"My Top 10 Failures as CEO [While Still Getting to $200m ARR]" Nick Mehta @Gainsight | SaaStr Annual

Nick Mehta, CEO of Gainsight, walks through ten mistakes he made scaling to $200M ARR: promoting the wrong people, hiring before validating the need, custom pricing instead of standard tiers, skipping digital customer success, and chasing shiny things instead of staying focused. He frames each as a lesson learned, not a lecture.
Chapters
Please welcome to the stage nick mehta, CEO at gainsight. Hi, everyone. How you doing? All right. I could not pick a more appropriate walk on song. Thank you for Shake It Off Acoustic edition. I appreciate that I'm a huge swifty, but it's very appropriate for. We're going to talk about because I am fired up to talk about something extremely motivational for Friday afternoon. I want to talk about failure. This is going to be amazing, everyone. It's all about failure because I don't know about you, but. But I failed a bunch of times. I've been doing SaaS and running companies for a while and I found this great quote on the Internet. I don't actually know who said it, but it said, I never make the same mistake twice. I make it five or six times just to be sure. And that's what I'm going to talk about is mistakes I've made over and over again and kind of what's gotten me to where we're at and a gainside and what we're all learning through together. Now. One caveat, sort of background I'll give you to this. Some of you may or may not know this. When we defined our purpose statement at Gainsight, we didn't go with the typical change the world or build a huge company or anything else. We said we want to be living proof you can win in business while being human first. And this is like something we talk a lot about. Human first and part of human first. The fact that we're all human beings is being open to vulnerability. We're not always perfect. To be honest, I've had a heck of a year both personally and work wise and it's hard. And I, I don't know about all of you, maybe you all feel SaaS is crushing it this year. And if that's true, I'd love to learn from you. But it's not an easy year probably for a lot of us. So I'd love to open up a discussion, maybe it is a good closing of the conference about being open about mistakes. And I'd love to teach you all the mistakes I've made. Now, I'll give you a little background to this, which is the way this talk started was maybe six or nine months ago. Jason Lemkin, who I've been very fortunate to know since the beginning of Gainsight, he emailed me and he said, nick, I'd love to have you write a blog post about the top 10 mistakes you've made. And I was like, okay, so I'm the Go to guy for mistakes. Apparently for Jason. Right. That's what he thinks in his mind about mistakes. He thinks about me. But you know what? I'll take that because I think I have made a lot, but also I've learned a lot. And hopefully you all are learning along the journey too, right? Raise your hand if you think you made a mistake in your business at some point. Okay. Thank goodness. And the rest of you aren't honest. So let's keep. Let's go through 10 mistakes and we'll do like an AMA at the end because I think there's a lot of questions we can all ask. And frankly, I'd love to learn from all you as well, because I'm still learning. Okay, so number one, these are in no particular order. They're just kind of random stream of consciousness. Number one, so many of you are building companies. Some of you probably have leadership teams. Maybe they're getting bigger. The number one mistake or one of the mistakes I've made is not holding our leaders to the highest possible standards. Yeah. Actually, just yesterday, an entrepreneur texted me and he said, what's the reason entrepreneurs fail to scale? Very common thing you hear about, people don't scale, they bring in other people. And I think it's not being able to hold people to the standards that you hold yourself. Right. And that's. You think about values, you think about performance. What are those things that matter a lot to you? Are you able to hold the people that work for you to those same standards? Right. And I think one of the things that's really important is in leadership, there's that great expression, some of you know, to those whose much is given, much is expected. And I always tell my leaders, you know, we have about 1300 people at gainsight. I say, you know, you're running a pretty large company, you're expected to do a lot, and it's hard. You should be super honest, actually. I just literally right before this, put a slack post to my leadership team and I said, this isn't an easy year and I have a lot of empathy for you. And we have to hold ourselves to the highest standards because our team depends on that. And so this first thing, what it's motivated by at Gainsight is, is we are a very values driven company. We have these five values. They're kind of zany. Some of you know them like one of them is childlike joy. Bring the kid in you to work every day. One of them is stay thirsty, my friends, which might be a copyright violation from DOSA Keys. I Don't know. Right. So I've always, we've had these since the very beginning of the company and I've always been really passionate about them. You know, I could recite these in my sleep. I could tell you an hour long. Talk about examples at Gainsight of what we've tried to do over the years and also where we've failed to live up to our values. These really matter to me. Funny little side note, I was in the early days of Gainsight, I was at a kind of a CEO breakfast trying to learn from all these other CEOs. And every CEO around and said, went around, said, our values are really important to our company. They're so critical. It's important to have values. And I asked one of the CEOs, so what are your company's values? And he said, actually, I don't really remember them right now. And I was like, well, for gain sight, these are really, really important. But I got, we do employee surveys, you know, every six months or whatever, Right. Many of you do them. And I remember doing a survey probably about five years ago and I remember asking people, you know, the normal stuff, you know, rate the