Darren [00:00:02]:

Hi and welcome back to another episode of One of one. I’m your host, Darren Gold, CEO of the Trium Group. My guest today is Dennis Woodside. Dennis has had an extraordinary career journey, including beginning as a corporate lawyer, a consultant at McKinsey, a senior executive at Google, COO of Dropbox, president of Impossible Foods, and now CEO of Freshworks, an AI enabled software company focused on disrupting, empowering the next generation of customer service and IT service management functions. We spend time covering this amazing set of experiences. We explore Denis’s unique ability to attract and grow top talent and we dive into his long history as an endurance athlete and how that has shaped who he is and how he leads. We had a lot of fun in this rich conversation and I trust and hope you will too. 

Dennis, it’s great to see you. Thanks so much for being here. I’m really excited about this conversation.

 

Dennis Woodside [00:01:08]:

Thanks for having me, Darren.

 

Darren [00:01:09]:

If my calculation’s right, we go back a long way and I think it’s 29 years. I think the year was 1996 when we first met.

 

Dennis Woodside [00:01:18]:

So I think that’s right.

 

Darren [00:01:19]:

It’s been a long time. We’ve got a lot of ground to cover. But it’s so nice to be having this conversation given that history.

 

Dennis Woodside [00:01:27]:

Yeah, it’s good to see you and yeah, it has been quite a while back in LA when we first met and we were both lawyers, so quite a different space now.

 

Darren [00:01:35]:

Yes, we were. That’s probably a distant memory for you as it is for me, but a formative one nonetheless. But yeah, it’s good to see you and you’ve had a pretty significant, illustrious, remarkable almost 30 year old career since then. And since those that are listening may not be fully up to speed, I’d love for you to take U.S. back to 1996, your early years as a lawyer.

 

Dennis Woodside [00:02:02]:

You know, it all got better after I met you, but, oh well. So I grew up on the east coast and grew up in Pennsylvania, went to school undergrad at Cornell and I was interested in the law actually was a competitive rower, was in contention for the national team which kind of got me into endurance sports and that became a theme throughout my life, but wound up going out to Stanford for law school. I think most important thing there is I met my wife Laura at Stanford who you know quite well and we’ll skip back and forth, but if we were to fast forward to recently, you know, our kids wound up going to school together, which is quite a, quite a coincidence. But now met Laura at Stanford, decided to practice law for A while, wound up in LA working for a firm called Munger, Tulls and Olson, which is where I met you and your wife. And I remember you were practicing as well at that time. Is that right?

 

Darren [00:03:01]:

Yeah, I was.

 

Dennis Woodside [00:03:02]:

And where were you? Just remind me what I was at.

 

Darren [00:03:05]:

The second best law firm in la. You were certainly the best. I was at Irel. Irel and Manell.

 

Dennis Woodside [00:03:11]:

Irel. Okay, so. And I think you were litigator, is that right?

 

Darren [00:03:14]:

That’s correct, yeah.

 

Dennis Woodside [00:03:15]:

Okay, so I think one of the first times, for those who are listening, that I met Darren. He was telling me about a case that he was involved in. I don’t know if you remember this, but you know, we were both like 26 and I was like, so what do you work on? He’s like, oh, I got this coolest case. I’m like, what is it? Well, you know how they at the time VHS tapes were a big deal?

 

Darren [00:03:39]:

Yeah. You’re dating us here.

 

Dennis Woodside [00:03:43]:

One of the studios decided to save money and reuse VHS tape and somehow they over recorded like a feature film for distribution through Blockbuster, but it was re recorded on top of an adult film and they were getting sued. Do you remember this? Something like that.

 

Darren [00:03:59]:

Of course I remember it. It’s close. Yeah, I was on the, on the. Yeah, I was the law firm representing. It was actually, it was not a motion picture, it was a Abflex, those ridiculous infomercial.

 

Dennis Woodside [00:04:12]:

Even better things.

 

Darren [00:04:13]:

It was their instructional video and went to some, some video duplication facility in the San Fernando Valley which happens to be the home of the adult entertainment industry. And rather than purchase new tapes, they, the duplicator used old tapes and it was an adult film. So it was. They showed up in targets, people would buy their thing, go home. The discovery on that case was interesting to say the least, but it brings back good memories.

 

Dennis Woodside [00:04:39]:

That’s kind of one of the early stories of me meeting Darren and anyway, went on from there. One of the things that happened was that my wife went to McKinsey and I had been working on a bunch of. I was a corporate lawyer, so worked on M and A stuff and was always a little more interested in what the business people were doing on the deals that I was working on. And then she kind of got me meeting a bunch of people from McKinsey. That seemed like a pretty interesting path. And McKinsey was recruiting lawyers at the time. So I wound up moving over to McKinsey and I thought of it as sort of a, a way to expand my education, learn a lot about business also, I like the fact that law is a very local thing. You’re licensed in a state. And I was very much interested in the more international aspects of things and wound up working a lot in tech. And that’s kind of my first exposure to the tech industry. First for companies like Disney that were being disrupted by tech, and then ultimately for technology companies, early web companies. And one of the partners at McKinsey wound up going to Google. And I had used Google as a search engine, but didn’t really think that it was. I didn’t know much about the company at all as an actual company. And she said, hey, you’re flying around a lot now. You might consider moving over to a company and taking a strategy role. And I need to hire somebody to do that at Google. And I was kind of skeptical because I worked with some startups before. I thought, I like, McKinsey’s an organized place, there’s a lot of structure and all that. But I went up, I met the Google team, and I was just really impressed. I met Eric Schmidt in my first. My interview panel. Sergey Brin interviewed me. Their cfo, Jonathan Rosenberg, who I’m friends with to this day, who headed up the product organization. And just the people that they had assembled in the company were amazing. And the activity level in the organization, you walked around the halls, it just felt really buzzy. It was still a small company. It was about 1,000 people at the time.

