The Exchanges

Q So am I, but I would love to kick off today with a little bit on you. So tell me, how did you make your way into the wonderful world of tech and startups and really come to found the unicorn and incredible company that is Gusto today?

A Thank you. Yeah. So I'm originally from Israel and my parents have a small clothing store. In downtown Haifa. And I actually got into startups and got into programming by just picking up a book, a visual basic six programming book to help me build something for our store. I was in charge of, I was a small kid. I was like, 11 years old. And my dad asked me to make sure that we have enough inventory and count all the inventory and the jeans and the shirts and the sizes and all that stuff. And I used to do it by hand. And then I just figured that, hey, I think we had a computer at home. And I was like, you know, computer should probably be pretty good at this. Anyway, I ended up going to this nearby bookstore. I got this Visual Basic Six book, and I built this inventory management software, and it worked, and it really helped my dad, and it really helped also other small businesses that my dad's cousins had, and my grandpa had, and, and it ended up kind of starting, funny enough, like this journey that I had with falling in love with software, and seeing that all the real impact that you can have on people's lives, and specifically on small businesses, and you know, I can't say that I expected it, but Fast forward for today, I am, you know, as a part of Gusto, we are here to help small businesses, and the software's ability is here to help them start, build, and grow their teams, …

AI assessment note: “got into startups and got into programming by just picking up a book”

Q So am I, but I would love to kick off today with a little bit on you. So tell me, how did you make your way into the wonderful world of tech and startups and really come to found the unicorn and incredible company that is Gusto today?

A Thank you. Yeah. So I'm originally from Israel and my parents have a small clothing store. In downtown Haifa. And I actually got into startups and got into programming by just picking up a book, a visual basic six programming book to help me build something for our store. I was in charge of, I was a small kid. I was like, 11 years old. And my dad asked me to make sure that we have enough inventory and count all the inventory and the jeans and the shirts and the sizes and all that stuff. And I used to do it by hand. And then I just figured that, hey, I think we had a computer at home. And I was like, you know, computer should probably be pretty good at this. Anyway, I ended up going to this nearby bookstore. I got this Visual Basic Six book, and I built this inventory management software, and it worked, and it really helped my dad, and it really helped also other small businesses that my dad's cousins had, and my grandpa had, and, and it ended up kind of starting, funny enough, like this journey that I had with falling in love with software, and seeing that all the real impact that you can have on people's lives, and specifically on small businesses, and you know, I can't say that I expected it, but Fast forward for today, I am, you know, as a part of Gusto, we are here to help small businesses, and the software's ability is here to help them start, build, and grow their teams, …

AI assessment note: “I actually got into startups and got into programming by just picking up a book”

Q Totally. And I'm very excited to see that newly announced product or iteration of some form. So that's exciting. Can I ask also, when I was doing my research, I saw there were 111 investors in the company. It is a lot. What advice would you give to founders when it comes to cap table management?

A Yeah, so that's a really good one. So again, I don't think there's one way of doing things. I think our way was we'd really try to guide the fundraising process around this idea of alignment and between in our In values and motivations. And I think a lot of these people are people that we've known before Gusto started and, you know, Gusto has been a long journey. So we got to meet a lot of people throughout the time. And we try to make sure to bring people on the cup table that can add some sort of value. And I know that that sounds probably like a cliche in the world of VC, but it's still true. Like, you know, when I look at it, when it's specifically, when I look at some of the angel investors that we brought in, I mean, one person comes to mind, like Adam Nash is right now VP of product at Dropbox. He's been immensely great sounding board to me. In making some big product decisions. And similarly, there's other folks that have made a real impact on the company. And when we try to bring someone in, or I guess the advice then to founders is be really picky because those people are going to be out there and they're going to be associated with you and make sure that you feel great about them bearing your name. It's exactly like recruiting. It's exactly the same thing.

AI assessment note: “the advice then to founders is be really picky because those people are going”

Q Yeah, hit me on MPS, because it's one where founders often kind of align to benchmarks to the industry standard, and I find it all quite bluffy, actually. So how do you think about MPS and using MPS effectively in terms of determining delight and customer love?

