#100 Arvind Jain, Founder of Glean — From Technical Leader to First-Time CEO, the Business Case for Culture and Selling as a Founder’s Superpower

And I have to learn how to focus on the big picture and learn to ignore some of the other things which, you know, even if you don't like what's happening in front of you, how do you sort of get yourself in the mindset that you know, you cannot go and solve every single problem that's in the company and you got to prioritize, you got to focus on the things that matter the most, count three things that matter the most and make sure that you work with your executive team on those three things and ignore, you know, the other ones, you know, trust your team that they will actually handle everything else.

Welcome back.

This is from Startup to Grown up.

My name is Alyssa Cohn and today.

I'm thrilled to welcome Arvind Jain to the podcast. Arvind is the co founder and CEO of Glean, an enterprise AI assistant that helps every employee find the right information and get work done across all their company systems. Before founding Glean, Arvind spent more than 10 years at Google and then co founded Rubrik, a cybersecurity startup. So Arvind is a second time founder and first time CEO and that is a steep learning curve as you can imagine.

We had a great conversation. We talked about the early days at.

Glean and what it was like when no potential customers would take a meeting and what allowed him and the team to maintain their conviction even during that challenging time. We also discussed his move from engineering leader to CEO and what a big leap it was.

He had to learn how to sell.

How to deal with all the different functions that make up a company like marketing, HR and finance, and how he had to grow to lead a business that's now approaching a thousand people. One of Arvin's key insights was that when he was working only with engineers, he saw himself as an easy person to work with. When he started working with these other groups, he discovered he was kind of a challenging person to work with. Another insight we covered was how Arvin saw that he had to reinvent his leadership playbook continuously as the company has been on such a steep trajectory. This is an incredible conversation with the founder of a company which is experiencing massive growth right now and and you're going to love it. So please enjoy my fantastic conversation with Arvind Jain, the founder and CEO of Glean.

Arvind, welcome to the show. I'm so happy to have you.

I'm excited to be here.

I'm excited to have you. You know Arvind, you're a second time founder. You were the co founder of Rubrik, a cybersecurity company. And now you're the co founder and first time CEO of Glean, the company which builds efficient tools for employees to search for the right information inside of their company. Both extremely high growth companies. And you've said you had to throw out your playbook from your first company to be a good leader for your current company.

Can you talk a little bit about that?

Yeah, I mean like look, every company, you know, always feels like a real new project for me at least, you know, that's how it feels. There were, you know, we built Rubrik, you know, into a high growth company or a few years. But the business there was so different than the business that we have at Glean. For one, at Glean, our product is a end user product. It's more like it's meant for, you know, enterprises but it's still a consumer like product. Every single person in the company uses our product. At Glean and at Rubrik it was the other way where you know, it was a again like you know every company required a product like Rubrik, but it was actually only a select few people inside the company that would use it and we would have a good relationship with them. So like the journeys were so different. You know, there we were able to build a business very aggressively and, and because you know every buyer, every user of our product we had a good relationship with. So we actually they allowed us to build the product with us versus at Glean we don't get that luxury. Like most of the people who use the product, we have no relationship with them, we don't know who they are. And, and so you have, there's a much higher power. You have to actually wait, you have to make the product, bring it to a really high quality before you can actually start to scale the go to market. So that's one, one of the key differences in like you know, how we approached the, the, the problem. But you know also roles are different. Like you know there, you know there I was not the CEO here, I'm the CEO. So I have to learn so many new things as part of building this company.

Yeah, I wanted to double click into that because you know you are a second time founder but a first time CEO. What are some of the key differences you would say this go around in terms of being the CEO. And I should also mention you were at Google for 10 years. So like Google for 10 years, co founder of a company, now CEO and co founder of a company. So like talk a little bit about the changes you had to make to kind through that journey. And what's different today about being a first time CEO.

I think the role typically forces you to sort of learn and adapt. And my role at Google and then my role at Rubrik as a co founder and somebody who ran the engineering team was sort of similar because I've been, I was running large engineering teams at Google and so it felt sort of a. There's a bit of a difference because here you are responsible for the entire company. You know, even as the head of technology and the. So there is a bigger sense of responsibility, a little bit bigger scope in like for example, you have to work hard, make sure that you, you know, like hiring people of course again like there's no support system for you initially. You have to actually go and do all of that, all of that work yourself. But it largely felt to me that I was able to learn without, you know, feeling that, well, like look, I don't know, I don't know how to do this thing. I don't know if I'm ever going to learn this versus now. At Glean I was a founder, so I knew how to start a company. I knew how to recruit people, build a really good team, build the initial product. And luckily like at Glean, the first few years, like it doesn't matter like the fact that you're the CEO, but well, we're still building the product. And so the journey felt very similar initially. And then as you start to make some progress, as you start to say that well now I'm ready to actually get customers, that's when the new skills, like I had to learn them but luckily like you know, you got like, you know, got to learn them one at a time. And I always felt that, you know, I had the time to do so. Yeah, you know, as much as I, you know, as I could learn, I mean I think one thing I do feel, um, the, the learning never finishes like in our company. Also Glean today is very different. Like now we are, now we're almost a thousand people and the, the business has grown. The company's, you know, valued over $7 billion. It's a serious enterprise. So like it does feel very different from the glean of two years back or the glean of four years back.

