How to Dream Big Enough to Find $100M Ideas, Not $2M Ones | Freshworks, Dennis Woodside

1. 0:00 – 1:29

   Intro

   1. DWDennis Woodside0:00

      I think the thing about the technology industry is that there's always an opportunity to have a very big impact. You can build products that affect everybody in the world, and you know, we are now a $1 billion scale business. So for new ideas, I need $100 million ideas, right? And that's what we're looking for. It's easy to come up with an idea that might have a $2 million impact. That's not going to move the needle for us anymore. You have to really focus on the big things and accept a little bit of inefficiency in some of the smaller things that might be going wrong. The people that have, I think, the most fulfilling careers and also the biggest impact are chasing the biggest dreams. And I think that's been true, and it was true at Dropbox, it was true, uh, at Google as well. You know, I'm not the kind of person that's gonna be able to come up with necessarily that big idea, but I can help them execute it, and I find that that's very rewarding. You can attract lots of amazing people to your cause when you're in that kind of a situation. So I'd say dream big. I'm Dennis Woodside. I'm the CEO of Freshworks. I have been the CEO for a little over two years. We're a multibillion-dollar leader in the spaces that we compete in, and we are driving huge value for our customers through AI. We have 75,000 customers, so we have industrial businesses, we've got thousands of universities, we've got baseball teams, and their adoption rate is gonna be different. So our job in that situation is to help them come up, up that curve and get the best value out of, out of what we provide and out of what the industry is providing for AI, and AI is gonna enhance the experience in some way.

2. 1:29 – 6:34

   From Lawyer to Google's Americas Sales

   1. DWDennis Woodside1:32

      I've spent 25 years in Silicon Valley in various roles. I actually grew up in Pennsylvania on the East Coast. I went to Cornell University undergrad. So when I was 22, I was, I was a rower in college, and I was trying to row and get on the national team. So that was my biggest dream, but that was... that didn't work. [laughs] Maybe I should have stuck with it longer. Maybe it could have worked. But that was my kind of the first dream, I would say. I don't think I was the kind of person who had, like, these huge dreams to start. It took a while for me to open up my horizons and start understanding that actually it's possible to do that. So I think it just, you know, not everybody's born that way. Not every-everybody is taught that that's possible. You kind of grow up and have maybe more limited horizons when you're younger, and then at some point you start realizing, "Wow, the world's a much bigger place. There's a lot more I can do." I remember one of my friends worked at Yahoo!, and her job was to actually help organize the index. It was manually created at that time. But that was my first exposure to technology and to kind of where the world was going. Practiced as a law- a lawyer for a while. Came in, back into tech a couple of years later at McKinsey, where a lot of my cu- my clients were in the tech industry or in media. And one day, one of my colleagues left to join a startup which I had used, but I didn't know much about them as a company. The name of the company was called Google. And she was recruiting for a strategy team within Google, and she asked me to join the company. I, I flew up to interview. I met Sergey Brin, Eric Schmidt, and David Drummond, and a bunch of the leaders who now are obviously, uh, pretty well known. So when I joined Google, there were, I'm gonna guess, about 1,000 people. This was in late 2020-- 2003, so that was a while ago. [laughs] Google was not public. There wasn't a lot of information outside of, uh, the company about kind of what it was doing or its scale. It was really a search box. That's how most people experienced it. And the question was, "Could it ever be more than a search box?" There was literally no other product other than Search at the time. But, um, mostly what I was attracted to, I met the people, and Larry and Sergey just had this very big vision for how eventually everybody's gonna be connected to the internet and everybody's gonna need to find information and learn. And what an amazing opportunity to create the, a set of products that help people do that. When I met the people who were also surrounding them, people like Eric Schmidt or Shona Brown, I was just very impressed by what they were doing and the commitment that they had to that vision. So I think that was a big factor in deciding to make that decision. And I think when you make decisions because of people, you tend to make the right decisions, right? We all work every day with people, and you want to be surrounded by people who make you better and motivate you and excite you. And that was the case when I was just meeting people for the first time at Google. That's why I chose it. And I remember we did a project for, for Larry and Eric where we said, "Hey, there's like 20 countries where we really should have people on the ground and we can, we can invest, we can, we can actually make money now." And Larry's response was, "That's the wrong way of thinking of it. We, we have searches everywhere in the world. At least one person in every country in the world where we're legally allowed to do business [laughs] because we're gonna learn from those people, and they're gonna teach us how the market's evolving." Um, so I wound up building out some of those teams. I went to Europe, uh, and my, my, my territory was from Russia to South Africa. But that's how I wound up getting into sales, uh, because there was a big sales component and business development component to that job. And then I wound up running sales in North and South America for Google, which was, I don't even know how big that was, multiple billions in revenue. And this was right at the time of the, the financial-- the first financial crisis back in 2009. So the world was melting down, and even Google had seen its revenue go- growth go from twenty, thirty percent to zero. So we had to really kickstart our business all over again and, and move from a world where the, the customers were coming to us to we really needed how-- to learn how to drive the business. Did that for a while. Uh, we-- Google wound up acquiring a company called Motorola Mobility. I became the CEO of that company. Before Google, you're kind of trained in school to think somewhat linearly, right? You-- Like, I was trained as a lawyer. A lot of that's case law. You're learning what came before, and you're trying to apply it to a new situation. But you don't really think exponentially. You don't think about, well, if this technology turns out to work the way it could, this could change the lives of millions, if not billions of people. And at Google, that's how the founders [laughs] thought, and that they built an entire company on the premise that the world was gonna eventually be connected and that search and information was gonna be super important, both for people but for society as a whole. And so I think for me, you know, following that vision was really important. But what I learned about myself is that I might not be able to-- I might, might not be the one to come up with that vision, but I can help execute against it. I am good at organizing teams and leading teams and, uh, having plans that actually get to the-- get to a goal. So I think that was the big lesson for me in Google that, that, that I, I needed, I needed that strong vision to go after, but once I had that, I, I, I was quite good at actually executing against it.