company, how likely are you to recommend the company, things like that, right. And then there's these like free text boxes, you know, what are the things we can do better, what are the things that we're not doing? Well, that kind of stuff. And I'm still that crazy person that literally reads every comment even though we have 1300 people. I read like the 5000 comments just to learn. And I remember reading those comments, maybe it was a few hundred back then. And one of the comments said, I wish, Nick, you would hold your leaders to the same standard of values that you hold yourself. And that was so brutal for me to read. Right. Because what that meant was we weren't living up to our values as a leadership team. Right. And I don't know what specific one they were talking about, but for me that was a wake up call. It was like whatever you care about in your business, whether it's being high achieving, whether it's being, being innovative, whether it's your values, or maybe it's just making money, make sure your team, the people that work for you, feel that same way. And if they don't get different people, the whole thing falls apart. When you have some vision as a founder, CEO, entrepreneur, or even if you're a functional leader and the people underneath you don't believe the same things, it's all a house of cards. And some of you probably Worked in companies where this was true. You know, maybe the CEO would get into an all hands and talk about how important these values were. And then day to day, you didn't see it, right? You didn't see it day to day because the leaders didn't live up to that. And so this first lesson for me is holding leaders to the highest standard possible. And that means it's hard to be a leader at gainsight. It really is. It's really hard to. I've actually got one leader in Gainsight in our sales team right here in the audience. It's not easy. You have to lead your team. You have to live up to the values. You gotta hit your performance targets. We're trying to get more profitable. It is not easy. But I'm also unapologetic because we owe that to our teams. So this is the number one for me. Now, what does that mean practically? What does that actually look like? So one of the things I try to do is say, okay, for our leaders, be really clear about the expectations. You know, we've got these five values. We've got an onboarding program for our employees about the five values. What are the behaviors to live up to the values? What do you need to do to avoid the negative things? But we have a even higher standard for the leaders. And it's actually something I edit each year. And when a new leader comes in, even before they take the job, I give them this document. There's actually a written form of this, but this is the one slide. Not going to read through all of it, but basically what you can see is the five columns are the five values of Gainsay. Right? These are the things that we hold dear since the beginning. And then I list out behaviors that represent these five values that are like 100% mandatory for the leaders. Now, some of them are pretty simple, like respond to emails within 24 hours or Slack posts, which, by the way, why do you have to tell people that? But apparently it's still a thing, right? Another one is being radically transparent. I tell everyone everything gain said about my personal life. Numbers we're missing, you know, whatever, right? A third one, like childlike joy, you know, bring laughter to what you do, bring creativity. Shoshin means beginner's mind. You know, embrace diversity, stay thirsty is all about your internal ambition and drive. And we have some examples there, like giving feedback and taking it. But then each year I define what are the new ways we need to live up to these values in the latest phase of the company. We're in a Different phase of the company than we were a few years ago. We're a different phase of the economy. So this year I said five things. Number one, golden rule is one of our values. It means treat people the way you want to be treated. I think part of that is taking care of yourself and taking care of others, right? Taking the time off you need, taking the space you need. So if you're a leader, you need to own your own balance against site. It's not acceptable to let yourself work all the time and get burnt out because that sends a signal to your team. And by the way, you're not a good leader when you're burnt out. So an example that I've tried to do this year is I have had a lot of personal stuff this year and I told people I'm just not going to travel hardly at all in the second half of the year. And I used to travel like two days a week. I told everyone this, I'm like, I'm going to take care of my family and that's it. And it's that kind of thing where you're willing to tell people I'm going to own my own balance. And that's something I expect from our team. Give you a couple other examples. Disagree and commit, that's a very common thing. I think it came was popularized by Amazon. But disagree and commit with compassion, right? It's one thing to be like, I don't think you're right and I don't think you're thinking about things right and that's disagree. But there's different ways to do it, right? About like, hey, I really like the spirit of your idea. I know it comes from a good place, but I don't think, I think the same way you do, right? A third one, just as an example in this stay thirsty concept is altitude is a huge thing in leadership. What that means is you need to be able to operate at 30,000ft which is like what's the long term vision of our company? And 10,000ft, which is like what's our plan to get to our next few years? And 100ft, which is like what are okrs this quarter? And 3ft, which is what am I going to do to close this customer or make them happy? Ship a feature and I expect my leaders to be able to operate at all those altitudes. So this isn't the right list for you, but an interesting question, whether you're CEO or you're a functional leader, what's the list of things you expect from your leaders? Is it On a slide. Is it is in an onboarding document? Is it something you really believe in? So that's one idea or mistake that I've made