Yeah, I mean I can imagine 2019, you weren't thinking like oh, $7 billion. I mean you probably weren't thinking it but like it was this tiny little Embry building from scratch. It wasn't a $7 billion entity.

Yeah, that's right.

What, so what if you just sort of think about that journey like you were learning the skills it took to be the CEO. Can you sort of talk about one or two specifically that you felt you had to learn, especially in light of the high growth?

Yeah, first. So the, the most important skill that you learned was how to be a seller. As an engineer, you don't really sell your product, products like this. That's the job of somebody else. We, you know, we build good products, we build products that we use ourselves. And, and that's a very different place to be at. Engineers rule the world. You get to be creative, you get to build stuff and versus selling, you know, I think I feel like, you know, it's a much tougher job. Like, at least for me, I had to actually go and work really hard to get attention to. I had to learn how to actually go and connect with people, pitch to them that I had something useful for them, like get, you know, request them to give me. And that was sort of one of the most difficult things for me to learn was how to be that seller, how to actually convince people that they should spend time with us, convince them that they should actually spend their money with clean, to add value. So. And I think I did learn, you know, that skill over the years. I got good at understanding what problems our customers face and match that problem with the technology that we build here. So that was one. The other thing which I'm actually still learning, like, I don't think I'm a, I'm a, I'm good at it yet, is I had to actually work with many different types of people, people who play different roles. Like, for the longest time, for. I have a long engineering career. Like, you know, I work for, you know, 20 years as a, as an engineer or engineering leader. But, but during all of that time, most of my interactions would be with R and D people. Folks actually build products, develop technology. And I think I understand that set of people very well because I'm one of them. And I always had good, easy relationships with everyone. And here as a CEO, I actually now work with marketers, with salespeople, with HR and finance and legal and, and, and, you know, people. Everybody, of course, thinks differently. And I had to actually, it took me a long time to actually understand how to actually interact in the best possible way with folks like, you know, from these different, different teams and adapt myself quite a bit. And in fact, like, you know, that's just still a struggle for me. Like, you know, I think people sometimes find it hard to work with me, especially like if they don't in R and D. And so I think like, you know, they are probably learning adapting how to, how to work with an engineer. And I'm trying to adapt like in order to work with a non engineer.

Right, totally. Well, when I saw you in May, you said that you always considered yourself easy to work with. And then suddenly you're dealing with all these different people and you find yourself hard to work with. And so like learning the skill of dealing with marketing or HR is something that, you know, I think all engineers go through and there are many engineer founders. What specific advice do you have for engineering focused founders? Founders who come from engineering to learn to work with people who are different from the marketing people, Sal people, HR people, finance people. What specific advice do you have?

Well, I think first, if, if you can understand that everybody has their own style and way of working, way of thinking, and it can be fundamentally different than yours, but that doesn't mean that that is, that is worse than yours. Like in terms of that you, you know, your approach, your way of thinking is better than them. Like, you know, if you sort of have that mindset, then always struggle. I think it's just like having that awareness and is a good thing. And then there are quite a few founders who actually talk to me about their struggles with the teams that they're managing. And when I struggle myself, I'm actually able to give them good advice. And one of the advice that I got was that every engineer turned CEO is a good idea for them to actually have a coach who has a different background because the coach will help you understand what's the best way to actually build greater relationships.

Love that. Yay for coaching everybody out there. Think about getting a coach. I totally agree. Do you have a coach and what have you learned from your coach about the best way to adapt to people's different working styles?

I have actually quite a few people who provide me coaching. Um, and the. I don't have a formal relationship, luckily. I mean, that actually makes it a little bit more comfortable, you know, for me. But the. But, but, yeah, so, but I do get advice from time to time and I think the advice, you know, so I think one of the things, you know, for example, for me, I'm a very detailed, oriented person. Oftentimes, you know, I will go on any given topic, I'll just go like, right to the bottom of the thing and like, you know, maybe it even worth, you know, me spending that time or actually knowing, you know, that information. And I have to learn how to Sort of focus on the big picture and, and, and learn to ignore some of the other things which, you know, even if you don't like, you know what's happening in front of you, like how do you sort of get yourself in the mindset that like you cannot go and solve every single problem that's in the company and you got to prioritize, you got to focus on the things that matter the most, count three things that matter the most and like make sure that you work with your executive team on those three things and ignore like, you know, the other ones, you know, trust your team that they will actually handle.