 

Darren [00:06:32]:

Yeah, I was gonna say that was not an obvious choice. And, you know, the other part of the story here is I was at McKinsey in the same office when you joined.

 

Dennis Woodside [00:06:39]:

Right, right. You went to McKinsey. Yeah, that’s right.

 

Darren [00:06:42]:

I left to another, more conventional path. And when I heard you were going to this small startup, right, like in the wake of the dot com implosion bust. That’s right, yeah. Right. I was like, what is he crazy?

 

Dennis Woodside [00:06:56]:

Well, that’s what everybody said. I mean, there was. Of all the people I Talked to at McKinsey, there was only one person who said, that’s a good idea. Everybody says a bad idea. So anyway, I listened to my instincts, which is lesson number one. Sometimes the people around you are biased by the experiences that they’ve had. And I just, I love the idea of helping build a company. That was what was intrinsically interesting. You know, when you’re in consulting or law, you’re seeing a piece of a company for a short period of time. But I liked the idea of being able to contribute over a sustained period of time. And Seeing what happened. And so my job was to build the strategy team and we didn’t have one. So I hired from consulting firms, hired engineers, people who were smart analytical thinkers. One of the first hires was a physics PhD. We’d never done anything like that before, but super analytical I hired another. One of our first hires was a fighter pilot in the Navy who was literally a top gun pilot. And our jobs were to work on whatever Larry and Eric thought were problems that weren’t neatly product or engineering or go to market problems. So an example was we helped Urs Hozel who built out the infrastructure for Google, all the data centers. We helped him build a supply chain. We didn’t have a formal supply chain for how you built data centers. We worked on a project for Eric which was how could Microsoft screw us and what should we do to prevent that from happening? So it’s kind of competitive dynamics and really interesting stuff. But one of the more interesting ones for me was I worked on a project around internationalizing Google. So where should Google have offices in the world? What should those offices do? And I remember I did this with Sukinder Singh Sukinder is now the CEO of Xero, which is like an Intuit competitor, Australian based, amazing executive.

 

Darren [00:08:47]:

She was on this show.

 

Dennis Woodside [00:08:48]:

She was on the show. There you go. So amazing, amazing person. And the project was okay, where should we go in the world? And we sort of split up the project and came back and said, look, there’s 25 countries that really ultimately will matter for Google. And I remember Larry Page and this is like the power of thinking different. He’s like, well look, we get searches in 196 countries. Why don’t we take out the seven countries where we’re not allowed to do business by law and come back with a plan to get into the 189 countries or the 169 countries where we’re allowed to do business. And that’s how we thought and we actually had to go back. We wound up hiring people in places where we had no near term commercial business like Nigeria and Kenya and Egypt, just to learn the Internet. And his whole thinking was if we learn what’s going on in the Internet and how behaviors are changing, that’ll make our products better over time and we’ll be able to compete. And eventually all those people are going to be online anyway. So we did some really cool stuff. It was a lot of fun. But that project, eventually they needed someone to actually go build out those teams. And I remember Omid Kardistani was looking for someone to take one of the roles. Sukindra wound up doing egypac and Latin America and building a bunch of teams there, but there was Emea. So from Russia to South Africa, that was open and I kind of pitched myself. And he said, well, have you ever been to any of these places like the Czech Republic or Israel or Turkey? And I was like, no. Like, do you ever speak any languages? No. He said, well, you know, we’re gonna find somebody who actually has done this, so come back, you know, come back when there’s something a little bit more suited to your skills. And like two months went by and they couldn’t find anybody. And it was like priority number 10 for him, I’m sure. And I convinced him to give me the job. So I wound up moving into sales and my territory was from Russia to South Africa and over the course of a couple years opened up like 13 offices across that region. Every, every we lived in London and every Monday I’d fly to a new country. So that’s how I kind of got started in tech and in Google.

 

Darren [00:10:48]:

What was it about you, do you think, that convinced him to take a leap of faith?

 

Dennis Woodside [00:10:53]:

When you’re in a fast growing company and there are people who have been successful, sometimes knowing the context of the company is more important than knowing the domain of what you’re going to go do. And in this case, I think you probably figured it’s kind of a low risk. We don’t have anybody in any of these places. Now I trust him and he has a good plan. Let’s see what he could do. I think that that’s, that was kind of the thinking behind it and it was an amazing job because, you know, part of it is hiring and building teams in completely different cultures. So we had a Turkish team and an Israeli team and an Egyptian team. Right, let’s talk about three different cultures. We had Polish leaders next to Ukraine and Russia. Right. All, all on the same team. And so building a team in that environment. And most of the people who would join Google were a little bit, they had a little bit of a creative streak. They weren’t in the mainstream or they had a reason to believe in the mission. So the person who headed up our Polish office, his parents were detained by the Polish police when he was a kid for disseminating information that was against the, you know, at the time, the communist state. So the idea of working for a company whose whole mission is to free information and get it into the hands of everybody, that’s really compelling and so we would find people like that that had a compelling reason to join the mission. And then it became easy. If you hired a mercenary, it didn’t work. If you hired a missionary, it worked really well.

 

Darren [00:12:21]:

Nice. That’s a good distinction. Yeah.

 

Dennis Woodside [00:12:23]:

So anyway, that’s how we got started and I wound up moving into more of a traditional sales role. The UK sales role opened up and that was the biggest role outside the US in sales. That was more selling to if you know any of the UK business like Marks and Spencer and Harrods and the traditional companies and convincing them of the power of the Internet because the Internet was still young. This is 2009, 2008 and then building a team that could evangelize what we were doing with ROI driven advertising, search advertising, which again at the time was all new. That led to be a role in North America where North and South America, which was the biggest region for the, for the company where I led all the field sales teams. Now you’re talking thousands of people, billions of dollars. And I took that role right in the middle of the financial crisis where our revenue, this is, you know, now it’s hard to believe this but Google’s revenue growth went from like 30% to zero. Our stock went from like, I think it was 700, went to 120. So it was, you know, this was total crisis in the economy and our goal was to get the company back to growth and to really kind of get on the forefoot of accountable advertising in a downturn and, and we redid a lot of things about how we went to market and wound up driving growth from that role as well. So lots of, I mean Google’s amazing experience.