that I've tried to live up to. Okay. Number two, which is some of these are kind of like paradoxical in a way, but in a way that makes sense to me. Number two is, you know, with your leaders, don't forget that there's some great people that have gotten you to where you're at that you don't always recognize, can do more in the company. Right? And this is like, gets me to one of the common mistakes every founder, including me, makes, right? Which is you get to a certain point in your business, but you miss your sales numbers. The product isn't what you want. You know, you have too much churn. Employees aren't happy. And you say one thing, you say, you know what to your board or whatever, you're like, everything is fine. Once we get a new head of X, a new head of sales, we're missing our sales numbers. We will hire a new head of sales. Maybe some of you been that new head of sales, we're missing our lead pipeline. We just need a new head of marketing. Right? And the truth is, sometimes that's true. Right. I've had some people that came into Gainsight that we hired that were incredibly legendary, you know, amazing people that like, really changed the company that were from the outside. They had the experience, they had the resume. But I got to admit, I have swung and miss on way more executive hires than I've actually hit on. And if you have to, don't feel bad. It's something that I think a lot of us do. I mean, I don't think my batting average is more than literally like 200, like 2 out of 10 or something like that right now. On the flip side, if you look at my executive team today were 1300 people. Let me just go through it. Chief customer officer seven years ago, was a CSM at Gainsight. Had a sales Nine years ago, was a sales rep at Gainsight. Chief marketing officer six years ago was the person that did sponsorship sales for Gainsight. CFO was our head of fp and a chief people officer was my chief of staff. Right. Like, I can go on and on. Almost everyone grew up in the company. Now, at some point, you want to bring in some outside talent, so we want to kind of go the other way. But at least for me, this idea that, like, everything is about bringing new people and hiring the person I need in the future, they've Been at Salesforce or Google or Amazon. They'll show us the way. By the way, those are great companies. I think often people miss more than they hit. And this is especially true now because before people would often say, and boards would say, you need to hire for the person you need four years from now. Right? Because you're going to be growing so fast and you need to hire that person that can help you get to where you need to be. I'd argue first of all, most of us aren't growing as fast as we were a few years ago. And second of all, I'd say you kind of have to hire for the person you need now and maybe the next year and then hopefully they grow in the company. Mistake number two, mistake number three is a big one for me. Startup financial perspective. Maybe you've made this mistake. A lot of people made this mistake in the last couple years. Not scaling based on leading indicators. Now this gets to one of the big fallacies I would say exists in software and maybe you've lived this. I want to generate 10 million of bookings this year. Okay, great. My average sales quota is $1 million. I need 10 sales reps and I will generate the $10 million. Some of you might have been there before, right? And why not hire 10 more and you'll get $20 million. Why not hire 1000 sales reps and you have $1 billion of revenue. Why not? You should all do that tomorrow. Right? And the truth is like that's such a fallacy. It's an old school concept when there's like one vendor in a space and infinite demand. And so at gainsight we have scaled up too fast many, many, many times without leading indicators. I'm going to share three, like in the spirit of vulnerability. Okay, first one, so 2015, 2014, something like that. We closed our first gigantic enterprise deal. $202.6 million of ARR. The biggest deal we'd done till then was maybe 300 grand, 400 grand. We're high fiving around the office. I'm sure champagne is being passed around. I don't remember right. But it was a big day and we said this is the beginning of the next phase of the company. Let's hire like 10 enterprise reps and SCs and so on. And we did. Built a team, hired a leader. We didn't close our next million dollar plus deal for like five years later. Literally. I'm not kidding. Right? And that team cycled through. There were great people, a lot of people left. So this idea that you get one big deal and it's the sign of something new. I'd encourage you to get two or three before you scale up a second one. Now, this is not as relevant for very early stage companies, but even if it's a new product you built, scaling up the go to market for that newly acquired technology or newly built technology before it's really ready, not just technology wise, right? Like technology has to be ready. You need to be at feature parity or have something competitive, but you don't really know how to market it. People don't know about you. You don't know how to sell it. Maybe it's a different Persona, maybe it's a different industry. A lot of people are like, this is awesome. We have this new technology and we're just going to go scale it. By the way, a lot of people includes me. So we made that mistake. A third one, maybe many of us made here was in 2022. It was, it was in 2021. Those were heck of a good years in SaaS, right? Amazing. For many companies. Our bookings shot through the roof. We thought we were so great. Like we did. I don't know about you all, but I thought it was such a great CEO because we're just, you know, soaring, right? We were like, we have an investor and we were like the number one performing company in their portfolio, right? And a lot of companies, including Gainsight, said let's just hire a bunch more people. Like literally we went from like, I don't know, 800 people that year to like 1300. And by the way, that's, you might be doubling your company, but at that scale, that's a lot, lot of people. And it was a big mistake. Like the market was like temporarily in this boom, right? You