Yeah, that is, it's so true. You have to really focus on the top things and like not quote, unquote, word with the details. But the notion of trusting your team, I always think a lot about that because I think a lot of founders especially, you know, when founder mode came out, like oh, founder mode this, founder mode that, you know, with that, that essay from Paul Graham came out, there was a sense actually from founders of feeling like relieved, like, yeah, you see I should be focusing on the details and at there is true that like actually sometimes it's important to focus on the details and cause if you get the details wrong, you get things wrong, but you can't focus on every detail. So to your point about prioritizing, but how do you know that you can quote unquote trust your team? Because sometimes you can and then sometimes you trust the team and it's like that didn't work out well. How. What's your spidey sense that tells you if you can trust the team or not and when it's important to lean in and when it's important to lean out.

Yeah, well, first on the founders mode, I've talked to so many founders who feel so relieved, as you said, you know, they're able to rationalize, you know, their weird behavior because of it. And for me too, I think I also, I'm getting a, you know, I get a pass sometimes, you know, with things, you know, that I do the. I think it's not that hard to know when you can trust somebody versus not. I think it just happens. In my opinion, it just happens over time and it happens automatically. You don't really put an effort. You start to build trust in an individual because in the past you had multiple interactions where they showed, for example, that you know, they have attention to detail, that they are able to think analytically and those experiences ultimately creates that trust. And that sort of then allows you to just, you know, step back and you know, your sort of mind automatically switches is off. Like you don't actually bother to even like you don't, you don't worry anymore that hey, like you know, hey, what's happening in the marketing team? You know, I, you know, because I know that there's a, there's a great leader like you know, who's going to take care of it. So the, I don't know if it's so much of a spidey sense versus just observations over time that helps you sort of get to that level of trust and confidence in your leaders.

Yeah. And experiences with them. That makes complete sense when you think about, I mean you, you have leaders now and you have a thou, you have a thousand person company and you know, on day one you were like what, zero or two people or whatever. And so that's quite a big growth. And obviously you've done a ton of hiring. Obviously. How do you think about hiring people? Early stage of your startup? As the startup's growing, as your startup kind of matures. What are the things you think about when you're hiring? And also, you know, at some point you're no longer hiring everybody. How do you translate those criteria to your team?

Yeah, for me, I think I don't actually change who we hire based on what stage we are in. I think the qualities of somebody who's going to make a great employee at Glean it has been the same because in a while, well, for one, I don't think we have actually grown that much either. Like you know, we still believe we are a early stage startup. There's a lot that we need to get done to build real durable success for the long term. So what we look for in people is all the standard attributes that you would think about like somebody who works hard, somebody who knows their trade. Like if you're looking for an engineer, somebody who's really good technically, we look at a lot of things like we look for evidence of hard work which sometimes goes all the way back to where they went and got their education. And so that's sort of like focus on those standard criteria. But and also like you know, the desire like you know, do you have, do they have the desire to actually succeed? I mean that's actually the most important one for me because startup journey is not easy. You have to work very hard and you don't even get paid reliably for that. Like you, you know, like a lot of your pay comes in form of equity which you like, you know, it can be zero. If you don't succeed at a startup. So you have to have somebody who has those attributes. And then there are a few more which may be something that may be a little bit more unique to us. Number one in that category is we're looking for somebody who wants to learn something that's unique to our environment. For example, somebody wants to be an entrepreneur in the future, and they feel that by being part of the Glean journey, they will get to learn a lot of things outside of their own core job. Like which maybe, you know, maybe which is being a software engineer or a product manager. So that actually is a, is a, is something that motivates me to see somebody like, who's looking at Glean, you know, as a place which will actually help them learn those special, special things that they want to learn. And second, this was one of the learnings I had at my previous startup. We built a product there which we didn't use every day. And, and as a result, there was a little bit of a distance between our engineers and the product. We didn't actually. We always had to rely on our customers to tell us what we should be building versus at Lean, we're actually building a product for ourselves. And when you build a product for yourself, it actually brings a different level of passion and excitement and energy. And so I always look for folks who are really interested in working on this particular problem that we solve. There is a personal pain that they have actually gone through in their work lives which they believe they're going to now solve by building this product at Glean. And so that's sort of like I always test for, like, what is what? Like, why do they want to work on this product? Is it like personal to them? Is it something that's super important to them? And so that's one of the other criteria that we use to recruit people. And that actually works a lot because we have an incredible sense of mission alignment. Nobody in our company actually ever questions, are we building a meaningful technology? Are we going to actually make a big impact in the world?

I see. Because everyone really knows it's a problem. Arvind, why don't you talk a little bit about what Glean actually does and how you had your kind of founding insight about Glean.