A Yeah, I think NPS is not the one metric. Like, it's not the one place you go and you know everything about how people think about your product or love your product at all. So there's a lot of really solid criticism about NPS, but it's really about the usage of NPS. I think we have different usage here with NPS. So I think this is really helpful is two things. One is seeing trends, and two is reading the comments. Trends are obvious. You see, you have more promoted, less promoted when you cut by different types of customers. So you learn about Who the different experiences are better for? Or perhaps specifically, if you think about the NPS question, when customers do use feature X, do they tend to then want to talk about Gusto positively outside or not? That is a really interesting question. If your go-to-market is through word of mouth, which is a huge part of how Gusto grows, that is one specific thing. The other thing is about comments, and you know, we have like a Slack channel in Gusto, it's open to everyone, where literally every single NPS comment has been read by many, many people in our Gusto team, and especially The product and design teams. And these really matter because these anecdotes can show some trends, they can show some specific situation we haven't thought of, and they can bring ideas and they can connect people that work in the day-to-day Customer happiness …

AI assessment note: “So I think this is really helpful is two things. One is seeing trends”

Q ask, and sorry for going off schedule here, but you mentioned about kind of investors having the time to talk about startups. I'm probably the biggest or biggest kind of enemy of VC Twitter and probably a big proponent in it. How do you as a founder feel in the rise of this VC Twittersphere that we've seen really in the last 18 months? How do you feel about it?

A I try as much as I can to not be a part of it, to not be a listener to it, to be honest. I think social media in general, like, you know, the amount of information, the amount of opinions, the amount of knowledge out there has a lot of positives, but it also has some negatives, and we talk a lot here about being in a bubble, and kind of the echo chamber, and people repeating each other's words, and I think when you're in it, when you're overly tuned to the kind of repeated opinions, and kind of the small debates, and the small conflicts that happen in this bubble of venture You just don't have the mental space sometimes to come up with something original, to be different, to think differently, to really just be contrarian enough in order to do something special and unique. So what I try to do is to be off of it and away from it as much as possible.

AI assessment note: “I try as much as I can to not be a part of it”

Q Yeah, hit me on MPS, because it's one where founders often kind of align to benchmarks to the industry standard, and I find it all quite bluffy, actually. So how do you think about MPS and using MPS effectively in terms of determining delight and customer love?

A Yeah, I think NPS is not the one metric. Like, it's not the one place you go and you know everything about how people think about your product or love your product at all. So there's a lot of really solid criticism about NPS, but it's really about the usage of NPS. I think we have different usage here with NPS. So I think this is really helpful is two things. One is seeing trends, and two is reading the comments. Trends are obvious. You see, you have more promoted, less promoted when you cut by different types of customers. So you learn about Who the different experiences are better for? Or perhaps specifically, if you think about the NPS question, when customers do use feature X, do they tend to then want to talk about Gusto positively outside or not? That is a really interesting question. If your go-to-market is through word of mouth, which is a huge part of how Gusto grows, that is one specific thing. The other thing is about comments, and you know, we have like a Slack channel in Gusto, it's open to everyone, where literally every single NPS comment has been read by many, many people in our Gusto team, and especially The product and design teams. And these really matter because these anecdotes can show some trends, they can show some specific situation we haven't thought of, and they can bring ideas and they can connect people that work in the day-to-day Customer happiness …

AI assessment note: “One is seeing trends, and two is reading the comments.”

Q because as we said, I came to the office, and it's another tenant of leadership, which is kind of culture creation and culture maintenance. You do have an amazing culture, and I spoke to Leila at Capital G, who's obviously invested in the company and a mutual friend, and she asked specifically, and I saw it specifically, what do you do deliberately to create the culture that you have done?

A Yeah, I think that that is the word, and that helped us kind of get to where we are. So intentionality. Intentionality is a huge part of how we think about culture, and I think just Understanding that is kind of half of the battle. Just knowing that, hey, culture is not just about the values that you put together, and what you say, it's what you do, and understanding that every single action that you do has repercussion, and especially as the company scales really quickly, and you don't have tons of time with new people, so they really read into what they see around them. So intentionality on how we hire, so I mentioned earlier, one of the biggest things for us is this motivation alignment interview, and really figuring out, like, Is the person coming? What's the motivation? Are they here to serve others? Are they here to challenge themselves and grow? Do they have the humility that you need in order to keep growing as a person, professionally and personally? These are the things that we're looking at, and that sets, obviously, a big part of the culture of how, kind of, we interview people in. Treating people with respect, especially in the tough situations, really, really matters. So how you handle when someone does not perform well in the company? How do you balance the situation where On one side, you want to give this person a chance to grow, be successful, but on the other…

AI assessment note: “intentionality on how we hire, so I mentioned earlier, one of the biggest things”

Q hope they didn't ask for discounts in the early days. Family always take liberties. I do want to start on maybe unsurprisingly for the show, though, the element of fundraising, because when we chatted before, you said something that actually really kind of stuck with me, and it's fundraising equals creating change. So I have to double click on this. What did you mean by this fundraising equals creating change?

