How to Dream Big Enough to Find $100M Ideas, Not $2M Ones | Freshworks, Dennis Woodside
In a Nutshell
Dennis Woodside's core message is that companies like Freshworks need to pursue $100M+ ideas, not $2M ones, by embracing exponential thinking and surrounding themselves with people who have both growth experience and world-class training. He emphasizes that leaders don't need to be visionaries themselves but must excel at execution, make tough decisions on strategy and talent, and stay connected to high-potential people for future roles. The biggest opportunities come during industry shifts like AI, when customers become open to new approaches and startups can gain ground against incumbents.
These notes were generated by AI and may contain inaccuracies.
The technology sector offers constant opportunity to make a very significant impact. Products can be built that impact everyone across the globe. Freshworks is now a multi-billion dollar company, and for new ideas, the company needs ideas worth hundreds of millions of dollars. It is easy to come up with an idea that could have a $2 million impact, but this won't change much for the company anymore. Focus is needed on the big things and accepting a little inefficiency in some of the smaller aspects that might go wrong. The people who have the most satisfying career paths are also the ones who make the greatest impact and have the biggest dreams. This was true at Dropbox and at Google. Not necessarily the person who will come up with the big idea, but can help implement it, which is extremely rewarding. A lot of great people can be attracted to the cause when in this kind of situation.
Dennis Woodside is the CEO of Freshworks and has held the position of CEO for a little over two years. Freshworks is a multi-billion dollar leader in the fields in which it competes, and delivers tremendous value to its customers through artificial intelligence. The company has 75,000 customers, including industrial companies, thousands of universities, and baseball teams. Their rate of adoption of technology will be different, so the job is to help them keep up with that development and get the best value from what Freshworks and the sector offer in the field of artificial intelligence. Artificial intelligence will enhance the experience in some way.
Dennis Woodside has spent 25 years in Silicon Valley in various roles. He grew up in Pennsylvania on the East Coast and studied at Cornell University. When he was twenty-two years old, he used to row at university and was trying to row and join the national team. That was his biggest dream, but it didn't work out. Perhaps he should have continued with it for a longer period. Perhaps it could have worked. But it was his first dream of its kind. He doesn't think he was the type of person who had such big dreams at first. It took a long time for him to broaden his horizons and begin to realize that it was really possible to do this. Not everyone is born that way, and not everyone learns that this is possible. You grow up perhaps with more limited horizons when you are younger, then at some point you begin to realize: "Wow, the world is a much bigger place." "There is so much more I can do."
Dennis Woodside remembers one of his friends worked at Yahoo, and her job was actually to help organize the index. It was created manually at that time. But that was his first encounter with technology and with a kind of direction the world is taking. He worked as a lawyer for a while. He returned to the technology field after two years at McKinsey, where many of his clients were in the technology or media industry. One day, a colleague of his left to join a startup he had used, but he didn't know much about it as a company. The company's name was Google. She was recruiting for a strategic team within Google and asked him to join the company. He traveled by air for the interview and met Sergey Brin, Eric Schmidt, David Drummond, and a host of other leaders who are now, of course, very well known.
When Dennis Woodside joined Google, there were approximately a thousand people. That was in late 2003. So, that was a long time ago. Google was not a public company at that time. There wasn't much information outside the company about what it was doing or its size. It was really just a search box. This is how most people have experienced it. The question was, could it one day become more than just a search box? Literally, there was no other product besides research at that time. But what attracted him most was that he met people, and Larry and Sergey had a very big vision about how everyone would eventually connect to the internet, and everyone would have to find information and learn. And what an amazing opportunity to create a range of products that help people do just that. When he met the people who were also around them, such as Eric Schmidt or Shona Brown, he was very impressed with what they were doing and their commitment to that vision. So, he thinks that was a big factor in making that decision. And he thinks when you make decisions based on people, you tend to make the right decisions, don't you? We all work with people every day, and you want to be surrounded by people who develop you, motivate you, and excite you. That was the case when he first met people at Google. That's why he chose her.