can think of all the companies that are amazing companies but went through this very publicly, like Zoom and others, right? Amazing companies. But they had this huge temporary jump and then it came down and now they're still great companies, but it's hard to go through that. So this learning about what are my early leading indicators. And, and there's a great way to think about this. So there's a famous author and business named Jim Collins. He's written good to great. Like some of you might have read his books and he has this great quote, fire bullets, not cannonballs. And the basic idea is when you have something new you're thinking about, it's like a new product, a new go to market. Maybe you're, maybe you're going to sell in a new region. Fire A bullet meaning make a small experiment, hire two sales reps or three, spend $100,000 on marketing. Right. Don't assume that just because you've gotten a lot of success in your first business, you can just go immediately into this next business. Fire a bullet, not a cannonball. Mistake number four. So this is a big one that many of you are probably the very beginning of. Okay. And if I had to give you one like lesson from somebody who's made huge mistakes that we can never really recover from, it's this. So you will have a customer, maybe you have one now prospect and they'll say okay, I get Your pricing is $200 a month, right. And it's like you have a one year contract. What I'd really like to do is have a three year contract with the one year, opt out in the beginning and pay you on quarterly terms and not pay you in the actual. The users you've signed up for, but the, the, the computed users based on consumption and actually have a max and a minimum. And you're like this entrepreneur that's kind of desperate, which I was. You're like, sure, we'll do that, right? It's like one customer and the one customer turns into three or four and then you have like gainsight where like 1300 customers, I don't know, 1200 different pricing models, something like that. And I would just say it's a trap, right? It is totally a trap. And now that doesn't mean you shouldn't be flexible to customers. You should. But I remember some of you probably know Atlassian, like one of the greatest software companies of all time. Somebody from Atlassian here. Go, go Atlassian. What's that? Aussie. There you go. It's Aussie. Atlassian's an Aussie company. And Jay Simons used to be the president of Atlassian. I got to know him, he's amazing. And he presented this like chart where Atlassian very famously did no contracts, no negotiation. You buy jira, you pay a certain price, that's it, right? And he showed this chart like Goldman Sachs buying jira. And Goldman Sachs just literally bought Jira like a seed at a time or whatever. And at some point Goldman Sachs presented offer to Atlassian that will pay a lot more and will get a discount and so on. And Atlassian said no. And Atlassian's revenue was much more than that contract could have been a few years later. That's not appropriate for everyone. We're not Atlassian. I'm not, we're not Atlassian, but I Think there's some element of having some level of discipline because frankly a lot of those deals at the end of the quarter that you push in because it's a special pricing model, you're desperate to hit your number. Maybe you buy their product if they buy yours. I'm sure none of you have done that before. Maybe we've done that a couple of times. Almost all of those blow up later on. They're bad customer success, they're impossible to scale. And specifically they create this problem where if you didn't invest in those pricing and those systems and all that upfront later on, you end up with a lot of complexity for your customers. Right. Like how do I even renew this thing? That your team becomes super frustrated like sales and cs. Cause they're like doing a quote takes like an hour. Right. And. And it becomes hard to do analysis like how much are we growing, what are our discount rates and so on. You probably aren't dealing with these problems now if you're early stage companies, but if you make these mistakes of doing whatever every deal wants, you will absolutely have them a few years later. So the lesson here is be really careful about custom deals that feel very tempting in the moment. Number five, this is such a frigging commercial. But in not investing in digital customer success early enough, that's what we do. Right? So of course. But I think I really believe in it because eventually you hire a ton of people and it's kind of chaos. And so obviously we think that like getting to the point where you really scale through digital, not just like what Gainsight does, but just every kind of self service thing you can do. Everything you can do to not hire a ton of CSMs and support people early on. Right. Make it way more self service. Then the people you hire will be much more value add. There are so many companies out there that hire CSMs as a band aid over the customer experience over the product. I would work on those things first. Even though that might lengthen your sales cycle for buying Gainsight. Right. And like, you know, we have a whole playbook and go to our website of things you should do to improve digital customer success. Some of them related to Gainsight, some not. I'm not going to go through this one in detail. Okay. Number six. Because I want to make sure you have time for Q and A. Number six, this one's very close to home for me. Matters because of this human first thing I talked about about not parting ways. Well, always. Now unfortunately in business there's a lot of parting ways this year there's been a lot. And that parting ways is hard. Now, there's two kinds of ways. You can part ways, right? The company can part ways with the teammate, which is tough, or the teammate can part ways with the company, which is also tough. Right? Both of those. Right? It's like, I'm from Seinfeld, I'm breaking up with you. No, I'm breaking up with you. Right? That's what happens. And you know that the truth is that a lot of companies don't part ways well, right? Some. It's very well known that some companies do the riffs well and some not. That's not what we're