Deep Dive with Nick Mehta

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This is a podcast episode titled, Deep Dive with Nick Mehta. The summary for this episode is: <p>Today’s guest is Nick Mehta, CEO of Gainsight. He and Matt are diving deep into Nick’s journey launching and scaling Gainsight to 1200 employees over 10 years. Nick considers himself a student of the craft of being a CEO—something that gives him an interesting and thoughtful perspective.&nbsp;</p><p>They also talk about being values-based from the beginning, keys to a healthy board, the stages of building a leadership team, and why careers are like jungle gyms. </p>
The journey to launching Gainsight
02:38 MIN
The scaling journey
00:56 MIN
Scaling culture as the company scales from 10 to 1200
06:27 MIN
Scaling culture as the company scales from 10 to 1200
06:27 MIN
The first phase of building a leadership team: hiring a team that's ready to prove themselves
02:09 MIN
The second phase of scaling the leadership team: bringing in more experienced players
02:38 MIN
The third phase: laying in new perspectives
03:18 MIN
Careers aren't ladders, they're jungle gyms
00:42 MIN
Getting the most out of your board as you scale
04:40 MIN
Balance is the key to a healthy board
00:45 MIN
The role of the CEO changes every single year
02:52 MIN
Be a student of what it is to be a CEO
02:39 MIN
Venture backed vs. private equity owned
01:10 MIN
Venture backed vs. private equity owned
01:10 MIN
If you did it again, what would you do the same and what would be different?
00:50 MIN

Intro: Welcome to the Daily Bolster. Each day we welcome transformational executives to share their real world experiences and practical advice about scaling yourself, your team, and your business.

Matt Blumberg: Welcome to The Daily Bolster. I'm Matt Blumberg, co- founder and CEO of Bolster, and I am excited to be here in Deep today with Nick Mehta. Nick is the CEO of Gainsight, a company that he started 10 years ago?

Nick Mehta: 10 years ago.

Matt Blumberg: 10 years ago, that has scaled to about 1200 employees, is an absolutely role model CEO, and it's a role model SaaS company, and I'm sure many of you have heard of it. Nick is one of my favorite fellow CEOs and someone I've always enjoyed sharing notes with and talking to over the years. So Nick, thank you for being here today.

Nick Mehta: Really appreciate you having me here. It's going to be a fun conversation.

Matt Blumberg: Yeah. All right. So let's start really quickly with the arc of your journey. So you've been doing Gainsight for 10 years, work backwards. What inspired you to start Gainsight? And then just so real quick hits of the things that got you from college to there.

Nick Mehta: Yeah, totally. Yeah. Maybe I'll give the quick chronologically forward narrative because you'll see how sort of fits together and you probably feel the same way. Your career path is a little bit of a random walk, but maybe in hindsight there's a little bit of a pattern. So yeah, I grew up around technology. My dad ran some small tech companies, so I was always around computers in programming. I always wanted to be in Silicon Valley and luckily I'm living my dream of being in tech. And I started that dream actually doing a startup in college in the late nineties where we founded a company from our dorm room selling golf clubs over the web called It was an early. com e- commerce pioneer and actually raise venture capital, almost went public. We were all these young kids but missed the IPO window and didn't end up making any money, but it was a great experience. But that brought me to Silicon Valley and at that point as you and I have talked about before, this was the doldrums of the post. com crash, right? 2001, 2002. And I had to get a real job even though I had done my own startup, I was basically just like a kid out of college. And so I went to be a product manager at a mid- size public software company called Veritas Software. And this is on- premise software, I'd sell this product and people would install it and it was their problem at that point, they would use it or not, it didn't really matter. The concept of customer success didn't exist back then because people were paying upfront for their software. And then I went to run my first SaaS company. I got hired to be the CEO of a little bit of a turnaround SaaS company called Live Office, which I ran. And then we sold about three and a half years later and we sold it actually to Symantec, the security software company. And so in running that company, this company live office, one of the things I learned was how different things are as you go from the on- prem model to the cloud bot. And one of the big differences was you can't just sell to your customers and walk away. You actually have to make sure they're using it, they're getting value, otherwise they won't stay with you.