A Yeah, I would say specifically for fundraising, what I've seen a lot is like in the ecosystem and meetups and conversations and other places is that it's really easy to confuse and look at fundraising as a goal, as a target, as something that you as an entrepreneur, the goal that you're trying to achieve As opposed to thinking about fundraising as more like a means to an end. What I mean by fundraising is really about creating change. For me, the most important thing for an entrepreneur and a startup founder early on, as well as you go and you grow, is to build a great business. You know, make sure that you find the product market fit, understand the customer build, the product customers love, get a product to market, and hopefully build a great business out of it. And fundraising is just a tool to use to create change. What I mean by that is, for example, let's say you're out in the market and you're seeing like, Hey, interesting. There's a new channel for us to go and acquire customers. And I really think it can scale and it can take my journey instead of getting to a hundred million ARR, instead of taking it, taking seven years, I can do it in four years. Well, maybe that's a good reason to go and get some funding, but without this type of hypothesis, I think it can actually be quite ruinous because you can just put yourself in a situation where you're making promises to inv…

AI assessment note: “fundraising is just a tool to use to create change.”

Q incredible few years, and the scaling has been amazing. As I said, I saw your office in San Francisco, and I mean, I didn't really want to leave. I think it was security that probably threw me out. But I do want to ask, because it's a big change to make as a leader. How have you seen yourself change and evolve as a leader over the last few years?

A Yeah. So I think the company eight years ago when we started, we were three and now we're around 1200 people. So my role has changed immensely and is changing every six months, I would say, when I look back. So it's really important for me and for my co-founders, Eddie and Josh, to be ahead of it. You know, I don't take for granted the opportunity that I have to do this job and my job then and what I pay a lot of attention to is thinking about, you know, what's going to be this new job requirement called like six months What would it mean to be chief product officer six months from now? And then make sure I spend a lot of time getting ready for that. So getting advice from mentors, learning from other folks that have been in similar situations, really getting myself prepared for the next level. This idea of, of kind of like firing yourself from your old role and hiring yourself to the new role is something that I think the three of us really took to heart and it's been really helpful. It kind of helps because you kind of set expectations with yourself that, Hey, it's all good and nice that you're good in coding, but that doesn't matter in the next stage. The next stage is really all about creating. A team that works really well together. And then the next stage that, oh, it's all good and nice that you can mentor and coach and kind of lead with a small team. But what really mat…

AI assessment note: “firing yourself from your old role and hiring yourself to the new role”

Q hope they didn't ask for discounts in the early days. Family always take liberties. I do want to start on maybe unsurprisingly for the show, though, the element of fundraising, because when we chatted before, you said something that actually really kind of stuck with me, and it's fundraising equals creating change. So I have to double click on this. What did you mean by this fundraising equals creating change?

A Yeah, I would say specifically for fundraising, what I've seen a lot is like in the ecosystem and meetups and conversations and other places is that it's really easy to confuse and look at fundraising as a goal, as a target, as something that you as an entrepreneur, the goal that you're trying to achieve As opposed to thinking about fundraising as more like a means to an end. What I mean by fundraising is really about creating change. For me, the most important thing for an entrepreneur and a startup founder early on, as well as you go and you grow, is to build a great business. You know, make sure that you find the product market fit, understand the customer build, the product customers love, get a product to market, and hopefully build a great business out of it. And fundraising is just a tool to use to create change. What I mean by that is, for example, let's say you're out in the market and you're seeing like, Hey, interesting. There's a new channel for us to go and acquire customers. And I really think it can scale and it can take my journey instead of getting to a hundred million ARR, instead of taking it, taking seven years, I can do it in four years. Well, maybe that's a good reason to go and get some funding, but without this type of hypothesis, I think it can actually be quite ruinous because you can just put yourself in a situation where you're making promises to inv…

AI assessment note: “fundraising is just a tool to use to create change”

Q least now I know why you don't like any of my tweets. I am brutally offended, Tom. I do want to ask though, we're talking about investors. I spoke to one of your fantastic investors before and him onto GC, and he said you have something called a values motivation alignment. So What is this mechanism? And I guess, how does it drive your decision around who to partner with?