Dennis Woodside remembers they did a project for Larry and Eric where they said, "There are about 20 countries where we should have employees on the ground and where we can invest. We can actually make profits now." Larry's response was: "That's the wrong way to think about it. We have research operations all over the world. We should have at least one person in every country where we are legally allowed to do business, because we will learn from these people and they will teach us how the market develops." So, he ended up building some of those teams. He went to Europe, and his region extended from Russia to South Africa. But that's how he ended up in sales, because that job involved a large part of sales and business development. Then he ended up managing sales in North and South America for Google, which he doesn't even know how huge it was, as it generated billions of dollars in revenue. This was during the first financial crisis in 2009. The world was collapsing, and even Google saw its revenue growth drop from 20-30% to zero. Therefore, they really had to revitalize their business, moving from a world where customers came to them to a world where they really needed to learn how to drive the business forward. He did that for a while. Google ended up acquiring a company called Motorola Mobility. And he became the CEO of that company.
Before Google, Dennis Woodside was trained in school to think in a somewhat linear way. As he trained as a lawyer, most of the work is based on case law, where you learn what happened previously and try to apply it to a new situation. But you're not really thinking exponentially. You're not thinking: "Well, if this technology works the way it's going to, it could change the lives of millions, if not billions, of people." At Google, this was the way the founders thought. They built an entire company on the premise that the world will eventually be connected, and that research and information will be of paramount importance to individuals and society as a whole. Therefore, he thinks that for him, following that vision was really important. But what he's learned about himself is that he may not be the person capable of creating that vision, but he can help in implementing it. He is good at organizing and leading teams and developing plans that actually achieve goals. So, he thinks that was his big lesson at Google, which was that he needed that strong vision, but once he had it, he was very good at executing it.
Girish Mathrubotham founded Freshworks in Chennai, India. At that time, there was certainly no history of technology companies starting in Chennai. Most technology companies in India are based in Bangalore, and started in Bangalore. Certainly, no successful and outstanding company has built a global business starting from Chennai, and very few have started from India. So, he thinks for him, having that vision and idea, then came his first product, Freshdesk, which is still their customer support product to this day. It found a market very quickly because it was at the beginning of the Software as a Service (SaaS) boom. There weren't many tools, especially for small businesses, that they could buy online, try out, and work well with. So, that boom continued for some time, and he took the company public in 2021. When Dennis Woodside met Girish, he was thinking that he had taken the company to an advanced level. If they want to become a multi-billion dollar company, there is a lot that needs to change over the next two years. He began to think about his next chapter. He is very passionate about investing in entrepreneurs, and investing in the next generation of Indian entrepreneurs in particular. He had already started a fund that would do that. So, he wanted to spend more time there, and was open to bringing someone in to eventually become CEO. They were on a journey to create India's first global-scale public software company. And they have already achieved that. So, for both of them, they had to think, what is our next task? Where do we go next? How do we truly take this work to the next level?
Dennis Woodside believes the role of the CEO is to focus on problems that no one else can handle. These could be strategic problems, such as: Where do we compete? Which products deserve our attention? What products are no longer worth our attention because they are not really part of our future? You have to make those tough decisions. Do we have the right business model? Do we have the right pricing model? Those are difficult decisions that must be made. Do we have the right people? Do we have the right organization? These are decisions that no one but you can make. Therefore, he thinks it's really important to focus as an executive. Don't do someone else's work, but focus on the things that really affect the whole company, and constantly think about the next step. What is the next decision he needs to consider that will bring about a transformation in the business? It was important for him to build that trust over time with Girish regarding how he thought about the company, and to make sure it aligned with how he thought. Therefore, he believes the operator's role in this situation is to build this kind of trust, deliver results, and prove that you are a good trustee of the company's future. That's what he tried to do. As for him recently, they have made some acquisitions. That could be an example of a very important field, wouldn't it? You won't be able to build everything yourself. You will have to go out and find emerging talent or products that may benefit your customer base. This is a decision that only the CEO can make. So, he thinks you should always consider: Am I focusing on problems that no one else can deal with?