Yeah. So Glean, you think of Glean as Google or ChatGPT, but inside your company, Glean knows everything about your business. It's connected to all of your technical systems. So it actually knows the different people in the company. It knows what the business is about. It is connected to all the knowledge that's inside the company, all the documents and conversations that you have in the company. And now with that connectivity to all of your enterprise data knowledge, information, as well as knowing everything about the world's knowledge and data, it's able to now answer questions for you. So you use Glean just like how you use ChatGPT but you know, you're using it inside the company so you can ask questions like, you know, hey, who's the subject matter expert on this topic? Or what did we accomplish in this particular project team or the last one month? Any questions about your day to day, you, you answered answer. You basically go to Glean. Glean becomes at one place which, which can give you answers to any questions that you have. And then of course, like, you know, as AI has become so powerful now, Glean is also a place, think of it as your personal assistant. You can actually also give it any work that you would like AI to do for you. And Glean will use all of that company's context and data and the world's knowledge to actually try to complete those tasks that you actually give to it.

So it's a part that's cool.

Yeah, so that's, yeah. So I guess like maybe to describe it again, it's a more powerful version of ChatGPT that has that, you know, and that extra power is that additional, you know, enterprise context that it has. And so it becomes like this really easy to use day to day AI tool for every employee in the company, helps them become more productive. And then also we had to do a lot of, a lot of hard work to actually build a product like this. We had to go and build integrations and connections into all of the different enterprise systems that companies typically use. And so that platform that we built to power this product now is also used directly by our customers as a AI agent building platform. So those are the two things we do. A really personal assistant, commerce AI assistant that we give to every employee and then an agent building platform that we give to businesses so that they can actually bring AI into all of their different business processes.

Yeah. Wow. Very slick. That's amazing. And I just want to highlight, you guys started in 2019 and I'm very aware that the people in the know knew about AI, have known about AI for decades, have thought about AI for decades. But in 2019, all of these things that you were thinking and building really weren't enabled. Like they didn't seem to be enabled in a popular way. And then suddenly, well, not so suddenly, but like in 2022, I think was when they really exploded. I guess I am curious, like, obviously you're a technologist, obviously you've thought about AI for a long time. What was the, what was the mo. What was sort of the, I don't know, the, the recognition in 2019, before we had ChatGPT and whatnot, that this was going to work.

Yeah. So the transformer technology, so AI is a very broad term and it's been around for 50 years, 60 years. Neural networks, you know, which is the core foundation of the current modern AI technology, also have been around for a long time. But I think in 2010s there was this wave of development in transformers and neural networks which, with sort of like, you know, these advances came because of a few different other technology factors like, you know, like the availability of very large scale parallel computing clusters. And so in Google, you know, a lot of this, you know, research started in 2010s and we had the goal there to really transform Google search and make it a lot more smarter. Google search was always the way it works is that when you ask it questions, when you type in a few words, it tries to match, like find, it tries to find the presence of those words in, in doc, you know, in documents. And, and that's how it does that matching. Like it's a word based matching algorithm. And then over the, over the, over 15 years, we built a lot of systems to make it smarter. We'd sort of, for example, expand people's questions with synonyms and other things to try to make it a little bit more flexible. But, but this technology, the transformer technology, it started to actually really show its impact. In terms of really making search more powerful in 2017, 2018. And we would see that you could actually, the AI had developed this ability to conceptually understand documents. So you no longer had to actually, if you wanted to sort of, you know, when you ask a question to find relevant documents, you didn't have to actually find documents that contained those words. Instead you could actually semantically understand what somebody's trying to ask. You could also semantically understand what a given document is about and you could do that matching at a conceptual level. And that was actually a big breakthrough for search. And we saw that many systems that we had built, you know, with a lot of effort, a lot of engineering resources over 15 years at Google, suddenly this AI technology was actually performing better out of the box than them. So there's a big moment and we knew that search was going to change fundamentally. And so for us at Glean. We knew that insight like most of us actually came from Google. Most of us have worked on Google Search for over a decade. And so we felt that this will fundamentally transform how people find information at work, how they get answers to their questions so it can work faster. That's when we embraced this technology before the rest of the world was really paying attention to it or even knew about it. So that's the origins of Glean. And in that sense, you know, we are the first Enterprise Gen AI company to start in early 2019, to the best of my knowledge.

Yeah. So you had a real earned secret of having been at Google and kind of seen all this, the way it's playing out and you kind of realized it sounds to me like your thesis for the future is this technology is going to get only better and we're going to be able to use it in this kind of way that people are not using it, they're not thinking about using it just now. Yeah, that's pretty, that's very cool. And I think it's so fascinating that you, I just like the idea of sort of all the different pieces that come into the prepared mind and to sort of realize the time is now. The idea that when you were at Google, I wanted to sort of circle back to your experiences at Google. You told me that when you were at Google you didn't really think it was very valuable to have culture and the values thing, and the culture thing, like whatever. But then when you started your own company, especially at gleam, you actually realized the value of. The value, I say, of values and culture. Walk us through why that became so clear for you and why for a while maybe that's still true. You don't even, didn't even have a chief people officer because you thought that was so important that you be responsible for that.