Matt Blumberg: You have to make sure they renew.

Nick Mehta: They renew, exactly. All that, right? And so I didn't realize that there was a whole profession around this. We were kind of making it up as we went, maybe similar to the early days of Return Path for you. And so we were just figuring it out. But I sold my company, I was like, there's a problem we solved here. And I was spending some time thinking about doing a startup. Met two other guys who had a quite similar idea through Battery Ventures who they had just pitched and we teamed up and launched Gainsight in 2013.

Matt Blumberg: Got it. And yeah, that's really funny. I don't think I knew about Chip Shot, so I definitely bought something from Chip Shot.

Nick Mehta: Yay. Awesome.

Matt Blumberg: There's no question about that.

Nick Mehta: There you go.

Matt Blumberg: And I did not realize that was you. That is very cool.

Nick Mehta: Awesome. I think we sold a lot of stuff at a big loss, so I'm sure many people bought from us at that point.

Matt Blumberg: Yes, the days of having negative gross margin, I think is behind us.

Nick Mehta: Exactly.

Matt Blumberg: So one of the things I really remember about one of our conversations early on in your tenure at Gainsight, a couple of years in, you said to me, " Man, I just love this. I just want to keep doing this forever." And one of the things that's so interesting about the scaling journey, which a lot of the people that are going to be listening to this are on that scaling journey, is they don't know what it's like yet. They know what it's like to start it. They know what it's like to get it to somewhere, 10 employees, 20 employees, a hundred employees. Very, very few people in the tech world get something over a thousand employees, usually you're just taken out. If you're doing well, usually you get taken out before that. Obviously they're a handful to get to where you have. But I'd love to focus the conversation today on what that journey has been like, both for you and your role as the CEO and the founder, and then also for the company. And I think rather than try to ask, well what was it like to go from 10 to a hundred and a hundred to whatever, let me focus on some topic areas and you can walk through for each topic area. All right, what was it like to scale that thing? And I guess the first question is what has it been like to scale culture? You and I did the short form of the podcast, which will have aired before this one does, about the quick tips on scaling culture. But what was it like running the 10 person company up to the 1200 person company in terms of the culture of what it felt like to go to work every day, what it felt like to go from knowing everyone to not knowing everyone? Those kinds of things.

Nick Mehta: Totally. Yeah. I mean I can tell you there's some visceral changes probably to some extent the more layers of the company you have in terms of depth, I think that's probably one of the biggest variables. In the beginning, we actually were, I think very similar to Return Path, very values driven from the beginning and having run another company before, I was like, " I want to do our values now." When we were just literally 14, 15 people, I remember us sitting around and saying, okay, we initially started with three values, the golden rule, success for all, and childlike joy. Those were our three early values. And then we iterated a little bit actually though, if you hear those three values, golden rule, successful, all childlike joy. I joked that sounds like we're running a bed and breakfast, so we should have something that's also business oriented. So we added in, stay thirsty my friends, and Shoshin, which is the Japanese word for beginner's mind. And so we did those values early on when literally the people creating the culture and the people living the culture are the same people. So that's a subtle thing because later on employees are coming on and they're still influencing the culture. They're evolving it, but they're not creating it. And I think there's a big change that happens. So when you can fit everyone in a room to actually figure out your values versus when you've got a thousand people, it's a pretty big difference. So that was, I think, one big era of the company was the creation of the culture. Then what ends up happening for us is there was a phase where it kind of organically just stayed true. We didn't do anything, it just sort of, everyone got it. And the new people learn through the existing people. But we were at that point, we weren't totally office bound, but we had some offices and you could hear in, that you would talk to people in the hallways, all the classic stuff, how culture gets shared. And then I remember, actually pretty vividly, I remember talking to a salesperson, maybe we're two, 300 people at this point, a salesperson who's leaving and he's like, "Oh, Gainsight, it's one of the best places I've ever worked." And I was like, " So why are you leaving?" And then he's like, " Well, I just don't see eye to eye with my manager." And so that's kind of the same aphorism that all about, which is people join companies and quit managers, right? And you're like, oh wow, this culture doesn't mean a thing if it's not carried forward at the next level. And so we started institutionalizing things. For example, we refer to our culture as Human First Business and we created a thing called Human First leadership as a training class. And so training managers on how to actually try to carry that culture forward, and all the other stuff. New employee onboarding and culture, all the things that you know and I have talked about before. And so you try to institutionalize and scale that. So a second phase is we just started thinking about some systems to make this more scalable at the manager level in particular. So that was, I would say, that first chapter break. I'll keep going, but I'll pause there.