Dennis Woodside remembers some early mobile phone experiences, watching YouTube in Manhattan on his phone and being amazed by it. How did this become possible and where will this lead? This will change the way many people live their lives. Therefore, he believes the same applies to artificial intelligence. He means, the industry, specifically hyperscale companies, will spend more than 700 billion on infrastructure to support the development of artificial intelligence this year alone, and estimates point to a trillion next year. This is an exceptionally large sum. They could simply say 700 billion, but that's a huge amount of money going into servers, chips, and data centers all over the world. The expectation is that this investment will pay off, isn't it? This investment will lead to a huge improvement in productivity for all of them. A technological revolution will change the dynamics of competition. He thinks it's really interesting that they're still in a very early stage of this development. He thinks the best mindset is to say, "Look, I can know as much about this as the world's experts, because those experts have only been around for a few years, haven't they?" There are companies they're competing with today that didn't exist two years ago. So, over the past several years, they have all been on a journey to embrace artificial intelligence in everything they do. Therefore, the way they write code is now fundamentally centered around artificial intelligence. They are rolling out their products at a much faster pace than they were 12 or 24 months ago, which is really important in a world where they are competing against giants, expanding in the market, and gaining bigger and bigger customers every quarter. He believes this momentum will certainly continue. So, if you adopt it now, and understand how to use artificial intelligence to improve your performance at work, you will outperform others. The world is a competitive place. Therefore, he always encourages people to embrace change. As you know, most of the founders he knows are excited about the pace of change and take advantage of the speed of innovation and transformation happening in the industry. When you go through such a moment in the industry, what also happens is that your customers who are used to doing things a certain way become open to doing them a different way. This is where the startup's opportunity for success lies.
Founders tend to be very loyal to the people they started with, and sometimes that loyalty is a really good idea, as you see people evolving; They were there when the team consisted of 100 people, and they are still there when the team has grown to 60,000 people. But sometimes this doesn't work. Therefore, he believes the mistake is to remain attached to people, to focus on them and be loyal to them, when they may not be the right leaders for the next generation of the company. You should definitely keep an eye on that. You must be open to the fact that the people who may have been with you at the beginning may not be the right people for you in the future. You need to find suitable roles for these people because they are extremely important to the company. But be prepared to find other talents who can strengthen your team. He is looking for people who have experienced growth because they are in a growing industry, and they work in a field that is constantly growing. You need to have experienced what it looks like to double the size of a business in two years. But he also wants people who have witnessed excellence, because there are companies in the valley that are world-class in how they train people, develop them, bring their products to market, and build them. So, if he's talking about someone in the field of bringing products to market, he likes to see that they've worked at Salesforce, ServiceNow, or Google, because he knows that the marketing departments at those companies are very prestigious, and that they've been well-trained to get where they are. If they're looking for engineers, they might be from Google or Amazon, because he knows again that those organizations have very rigorous engineering teams, who know how to scale and how to build great products. Therefore, a vision of growth and a vision of excellence are extremely important. He thinks the most important thing you can do as a leader is to surround yourself with good people. Going back to why he joined Google in the first place? Why did you join Freshworks? Because he was inspired by Girish here and by the people around him. So, the focus is really on staying in touch and looking for people you might be able to work with in the future and who can help you. For example, they brought in Kitty Evanson who worked with him at Dropbox. At Dropbox, she was a marketing manager and she did her job very well. Over time, she became the marketing manager at Clavio and another company. They stayed in touch, brought her to the company about 9 months ago, and she has done an amazing job. Therefore, he always likes to stay in touch with people who have a lot of potential, because you never know how things will develop in the future. He believes that the leader's duty is to find these people, bring them into the organization, and ensure their success.
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