Yeah, I think a startup journey is actually a very difficult one. You are, you're trying to build something meaningful. But like building something is hard. Like, you know, it takes time and it takes a lot of belief on part of like everybody who's going to be building, you know, that technology, that it's going to work. A lot of uncertainty and like if you think about the tech industry, there's no shortage of great jobs, like very well paying, lucrative jobs, you know, that are out there. So how do you, how do you build? How do you actually attract people? How do you, you know, keep them motivated to go on that journey that requires them to work much harder, get paid much less, have a lot of uncertainty that it requires A few different things. It requires you to build an environment where they believe that they're learning something. That's a great experience. Yeah. It requires you to build an environment where they really like their interactions with the rest of the team members. They build those deep relationships and they feel that sort of agency, they feel that ability to make big impact. And these are some of the things that you have to think deeply about. But because this is what the best people in the world care about. And so it's really important to actually build that right culture which creates that sort of feeling of positivity and these attributes that I just talked about. And then as you start to grow, you have to. I heard this observation from someone that if you put the, the hundred, you know, top scientists or engineers in one room and ask them to solve a simple problem and you know, after one hour you'll, you'll come out and they would have not solved it. Even though they were all the brain power of, you know, of the, you know, of the world was in that one room and you'd really given them a simple problem to solve and they still couldn't do it because like, you know, they were not working together with each other. They were, everybody had their own ideas and they just didn't know like, you know, how to actually get to, you know, get to alignment, get to agreements. And the same thing is true for, for a startup. If you don't build a, build a, a shared of values that, that makes everybody sort of think the same way, work the same way you will, you won't build a successful, high, high performing team. So these are, these are some of the, the key attributes for, you know, that, that actually makes, you know, that's the foundation, you know, that allows you to build the foundation which will then help you build a great company. And I felt that that was very important. Like part of my, I saw some of my learnings from Google as well on when we started to sort of lose our way on certain topics and what were the things that I wanted to avoid and I was really particular about that as we started building clean. So yes, that's a really important aspect of building a company and we didn't have a chief people officer for a long time. We, they sort of think about the whole concept of building the culture, the values. We think of that as a shared responsibility that all of us carry and build towards. Maybe I'll share some anecdotes. So when we started this, so it's not as if I was doing this work but as we Started to get a little bit bigger in the company. Somebody felt that, well, we need to actually document our values. We need to make sure that, you know, everybody understands, you know, like what's the best way to actually work at Glean. And you know, there was this person, like she's our first designer and then she wrote our, the first culture sort of manifesto or our values and which sort of, you know, still exists as the core sort of guiding principle for how we work, you know, at the company.

That's amazing. By the way, on the topic of bringing all the best scientists and people and engineers into the room together and solve our simple problem. One of my clients a long time ago, he said, and he was a multi time founder and he said, I hired the best people I could find. Stanford PhDs, all of them. They are the best rowers in the world, you know, like in terms of crew, like the best rowers in our, in the world. And yet the boat is going around in circles because we can't figure out how to work together. And that was a big insight. It's a lot of what you're saying, like just solving the problems and learning to work together. So when you thought about what are the key values that either you wanted to discover or you know, nudge the like because you know, your company probably had values without even you're realizing it. So you had to discover what they were. But then also you probably wanted to articulate and formalize what they should be. What did those turn out to be? Because you have a very nice sort of framework for your, the way your values and your culture are.

Yeah, so specifically what our values are. So we have, we have four the key principles in that and those are sort of. And then you know, like, you know, we, we go and like, you know, also further expand, like you know what they mean. But the four values, the four guiding principles for us are make it customer driven, make it happen, make it better, and make it together. And what it really means is, I mean like I can go one by one. Make it customer driven is, I think there's a very simple principle for any company. Customer is always right. They are, they are the ones that should define what you build in terms of your products, how you actually build your company. And so keeping that focus on them and adding value to them is always something that should be on our mind. The second value is make it happen. Which is the point that you were talking about that. Well, I mean it's not always that for any given problem, don't spend one year trying to figure out what the perfect solution is at a startup. Like, you got to move fast and make it happen. Like, you know, take baby steps, you know, do something fast. Have the, have the attitude to actually get something done as opposed to deliberate or as opposed to sort of like, you know, hoping for somebody else, you know, that they're going to do it. Make it better is, you know, perfection is achieved over time. And if you find something that you don't like, well, just go and, you know, change it. Make it, make it better than what it is and then finally make it together. This is, this is actually the one that I actually care the most about personally. In my opinion, it's the most important one, which is that, you know, you, you could be, you know, you could be really, really good. You could be the best engineer in the world, but that doesn't matter. You won't be able to go and build any amazing product, you know, just by yourself. You have to, of course, work, you know, as a team. And for us, like when we recruit people, we actually look for that attribute. We look for folks who, who sort of have this humility around them who know that. Well, yes, you know, I was part of, you know, you know, I actually helped, you know, for example, I built, you know, I helped build Google Maps or I built Google Search. But they know that, you know, their role in that was very small in the sense that there are so many other people who actually also worked on it, you know, along with you. Like, no, no one person plays a huge role in any product, in my opinion. And so that, so like, having that awareness and actually, you know, putting the team first, respecting them, respecting every team member for what they bring to the, to the team. That is actually very, very important if you're going to actually continue to scale and, and build that healthy culture inside the company.