going to talk about. I would talk about the other side at this LinkedIn post. It said, serious question, why are so many companies weird to teammates when they leave? And you can see more of this. And it is the most commented shared post I've ever read, ever. Posted thousands of comments. And it was heartbreaking. Cause everyone's sharing stories about they left a company and they never spoke to me anymore. They walked me out the door, they treated me like I was dead to them. They would never, ever help me in the future. And it just breaks my heart. It's just like really sad that somebody that works for you, that did so much for you leaves the company after doing some great things and you treat them like they're dead. Right? That's just horrible. Right? And so for me, I've even made this mistake once or twice. I never treat anyone like their dad. But I remember making people, two people actually in our history, feel bad for leaving and then later on with good relationship. But for me, I would say, and again, I'm biased, but end every relationship with a teammate in a human first way, whether it's you doing a riff and somebody leaving. And honestly, like when we've done those, I try to call every person and say, how can I help you with your job search? Try to help. Or they leave and they announce their new job and you, like, celebrate them on LinkedIn. You know, sometimes I literally, it's crazy. I will send the person a bottle of champagne for getting their new job. I know, it's weird, right? Why would you do that? But eventually you build a great alumni network. I'll just pick one. My favorite. Brian Hamblin was our head of sales several years ago. He's amazing guy and, you know, like, I celebrate him on LinkedIn for his new job. I'm talking to him on Thursday about career advice. Right now he's happy with his job. But just like, how does he keep growing his career? How to become a CEO one day, right? I talk to probably hundreds of gainsters, ex gainster alumni about their career advice. Like, people will call me three jobs later for advice. And it feels so great for me, it's not about me, it's about building that relationship. By the way, your alumni can be referrers for jobs, they can be customers. So treat your people well when they leave. Getting back to a little more intellectual part of business. Not being prescriptive enough, early enough. So many of your early stage entrepreneurs we were at some point and we built some of, you know, our first product was like software to scale customer success teams. 2013, people didn't even know what a customer success team was. Now why did we build software for teams that didn't exist? I don't even know. That probably wasn't a good idea at the time. We had to wait a while. But early on we had this software and it was like, you know, score your customer risk or manage workflow. And we would go to an implementation and the customer would say the following, which you all hear, how should we implement your software? And we would say, I don't know, what would you suggest we do? And the customer would say, well, what would you suggest we do? And we had no idea because we're this little startup. But the problem is we went too long with that, like letting everyone implement in totally different ways. Some of you might have done this, right? Customer A wants to implement a certain way. Customer B randomly wants to do a different way, right? Here's the problems over time. The back and forth is where long time to value comes from. People always talked about time to value. I'd argue the biggest part of time to value is not your technology, it's how people implement it. Because people spend a lot of time on indecision. How should I use this? You know, you've all used products where you're like, okay, what do I do first? Right? And sometimes an in app guide can help, sometimes your community can help, sometimes just a methodology and best practice can help. What does your implementation team do? Or your customer success team do? They get on the call and say, how would you like to implement this? Or do they say, here's a methodology for what our other customers do, we'll do it whatever way you want. But here's our recommendation. Customers want to do things in the way that other customers do things. They don't want to be like the snowflake, totally different, right? And one of the things that happens is if you let people be different, they will all be different. And it's really hard because they can't all learn from each other. They give you different product roadmap requests that don't even make sense. It's hard to ramp new teammates because new people come in. They're like, okay, so how do we implement this? What's our methodology? You're like, well, if you spend five years here, you understand it, right? Because you need to know all these things. And that doesn't make sense. Now it's hard too, because you kind of need to get everyone on the same page. Sales, marketing, like, what is our value prop? How do we implement this stuff? You need to have like the implementation for each stakeholder. That might mean different things for like the C level person versus the end user. You have to keep it up to date as your product changes. And we have to like, coach our team to be brave, to tell the customer, yeah, we'll do whatever you want. But here's what we Recommend. We have 1300 customers at gainsight. Most likely, we've done this more often than you. So here's our recommendation. The bigger you get, the more you have opportunity to do that, right? And so I would recommend that if you're in the early days, do this soon. Because all this is easier when you have 50 customers and it's much harder when you have 1300 or 5000 or whatever. So what does this look like a GAIN site? You actually can find this on the web, like a code. A site code is like a documentation, you know, collaboration thing. And you can go find or go to our website and it'll say, what are the business outcomes you want in terms of customer success? Reduce, churn, drive expansion. And it'll literally go. And this is how you should implement Gainsight. For that, here's the workflows, here are the best practices. And our team uses this to basically