A Yeah, so in Gasto, you know, we've been in a very fortunate situation ever since Y Combinator. We started in Y Combinator in winter, and I think ever since we had, we were in this really fortunate situation where we had options. We were out there raising, and we've had folks that we knew for a long time, and we've had good traction, and as a result of that, we were oversubscribed, and we were in this nice situation where we needed to ask ourselves, Josh, how do we choose our investors? And Josh came up with This thing that I feel like is just really wonderful, and it's definitely the way we're working on. We're still doing this today, which is thinking about investors as team members. When you bring in a new Gusti, that's how we call our own team members. When you bring in a new Gusti on board, there's an interview process, right? And there's like a whole lot of criteria that when we think about culture fit, when we think about, is this the right person for the company? And that type of process we call is the values and motivation alignment. The idea is to make sure that the person that's entering and now is being a part of Gusto Um, shares the same type of values in how they want to live their lives, and how do they look at distance, Motivations that align with what we care about. And that is the most important interview in the gastro interview process. And we take the same ty…

AI assessment note: “we take the same type of criteria and we apply it when we talk”

Q I love that in terms of the perspective of, like, adding an investor as a new hire. I do want to ask, in terms of the rounds themselves, the latest round you raised was two hundred million dollars. You fundamentally have to shift your mindset when you raise that much How do you know when's the right time to go big?

A That's a really good question. I think, you know, we reached basically this scale over, we're serving over a 100,000 small businesses across the country, across all these different industries. We have dentists and lawyers and tech companies and barber shops and, you know, anything that you can imagine. And we're fortunate to see that working. Like you see it in the numbers, you see it in our ability to kind of scale our growth engines, our ability to Bring a really, like a product to market that people really love and talk a lot about. And when that happens, you feel like you have all the signals, and that's where it kind of starts looking for these opportunities that I mentioned earlier in our conversations. It's really about, again, this fundraising is all about in order to have a specific purpose to it. And for us, like this two hundred million dollar raise was less about going big, because I think that we were already going big before that. I think it's a mindset that was true from day one, but it's more around specific opportunities that we've seen. I think we've seen two specific opportunities. One is around R&D. So we have this really exciting new initiative here that we haven't launched and announced yet, so I can't share too much about, but the world is going to hear about it. It's what we're going to hear about next year. Investing in that requires funds and requires …

AI assessment note: “when that happens, you feel like you have all the signals”

Q But can I ask, we often hear the term like time to value being so crucial. Time to value is the most important thing for enterprise products I always hear. How do you think about time to delight? Does it have to be in one of the first few interactions or can it be at the later end of the user workflow?

A Right. That's a great one. I think, yes, I think like, you know, the fastest you can, of course, delight the customer and show them what you're about. The better. And for me, the, the way I think about this is a brand or a product experience is really like some, like a product is like a personality. It's like a person. And when you meet someone for the first time, the first 20 seconds, the 1:30 seconds really, really matter. And after the personality shines, even in the dull moments of whatever, waiting in line or the dull moments of just randomly seeing someone crossing eyes. And I think that if you really understand the personality of your brand, the personality of your product, you can bring that in very, very early. Through simple things like copy, through simple things like illustrations, and these things can make a really big difference.

AI assessment note: “the fastest you can, of course, delight the customer... The better.”

Q incredible few years, and the scaling has been amazing. As I said, I saw your office in San Francisco, and I mean, I didn't really want to leave. I think it was security that probably threw me out. But I do want to ask, because it's a big change to make as a leader. How have you seen yourself change and evolve as a leader over the last few years?