Yeah. And how do you, how do you test for these different values when you're interviewing people?

Yeah, so going back to the values again, the first one is make it customer driven. And so we, that, that actually like, maybe for engineers sometimes, you know, it's not as applicable. Although, like, you know, in that case, you know, the, the customer basically is the end user that they build the product for. So we look for examples of, we'll ask them questions around like, you know, hey, like, tell me one thing, you know, that you did, you know, where you, where the customer or the user told you something and like, what is it? What was the interaction on it, Making it, making it. I think all of those values are easy to Test. In some ways, making it together is, as I said, like, you know, is the main one. And that's where we, like, you know, if you ask somebody about the project that they worked on and, you know, if they describe that project as how they did the design and they did the implementation and they get it all done by themselves, you know, you start to wonder, like, okay, well, like, you know, I'm not seeing any recognition of, like, you know, the fact that they had good colleagues, you know, who did that work. And, you know, that could be like, one of the red flags. So we. So you sort of like, you know, orient your questions around those questions. You try to learn for evidence on, like, are they a good team player? Or, like, how do. Like, you know, like, it's very easy. Like, I'll give you an example. Like, when somebody changes a job, I will always ask them, okay, why did you change, you know, from company one to company two? And, you know, somebody will answer to me that, well, like, look, I wanted to learn new things, and that's why I changed. I love that answer. And somebody else will sometimes will say that, hey, like, the company got too slow and difficult and, you know, like, I was having. And that's when, like, you know, I sort of, you know, for me, that's not necessarily like a, you know, some reason to reject, you know, that person. But then you have to go, you know, dig deeper into it, because at a startup, like, again, like, you know, you know, we may have the same issue, like, we may have the same kind of challenges, and if somebody's just going to come and leave, you know, that's not the thing that we want. So we always go and dig into, you know, when, you know, when you change jobs, like, what were the reasons? And that'll actually allow us to, you know, both identify. Like, do you have the mindset to actually go and fix things or face problems, but then go and solve them as opposed to sort of run away from them?

Yeah, it's a way to really. It's an opportunity to dive deep into what their values are and to really understand what their makeup is. Yeah, yeah, that's. That's very helpful. You know, Arvind, you said several times, both when we first met and this time, that the startup journey is hard. And I would say that literally every single founder would agree with you. The startup journey is very hard. What are some things that have been super hard for you? What are some lows that you had? What was sort of like a. Like a war story? And how did you Deal with it.

Yeah, the. I think for Glean, like, at a macro level, you know, we have been very fortunate. The journey has been largely positive and we keep growing. And it's like, I think we all are also very fortunate in terms of technology trends. You know, they're all actually becoming more and more helpful to us. But I'll. I'll share a few moments. So first was the, like, trying to get people to pay attention to us. So we, we wanted to solve this problem because. Well, I started Glean with our team because it was a pain that I, you know, that I felt personally in my. All of my jobs before. Like, I, I always found it super hard to actually find the information that I needed to do my work. And so, so it made all the sense to me. It made all sense to, like, you know, our, you know, our founding team. And so we're building this product, but then it turns out that the market was not really interested in it at all. I mean, like, I would go and talk to CEOs and CIOs, try to actually get time from them and explain to them that, hey, we're building this really good search product. It'll actually help your employees, you know, save a lot of time. Would you. Would you like to try it? I'm not even asking them to pay me money. Like, I'm just trying to say that, hey, can you actually just try this product out, give us some feedback? And I would get very, very little attention on that. Like, you know, people want to respond. I had to, like, I would send, you know, hundreds of thousands of messages on LinkedIn to people trying to sort of find our first few design partners. And, and was very difficult. And it, like, often during those days, you know, like, oftentimes, you know, I would actually wonder that, hey, are we working on the right problem? Like, if people are not going to take interest, if everybody thinks, you know, this is a vitamin, this is not a painkiller, this is not the top priority, how are we going to actually build this? But I think, you know, luckily, you know, we had the conviction because we went through the pain ourselves, like, you know, you know, every single day of our own work life. So we knew that we were building something important. And so we persisted. And over time, of course, like, you know, the people, we found people who were actually interested in being the pioneers and bring a solution like that into their businesses. And then in 2022, everything changed where with the power of AI, we could show that we could do so many big, amazing things. And it was a 180 degree shift for us. And we went from a place where we had to evangelize, where we had to actually convince people that, hey, we're building something interesting, to now where everybody believes that they need a product like ours. So, yeah, so patience sort of helps. Ultimately, you'll find your day. And so that was like one of the big challenges for us. The second one was actually the ChatGPT moment where suddenly we felt that, like, look, all this work that we did over the years did suddenly become worthless in the sense that, you know, the model, the LLMs, the language models actually became so good. And people started to talk about that, hey, well, like, instead of building a search solution like the way we had done it, there's a new way of doing it, which is just take all the data from your company and just dump it into and train a language model for your own company. And so we had this period of a few months where we felt that, well, the four to five years of hard work that we had done, maybe it's all obsolete in one fell swoop. Everything's become obsolete. And we had this question about like, this existential question for our company, but only like, you know, that only lasted for maybe a month when we realized that actually, no, like, you know, this new technology advance that we saw was actually a big enabler and a positive thing for us as opposed to something that made our technology that we built obsolete. So. But overall, like, you know, we don't have that many moments at glean luckily, like which, like, you know, which have been the difficult ones. 1.