Matt Blumberg: Yeah, no, that is the journey. It's from creating it, watching it flourish to figuring out how to institutionalize it.

Nick Mehta: That's right. The third phase for us was, I think companies naturally go through phases where you have a lot of hiring and maybe there are just all of a sudden a lot, people have to be brought up to speed. And so for us, it was actually interesting convergence everyone went through, which is crazy growth from basically three, four years ago to now and hired hundreds of hundreds, hundreds of people. But we had moved to a fully distributed model, so none of them were seeing each other. And so I think this third phase then becomes how do you quickly create the same culture but with a whole set of new people? Because I think over time, especially in tech, and especially the last few years, there's an incredible amount of the company that ends up being new because we have the mix with a lot of people out of a lot of attrition with the quote- unquote, grace resignation and a ton of hiring. And the net was you look around, you're like, wait, so those people from those early photos I don't know. I have some of that melancholy feeling, we're like there's early photos, you're like, " Wait, there's two people. There's me and I can find the two other people in that photo that are still here and everyone else is new." So then you were like, okay, now you've, you've got to remember that as a CEO, you've been on this journey 10 years and they're brand new. I wrote this blog post a while back that it was actually kind of random, but I had this dream and it was dreaming about how they say the CEO job is lonely, and no one cries a tear for CEOs, nor should they, but it is lonely. And part of the loneliness is if you're really passionate about it, I had this dream where the analogy was you're like a train conductor and you've kind of handcuffed yourself to the train wheel so you're not leaving. But for a lot of the people, the train is of means to get to a destination.

Matt Blumberg: They get on, they get off.

Nick Mehta: They're going back for their MBA, they're moving for their family. They got a new job, they got their first CRO job, which is awesome. You're so excited. But you have to remember all these new people come on the train and they're just super excited to be on the train. And every time you have to greet them with that excitement, even though knowing that, gosh, you said goodbye to so many other people that have left the train. And so that this third phase, it really hit me the last few years of like, okay, you've got to get great at being great for new people. And remember that this company isn't about the long timers only. I remember there was a story about an intern, this is one of these famous Steve Jobs stories. An intern emailed Steve Jobs, an Apple intern, and he said, " Hey, it's the 20 something anniversary of Apple, maybe 25th or whatever. Do you want to do a party at Apple?" And Steve Jobs wrote back, " Apple's about the future, not the past." And it's not to say you don't celebrate the past, but you have to remember that for a lot of the employees that are new, the past is just history to them, the future is what matters. So those are the three phases I can think of.

Matt Blumberg: Yeah, that's so true. And it really does change. And by the way, when you get to 20 years.

Nick Mehta: Yes, I can only imagine, right?

Matt Blumberg: inaudible

Nick Mehta: Seriously.

Matt Blumberg: Yeah, that's right. All right, so let's talk about team no, and let's focus on leadership team. So you've built your first leadership team 10 years ago and you probably have shaped it over the years. Maybe you had moments of broader overhaul.

Nick Mehta: Totally.

Matt Blumberg: How do you think about the scaling of the leadership team?