A Yeah. So I think the company eight years ago when we started, we were three and now we're around 1200 people. So my role has changed immensely and is changing every six months, I would say, when I look back. So it's really important for me and for my co-founders, Eddie and Josh, to be ahead of it. You know, I don't take for granted the opportunity that I have to do this job and my job then and what I pay a lot of attention to is thinking about, you know, what's going to be this new job requirement called like six months What would it mean to be chief product officer six months from now? And then make sure I spend a lot of time getting ready for that. So getting advice from mentors, learning from other folks that have been in similar situations, really getting myself prepared for the next level. This idea of, of kind of like firing yourself from your old role and hiring yourself to the new role is something that I think the three of us really took to heart and it's been really helpful. It kind of helps because you kind of set expectations with yourself that, Hey, it's all good and nice that you're good in coding, but that doesn't matter in the next stage. The next stage is really all about creating. A team that works really well together. And then the next stage that, oh, it's all good and nice that you can mentor and coach and kind of lead with a small team. But what really mat…

AI assessment note: “firing yourself from your old role and hiring yourself to the new role”

Q ask, and sorry for going off schedule here, but you mentioned about kind of investors having the time to talk about startups. I'm probably the biggest or biggest kind of enemy of VC Twitter and probably a big proponent in it. How do you as a founder feel in the rise of this VC Twittersphere that we've seen really in the last 18 months? How do you feel about it?

A I try as much as I can to not be a part of it, to not be a listener to it, to be honest. I think social media in general, like, you know, the amount of information, the amount of opinions, the amount of knowledge out there has a lot of positives, but it also has some negatives, and we talk a lot here about being in a bubble, and kind of the echo chamber, and people repeating each other's words, and I think when you're in it, when you're overly tuned to the kind of repeated opinions, and kind of the small debates, and the small conflicts that happen in this bubble of venture You just don't have the mental space sometimes to come up with something original, to be different, to think differently, to really just be contrarian enough in order to do something special and unique. So what I try to do is to be off of it and away from it as much as possible.

AI assessment note: “I try as much as I can to not be a part of it”

Q about kind of inserting delight from day one. I'm always a big proponent of what is the leanest, leanest product that we can get out the door as fast as possible, and then test and iterate. Does that element of delight go against that incredibly lean MVP, given delight may be Feels more like a luxury. How do you think about delight versus MVP and that kind of balance? Right.

A I think high level, if you, you know, again, we're in generalization, I would say every industry is different. Every product is different. I'll tell you for us, for us, what happened is delight is not a nice to have delight. We have to have delight. That is our differentiator. People come to us because they've heard from someone else who is a customer that they absolutely love their payroll experience. They love their benefits experience. Who says that? Who says they love payroll? You know, it's something that was never sounded crazy earlier on, and I think that that is a very important insight. You have to ask yourself as the founder or product leader, what is the role of delight in my business model? If delight is the way you end up acquiring new customers, well, guess what? It's as important as just So I think that is something that we understood early on, and, and we spent a lot of time on. And as a result of that, we don't use the word MVP here. You know, MVP was all the rage in Silicon Valley with the lead startup and all that. And I think I saw another term a few years ago in someone's blog post, and we use it now here internally, is just like, it's not MVP, it's MLP. So minimal lovable product. And the idea is that the minimal product needs to be lovable in gusto. Otherwise, it's It's a really good one. The idea is don't waste time building stuff that no one's going to …

AI assessment note: “it is not like cut the delight element out. It's got the functionality down.”

Q I love that in terms of the perspective of, like, adding an investor as a new hire. I do want to ask, in terms of the rounds themselves, the latest round you raised was two hundred million dollars. You fundamentally have to shift your mindset when you raise that much How do you know when's the right time to go big?

A That's a really good question. I think, you know, we reached basically this scale over, we're serving over a 100,000 small businesses across the country, across all these different industries. We have dentists and lawyers and tech companies and barber shops and, you know, anything that you can imagine. And we're fortunate to see that working. Like you see it in the numbers, you see it in our ability to kind of scale our growth engines, our ability to Bring a really, like a product to market that people really love and talk a lot about. And when that happens, you feel like you have all the signals, and that's where it kind of starts looking for these opportunities that I mentioned earlier in our conversations. It's really about, again, this fundraising is all about in order to have a specific purpose to it. And for us, like this two hundred million dollar raise was less about going big, because I think that we were already going big before that. I think it's a mindset that was true from day one, but it's more around specific opportunities that we've seen. I think we've seen two specific opportunities. One is around R&D. So we have this really exciting new initiative here that we haven't launched and announced yet, so I can't share too much about, but the world is going to hear about it. It's what we're going to hear about next year. Investing in that requires funds and requires …

AI assessment note: “when that happens, you feel like you have all the signals”

Q about kind of inserting delight from day one. I'm always a big proponent of what is the leanest, leanest product that we can get out the door as fast as possible, and then test and iterate. Does that element of delight go against that incredibly lean MVP, given delight may be Feels more like a luxury. How do you think about delight versus MVP and that kind of balance? Right.

