to say? And so for me that's always been an important part of my day. I schedule it all in. I collect all the data. Now I'm using AI to plan my, uh, plan my, do my training plan for the year. It's all done on cloud, so I try to mix work and the and the sports stuff in together, and I find it, I just find it rewarding and I like to compete. So that's why I do it. Let's go back to the business and. Especially not just the business you're in and how you are reforming it, but AI generally and the fact that a lot of people are spending a lot of money right now and not seeing the return, you get a frontline view of that. What do you see going on? What advice do you have? Yes, I think so. Recognize how big this is. I think if you're not right in the middle of it. Hard to, it's hard to fathom. We are going to invest $1 trillion in caps and systems and chips for AI. The semiconductor industry has added $1 trillion in market cap in the last year. The software industry, like I said, has gone down by $1.3 trillion. This is a massive transformation. Every business here is going to be affected as the COO. It's your job to figure this out because it's going to define how business is done for the next several decades. It's bigger than the internet. It's bigger than mobile, and it's important to start. Re start acting now in a way that makes sense. Business sense. There's a lot of hype. I guarantee you, a lot of companies are gonna go completely under. You don't wanna partner with them. You wanna find trusted partners that are gonna be around for 10 years that have strong business models that have understand your business and understand what you're trying to accomplish and can drive real business outcomes. But I think if you're the COO, you need to take AI very seriously and personally learn how to use cloud, understand what MCP is, build your own software. You can do all that right now. You do that, of course. I use, I use Cloud. I use Lovable, which is a prototyping app. I send ideas that I've created just on Lovable, you know, in my spare time to the product team, and then they figure out, is this a good idea? It's usually a terrible idea. But um, but I think you have to. Have to walk the walk and talk the talk, and the value of AI is it allows people who don't have deep programming backgrounds to build things and to build tools that you can use internally to build tools that you can ship to your customers. You have to, you have to get your hands dirty on this stuff. And one other thing in the final minute or so we have is you are somebody who also likes to in some ways represent the industry. A COO job is very internal. I mentioned at the start. The narrative around AI, the narrative around software, give me a sense of how important it is you feel to be getting out there and helping to shift that narrative right now. Yes, that's one of the things that you know as a COO you typically don't have to do a lot of your communication probably is internal to your own don't have to deal with the likes of me, no, or investors. You probably aren't, but if you get a chance, spend time with investors, understand how they think because they think very differently than maybe. Than your board does, uh, and, and I think shaping the narrative externally is super important. I probably spend a third of my time on communication to investors, to media, or to the teams internally, and that certainly wasn't true as a as a COO or as a president. Great, please join me in thanking Dennis Woods. Oh wait, do we have what? No, you know what? Can I, um, in 30 seconds just give us a quick comment and then you can continue after. What would you like to say? I wanted to ask a quick question. Is probably not gonna fit in 30 seconds, but, uh, wanted to know you work with thousands of companies that try to automate their operations, right? And I wanted to know from your point of view what differentiates the ones that are successful versus the ones that are not successful, that is a haiku, is it OK. You've got 10 seconds. 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, and that is not you, Dennis Woodside. So there you go. Thank you very much to be continued and thank you thanks for.