Nick Mehta: Yeah, absolutely. So obviously it's a constant work in progress and so I think there's some element that's such a truism. I think broadly what ends up happening is the very early days of a startup, especially if it's your first time, you're not able to, nor do you necessarily want to hire all these incredibly super experienced people. In fact, a startup is the person takes a chance on the company and the company takes a chance on the person in the very beginning, and then later on, you have some proof that your business is real. You've raised a certain amount of funding, you've got revenue and you can have more experienced people. So interesting enough, I'd say that we started out with a lot of people that were kind of proving themselves. So for example, we had our head of sales, Mike Schmidt, who was so great. Our first one was basically a sales manager before, managed maybe five, six people. The person who would eventually become our COO, Allison Pickens was straight out of Stanford Business School, she'd worked in private equity. She'd done one brief tech startup, but she'd never worked in a tech company at scale. Our head of marketing who became a legendary head of marketing, Anthony Canada, had literally been a biz dev person in my last company. So all these people that are proving themselves and frankly early on, a lot of mistakes you'll hear in startups are people that you hire somebody too experienced and they want to jump into something much more fully formed. But these people that are really creative and willing to try things and obviously you want to hire the right people. So there's that first phase that I think is pretty organic because you're kind of hiring who you can. And I'd rather in that first phase, hire somebody who's less proven but has a lot of grit, hustle, creativity over somebody that has a stronger resume in those early days. So that's it.

Matt Blumberg: I totally agree with that for the beginning. Yeah,

Nick Mehta: Totally. And so then you get into this next phase, which is I think where a lot of mistakes happen because you're trying to bring in the experienced people, you're trying to quote- unquote, scale. We made a bunch of mistakes in that area, probably other people have as well where you're trying to bring in the perfect head of sales who's done it a million times before. But you don't realize that some of those heads of sales were in environments where everything was perfect and they were good people, but they were set up for success with a great tailwind behind the back. They worked at big company X, Y, or Z, but big company X, Y or Z was going to be great with or without them. And so sales, marketing, a few these areas, I think, a lot of companies make mistakes in where you're trying to find the panacea based on resume. And so interesting enough that second phase, I think we wandered in the darkness a little bit. We had made a few mis- hires here and there.

Matt Blumberg: I think there are a lot of companies that stumble in that phase. I mean obviously a lot of companies stumble early at scaling your team, but they play through. I think everybody stumbles in that second phase.

Nick Mehta: Totally stumble. And I think that especially in the sales and marketing role, if you're a kind of a B2B company, because it's such an important area, but there's no quick fix. I'd argue actually it's a little easier to hopefully find a great CFO, chief people officer, because those can go the distance. But sales and marketing, there's just a little bit more churn in finding the right person. And so for us, interesting enough, we've had an experience where we'd hired some people who weren't the right people, but then other people emerged at internal promotions. So that actually we had a lot of success then with the next level down stepping up. The RVP or the SVP or whatever underneath the C level person. And so, for example, after trying to bring somebody in from the outside didn't work, we promoted one of our sales leaders who is a first line leader and said, " You run all of sales." And it was one of those people had proven themselves amongst the team already. The team already respected him, his name's Brian. And so everyone respected Brian and it was much easier to just promote him through that. And so I think this middle phase is actually hard because you're not really a proven company yet, most likely you don't have total product market fit. Product market fit isn't something that just happens overnight. It happens gradually over time, and yet you want to scale. And so I think that's where you have maybe give yourself some permission that you're going to make mistakes. I mean, if you somehow don't whiff on a head of sales or head of marketing or whatever as a CEO, more power to you, you're batting way above average.

Matt Blumberg: inaudible That's right. All right, so now then what does phase three look like?

Nick Mehta: Yeah, so then I think there's this interesting thing about, then there's a question of, okay, you've been around for a while and now it's like you've had some great people, but sometimes new ideas, putting aside the tenure of a person or whatever, sometimes new ideas do help. And by the way, that probably applies to CEOs too, it's always good to get a new perspective. And so we were fortunate that we actually did as we did a deal with Vista, a private equity firm. And that was actually a great opportunity because the way these deals work often is that there's a chance to make everyone that's been there for a while, able to make money from their stock and all that. And there's a chance to almost restart with your new equity plan and all that. And it allows some of the people that maybe they've been sticking around but they're ready to go do their new thing and they can healthily opt out. Great people, but they can go do their next thing and then new people can step up. I think there's always a forcing function opportunity in a company, whether it's a new CEO, whether it's a new investor, whether it's something that's causing you to say, " Hey, let's look at this next phase." So what we do at Gainsight, to make that a little more real, is we divide the company up into chapters of history. We call these chapters Gainsight phase one and Gainsight phase two. And we call for short G one, G two, G three, G four, G five, G six. And so what we did when we did our vista deal, we said Welcome to G five, here's this new phase of Gainsight. We had just crossed a hundred million of AR. We wanted to build a profitable company, we want to be around for the long term. We had certain goals we want to continue to have a great culture, all that stuff. And so we basically said, let's build out what G five means and then I went around to everyone in the management team and said, this is G five. We've all had incredible success today. You all made great money and everything else, it's up to you, do you want to opt into G five? And there's no negative if you don't. I told everyone, the whole company, the entire company, I was like, " Are you in for G five and no sweat if you're not." And so I think there's an opportunity to be bold sometimes and let the team opt in and maybe every couple of years opt into the strategy.