 

Darren [00:13:45]:

You’re really leading at scale at this point in your career.

 

Dennis Woodside [00:13:48]:

At that point. Yeah, at that point definitely leading at scale, working with some amazing people. I work very closely with the CFO of Google, guy named Patrick Bashette. I work with Nikesh Arora, who’s now the CEO of Palo Alto Networks. So learning from people who are world class all around you, super important because Google at this point is off to the races. Public growing really quickly, able to recruit amazing people into the organization who then go on to amazing leadership roles as well. And now it’s all about like how do you find world class people, build a world class team, how do you scale that world class team, put the process in place to drive performance, build relationships with your partners and your customers that are lasting and benefit them. All that stuff comes more into play in that role. Both the UK role, but the Americas Role was really the first role where it’s literally thousands of people on the team.

 

Darren [00:14:42]:

Yeah. So I’m interested to understand your emerging leadership style, approach, philosophy and how would you describe that? I’m also going to imagine that if I ask you that when we get to the present day, there’s probably some evolution in that. But if you wind the clock back 15, 16 years ago, you’re leading at scale. How would you describe yourself as a leader? How do you think about leading people at scale at that time?

 

Dennis Woodside [00:15:08]:

Yeah, I think so. I think it’s just different in different phases. In that first kind of that emerging markets role, it’s finding the evangelists and the missionary. When you got to the Americas, you need people who can think strategically longer term. Also are focused on their talent and how do they build their talent, how do they create consistency in the process of how they run the business so they create predictability for their teams because people thrive, thrive when they know what’s expected of them and they know when is it expected, how is it expected. That kind of consistency of performance. That’s very different than a super early stage startup where everything’s changing all the time. So a lot of it was finding people who, who had that and then finding complimentary people. So I, you know, one of the people that wound up working for me was named Benita Stewart. And Benita I gave, she wound up running all of the businesses or the, she had the customer base that was not quite ready for the Internet. They didn’t have. You couldn’t buy the products online, like automotive as an example. But she came from more of a branding background and I did, I didn’t come from that background at all. So she was able to complement our team overall and bring a set of skills and characteristics that we just didn’t have into the organization and then hire a bunch of people like that, which when Google got into YouTube and video and more brand building ad formats became super important. I also like taking people, you know, the thing about a growth company is you get very ambitious people and people are always looking for a challenge and I always like to find people who kind of raised their hand and said I need a new challenge and try to find them that challenge. I took that as my personal goal. And I remember there’s a guy named Jason Spiro who was super talented salesperson, kind of raised his hand and we said, well, I said, well why don’t you, you know, mobile’s a new thing, mobile advertising is a new thing. Why don’t you run mobile advertising and he just, he knew nothing about mobile advertising, but he learned it and he just threw himself into the role and it became a huge, huge boost for his career and also for the company. So at scale, you need to constantly be cultivating leaders who can help you and who can, who can drive the business forward. And your job is really as a talent manager more than anything else because you don’t directly, you know, influence thing. You don’t directly sell that much. You’re relying on the people around you to do that.

 

Darren [00:17:31]:

Yeah. Okay, so your career at Google takes a little bit of a turn at some point soon, is that right, in terms of your next role?

 

Dennis Woodside [00:17:40]:

So I’d been in sales for a while and I was like, well, you know, I’d like to do something else besides its sales. And, and I’ve been talking to Nikesh and others. And by coincidence, Google wound up buying Motorola Mobility. And the story behind that was Google had acquired a company that ultimately built Android. The operating system put Android out into the world, had gathered a bunch of partners like Samsung and LG to build their devices on top of Android at the time, you had iOS, you had BlackBerry, you had Windows Mobile, you had Nokia, had an operating system. So the operating system environment for mobile was very fragmented. And Google’s strategy was, we’re going to open source Android, it’s going to be free. And the only catch will be you’ll need to take. If you want to use Android as your operating system, you’ll need to participate in our marketplace and make Google search a default, make YouTube a default, and so forth. And that strategy worked really well, except that Google got sued by all the other operating systems for IP infringement. And Google didn’t have a habit of patenting its own ip, so it didn’t have anything to defend with. And as a lawyer, you’ll kind of understand this. So its choices were to its partners were going to get sued potentially to the point where they would not find Android attractive and Android would die. Or Google could defend by going out and finding IP and then using that IP as a defense. And that’s what it did. So Motorola had been a struggling mobile device manufacturer that was recently spun out of the bigger Motorola corporate. There’s a long story there. There was a corporate activist, Carl Icahn, who was a big shareholder, who was actively pushing the company to sell, but based on the IP that it had, and ultimately Google bought the company for 12.5 billion. And with that, with the IP came 20,000 people, came a business that was losing a billion dollars A year and was actually more than one business. It made mobile handsets, it made set top box devices, and it made infrastructure for the cable industry. So very different set of businesses and very different than what Google had ever done. And Larry asked me to kind of put my strategy hat back on. And as a secret project before we closed the deal, we had signed a contract, but we had to go through the regulatory process, figure out what’s the strategy for this company, what are we going to do with the actual operating unit. So we kind of came up with a strategy and we knew from the beginning that the business that was in cable, set top boxes, cable infrastructure, that was exactly opposite of the YouTube strategy, you could not actually own both of those. Your customers would go away. And so we decided from day one we were going to sell that business. And then that left the handset business. And there was some potential synergy like there was some talk about, well, we should compete directly with Apple. But there wasn’t consensus, I would say internally as to what we should do with it. And I ultimately became the CEO of the company. And so the day that we closed, all of the Motorola employees, they were technically Google employees, but we, we managed the company as if it were just a wholly owned subsidiary of Google. Google owns the shares, but we did not integrate the company in any meaningful way because we couldn’t, we didn’t want the partners of Android to feel we were competing against them. But as a result, Motorola didn’t have much strategic advantage of being part of Google and we had to compete on our own. So we wound up building a new team there again bringing in a lot of new talent, bringing the company from the smartphone era where it was the, I mean this is a very proud company that had shipped the razr, which was at one time the best selling phone in the world. And all of a sudden iPhone comes around and they’re way in the rearview mirror. So we had to bring them into the smartphone era and very drastically simplify their portfolio and figure out a bunch of product stuff. And culturally it was super hard because you have people who were used to like five years ago, they were the leader, they were one of the technology innovators. And iPhone comes out and all of a sudden it’s all different, right? Android comes at Samsung, gets in the game, it’s, it’s a completely different competitive environment. So you have to explain, do a lot of explaining as to how we’re going to improve and what we can do. And I had to explain what Google’s relationship was With Motorola, it was, it was a very hard job. We’d lay a lot of people off because we’re losing $1 billion a year. Like that was not a sustainable business even for Google to kind of hold on to. Or to. Yeah, to, to continue to sustain those losses. So ultimately I remember talking to Larry and saying, look, unless we’re willing to invest a lot more money and you know, make our own screens, make our own cameras, we should not be in the business. And we wound up selling, selling the business to Lenovo about two and a half years after. After buying it.