Yeah, I can understand that. And then also what that brings up for me is like early days when you were trying to get like, you knew it was a problem, but you were trying to get attention from people and they were like, nope, not a problem for us, or I'm not going to spend the time. What made, I guess I'm curious, like, what made you stick with it as compared to trying to, quote, unquote, read the market and pivot?

Yeah, I think it's the, I think we had conviction in our product because, like, for a few different things, one, it was a problem that we faced ourselves, and it was not a problem that we faced for two months or three months. I faced it for two decades of my, my career. Like it was the number one problem. Like, you know, I felt that I spent a third of my time just looking for information. And so that personal experience of facing a problem actually brings that true conviction. And, and that conviction was shared, like, not just Mine, but everybody else. Sometimes I would actually tell our team members that like, look, you know, I just this call with the customer and they're not interested because of X, Y and Z reasons. And I never heard from my team ever that, oh well, should we actually do something else? Because they also believe so much in it. And then the second thing was that, you know, as we were building this product, we're also using it internally. Like our team was growing and we were finding utility from it. We knew the product actually was helping us so much on a day to day basis. It was actually making all of us more productive. It was making all of us on board so quickly onto new technologies inside the company. So the utility of actually after having built it was also very clear to us that it was, the product was helping us. So, so that is sort of what kept the, kept the conviction. And that's, that's why we didn't pivot despite, you know, the, the early struggle from every prospect, you know, that we talked to. And that's an important thing. And I always tell founders like, if somebody's listening, like the, I think like in any journey, like in a startup journey, you will have those moments where you will, you'll be forced to question, like whether you're building the right thing or not. And you always have to go back to the day one on why you started this thing in the first place. You had, you had thought you had observed you'd found something. And unless if the word has dramatically changed, that problem still exists and you have to stick with it. More often than not, people pivot too fast, in my opinion.

Yeah, I can really see that you're a really reflective person. And one thing, when we, when I saw you in May, we talked about, you do like almost like a six month review of yourself as like, am I still the right CEO for this company and am I, you know, sort of still. Are we still working on the right thing? Can you talk a little bit about your process and how formal or informal that is?

I mean. Well, we have formal processes around product strategy and what we should be building. Like look in the, in the world of AI, if you don't have that, if you don't revisit, not six months like now, it is more like every month. Every month you have to think about both your product roadmap, the technologies that you're using, how you're building your product, and you have to actually continuously see what new things are available in the market that you can use and redesign your systems and throw away your Old technology. So we have to. So that's, that's one of the things we changed. Like you know, our product planning process now is monthly. It used to be, it used to be quarterly before and that itself was too slow. And the, and like, you know, largely the concept of annual planning and setting goals are not that relevant to day to day. Like you know, this is all about every month, you know, we decide hey, what are the most important things for us to do this month? And then we go into it. The. So yeah, because you know, the industry changes so fast.

Yeah.

Now for me personally, the. And actually for our executive team, for everybody in the company, like we do have this self assessment process like you know, that you would hear most companies have like you know, every six months. We, every six months, you know, we think about, everybody thinks about like, you know, the work they've done. They actually form, you know, formally write it. And that's the moment to actually also think about. For me as a CEO, I have to think about every executive as well as myself, like you know, the right people to lead the company, you know, in this new phase. Because every six months, you know, we also change as a company, the rate of change, the size of the business, the complexity of the organization, like you know, sort of keeps going up every six months. So it's sort of like, you know, tied to our, the formal performance review processes. But for me personally, like whether I'm the right person or not, like you know, that's a, that is something that like maybe I think too much, you know, I think you know all the time about it. And the reason I do that is that the, like we have a. We've been very fortunate at Glean. We started working on leveraging, you know, generative AI language models before anybody else. And we built a product that the entire world wants now. And so the timing, timing has been great for us. We're fortunate to have a great team, great customers, amazing traction, user love. And it feels like, you know, we have the opportunity to be. We are one of the most important enterprise AI companies today and we have the opportunity to actually be one of the most important enterprise companies in the future. A company that's one of the world's most valuable one. Valuable one as well, the one that makes a huge impact. And so when you sort of think about that, then you realize your own role and how much that actually is going to especially as a CEO. Like it's sort of like, you know, you are steering the boat or the ship as you said, and you play like, your. Your actions may have, you know, a huge impact, you know, positively or negatively. And so. And that's sort of like, for me personally, it always creates that doubt in my mind and that sort of. I have to think really seriously about it because, you know, there's such a great opportunity and I should not be the one that sort of become, you know, you know, who becomes the reason for us to not realize it.