Matt Blumberg: And what was your opt- out rate?

Nick Mehta: So out of the executives, so if I did VP and hire, over the course of maybe a year and a half, 25%, something like that. So not a crazy amount, but a decent amount.

Matt Blumberg: No, not at all. Like 75% recommitted. That's pretty impressive.

Nick Mehta: Yes. Something like that. And by the way, after that maybe the cohort might have dropped to 60%, but still that actually has been pretty strong at that point. And then last things I'd say is one things I feel like we're in now is as you build a company that is trying to be built to last, one of the interesting things is you look at these big companies, a lot of the talent is grown within. Eventually it's not about hiring people from the outside. Frankly, most of these big companies, you look at the executive teams hiring, very few people are hired from the outside, they're grown from within. And the way they're grown from within is you have really strong early career programs to recruit, but also to make early career people successful. But then the other thing you have is a willingness to rotate people. So as an example, I just had my chief of staff become our chief people officer. We just had our head of support become our head of professional services.

Matt Blumberg: I love that. I love that.

Nick Mehta: And that idea of, okay, yeah, I could have find somebody who's done that exact job before outside, but they don't know Gainsight.

Matt Blumberg: Right.

Nick Mehta: And you think about these big companies, it's actually more knowledge to know IBM or VM ware or GE or ADP than it is to know that function. And so I think this idea of building the institution internally, I think that becomes a new phase. We're in the beginning of that phase.

Matt Blumberg: Totally. We did that a lot. I used to tell people, part of one of my speeches internally was that careers are no longer ladders, they're jungle gyms.

Nick Mehta: Yes. Jungle gym. Exactly.

Matt Blumberg: I think, when we were at our peak, we were moving about 10% of the company around laterally every year.

Nick Mehta: Oh, I love that you even measured that.

Matt Blumberg: Oh, yeah, we measured promotions and terminations and everything and we measured lateral moves and we found it incredibly helpful. Engineers can make great product managers.

Nick Mehta: Yes, totally.

Matt Blumberg: Product managers can be killer product marketers, good sales reps can flourish in customer success. So giving people those opportunities is so good for the culture and the company.

Nick Mehta: Well, I think a key thing on that, by the way, and that's what I've struggled with but also had some small success is hiring leaders who value that versus the leader that wants that person to have done that exact job before. And so that's something that sounds like you did a great job of that. And how do I make sure that I have leaders that accept the jungle gym? Because a lot of leaders they're like, " Wait, no, I want somebody who's done this exact job because that's what I'm hiring them for." So yeah, I like that spirit.

Matt Blumberg: Yeah. All right, so we've talked about culture, we've talked about scaling team, let's talk about board.

Nick Mehta: Yes.

Matt Blumberg: So my guess over 10 years is your board has had a few revs to it. And I'm not actually sure what it looks like at the moment with a control owner. And so whether that chapter is relevant...

Nick Mehta: I can talk about both.

Matt Blumberg: Yeah. How did you think about growing and scaling and getting the most out of your board, small stage, mid- stage, larger stage?