sell Gainsight. Our recommendations, implement Gainsight, manage the CSM process, renew, show the value of Gainsight. So for me, this prescriptive methodology is something very practical you can all do in the next year or two. Okay, Number eight, getting towards the end. So one of the things that happens in the early days of a company is you're like growing like crazy. Like, I think our ARR early on was like 1 million and then 5 million and then 16 and then 30. That was pretty good, right? Not Snowflake, but it was pretty good. But then one of the things that happens is every business gets to the point where they need what people call an Act 2. Act 2, which is basically like, what's the next thing you're going to do? An Act 2 could be a new geography, a new segment of the market. Maybe sell to enterprise. You want to go to SMB, it could be a new channel, maybe there's a partner for you, could be a new product. Right? And one of the problems is if you don't think about that stuff early, you end up dealing with gravity. And the gravity is this. Every market has a certain number of buyers and eventually get to the point where you started selling to a lot of those buyers. Now doesn't mean you won't sell to more buyers. But often, like the number of new buyers, like the number of new logos grows, grows, grows, and then flattens out, right? And so that logo count, maybe you did the first year you did 10 logos, second year did 20 or 30. The next year you did 60, then next year you did 80, but then you did 85 and then you did 87 and then you 90. So again, tying to our, er, I think it was 1 to 5 to 16 to 30, and there's like 48. That was 61. Right. And we didn't do anything wrong. It's just like they started having the same number of logos a year. So what that means is, like, your new bookings flatten out if you have one product. And this is tough because, like, if you wait too long, it'll look like your company is flattening out. And by the way, it's much harder to raise money when your company's slowing down. It's much harder to get people excited when you're slowing down. And so for us, we saw this slowdown roughly around 50 million of AR. I have a whole blog post on this, by the way. And what happened was, honestly, we were selling to SaaS companies. There was only a certain number in 2016, right. A lot more now. And we're just bound by the tam. I would drive up, like, I live here and you know, there's Highway 101. I drive up and down it and they, you know, back then people had offices, right? And there'd be the logos on the top of the building. I'd be like, okay, I pitched that customer, their customer, their customers, their customer. I pitched that customer, everyone, every single company, we'd either pitched or they'd buy every single one. I was like, oh, geez, we're tam constrained now. Eventually our TAM grew, and then for us, we became what I call platform company, meaning we have four products now. Community education in app guides, customer success, more coming, right? But I wish we'd started all that earlier. And for you it might not be more products, could be more geographies, something. But don't let it wait till you start flattening out, till you figure out your next act. Because if you don't like, you are going to slow down. And one of the things, very practically I wish I'd done is build a database of your addressable market. Now, I don't mean that BS slide you show to investors that says your addressable market's like $10 billion or a trillion dollars. I mean the real one, who are the buyers that could buy from you? There's maybe a thousand. Like back in the day there, Frost, there were probably like 200 companies that could buy from us and maybe now there's 5,000. Who are they? Where are they in their process? Track the people at those companies. So for us it's like, who is the head of customer success, that company? How many CSM are they hiring? What do we think we could sell them, right? Build that TAM database. Now you can use a third party data set, like a zoom info or whatever, which are great, but they take that data and build your own database. I wish we'd done that earlier. We're doing that now, actually. Number nine, huge one for me. I particularly a few years ago had massive, massive fomo. Like, like I would be here speaking here. I'm like, is there a brother speaking engagement in one of these other stages I should be at, right? I would always have fomo. And one of the problems is there's all this FOMO in tech and people aren't really open about the challenges. This company just raised a lot of money. This company just went public. Like Klaviyo is this amazing company going public. You look at their numbers, like, how could I ever be like that? Snowflake, right? Data bricks. And so you have this fear of missing out. What's wrong with me that I'm not like that? Now, I would say at the beginning of Gainsight, again, this is way before many of you are working 2013, there's all these companies that were super hot, like super hot, raise money, TechCrunch or whatever headlines, billion dollar startups. And you know, some of them are gone. Honestly, we're still here. And so I'd say, to quote one of my other favorite influences, Hamilton, sometimes you gotta wait for it. Just like Aaron Burr, right? You got to wait for it and be patient. That doesn't mean, like if there's no market. You should spend your whole life doing nothing. Right? But be willing to be patient. I would say gainsight and me, we're definitely the tortoise, not the hair. There's no way we're not the hair. But we just kept going. Kind of persistent, right? And just like waited for it, for our market to arrive, for our business to be there. And if you don't believe in your business, don't wait for it. But for me, I was like, look, this is gonna eventually happen. Like customer success SaaS. It's gonna eventually happen. And honestly, it would piss me off if we threw in the towel and somebody else took advantage of that. Right? So we just kept going and going and going. Right? Okay, last one. Number ten. Not being myself. This is very easy for all of us to do, right? You can tell I have a certain style, certain style of wardrobe, whatever, right? And