Yeah. Holding you, holding you back. What insights, if any, have come out of that sort of reflection process that you've done.

Well so far? Like, you know, the answer is that I feel like, you know, yes, I can still do the job. You know, that's why I'm still here.

You haven't fired yourself yet. Yeah.

Yeah. And it's sort of like, when I think about it actually does give me ideas for. Okay, what are the. What are the. What is that one thing that I need to change right now? Yeah.

What are some examples?

Yeah. And actually, by the way, like, you know, it's important for me, like, I should typically only think about one thing, like, every time I think. Not like, you know, hey, here's a list of, you know, 10 things I need to change because that system, that's. That's too much. And then I probably won't do, you know, any. Make any changes. So one of the changes is that I've made is about the. How do I actually. And I don't, like, I won't. I won't claim that I've been successful, but the, like, it's very much a desire for me is how do I, again, like, you know, work well with my. With. With my. With my executive team? How do I, like, make them feel the agency, the independence, the authority, and the ability for them to sort of drive their organizations without, like, you know, constraints, you know, from that are coming from me. And so I put a lot of effort, you know, into that. And oftentimes, you know, I go against my instinct to not get involved in a certain topic. Sort of like, you know, in fact, sometimes I have, like, I feel. I feel very strongly that, well, you know, this particular project should have been done this way versus other, but I still won't actually share those learnings because I feel that, you know, like, maybe it'll. It will sort of reduce the confidence that the other person has in what they're doing. Like, you know, it was okay. Like, you know, maybe you could have done, you know, done it 10% better, but it's not worth talking about that right now. And so that's One of the main learnings is like, you know, that I need to actually just change my own working style in terms of how I work. And then the second one is also I'm a conservative person by nature. And as we build businesses, we want to build them. In a good manner, fiscally responsible manner, we generate profits over time and actually that. But sometimes it's not the right strategy anymore, especially in the AI world. In the world where when there's a fundamental shift in technology that happens, like the one with AI today, land grab becomes much more of a strategy. Like you won't actually go really, really big, you raise huge amounts of capital, don't worry about are you making any profit and just acquire users. Right. And that's the right strategy. And that's sort of like for me it's always hard to actually go and think that way. And I have to sort of over the years get myself to feel comfortable doing that. So that, and because you have to, you have to really adjust and go against your own instinct. Against your own instinct. Like you need to understand what you're weak at and sort of actively work against that. You know those weaknesses.

Yeah, I mean what you're weak at, but also how your natural inclination is as compared to what they call the game on the field. Like as, as, as compared to like what's necessary from you right now.

Yeah, yeah.

Arvind, just a couple more questions. What do you wish you had known earlier on your journey?

That's an interesting question. Well, I mean I think the one thing that I I wish, I wish I actually got more coaching and Talked to more CEOs who had led their companies through hyper growth before than I actually did. I was very inverse focused. I was always just focused on building our own product, working with our own customers. And I felt that at glean be under invested in marketing, we under invested in go to market and sales teams for a long time and if we had not, we would actually be much larger today. We waited for building a really good product and until we had it, we didn't want to actually go and invest in those things. The right answer now in the hindsight was that sometimes you have to get out of that again, do things which are uncomfortable. And even before you have full proof that your product actually works beautifully, you have to actually go in parallel and invest and build your other organizations so that by the time you get ready with your product, you also have a team that can actually go and sell it in a big way. So like, but we serialized it which was Actually probably, like, you know, like, probably put us behind by a year or two in terms of where we could be in terms of our size of business.

Yeah. Yep, That's a good insight, good learning. And the last question, what advice do you have for other founders as they embark on their journey to grow into leaders?

Well, my main advice to every founder is, well, first, like, you don't give up on your own ideas. When you start something, it's for a reason. And there'll be a lot of times where those reasons will be in question. But keeping that conviction on is actually the most important thing. So that's my number one advice. And number two is, as I said, get like, build a team. There is a lot of help. Like, you know, there's so many amazing leaders in the industry who are now, maybe they're retired, they're bored, and they're very eager to help, you know, young founders. And so just finding those people and bringing them, collaborating with them can actually go a long way. Like, it can actually help you avoid mistakes, you know, which are costly, which takes years from your companies. So the more you can interact with, you know, experienced CEOs from the, the better it's going to be for you.

Amazing. Arvind, such a great conversation. I so appreciate your time today and a lot of people are going to learn a lot from this discussion. So thank you.

Thank you so much for having me.

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