#100 Arvind Jain, Founder of Glean — From Technical Leader to First-Time CEO, the Business Case f...

And I had 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 3 things that matter the most and make sure that you work with your executive team on those 3 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 Grownup. My name is Alisa 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's 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 1,000 people. One of Arvind'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 Arvind 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 you're gonna 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, 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, uh, every company, you know, always feels like a, a real new project for me, at least, you know, that's how it feels. There were, you know, we built Rubrik, uh, uh, you know, into a high-growth company over, over, over 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 an end-user product. It's more like it's meant for 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 it was again, like, 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 the journeys were so different. 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 Gleam, 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 so you have— there's a much higher bar. 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 of one of the key differences in like, you know, how we approached 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 of go through that journey and what's different today about being a first-time CEO.

I, I think the, 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. It was sort of similar because 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, even as the head of technology. And 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 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 work yourself. But it largely felt to me that I was able to learn without feeling that, well, like, look, 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, 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 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 The learning never finishes. Like, you know, our company also, Glean today is very different. Like, now we are almost 1,000 people and the business has grown. The company's, you know, valued over $7 billion. So it's a serious enterprise. So like, it does feel very different from the Glean of 2 years back or the Glean of 4 years back.

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

Yeah. That's right.

What, so what can I, 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 to learn was how to be a seller. As an engineer, you don't really sell your product. Products like this. That's a job of somebody else. We, you know, we build good products. We build products that we use ourselves. 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 time. 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 Kleen 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 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, I have a long engineering career, like I've worked for 20 years as an engineer or engineering leader, but during all of that time, most of my interactions would be with R&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 like, you know, good, easy relationships with everyone. And here, like as a CEO, I actually now work with marketers, with salespeople, with, you know, with HR and finance and legal. 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 teams and adapt myself quite a bit. And in fact, like, you know, that's still a struggle for me. Like, you know, I think people sometimes find it hard to work with me, especially like if they're not in R&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 them, marketing people, sales people, HR people, finance people, what specific advice do you have?

Well, I think first, 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 worse than yours. Like in terms of that, you know, your approach, your way of thinking is better than them. Like, you know, if you sort of have that mindset, then you're always struggle. And so that's that. 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, like I'm actually able to give them good advice. And like one of the advice that I got was that every engineer turned CEO, is a good idea for them to actually have a coach that, you know, who has a different background. Because, you know, the coach will help you understand, like, you know, what's the best way to actually build great 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 and I don't have a formal relationship, luckily. I mean, that actually makes it a little bit more comfortable for me, 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 detail-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 was not 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 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 3 things that matter the most, and make sure that you work with your executive team on those 3 things, and ignore the other ones. 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 not quote unquote worry about 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, uh, 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. 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 founder's mode, I've talked to so many founders who feel so relieved, as you said. They're able to rationalize their weird behavior because of it. And for me too, I think I also— I get a pass sometimes with things 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 like over time and it happens automatically. You don't really put in 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 step back and your sort of mind automatically switches off. Like you don't actually bother to even, like you don't worry anymore that, hey, what's happening in the marketing team? Because I know that there's a great leader who's going to take care of it. So 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, or whatever. Yeah. 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 Gleam, it has been the same because, you know, 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 like, you know, where they went and got their education. Like, and, and, and so that's sort of like, you know, 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 your startup journey is not easy. You have to work very hard and you don't even get, you know, 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's It can be zero if you don't succeed as 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, you know, we are looking for somebody who wants to learn something that's unique to our environment. And so why, like, you know, like for example, like 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, which maybe, which is being a software engineer or a product manager. So that actually is something that motivates me to see somebody who's looking at Glean as a place which will actually help them learn those 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 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 Gleam, 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, like, why do they want to work on this product? Is it like personal to them? Is this something that's super important to them? And that's, so that's one of the other criteria that we use to recruit people. And that actually It 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, you know, that you have in the company. And now, you know, with the, with, you know, that connectivity to all of your enterprise data, knowledge, information, as well as You know, 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, like, you know, hey, who's the subject matter expert on this topic? Or what did we accomplish in this particular project team over the last one month? Any questions about your day-to-day, you answer, you basically go to Glean. Glean becomes that one place 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 the company's context and data and the world's knowledge to actually try to complete those tasks that you actually give to it. Wow, I didn't know that part. That's cool. 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 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 like, you know, we had to do 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 to power this product now is also used directly by our customers as an AI agent building platform. So those are the two things we do. A really personal assistant, e-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 recognition in 2019 before we had ChatGPT and whatnot that this was gonna work?