 

Darren [00:22:35]:

Yeah. Any big, other than maybe whether to buy it. Strategic considerations. But in terms of your, your leadership, your evolving leadership approach philosophy, were there some lessons from that period of time in particular?

 

Dennis Woodside [00:22:50]:

Well, I think in retrospect I was definitely naive about having consensus among the team as to what the longer term game plan needs to be. And I think that, I sense that we didn’t have that kind of consensus, but maybe it was an aversion to conflict, but I didn’t lean into it and really make sure that we all had a alignment on what’s the long term plan. Are we going to integrate this company in with Google? Is it going to become part of Google or is the plan. We really just want the IP and we want to kind of move on from there. So I think that was definitely a lesson in. Okay, you need to walk into situations with your eyes open. You need to make sure everybody’s aligned and what’s the long term goal? What is a win here? Because it took a lot of work after the fact to figure all that stuff out. And the other thing is that some situations are just very hard to come out and really declare a clear win. When you’re the number five player in a hardware market, it’s really hard to compete. It doesn’t matter what the leadership team looks like, who they are, it’s hard to compete. There are some businesses that are just really, really tough.

 

Darren [00:23:57]:

Yeah. So does that bring your Google career to an end? And at some point you’re. I know we kind of reconnect in some ways professionally.

 

Dennis Woodside [00:24:04]:

Yeah, that’s right. But yeah, so, yeah, so I wound up going to. So I was introduced to Drew Houston, who is the founder of Dropbox somewhere along the way and once we had sold Motorola, he kind of started reaching out and saying and talking. And I always liked the idea of helping a founder like scale a business from a really early stage. And I was at Google early but I wasn’t working directly for Larry and I wasn’t like there at the genesis where they were really trying to figure out a bunch of things from first principles and create a lasting business. So I like the idea of doing that and helping a founder do that. And I had the background to do it. So Drew and I just started talking and you know, Dropbox at this, at that point was maybe 200 million in revenue, but just a skyrocketing business where this notion that now it seems like obvious and we’re so used to it that it’s not as revolutionary in our minds. But at the time, all of our information was on a hard drive and we have multiple hard drives. So you could have things on one computer that the other computer didn’t have access to on your phone. It was really a pain. And people would walk around with thumb drives and all that. And his whole idea was, let’s put all that in the cloud, make it super easy to sync information, share information. Much easier. And he was first to build a product that did that. And coming from mit, he had the technical chops to engineer a solution to a very, very hard problem and he was off to the races. But he also realized that he wanted to build a multi billion dollar business and he needed to scale well beyond the technology, all the different functions that you need to build a lasting org. So he and I started talking. I met Arash, his co founder and they brought me on as a COO and what that means a lot of things in a lot of places for us. I had everything other than engineering, product and design, which reported directly to Drew. So all the go to market functions, hr, comms, marketing, that sort of thing were with me. And basically we just got about kind of building that business up and creating another product line which was focused on businesses Dropbox for teams, which is a big driver of their growth today, doing all the things you need to recruit a team that can take a company public and then ultimately going through the process of positioning the company with investors and going public in 2018. So that was an amazing experience as well in recruiting leadership who wanted to be part of growing a business, building a business. We brought in some amazing people there as well. I always view my job as like, first thing I have to do is build the team around me. That’s a really amazing team with amazing people. Some of the people we wound up hiring, like Arden Hoffman was our Chro. She came from Google. I worked with her a bit, but she’s now the Chro at General Motors, one of the biggest companies in the world. And think about that job is incredibly hard. You’re dealing with unions, you’re dealing with the same kind of war for talent that you’re dealing in the tech industry. Just a super versatile, amazing executive. Yamini Rangan was also on the team. She’s now the CEO of HubSpot. So it’s a lot of fun to look back and see people who kind of, you put in roles. Obviously you knew they were going to be successful, but then you had no idea how successful they were going to be. And to see that happen has been really rewarding.

 

Darren [00:27:16]:

Yeah, I’m starting to see this theme around having a discerning eye for great talent and then creating sort of breakthrough growth opportunities for them and then to sort of see the dividends years later has got to be very fulfilling for you.

 

Dennis Woodside [00:27:29]:

Yeah, I think giving people, putting them a little bit over their heads and recognizing not everybody’s going to be able to handle it. But for those who are, often it’s a breakthrough experience for them and often you get way better results than handing something to somebody who’s done something five times.

 

Darren [00:27:45]:

Yeah. So I want to keep going and get to the present moment here. I know there’s a stop between where you are today and where you are now, but let’s get us there and then I’d love to get into bringing to life like you as a leader, but let’s complete the kind of the career journey here because it’s just a fascinating one.