Nick Mehta: Totally, Yeah. I think that early on, not everyone's doing the venture back path, by the way. Obviously more power to you if you're not. If you're in the venture back path, you naturally typically start out with a series A investor or some early investor. So one or more co- founders, early investor. And then I think you've got these different sort of paths that you could end up being on. So you have paths of adding on more investors. Now just because you add more investors doesn't mean you add any more board members. I think a lot of entrepreneurs I've talked to have been smart about, you know what, I wanted more money in the company, but I don't necessarily want more board members. I'm willing to take a lower valuation just so that I can actually get more focus in the board. Because we all know that the more people you have on a board, the more people to talk to, the more coordination cost, just potentially the less agility you have. And so there's a path of how many investors do you bring onto the board and does that have to correlate with the number of rounds you do? And then there's a separate path of how many independents you bring on the board and when do you bring those on. For me, what our story was, we brought on our series A investor, a battery ventures; series B, bank capital ventures; series C, investment venture partners. Those were our three official board member investors. And then we had observers for some other investors like Insight and Lightspeed, which I think works out great because you could still get their help but formally you could still do some meetings just with the board. And then on the independent side we brought on a gentleman named Kirk Bowman who was a longtime operator sales leader and he sort of had that sales expertise and we brought on somebody, Kirsten Helvey, she'd actually run customer success. So she'd been on our domain and then at a company called Cornerstone. And then we brought on a longtime CMO and general manager named Sue Barsamian. She was at HP most recently. And so we had these three operating executives and three venture investors and me. So that was the board. And I think a couple of learnings on that. So number one is the board. We're so lucky, I'm super close to all six of those people still. We do things together, we get together and it's actually great if you get a chance, as a CEO, to actually become friends with your board. And obviously you still have to have the appropriate governance and separation, but it really makes the job a lot more fun. The second thing that I learned though is I do think that there's value to boards being as small as possible. So one of the things that's nice in our new world, we did a deal with Vista and with the Vista type relationship, what ends up happening is you basically have Vista as the investor is on your board. Now there might be multiple people but they kind of act as one and then you can bring in a couple of independents. So I've got basically two independents on my board, one CEO and then one of the people I had mentioned before. And so the board's actually much smaller and easier and the advantage is decision making is really fast because you don't actually have to have too many calls to make. So I've talked a lot of entrepreneurs who've kept their board small and I think there is a benefit to it. So I just encourage you to not go too aggressive on making your board too big too quickly. A second thing I think to think about then is whatever board members you have, they all want to be part of a team. I'm on a couple of boards, I know you've been on boards too. You want to help too. When you're on a board, you're sort of on the team, you're not really on the team but you want to feel like you're on the team. And so how do you actually make them feel like they're on the team? A couple of things. There's, I think, the practical and the emotional. Practical, give every board member a specialization. So for me, in the early days, Ajay Agarwal from Bain Capital Ventures would spend time with my chief product officer and he'd be our product specialist on the board. Roger Lee from Battery would spend time with our chief marketing officer. And so they would actually get together once a quarter outside of the board meeting. And then when we got into the board meeting, they had a little bit more depth in one area. So specialize is one way they can get involved, but then also just get them involved for fun. We make jerseys for all our Gainsight teammates, we made jerseys for all the board members. We obviously bring them to all your hands meetings. They love coming to talk at your kickoffs. Use them and use them as evangelists for a company because then that makes them feel better as well. And then in the board meeting, as you think about content, obviously there's a million blogs about how to run a good board deck, et cetera. But don't forget you want to have them be excited about your business just like you do in an all hands. In all hands. You're talking about updates and metrics, but you're also talking about why you're excited and what excites you. Maybe showing a demo or whatever, try to have some part of the board meeting that's inspiring.

Matt Blumberg: Yes to everything you just said.

Nick Mehta: Awesome.

Matt Blumberg: Although it is interesting, keeping the board small is not something I talk about much because for the most part CEOs have boards that are too small because it's just like them and a a couple inaudible.

Nick Mehta: That's a good point. It depends on the situation. If you raise a lot of money they can get big. But yeah, you're right.

Matt Blumberg: Yeah. But that balance of the investor director and the independent director is really, really important. And it's not that one is better than the other.

Nick Mehta: No.

Matt Blumberg: It's that balance is pretty key to a healthy board.

Nick Mehta: Totally agree. By the way, right now a former CEO on my board for the first time, that is incredibly valuable. That's a very specific thing. It's great to get functional operating executives and investors and all that's awesome. But there's nothing that substitutes for another CEO that's been in your shoes.

Matt Blumberg: Yeah, that's for sure. All right, so we've talked about scaling culture, scaling leadership team, scaling board, let's talk about scaling you.