3. 6:34 – 8:05

   Decisions Only a CEO Can Make

   1. DWDennis Woodside6:36

      Girish Mathrubootham started Freshworks in Chennai, India. Now, certainly at the time, there was, there's not a history of technology companies being started in Chennai. Most technology companies in India are based in Bangalore, started in Bangalore. And there certainly had not been a breakout company that built a global business out of Chennai, and very few out of India. So I think for him, you know, having that vision, having that idea, and then his first product was Freshdesk, which is our customer support product to this day. It found a market very quickly because he was early in the SaaS boom. There weren't a lot of tools for smaller businesses in particular that they could just buy online and try and get to work with and that worked well for them. So that boom lasted for quite some time, and he went public with the company in 2021. When I met Girish, he was thinking, "Well, you know, I- I've got the company pretty far. If we wanna be a multi-billion-dollar business, you know, there's a lot that is gonna need to change over the next couple years." And he was starting to think about what was his next chapter. He's very passionate about investing in entrepreneurs, investing in the next Indian generation of entrepreneurs in particular. He had already started a fund that does that, so he wanted to spend more time there, and he was open to bringing someone in to eventually becoming the CEO. You know, they had been on this journey of creating the first public software company out of India that was global, and then they'd accomplished that. So for me and for him, we had to

4. 8:05 – 9:30

   Not the Founder's Call. The CEO's.

   1. DWDennis Woodside8:05

      think, "Well, what is the next mission for us? Where are we going next? How do we, how do we truly take this to the next level?" Look, I think the role of the CEO is to focus on the problems that nobody else can take on. Those can be strategy problems, like where do we compete? What, what products deserve our attention? What products do we or do not deserve our attention anymore because they're, it's not really our future? Um, you have to make those hard decisions. Do we have the right business model? Do we have the right pricing model? Those are hard decisions to make. Do we have the right people, right organization? Those are decisions nobody else can make. So I think it's really important to focus a- as a CEO, don't do someone else's job. But focus on the things that truly affect the whole company, and constantly be thinking about, "Well, what's next? What's the next decision that I need to be thought- thinking about that's gonna transform the business?" And, and it was important for me to establish that trust over time with him about how I thought about the company, making sure it was aligned with what, how he thought about it. So I think the, you know, the role of the operator in that situation is to establish that kind of trust, to deliver results, and to show that you are a good steward for the company going forward, and that's what I tried to do. For me recently, we've made some acquisitions. That can be an example of an area where super important, right? You're not gonna be able to build everything yourself. You're gonna need to go out and find talent or find products that are nascent and that potentially could benefit your customer base. That's a decision only the CEO can make. So I think you always have to think, "Am I focused on problems that only I can handle?"