A I think high level, if you, you know, again, we're in generalization, I would say every industry is different. Every product is different. I'll tell you for us, for us, what happened is delight is not a nice to have delight. We have to have delight. That is our differentiator. People come to us because they've heard from someone else who is a customer that they absolutely love their payroll experience. They love their benefits experience. Who says that? Who says they love payroll? You know, it's something that was never sounded crazy earlier on, and I think that that is a very important insight. You have to ask yourself as the founder or product leader, what is the role of delight in my business model? If delight is the way you end up acquiring new customers, well, guess what? It's as important as just So I think that is something that we understood early on, and, and we spent a lot of time on. And as a result of that, we don't use the word MVP here. You know, MVP was all the rage in Silicon Valley with the lead startup and all that. And I think I saw another term a few years ago in someone's blog post, and we use it now here internally, is just like, it's not MVP, it's MLP. So minimal lovable product. And the idea is that the minimal product needs to be lovable in gusto. Otherwise, it's It's a really good one. The idea is don't waste time building stuff that no one's going to …

AI assessment note: “for us, it is not like cut the delight element out. It's got the functionality down.”

Q because as we said, I came to the office, and it's another tenant of leadership, which is kind of culture creation and culture maintenance. You do have an amazing culture, and I spoke to Leila at Capital G, who's obviously invested in the company and a mutual friend, and she asked specifically, and I saw it specifically, what do you do deliberately to create the culture that you have done?

A Yeah, I think that that is the word, and that helped us kind of get to where we are. So intentionality. Intentionality is a huge part of how we think about culture, and I think just Understanding that is kind of half of the battle. Just knowing that, hey, culture is not just about the values that you put together, and what you say, it's what you do, and understanding that every single action that you do has repercussion, and especially as the company scales really quickly, and you don't have tons of time with new people, so they really read into what they see around them. So intentionality on how we hire, so I mentioned earlier, one of the biggest things for us is this motivation alignment interview, and really figuring out, like, Is the person coming? What's the motivation? Are they here to serve others? Are they here to challenge themselves and grow? Do they have the humility that you need in order to keep growing as a person, professionally and personally? These are the things that we're looking at, and that sets, obviously, a big part of the culture of how, kind of, we interview people in. Treating people with respect, especially in the tough situations, really, really matters. So how you handle when someone does not perform well in the company? How do you balance the situation where On one side, you want to give this person a chance to grow, be successful, but on the other…

AI assessment note: “intentionality on how we hire, so I mentioned earlier... motivation alignment interview”

Q least now I know why you don't like any of my tweets. I am brutally offended, Tom. I do want to ask though, we're talking about investors. I spoke to one of your fantastic investors before and him onto GC, and he said you have something called a values motivation alignment. So What is this mechanism? And I guess, how does it drive your decision around who to partner with?

A Yeah, so in Gasto, you know, we've been in a very fortunate situation ever since Y Combinator. We started in Y Combinator in winter, and I think ever since we had, we were in this really fortunate situation where we had options. We were out there raising, and we've had folks that we knew for a long time, and we've had good traction, and as a result of that, we were oversubscribed, and we were in this nice situation where we needed to ask ourselves, Josh, how do we choose our investors? And Josh came up with This thing that I feel like is just really wonderful, and it's definitely the way we're working on. We're still doing this today, which is thinking about investors as team members. When you bring in a new Gusti, that's how we call our own team members. When you bring in a new Gusti on board, there's an interview process, right? And there's like a whole lot of criteria that when we think about culture fit, when we think about, is this the right person for the company? And that type of process we call is the values and motivation alignment. The idea is to make sure that the person that's entering and now is being a part of Gusto Um, shares the same type of values in how they want to live their lives, and how do they look at distance, Motivations that align with what we care about. And that is the most important interview in the gastro interview process. And we take the same ty…

AI assessment note: “apply it when we talk and when we get to know investors”

Q But can I ask, we often hear the term like time to value being so crucial. Time to value is the most important thing for enterprise products I always hear. How do you think about time to delight? Does it have to be in one of the first few interactions or can it be at the later end of the user workflow?