 

Dennis Woodside [00:28:01]:

Sure. So I gotten to know Vinod Khosla who’s the Khosla Ventures and co founder of Sun Microsystems. He, after we went public, he was like, hey, you got to work for one of my portfolio companies. And I, I talked to him for a while and eventually introduced me to the founder of Impossible Foods. And this was back to sometimes businesses are really hard for a reason. But this was completely different. The whole idea is that you can re engineer meat from plants that’s as nutritious and delicious as the animal, but that’s healthier and at lower cost to the environment. That’s the thesis behind the company and they’ve done reasonably well. So I went in and helped him scale that business to a couple hundred million in revenue. But at the end of the day, the challenge for that business going forward is a consumer marketing problem, which I am not the expert on. So how do you change consumer behavior? That’s the hardest thing that they have to do the product in blind taste tests. It’s very, very close to the animal. The nutritional value is actually better. But how do you convince people who are used to eating animal meat to eat plant meat? That’s the challenge. So wound up bringing in a CEO who comes from that world, came from Chobani. And then I left to join freshworks.

 

Darren [00:29:14]:

Yeah. Again joining another founder and Yirish. And so that’s three years ago that you joined. Tell us the arc of that experience so far because you’re now leading it and have been, I think, for a little over a year.

 

Dennis Woodside [00:29:28]:

Yeah. So Juris is an amazing founder. He did not go to Stanford or mit. He grew up outside of Chennai, India. And Chennai is not the tech hub of India. Chennai is like the Philadelphia of India of an industrial city. Its former name is Madras and there was a lot of textile there kind of back in the day. It’s a port city. And he grew up and he saw technology changing India early on with the Internet. He started a company to educate people in Java how to program Java. That was his first company. He wound up getting educated mostly in India, but then working in the US for a business process outsourcing firm, which a lot of, you know, those were the first tech jobs that were coming out of India. And he wound up educating himself on product management, the art of product management. He was a sales engineer by early training, so he spent a lot of time with customers, but he also spent time with the engineering and product teams. And he had this idea for when SaaS became a thing for a customer support tool that any company in the world could use that’s entirely SaaS based, which was unique at the time. There weren’t tools like that or there weren’t many at the time. So he left his company, which was Zoho, which is another tech company in India, and started freshdesk at the time as a customer support tool for any business in the world. And his first customer actually was from Australia. So from day one, they were an international business. His thesis was, anybody’s going to be able to access software made in India. So let’s build software here. Let’s create a global business. And it worked. The product took off. He wound up going from a product for support and SMB to support and larger businesses. So today, you know, companies like Klarna in B2C and Discover cards in B2C and big divisions of Airbus in B2B use the same Fresh Desk tool that he built back then. And he also saw that being pulled into it. And so he built a separate product called Fresh Service, which is for any IT department. Every IT department has at most have. Have something called An IT service management platform. It’s how they answer questions, receive questions from their employees, escalate issues and problems and ultimately resolve those problems. And so that’s what he built and, and those products took off, took the company public in 2021 and then we met in 2022 when he was thinking about bringing someone in who could help him scale the company to the next level. So I joined in September 22 as president and there was some thinking that over time Gears might want to do something slightly different. And then I became the CEO just in May of last year.

 

Darren [00:32:13]:

Got it. Well, congrats on that. Congrats on, you know, an incredible three decades of your career. It’s hard to, hard to believe because.

 

Dennis Woodside [00:32:21]:

We’Re in that third. Right?

 

Darren [00:32:23]:

Yeah, exactly. I want to bring to life you as a leader and sort of three dimensionalize you a bit. For listeners that are curious, what is it like to be led what is it like to be part of a senior management team or part of a company that’s led by you? Maybe in the current company, freshworks.

 

Dennis Woodside [00:32:43]:

So freshworks. So just to finish that kind of what we do. And then I’ll get to the leadership side. So we compete in two spaces, customer support now and IT service management. We provide an AI enabled product to enable any customer support or IT team to provide world class service to their employees and their customers. And we’ve got 73,000 customers around the world headed towards a billion in revenue. I like to say we compete with, and this will get to the personal side. We compete with about 500 billion in market cap. So our top competitors are ServiceNow, Salesforce, Zendesk, Atlassian and HubSpot. My friend Yamini runs HubSpot. So those companies combined are well over 500 billion in market cap. Our market cap is about 5 billion. So we are the upstart, the challenger that’s trying to disrupt that space with a product that’s easier to use, faster time to value. It’s about half the cost of our competitors. And my view in that world is we have to think of ourselves as competitors. We have to train as competitors. Every situation where we’re in front of a customer is a situation we can advance the ball in the right direction or we can kind of go backwards. And so what I’ve tried to do is bring that competitive spirit, that competitive ethos, which also kind of is my background from the triathlon stuff, which I’m sure we’ll, we’ll get into. But that is really important, I think in a business like ours. You have to, you have to show up and be willing to compete and be willing to learn and think like an athlete. And you know, world class athletes always talk about being coached and trained and learning and adapting and then, you know, understanding that you’re not going to win every, every game you go into, but when you don’t win, learning from it, coming back and then going out and winning. And so I think that’s a very different company than let’s say I’m working for Microsoft today or I’m working for Google today. You know, Google’s not going to win, not going to lose many, many deals at all. Microsoft’s not going to lose any deals at all. So you’re not going to learn the same things that you’re going to learn in a company like ours where you’re really trying to build the business in a way that hasn’t done before. We’re constantly going after bigger deals, bigger companies, companies that feel like they’re too big for where we are now. That’s what I want. Those are the situations I get involved with because that’s where you learn the most. So that’s the ethos that I’ve tried to bring, is that you have to compete. I like people who have been in competitive sports team environments because they have that ethos, they have that competitive drive and they also, they understand they’re not going to win it all the time and that, you know, some people who haven’t lost, when they do lose, it really hurts them and you need to be resilient and able to bounce back from that and brush it off in order to be able to be competitive. You talk about like Girish is a good example. You know, his, his first business ultimately failed and his second business ultimately failed. But here he is, he’s probably one of the most famous entrepreneurs in India having built what is now a, you know, billion dollar software company.