5. 9:30 – 13:24

   Third Shift, Same Playbook

   1. DWDennis Woodside9:34

      I can remember, like, some of the early mobile experiences, watching YouTube in Manhattan on my phone and being blown away. Like, how is this possible, and what, where is this going to go? This is g- you know, this is gonna change [laughs] the way a lot of people live their lives. So, uh, I think it's the same with AI. I mean, the ind- our industry is gonna spend, and, and specifically the hyperscalers, are gonna spend se- over $700 billion in infrastructure to support the AI build-out just this year, and the estimates are a trillion next year. That's an extraordinary, like, extraordinarily high amount. We can just say $700 billion, but that is a huge amount of money going into servers and chips and, and data centers all around the world. The expectation is that that investment's gonna pay off, right? And that, that, that investment's gonna yield massive productivity improvement for all of us. Technological revolution, the competitive dynamics are gonna change. I think it's, I think it's really interesting to be still pretty early in that evolution. I think the best mindset is to say, "Look, I can know as much about this as the [laughs] world's experts," because the world's experts have only been around for a handful of years, right? There are companies that we compete against today that didn't exist two years ago. So for the last several years, we've all been on a journey in embracing AI in everything we do, so the way we write code now is in- inherently AI-centric. We're shipping at a much faster pace than we did 12, 24 months ago, which really matters in a world where we're competing against giants and we're moving upmarket and we're winning bigger and bigger customers every single quarter. And I think that momentum's just gonna continue. S- so if you embrace it now, you understand how to use AI to make you better at your job, you are gonna be better than others. And, and w- the world's a competitive place, so I, I always encourage people to embrace the change. You know, most founders I know are excited by the pace of change and taking advantage of the speed of innovation that's happening in the industry and the speed of change. And when you have that kind of moment in industry, what also happens is your customers, customers who had gotten in the habit of doing things one way are open to doing it a different way, and that's when a startup can be successful. Founders tend to be very loyal to the people that they started with, and sometimes that loyalty is really a good idea, and you see people scaling from, you know, they were there when the, the team had 100 people, and they're there when the team had 60,000 people. But sometimes that doesn't work. [laughs] And so I think that, I think a mistake is staying attached to people, really focused on people, l- loyal to people, when they might not be the right leader for the next generation of the company. And so you have to watch for that for sure. And you have to be open to the fact that people who maybe were with you at the beginning might not be the right people for you in the future. You have to find the right roles for those people because they're super important to the company. But be willing to, to find other talent that can supplement your team. I look for people who have seen growth because- We're in a growth industry. We're in a growth business. You need to have experience what it's like to double the size of a business in a couple of years. But I also want people who have seen great because there are, you know, there are companies in the Valley that have, are world-class in how they train people, how they develop people, how they, how they go to market, how they build products. So if I'm talking about someone in go-to-market, you know, I like to see that they've worked at a, a Salesforce or a ServiceNow or a Google because I know that the go-to-market organizations in those companies is, is very well-regarded and, and they, they got good training to, to get to where they are. If, if we're looking at engineering people, it might be people from Google or people from Amazon because again, I know that those organizations have really rigorous engineering teams that know how to scale and that know how to build great products. So seeing growth, seeing great, super important.

6. 13:24 – 14:43

   Surround Yourself with Great People

   1. DWDennis Woodside13:24

      I think the most important thing you can do as a leader is to surround yourself with really good people. Going back to, like, why did I join Google in the first place? Why did I, I join Freshworks? Is because I was inspired by Girish here and the people around him. And so really focusing on constantly being connected and, and looking for people whom you might be able to work with down the road who can help you. So an example for us, we brought in Katty Sriinivasan who worked with me at Dropbox. At Dropbox, she was a marketing manager, and she was doing quite well. Time went on, she was the, the CMO of Klayvio and another company. We stayed in touch, brought her into the company, uh, about nine months ago, and she's done an amazing job. So I always like to stay in touch with people who have a lot of potential because you never know how things are gonna develop down the road, and I think that that's the leader's obligation is to find those people, bring them into the organization, and make them successful. [upbeat music]

Episode duration: 14:43