A Right. That's a great one. I think, yes, I think like, you know, the fastest you can, of course, delight the customer and show them what you're about. The better. And for me, the, the way I think about this is a brand or a product experience is really like some, like a product is like a personality. It's like a person. And when you meet someone for the first time, the first 20 seconds, the 1:30 seconds really, really matter. And after the personality shines, even in the dull moments of whatever, waiting in line or the dull moments of just randomly seeing someone crossing eyes. And I think that if you really understand the personality of your brand, the personality of your product, you can bring that in very, very early. Through simple things like copy, through simple things like illustrations, and these things can make a really big difference.

AI assessment note: “the fastest you can, of course, delight the customer”

Q Totally. And I'm very excited to see that newly announced product or iteration of some form. So that's exciting. Can I ask also, when I was doing my research, I saw there were 111 investors in the company. It is a lot. What advice would you give to founders when it comes to cap table management?

A Yeah, so that's a really good one. So again, I don't think there's one way of doing things. I think our way was we'd really try to guide the fundraising process around this idea of alignment and between in our In values and motivations. And I think a lot of these people are people that we've known before Gusto started and, you know, Gusto has been a long journey. So we got to meet a lot of people throughout the time. And we try to make sure to bring people on the cup table that can add some sort of value. And I know that that sounds probably like a cliche in the world of VC, but it's still true. Like, you know, when I look at it, when it's specifically, when I look at some of the angel investors that we brought in, I mean, one person comes to mind, like Adam Nash is right now VP of product at Dropbox. He's been immensely great sounding board to me. In making some big product decisions. And similarly, there's other folks that have made a real impact on the company. And when we try to bring someone in, or I guess the advice then to founders is be really picky because those people are going to be out there and they're going to be associated with you and make sure that you feel great about them bearing your name. It's exactly like recruiting. It's exactly the same thing.

AI assessment note: “advice then to founders is be really picky because those people are going to be”

Q No, I do love that in terms of really nailing down the functionality and really honing that in and focusing. You mentioned obviously delight and lovable product there. It sounds great. How do you test it? Is this NPS? How do you think about determining what is delight versus not delight? And the standard of delight that you want.

A Yeah, that's a great one. I'll give one example. So folks have an idea of what I'd talk about when I say delight. So I remember when we were like in the early days, so we had this gusto started with as a payroll product and then expanded into benefits and employee onboarding and other HR functionality. And now we're this all in one HR platform. In the early days in payroll, we had this interesting moment where we were like, well, let's look at our, how does it feel like as an employee to get paid? And instinctively, you know, we saw all of our competitors and the way it It actually doesn't feel like anything at all. Maybe there's a line item on your bank account if you check this that day, or maybe there's like a really, really boring notification or something, or like an email. And that felt like a missed opportunity. So then what we did is we basically said, hey, you know, this payday is just inherently a wonderful thing. You get paid. You get money. You can do a bunch of really good stuff with that money. So what can we do there? So we did this design sprint, and I'm actually a really big proponent of the Google Ventures design team's design sprint. There's a book there, and they have, like, a bunch of content about it, and basically, it's a short period of time, defined period of time in the process, where you can solve a design problem. So, we ended up building this now ve…

AI assessment note: “I'll give one example. So folks have an idea of what I'd talk about”

Q No, I do love that in terms of really nailing down the functionality and really honing that in and focusing. You mentioned obviously delight and lovable product there. It sounds great. How do you test it? Is this NPS? How do you think about determining what is delight versus not delight? And the standard of delight that you want.

A Yeah, that's a great one. I'll give one example. So folks have an idea of what I'd talk about when I say delight. So I remember when we were like in the early days, so we had this gusto started with as a payroll product and then expanded into benefits and employee onboarding and other HR functionality. And now we're this all in one HR platform. In the early days in payroll, we had this interesting moment where we were like, well, let's look at our, how does it feel like as an employee to get paid? And instinctively, you know, we saw all of our competitors and the way it It actually doesn't feel like anything at all. Maybe there's a line item on your bank account if you check this that day, or maybe there's like a really, really boring notification or something, or like an email. And that felt like a missed opportunity. So then what we did is we basically said, hey, you know, this payday is just inherently a wonderful thing. You get paid. You get money. You can do a bunch of really good stuff with that money. So what can we do there? So we did this design sprint, and I'm actually a really big proponent of the Google Ventures design team's design sprint. There's a book there, and they have, like, a bunch of content about it, and basically, it's a short period of time, defined period of time in the process, where you can solve a design problem. So, we ended up building this now ve…

AI assessment note: “I'll give one example. So folks have an idea of what I'd talk about”