 

Darren [00:35:39]:

Yeah, I’m picking up there’s an intensity to that way of leading. Right. Holding people to really high standards, setting the bar really high. Is that true for you? What does that look and feel like in the everyday?

 

Dennis Woodside [00:35:54]:

I think what I like to do is find other people, surround myself with people who also have the same commitment to doing things the right way. And then it’s less on me. Right. I think the team that I built at Fresh, the team I built at freshworks, the team I built at Dropbox, like the people on that team, they had high standards before I ever met them. And so it wasn’t about me teaching them how to have those high standards. They kind of brought those in to begin with. And so then it’s about coaching them and helping them be successful in their role. And a lot of what I do at this level, when you’re the CEO, ideally you have a team of stars who are absolutely amazing in their function and your job is to help them execute as a team. And that’s very different than when you’re kind of like lower down the organization and you have to teach people their jobs. I don’t have to teach my CFO how to be a cfo. What I have to do is create the environment where you can be the best possible CFO and work well with our head of sales and our head of marketing and be successful as a team. That’s where I spend more of my time. Are we creating the right environment for the team to be successful and for all the individuals to be successful within that team?

 

Darren [00:37:02]:

And how much of this ethos was in place when you joined in 2022? How much of it needed to be built and what was the process you went through to evolve the culture to the extent it needed to be evolved?

 

Dennis Woodside [00:37:14]:

So Girish had absolutely similar focus on team. He talks a lot about team sports. He’s very involved in the community around Chennai to the extent that he has started a soccer academy for young kids who otherwise wouldn’t have the opportunity to. To kind of learn soccer and develop. His goal is to create players who can play on the national team. So that’s. He is very, very goal oriented, very team oriented. I think the shifts that we’ve made, you know, in an entrepreneurial business, success often comes by trying a lot of things and seeing what works. But when you get to a certain size and scale, you have to try things that have a good probability of being like hits like I need to find the next hundred million dollar business. That’s I was with our product team today. It’s exactly what I challenged them like we have, we already have a line of sight to multiple new hundred million dollar businesses in our portfolio. But we need to find the next one. Right. And so I think one of the things that we’ve changed is we can’t fund everything. We have to be a little bit more thoughtful about funding big ideas that have the opportunity to make a big impact on our customers and solve bigger problems. So that means you need to be a little bit more thoughtful about longer term strategy and planning. And sometimes you can’t be as quick to change course in that environment. That’s the kind of change that I think I’ve brought. And you also have to think at a different scale. We have close to 5,000 people now, and the people who are on my leadership team, three of them, lead roughly a thousand people each. So the scale of how they lead is very different than when we were a younger company. So I wouldn’t say it’s a massive change. It’s just a, a refinement of the path that we were on that Kanagira set us on.

 

Darren [00:38:59]:

And are you methodical about this? Take your time, you’re gradual. Or do you hit things sort of like head on and are sort of demanding of change immediately?

 

Dennis Woodside [00:39:10]:

I think it’s a little of both. I mean, you can’t, you have to know when to say, hey, we’re doing this and we’ve talked enough, let’s go. But at the same time, for my team to be effective, I need to make sure that they are all aligned on the direction, the right direction to go in and the choices that we’re making. And so we spend a lot of time as a team talking about what are the actual choices that we have in front of us and how do we think about the different paths that we might take before we completely commit and dive in and go. So I think that planning phase and process and being methodical, soliciting people’s views, often you hear things that you didn’t think of in that process. I think that’s super important before you just fire off and say, go, I’m not. Rarely am I just like making a decision off the cuff. CEOs shouldn’t need to do that. That’s not the job. The job is to create the environment where collectively you can make the right decisions that pay off over time.

 

Darren [00:40:08]:

Is there anything unique about this role of being CEO? I mean, putting aside the Motorola Mobility, which was earlier in your career, and maybe a bit of an outlier, you know, in terms of, you know, your experience. Anything that, you know, being at the helm of a company at this size as CEO for the last year and a half, that’s unique, perhaps surprising or different than you’d experienced before.

 

Dennis Woodside [00:40:30]:

I mean, I think one thing that’s unique about us is so we have, like I said, about 5,000 employees, about 3,800 of them are in India. Yeah, company was started in India. All of our, nearly all of our engineering, nearly all of our product development happens in India. And that gives us tremendous advantage because we have a talent brand in India for getting world class engineers into the organization who can build and ship products Globally, you’re not working on like an unimportant product. You’re working on our core product in India. Whereas if you go to work for some of our competitors, you’re going to work on for the periphery. And so that’s super important for us. It allows us to move fast, There’s a cost advantage. All that’s. But it also creates like a lot of. It’s just different. Right. Because we do meetings, like typically there’ll be meetings going on at 6 in the morning through 10, because that’s the evening for India. And our teams in India prefer to work evenings. But like after I’m done with you, like there’s nobody. It’s the middle of the night in India, so there’s nothing going on there. So you have that aspect and that particularly affects teams like product management and engineering, where the teams are largely not here, but a lot of the leadership is here. The customers are all here. Right. So all the customer interaction is here. And we need to be close to the customer, we need to be spending time with the customer. So that’s a unique challenge when you have development so far from the kind of the majority of your customers. And we spent a lot of time trying to figure out how do we create that intimacy between the engineering and product teams and the customer in this sort of setup. I think the competitive dynamics in this space are unique. I mean, it’s got to be one of the most competitive software, one of the most competitive industries in the world. And the talent that is arrayed in the industry and sometimes directly against you is just incredible. There are very few companies that you can say, oh, they’re really a laggard, they’re not going anywhere, they’re kind of on their way out. There are those companies exist. But software is such a competitive space and so that dynamic is interesting. It’s always changing. AI completely has changed every software roadmap from every player in the industry in the course of the last 18 months. And that’s unique, I think, about the space and about the industry. So I think all those things are quite interesting, quite unique to the situation, to freshworks and where we are.