Nick Mehta: Yes.

Matt Blumberg: So again, not a lot of CEOs go from zero to where you are, 1200 employees. One change of control, probably contemplating going public in the future. You want to go the distance. Give us a couple of the things that you've relied on over the years to be your own development mechanisms or support mechanisms. How have you scaled with the job?

Nick Mehta: Totally. I think about this one a lot actually. I wrote this blog post a while back, which got a lot of attraction because I think it touches on what we all do with, and it was called, I guess it was a total clickbait headline. It said Attention CEOs: fire yourself. And the idea basically that

Matt Blumberg: That's good clickbait, that's

Nick Mehta: A good clickbait every who doesn't love a CEO getting fired. And so in the blog post I talked about the fact that every year at Gainsight, it's kind of like a new company, it has new needs and theoretically if you're writing a job description for the CEO, it would be slightly different. And so one of the things I did is I said, okay, let me write the job description for what Gainsight needs now and kind of interview for the job so to speak and hope I get the job. And it forced me to say what needs to be different? And we actually institutionalize this now. So I have myself and all my executives, we write the job description every year for ourselves and we highlight what's changed in red, basically what's different this year and we share it with each other and it's a good exercise to really try to help figure out what is changing, what needs to change. And so for me, along the way, a ton change. I mean everyone knows, you know, go from very hands on to having a lot of scale. You can't talk to everyone directly anymore, you don't know everything that's going on. But I think you, to answer your question, some things that helped along the way in terms of support, a few things. Number one is I think there's this, you and I have talked in separate sessions about this idea of having kind of a cadence, I think you call it an operating system, we call it Gainsight rhythm. Having a really organized way that everything in the company fits together in terms of the operating rhythm. So for us it's, literally I do a weekly email to the company on Sunday nights and we have a weekly morning, we call it a huddle, which is getting everyone together. And then we have my direct staff meeting and we have a business review, then we have a quarterly business review and all hands at a board meeting and everyone does those things, but ours are sequenced together to the extreme. So we know and we reuse the content and really organize. And I think a part of the job is improving that process. That's the machine that runs the company. How do I improve the machine every year with my chief of staff? How do we make it better every year? So that's one thing that I think is good is thinking about the systems that run your company and how do you keep making those systems better. So that's something that I think how is a way to think about how to evolve. Early on the system might literally be we do OKRs once it's a quarter, that's fine, or it could be whatever it is, but how do you constantly make that system better, learn from other people on how their systems work? That's a good thing to talk to other CEOs about because every CEO has a system, whether they've written it down, whether it's canonized, there is some way that the company runs, how do you study that and constantly get better. So that's one thing I've delved into. Sounds like you have as well, right?

Matt Blumberg: For sure. Yeah. And I mean the thing you just said at the end, let me build on that, which is you're constantly learning and trying to learn from...

Nick Mehta: Right, totally

Matt Blumberg: Right. So my guess is over the years you've had good, not just coaches, like developmental coaches, but you've also had good mentors, good role models and just sought out other people's like, " How do you do this? How do you do that? How important is that then for you?"