Yeah, so the transformer technology, so AI is a very broad term and has 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 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 research started in 2010s and 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 documents. And that's how it does that matching. Like it's a word-based matching algorithm. And then over 15 years, we built a lot of systems to make it smarter. We would sort of, for example, expand people's questions with synonyms and other things to try to make it a little bit more flexible. 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, when you ask a question to find relevant documents, you didn't have to actually find documents that contain 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 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 they 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, we are the first enterprise GenAI 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 gonna get only better and we're gonna 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 wanna just 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 should 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 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 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, you know, their interactions with the rest of the team members, they build those deep relationships. And they feel that sort of agency. They feel, you know, that ability to make big impact. And these are some of the things, you know, 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, you know, I heard this observation from someone that if you put like, you know, get the 100 top scientists or engineers in one room and ask them to solve a simple problem and after 1 hour you'll come out and they would've not solved it even though all the brain power of the You know, if the world was in that one room and you had 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 a startup. If you don't build a shared of values that makes everybody sort of think the same way, work the same way, you won't build a successful, high-performing team. So these are some of the key attributes for, you know, 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, you know, from Google as well on when we started to sort of lose our way on certain topics and what were the things, you know, that I wanted to avoid.. And I was really particular about that as we started building Kleen. 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 still 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. Like, you know, one, maybe I'll share some anecdotes. So like when we started this, so it's not as if I was doing this work, but, you know, 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 Gleam. 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 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 a 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 your 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? 'Cause 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 4, um, the key principles in that, and those are sort of, and then we go and also sort of further expand what they mean, but the 4 values, the 4 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, I can go one by one, make it customer-driven is I think there's a very simple, there's a very simple principle for any company. Customer is always right. They are the ones that should define like 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, like, you know, it's not always that like for any given problem, like, you know, don't spend like 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 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, that is the most important one, which is that, you know, 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 sort of have this humility around them, who know that, well, yes, you know, I was part of, 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 were so many other people who actually also worked on it, you know, along with you. Like, 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 team, that is actually very, very important if you want 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 actually like maybe for engineers sometimes, you know, it's not as applicable. Although like, you know, in that case, you know, 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 was 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 start to wonder like, okay, well, I'm not seeing any recognition of the fact that they had good colleagues who did that work. And that could be like one of the red flags. So you sort of like 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, 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? Why did you change from company 1 to company 2? And 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 I was having, and that's when I sort of, for me, that's not necessarily like a 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 will 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. 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 war story and how did you deal with it?

Yeah, I think for Gleam, 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 share a few moments. So first was the like trying to get people to pay attention to us. So 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 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 won't 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 it 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 build this. But I think, you know, luckily, you know, we had the conviction because we went through the pain ourselves, like, you know, every single day of our own work life. So, we knew that we're 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, you know, where, you know, with the power of AI, we could show that we could do so many big, like amazing things. And like 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 are building something interesting, to now where everybody believes that they need a product like ours. So yes, the patience sort of helps, like ultimately, you'll find your day. So that was like one of the big challenges for us. The second one was actually the ChatGPT moment where suddenly, you know, we felt that like, look, all this work that we did over the years, did it 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 a company and just dump it into a— into and train in a language model for your own company. And so we had this period of a few months where we felt that, well, like the 4 to 5 years of hard work that we had done, maybe it's all obsolete, you know, in one fell swoop, like, you know, everything's become obsolete. And we had this question about like, you know, like, 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.

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 gonna 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 2 months or 3 months. I faced it for 2 decades of 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 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 had 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 believed 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 onboard 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 conviction. And that's why we didn't pivot despite, you know, the early struggle from every prospect that we talked to. And that's an important thing. And I always tell founders, like if somebody is 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 thought, you had observed, you had found something. And unless if the world 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 we'll When I saw you in May, we talked about you do like almost like a 6-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, and not 6 months, like now, now it is more like every month, every month you have to, 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 technologies. So we have to, so that's, that's one of the things we changed, like in our, our our product planning process now is monthly. It used to be quarterly before, and that itself was too slow. And largely the concept of annual planning and setting goals are not that relevant to day-to-day. This is all about every month we decide, hey, what are the most important things for us to do this month? And then we go and do it. So yeah, because the AI 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 6 months, we, every 6 months, you know, we think about, everybody thinks about, like, you know, the work they've done. They actually formally, 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 6 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 6 months. So, 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 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 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 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 becomes, you know, who becomes the reason for us to not realize it. Yeah.

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. So that's, you know, that's why I'm still here.

You haven't fired yourself yet.

Yeah. And it's sort of like when I think about it actually does give me ideas for like, hey, what is that one thing that I need to change right now? Yeah. And 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's just an that's too much. And then I probably won't do any, 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 I said, 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, or 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 maybe it will sort of reduce the confidence that the other person has in what they're doing. Like, it was okay, maybe you could have done it 10% better, but it's not worth talking about that right now. And so that's one of the main learnings is 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 the, like as we build businesses, we want to build them in a good sort of, in a good manner, fiscally responsible manner, like we generate profits over time, and actually like that sometimes it's not the right strategy anymore, like especially in the AI world, in the world where, you know, when there's a fundamental shift in technology that happens, like, you know, the one with AI today, land grab becomes a much more, much more of a strategy. Like you won't actually go really, really big. You like raise, raise huge amounts of capital. Don't worry about like, you know, are you making any profit and just acquire users, right? And then, and that's the right strategy. And, and that's sort of like, you know, for me, it's always hard. 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, go against your own instinct. Like you need to understand like, you know, 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, um, one thing that I I wish I actually got more coaching and talked to more CEOs who had led their companies through hypergrowth before than I actually did. Like 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 Gleam we underinvested in marketing. We underinvested in go-to-market and sales teams for a long time. And if we had not, like, you know, we would actually be much larger today. We waited for building a really, really good product and until we had it, you know, we didn't want to actually go and invest in those things. The right answer, like now in the hindsight, was that sometimes you have to get out of that again, like, you know, like do things which are uncomfortable. And even before you have full proof that a 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 the 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. Yeah. 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 know, don't give up on your own ideas. When you start something, you know, it's for a reason, and there'll be a lot of times, you know, where that, you know, those reasons will be in question, but like, you know, keeping that conviction on is actually the most important thing. And so that's my number one advice. And number two is, you know, as I said, like, you know, get like build a team, there is a lot of help. Like, you know, there's like, 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, it 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, the better it's gonna be for you.

Amazing. Arvind, such a great conversation. I so appreciate your time today, and a lot of people are gonna learn a lot from this discussion.

So thank you. Thank you so much for having me.

Thanks for listening to From Startup to Grownup.

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