 

Darren [00:42:56]:

Yeah. And about the role itself, though, as CEO, anything sort of that presents a unique challenge or.

 

Dennis Woodside [00:43:04]:

Well, I mean, I think so most CEOs are coming up through a function. Right. So for me it was sort of strategy and then sales. And so you deeply understand that part of the organization. And I think a lot of people’s biases is to, when all else fails, go back and try to do the function that you used to do better on behalf of the leader who’s actually supposed to be leading that function. So I think you have to get away. I got away from that pretty quickly. I had to do that at Motorola, where, you know, I had not done anything in the mobile business before, so it was a little bit easier. I had to do that at Dropbox, because in each of those roles, I have multiple functions reporting in. It wasn’t like I was head of sales at that time. But I think that’s the thing that you have to. You have to kind of quickly get away from, and then you have to start thinking about, well, what decisions should I be making versus what decisions should I. Should the team be making? And if I make them, it actually, you know, disempowers the team. I think that’s really important to get right. The stakeholders that you are dealing with are just, you know, they multiply by a factor of 10. Because you’ve got investors who you’re somewhat distant from. You can only interact with them. And we’re a public company. The way you interact with them is constrained to some degree by law. You’ve got your directors, you have more interaction with them, but they come in, you know, maybe six times a year and are truly spending intensive time with you six times a year. So they’re not going to be as understanding of the intricacies of the business. At the same time. Our board’s amazing with people with CEO experience and multiple different industries, and so you can rely on that a lot, and it’s good to tap into that. But you’ve got that aspect. You’re constantly engaging with customers and partners. And a lot of the job is to bring what you learn from the customer conversations and the partner conversations back to the team, both the good and the bad, and help them understand. You guys are doing great on these areas, but we got to figure out our support motion. I’m hearing a lot of complaints about not being able to get in touch with people or whatever it might be. So I think the job is unique in that you’re not a master of any single function. You’re not expected to be, but your real job is to help that team be as effective as possible and. And make the right collective decisions for the business.

 

Darren [00:45:15]:

So can we go back to the competitive endurance aspect of you? You said you were a competitive rower and have been a triathlete for some time. Tell us a little bit more about that part of who you are and how it’s influenced you.

 

Dennis Woodside [00:45:30]:

After rowing, I was a good endurance athlete. But it’s hard to row when you’re not, you know, when you’re not in college. It’s just not a sport that many people continue with. And so a friend of mine at Stanford was like, hey, let’s enter this triathlon. It’s down in San Luis Obispo. It was called Wildflower. So we signed up for it, not knowing what we were getting into. But I thought it was really fun. There was all these people who were kind of like minded, was competitive, but also social. And I just sort of started just entering these things and then, you know, as life goes by, it goes on and off. Like there were years when I didn’t do anything. When our kids were little, it was more about spending time with the kids. And then they started getting older. I had a little more time. I got back into the triathlon thing. And so at this point, I’ve done over 100 triathlons, but I’ve done the Ironman 17 times. I’m going to do the 18th in October. And it’s like anything else. If you stick with it long enough, you get reasonably good. So I’ve gotten pretty good at them. I usually finish in the top in my age group and usually close to the top overall. For me anyway, I like the reward of competing and actually coming close to winning. And also the reality of, okay, I didn’t do so well. Why, what could I do better? So I did a race this past weekend in Central in Harold, which is like the middle of nowhere, it’s kind of cattle country in Central California. And I usually win and I didn’t do that well. And I was like, well. And I’ve got another race on Sunday, so what can I do between that race and the Sunday race to improve? What are the things I need to change? And I like that kind of puzzle outside of work where you’re, you’re challenged but you know, you’ve got. You’ve got something that’s healthy, obviously, but it’s also at this point more about. To be honest, it’s like, how long can I actually be good at this? At some point, not gonna be that good at it. And then my daughter has gotten into it. So she has done a bunch of races. She’s done the Ironman once, she’s done a half. I think she’s done two or three halves. So every now and then she’ll jump into a race with me, which is a lot of fun too. So it’s just been something. I’ve stuck with it’s a good, the training is a good time to think too because as a, as a CEO, you know, you’re. I’m constantly looking at my screen of some sort. There’s always new news. You got to digest what’s going on in the world, what’s going on in your business. You’ve got customers contacting you, so. But when you’re on a bike, you know, I’m not looking at a phone and it’s a good time to think about, okay, what, what do I need to accomplish? What did I miss? What could I do better? What am I going to do this week? What happened last week that went well? You know, it’s a good time. Even if you’re not consciously processing information, I think subconsciously it’s good to have that time where you’re just not looking at a screen, you’re not talking to anybody. Pretty much you’re just thinking maybe listen to a podcast or listen to music and you’re outside and enjoying it.

 

Darren [00:48:13]:

Yeah. I’m curious what your sort of daily routine looks like. How do you squeeze this in?

 

Dennis Woodside [00:48:18]:

You know, it’s not like it’s a regimented thing. My work routine dictates whatever the workout is. So today I actually had time. Usually I don’t have time in the morning because we start so early here. Usually I have time in the afternoon, but today I didn’t start until 8. And so I actually got on my bike. I needed to make sure that the bike is ready for the race. So I needed. And that means I needed to ride it in a certain way outside. So I did that in the morning and I’ve got a dinner or a drink with a customer. So I don’t think I’ll get anything else in. But typically it’s the afternoons during the week, maybe an hour to two hours a day, Monday to Friday and then weekends are when I put the real time in. So I could do a five hour ride on a weekend, a two hour run, that sort of thing. But the main thing is consistency. You have to do this for. If you want to be good at it anyway, you have to do it for like a long time. Like it’s not like a, hey, I’m going to build up for this thing in three months. To do an Ironman, you have to kind of build for it. If you want to do it and actually feel decent, you have to build up for 10 months and you pretty much need to train year round in my view. And so I’ve just been training continuously since we moved back From London, which was 2009.