Nick Mehta: Yeah, so in that realm, I'd say there's three areas, three ways I've gotten consistent help and support beyond board. I think board's great, but three that are a little bit outside of the board context. So number one is I actually do use a coach, I've used her, her name's Kayleigh Warner, forever, literally 14, 15 years. And that's been about understanding who I am. And so that's a lot of that personal work around what is driving me, what are my insecurities. There's a lot of different personality tests out there. The one that we use the most ISS called Enneagram, which is a way to understand what drives you, it actually goes back to your childhood and stuff. So it's all psychological stuff, but it makes you much more comfortable with who you are. And I'd say whether it's coaching or yoga or meditation or exercise, you have to figure yourself out or you'll never be a great leader. That's the number one thing. Then number two for me is a consistent group of peers that I can meet with on a regular basis who really get to know me and what makes me tick and hold me accountable. So in my case that's YPO, which is a CEO group. But it doesn't have to be something formal, it can be a group of people you have lunch with once a month. But I think the consistency helps a lot because then you actually have some accountability and really understand each other's stories. And then you've got that kind of episodic you're at a CEO event and that's why I really focus on learning. That's where I'm like, okay, I'm not going to see these people again for a year or two, but I want to learn everything about what they're doing. So I was at an event just a week ago and I was like, how do you deal with the balance between diving deeply into your team's stuff but also not feeling like a micromanager? That's a genuine question every leader deals with. And so how do you deal with them? By the way, I heard lots of answers. For example, somebody was like, yo, I came from Amazon, they have a principle called Dive Deep and here's how they explained it. Another one's like, " That's just what I do. And I tell my team, that's just what I do." And I was like, well that's not very useful for me, but good for you. And so you learn and I almost feel like you're trying on different outfits of being a CEO, different things that you could be wearing and not all those are going to fit you. A lot of people I meet, I'm like, oh that's awesome and it works for them and that would never work for me. But this other thing, oh I actually learned something from that person. And by the way, a hundred percent of what I do is crowdsourced from people like you, Matt and other. It's studying other people, reading their books, reading their blogs. So I guess I'm a student of what it is to be a CEO.

Matt Blumberg: That is the number one thing around scaling yourself I think, is being a student of the craft-

Nick Mehta: Of the craft.

Matt Blumberg: ... And theone thing you said that the beginning that's so right is you can have the same business card for 10 years or 20 years, but you might have a different job every year.

Nick Mehta: Totally.

Matt Blumberg: So building that routine that you and your team have about like, hey, it's a new year, it's a new job description, let me red line last year as, so let's start, is a great practice. I love that. All right, I have a couple of shorter questions to start wrapping things up. What do you miss most about the early stages?

Nick Mehta: Yes, we were all together in person at that point back in the old days, so I definitely miss celebrating in person where everyone is together and you have a big win and you're all together.

Matt Blumberg: What changed the most when you went from venture backed to private equity owned? And you can have a couple of things for that, I'm sure there's a lot of different things.

Nick Mehta: So part of it is I think it was a chance for us to make decisions on our own. There was a step function that independent of whether it's PE or venture backed, there was just a chance for us to all of a sudden do the right things for the company. So that was one. But the second one is I think focus. So we have a real clear goal and really good partners on how to get to that goal. So rather than having a hundred different goals, it was like, oh, clarity. That's the second thing.

Matt Blumberg: Interesting. All right. And as you think forward to going public, getting to 2000 employees, 3000, 5, 000, what is the most exciting thing about that and what is the most daunting thing about that?

Nick Mehta: Yeah, so most exciting is, if we're able to scale our culture, impact more people both inside the company and outside. And most daunting is us failing to scale our culture and values and not living up to who we are.

Matt Blumberg: All right. Now here's the last question. If you do another startup someday, what would be the first thing you would do that's like, " Oh, well the thing that I absolutely have to do is X."? And then what's the thing that you would do that's the most different? The next time around. And I'm not suggesting you'll have a next time around, like, " Man, I am not going to X."

Nick Mehta: Okay, so first thing I would do, again, like we did this time is really understand and define the values and culture. And then the thing I would do differently or learn from is institutionalize those more directly early on in terms of how we think about things like hiring, performance management, compensation. I always thought that stuff is so bureaucratic and boring, but as you scale, that's actually what turns your culture into reality.

Matt Blumberg: Nick Mehta, this is such a great conversation. I have always maintained that you are my kind of CEO, you and I think very similarly about a lot of things. I really enjoyed talking to you. This is going to be such great content for our audience. So thank you for spending the time.

Nick Mehta: Thanks Matt. This is awesome. I feel the same way about you.


Today’s guest is Nick Mehta, CEO of Gainsight. He and Matt are diving deep into Nick’s journey launching and scaling Gainsight to 1200 employees over 10 years. Nick considers himself a student of the craft of being a CEO—something that gives him an interesting and thoughtful perspective. 

They also talk about being values-based from the beginning, keys to a healthy board, the stages of building a leadership team, and why careers are like jungle gyms.

Today's Host

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Matt Blumberg

|Co-Founder & CEO, Bolster

Today's Guests

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Nick Mehta

|CEO, Gainsight