I remember we did our. We do this conference called Pulse. It's kind of like the industry event for customer success. The first year, 300 people showed up. We're in this, like, ballroom in a hotel, maybe something like this in a hotel, though not like an outdoor amphitheater here. And I did this talk, and this talk was like the one I'm doing now, like, not scripted. I think I came out in like a football helmet for some reason. I don't know why, but it was me, right? It was just me, like the zany cheesy dad joke me, right? That was me. And I remember it went really well. And we like, you know, that conference went well. And yeah, I know we got some articles or something. And I remember me saying, I'm going to be a grown up CEO now. I'm going to get a speaking coach. And the speaking coach looked at me and said, nick, you're way too, like, whatever this is. You talk too fast. You're too high energy. You're too unscripted. Why are they all these memes and jokes and gifs in your talk? And she said, write out your talk. Stand in one place. Like a little bit like a politician. Get electron. Is that. That's a thing? Is that what it's called? Electurn. I don't know. And stand there and so you could go watch on YouTube on Pulse 2014, my worst keynote ever by far. It's like so stiff, so boring, right? It was literally I was bored while I was doing it. That's a big part of, like speaking or being yourself. Like, you don't want to be bored with yourself, right? So what do we do at Gainsight, we just embrace this weird company that we are. Did carpool karaoke with Aaron, the CEO of Box. I literally made a rap video, rap single. It's on Spotify. There's probably been five downloads so far. All them my mom. But, you know, like, we made a rap single about customer success. We did Taylor Swift, many, many parodies. We did a TED Lasso spoof called Ned Sasso. I don't make this up. Right? This is legit. And so I just say being yourself is very powerful, right? Like, you hold yourself back and try to be somebody else. Like, try to be me or anyone else here in this conference. Be yourself. Maybe that's somebody really analytical. Maybe that's somebody about empathy and warmth. Maybe it's somebody that's, you know, trying to have fun on stage. Be yourself. Right? So just to close this out before we do ama, I just feel like, overall, we don't talk enough about mistakes in tech, and many of us make them, right? Many of us make them. But we don't openly talk about that many of these speeches here about how amazing things are, how we're all doing so well. Let's show up into the right charts. Let's be honest. This year, a lot of mistakes have been made. Last year, a lot of mistakes have been made. Sometimes it's nice to open up that conversation. We can all be a little more human first together. So thank you for listening this. Happy to do some questions. I think you go up to the microphone like this is some political convention. So please come up. I hope I'm not too stiff. Nick, love your chat, man. This is related to insight 10, which is mainly around. I'm curious, how did you change as a leader, your leadership style over the course of these mistakes, these learning opportunities? And I guess last thing is, what are you, like, working on now as a leader? What's the challenge for you? What are you trying to improve on? I love that question. What's your name, by the way? Sammy. Sammy. Thank you. And by the way, you can hide the slides so you don't have to watch the Taylor Swift Jeff for, like, forever. So great question. How do you change as a leader now? I'll tell you a few things about that. Like, how did I change? And then also, what have I actually changed? So the how for me is I'm a huge believer in, like, learning and feedback. So I do like a360 on myself every year. You know, I use a consultant now, but they'll, you know, reach out to my board and my team and what can I learn? What to do better, by the way, in the past, I'll probably do it this year, too. I literally share that with the whole company. Like, hey, this is what I am. One of the things I started doing a few years ago was like, I wrote this blog post called attention CEOs fire yourself. Very popular blog post. Mostly because most people want to fire their CEOs, I guess, but, like, it was about, like, rewriting your job description every year. Like, what does Gainsight need from me right now? Probably different than what we needed a few years ago. I'll get back to your last question because that's relevant. So what does it practically mean? How have I changed over the years? Well, you know, the early days, it was about evangelism, figuring out what this company was going to be. Then it was about scale. Then it was like unscale because we grew too fast. Then it was like new products and new markets, which still a lot of it now. And today, though, it's also about building a sustainable business. We're actually profitable now, which is pretty cool, generating cash. But you know, when you're profitable, you have to generate more. And how do we build a business that's durable and efficient and we're doing the right things, so we're not just throwing money at things, but still preserve our culture. So that's some thoughts on that. Great question, Sami. All right, next up. Hey, Nick, this is abhi. First of all, heartiest congratulations on being voted number one on Glassdoor. That's a huge achievement. I want to double click on mistake number one that you mentioned, but I don't want to restrict it to just the leaders part. Right. How do you hold everybody accountable? But it seems you've really aced the game of empathy as well. Like, you're number one on Glassdoor, which is a huge thing. And I also follow you on LinkedIn. It seems you have a very charming presence. So what has changed in your personal journey over the years and how do we get that right? Like, I want to disagree and commit, but I really want to be liked as well. So what's your philosophy behind. Oh my God, I'm going through such a personal journey on that this year. I think I definitely. One of the, like, strengths and weaknesses I've had is like a desire to be liked for sure from childhood or something like that. And it's