 

Darren [00:49:26]:

Yeah. This theme of endurance, I think, sort of has run through your life and your career, and has it always been part of you? If you go back to the younger version of Dennis, I don’t know endurance.

 

Dennis Woodside [00:49:38]:

It sounds like you’re enduring something painful or bad. Look, I read Bill Belichick’s book, and I don’t know if you’ve read that, but it’s worth reading. As a coach, I didn’t know what to think of him, but when you read the book, you really understand it. The commitment to being really great at what you do is not a, hey, I’m going to wake up one day and decide that’s what I’m going to do. He decided early on that he was going to be an amazing football coach. And he dedicated every hour of his work life to figuring out what did he need to do, who did he need to surround himself with, to becoming who he became. And so I don’t think he thought of that as endurance. I think he thought of that as, I have a goal, and if I want to achieve the goal, then I have to. You know, I need to do these things. It’s not even I need to. I want to do these things. So for me, I never. I used to early on, like, when I was training, I would think, oh, I have to do this. And some days, yeah, you’re tired. I have to do this. But increasingly, I just feel really. I guess, I don’t know if the word’s honored or lucky. Fortunate to be able to do this. And I see friends who can’t for health reasons or whatever. And so whenever I find my mind saying, hey, you have to do this, I kind of say, no, you don’t. You’re choosing to do this because you like the sport. Ultimately, you like kind of what you like to compete, and you like to compete, and not just compete, but actually to win. And so I think that that’s a different. That’s something that I’ve realized over time about how I think about things. And, yeah, I don’t think of it as endurance at all, though.

 

Darren [00:51:13]:

Yeah, it’s a great reframe. I’m curious, does this apply equally to your leadership and being the very best CEO? Do you carry the same sort of ethos into that?

 

Dennis Woodside [00:51:23]:

I think you have to. I mean, I think you have to. I think you owe it to the people around you. Like, I’ve hired most of my team now, and I don’t want to let them down. And so I have to do my job as best as I can. And that might mean you do things that you’re not as comfortable with or you have to learn new skills. I’ve had to learn the whole investor relationship side. I sort of had that at Dropbox, but not as much. So we are trying to build the brand. How do we build the brand in a world that’s so noisy? That’s a set of skills that I’ve had to learn. So I think they expect their leader to be learning and getting better. Right. Just as I do of them. And so I think that that ethos is really important. And if I think about leaders, who I’ve learned from. Yeah, I was talking to Nikesh, Nikesh Arora, who is the CEO of Palo Alto Networks, super successful security software company. He was at Google with me for a long time. I could see him from the time I met him, you know, in 2004 to where he is today. And that’s like huge growth and that, you know, you got to respect that. And also there’s a lot to learn from seeing someone else go through that path.

 

Darren [00:52:31]:

Yeah. If you project out five years from now and imagine we’re having this conversation in 2030, what would you want to be true about yourself and how you lead?

 

Dennis Woodside [00:52:42]:

Well, I think what would be really fun for me is if we are, as an organization, are as competitive as we can be, and that leads to amazing success in the marketplace and recognition that we are serving a need and truly transforming our customers in a way that no one’s doing now. So I think that in five years that ultimately there is a scorecard. Right. There are wins and losses. And in the tech industry, winning is growing the business. And so in five years, I think, okay, we should be a multi billion dollar company or billion now. We should be clearly multi, multi billion dollar company. And we should be affecting a large number of customers, important customers around the world, helping them run their business, perceived as a leader in AI, perceived as a employer that people want to work with around the world. Those are the kinds of marks of success that I think we can achieve. And what’s great about our phase is that that can happen rather quickly and it hasn’t already been done. Right. If I went and said that if I were working at Google, that’s already been done. It happened years ago. So you can’t really do it. You can only do it in these companies that are at this kind of phase of growth, which is why this is the kind of company I want to work in.

 

Darren [00:54:03]:

Yeah, it’s wonderful. Well, We’ve covered a ton of ground. 30 years of your career, aspects of your personal life, your professional life. Anything we haven’t covered that you think would be important for us to.

 

Dennis Woodside [00:54:15]:

Yeah, I have to have my other story about Darren, so maybe this goes and we should have a. I should do an interview of you. But I remember when we, when we were working together in LA and we were lawyers, you were like, there was some job. I don’t remember exactly what it was. And they were like, yeah, that, that, that job pays $200,000. And you were like, $200,000? I will bang on a pack of rocks all day long for $200,000. I was like, that image stuck in my head of you with like a hammer just banging on a bag of rocks all day long.

 

Darren [00:54:50]:

So that’s, that’s funny.

 

Dennis Woodside [00:54:52]:

You might not remember that, but I.

 

Darren [00:54:53]:

Don’T remember and I’m not surprised given, given my upbringing and money motivation of my 20s. But that’s really funny.

 

Dennis Woodside [00:55:03]:

That’s my other story.

 

Darren [00:55:06]:

And anything else about you that you’d want to make sure you bring into the conversation.

 

Dennis Woodside [00:55:10]:

I think we hit everything.

 

Darren [00:55:11]:

Yeah. Okay. Well, I’ve, I’ve so appreciated our friendship and watching your career evolve and so glad that we got to get into this conversation so that we could share for others the secret to a lot of your extraordinary success. I want to thank you and thank you for the, for the time, Dennis.

 

Dennis Woodside [00:55:31]:

Thanks, Darren.

 

Darren [00:55:38]:

What a treat to cover the three decade journey of such an accomplished leader, particularly given our friendship and history. I learned a lot in this conversation, but the one thing I’m taking away is the responsibility, almost sacred responsibility that Dennis appears to hold as it regards his privileged role of being a CEO. I hope you got a lot out of this conversation and I look forward to being with you on the next episode of One of One. Until then, I hope you live and lead with the same sense of responsibility and privilege and as always, with courage, wisdom, and above all, with love.