really positive in that you can end up with like a charisma or whatever, but it can also hold you back. Right. And I would say Gainsight's weakness Historically has been a lack of candor. Like, we were very positive. Like, nobody would ever say we're not positive, but did we address the hard issues quickly enough? I wouldn't say so. Yeah, not, not. Not in general. Now do we give feedback? For sure. Like, we have feedback process and all that, but I think we haven't been great. I'm being honest. Like, we haven't been great at that. And so one of the things we're trying to get better at is that, you know, radical candor. Many of you read the book, but it's basically like candor with compassion, right? And it's not about, you are a bad person and your bad salesperson. It's about, hey, like, we can all agree that that wasn't our best work, right? Or we can all agree this product isn't going well. Like, does anyone disagree with that? Right? Like, anyone tell me that it's going great? And I think there's something, some power in that where you ask the question, does anyone think this is going great? Anyone think we're doing our best work? I think there's something about that because most people will admit, like, yeah, no, this isn't our best thing. You know, And I would say earlier, actually, it's funny, I just talked to a teammate who's an alumni and she's like, nick, before I had to decode your messages, if. If you said great, it meant it wasn't good, and if you said awesome, it meant it was good or something like that, right? That's terrible. Like, how do we be more candid early on something? I think you can be positive and candid at the same time. I think people value it. One of the things I love, I don't know if people from GONG or hear anyone from GONG here, they have this value which I love, called no sugar, which is like, we're not going to. We're not gonna like add sugar to this feedback. I'm just going to tell you what it is. I think that's cool. Next question. Thank you. Hey, Nick. I had a coffee with Mike Burger this morning. Oh, Mike. He wanted me to tell you hello. I love Mike. He's our old head of product marketing. Yeah, he's great. So I think in the early, early days over seed stage startup, you have a lot of pressure, especially as a revenue leader, to sell and like, sell a lot and always been a seller. Have you ever found yourself overselling what the technology actually can deliver and how do you manage expectations better so you don't find yourself in that spot? Obviously that's never, ever happened to us. Never. I can't imagine what are you talking about? Nobody here has gone through that. I think the truth is like one of the great business books of all times called Crossing the Chasm. Some of you read it. I'd recommend everyone read it. They talk about this idea that there's a certain type of buyer demographic that loves being those early adopters. Right. And these are the people that like Trout the first iPhone when it came out. Right. The first, you know, first version of a Tesla or whatever. Right. Those people are willing to take the lumps in terms of the technology. And so one of the things I think about is who are the early adopters, by the way, they're the easier to sell to too. Like, one thing I always think about practically is if you're a certain domain, think about those companies that are like, you figure out who their early logos were. So gainsight, there's a company some of you probably know called Marketo Marketing Automation. And they were kind of a little bit before us. And so I was like, okay, what logos did they get early on? They're probably the ones that are willing to deal with the lumps. So I think the key thing is don't sell to a big old company that's not willing to do deal with those lumps. Sell to the companies that are okay with it. That my quick answer there. Awesome. Thank you. And probably last question, perfect timing. The last one. It's all you. All right, Nick, good to see you. You, I guess. Thank you. Founder of Growth Q so awesome question for you, for the operators or even longtime operators turned technology founders. Now one of the things I am finding is that there's a lot of unlearning that has to come from working in big, large companies to now scrappy startup. Even how you hire, how you allocate capital, things like that. I would love your feedback in the last thing you mentioned of be yourself, but how do you be yourself and when you're having to be kind of something you've never been before. Yeah, that's a great question. And definitely like that idea of like scrappiness is so true. And coming from a large company, some people are very scrappy in large companies, but you sometimes get a lot of support there. And so I would say that most of these things, like being yourself can be a little misleading because we can all grow, right? Growth mindset. I'm sure many of you know about it. And so I think scrappiness can be inspired in people. And I think that Sometimes there's one person that can inspire in others. I'll pick a person at Gainsight named Scott Salkin. I mentioned he was our. He's our CMO now. He started as like a sponsorship salesperson, and he's incredibly scrappy. Like, we'll be like, hey, what do you think about new pricing model? And like, something, something, right? And he'll be like, here's the slides on the new pricing model tonight. And he'll make the slides, right? He has a pretty big organization. You know, somebody else will be like, in sales, the sales leader and just go do a sales call themselves, do a demo themselves. And I think that if you have some people in your organization are like that, they inspire everyone else to do that. If everyone in your organization is like, okay, let me go delegate this to somebody else, everyone's going to be like that. So that'd be my quick version. So let me close out with a quote that I love. Very wise person said this. Be yourself and believe in what you do, but also believe in your mistakes and learn from them. Now, the philosopher was Taylor Swift, who's always the most wise person in the room. But I would say, embrace your mistakes, learn from them. I love learning from you. Thank you so much, Sam.










