The Exchanges

Q Can I ask, was that a daunting thought when scaling through and having all the multiple different challenges and problems with scaling? Was that a daunting thought for you personally, having to realize about that continuous upscaling of yourself when, as you mentioned, apparently it's so difficult for so many others?

A Yeah. I think the, the hardest thing about this, at least one of the hardest things about doing this is that when you're up leveling your team, you are saying goodbye to people, which puts more on you as a founder. There was a point not so long ago where I had more than two dozen direct reports because I was managing people out at the same time that I was trying to recruit to replace those positions because I don't believe in recruiting surreptitiously in the background to fill a position. I believe in being upfront with the person that's here and Saying goodbye, and then going out and recruiting. I just think it's a more upfront way to do it. So what that leads to is as a founder, as a CEO, you end up having dozens of direct reports and then hundreds of interviews to fill the positions that you do. What was daunting was just how do I do that for six to 12 months through each of these transitions.

AI assessment note: “What was daunting was just how do I do that for six to 12 months”

Q Can I ask, was that a daunting thought when scaling through and having all the multiple different challenges and problems with scaling? Was that a daunting thought for you personally, having to realize about that continuous upscaling of yourself when, as you mentioned, apparently it's so difficult for so many others?

A Yeah. I think the, the hardest thing about this, at least one of the hardest things about doing this is that when you're up leveling your team, you are saying goodbye to people, which puts more on you as a founder. There was a point not so long ago where I had more than two dozen direct reports because I was managing people out at the same time that I was trying to recruit to replace those positions because I don't believe in recruiting surreptitiously in the background to fill a position. I believe in being upfront with the person that's here and Saying goodbye, and then going out and recruiting. I just think it's a more upfront way to do it. So what that leads to is as a founder, as a CEO, you end up having dozens of direct reports and then hundreds of interviews to fill the positions that you do. What was daunting was just how do I do that for six to 12 months through each of these transitions.

AI assessment note: “What was daunting was just how do I do that for six to 12 months”

Q Okay, so let's start with the favorite book and why. On a desert island, what are you taking away?

A So, obviously, there's lots of books out there, lots of business books out there, and I've got a bunch that I love, but I've recently read a book called 438 Days by Jonathan Franklin, and it's about a fisherman that gets lost off the coast of South America and is at sea in the Pacific for 438 days, all alone, and manages to To traverse the entire South Pacific ocean and managed to live through it and tell the story. And for me, I just love survival stories. And to me, they're also sometimes even more instructive than business books about being a CEO and founder. So I love, love stories like that. And right now that's one of my favorite books.

AI assessment note: “recently read a book called 438 Days by Jonathan Franklin”

Q Okay, so let's start with the favorite book and why. On a desert island, what are you taking away?

A So, obviously, there's lots of books out there, lots of business books out there, and I've got a bunch that I love, but I've recently read a book called 438 Days by Jonathan Franklin, and it's about a fisherman that gets lost off the coast of South America and is at sea in the Pacific for 438 days, all alone, and manages to To traverse the entire South Pacific ocean and managed to live through it and tell the story. And for me, I just love survival stories. And to me, they're also sometimes even more instructive than business books about being a CEO and founder. So I love, love stories like that. And right now that's one of my favorite books.

AI assessment note: “I've recently read a book called 438 Days by Jonathan Franklin”

Q Well, I mean, now we've got David Hasselhoff in our mind, uh, we can finally talk about internal processes, which is such a smooth transition. You've said before that, that HR and people ops are of the most importance during this stage. So what leads the thinking around kind of the centrality of HR and people ops at this scaling phase?

A Yeah. So I think a lot of it comes down to the fact that what worked as a founder and a CEO early on, which is being able to interact with almost your entire team on a daily basis, that's no longer possible. You need to find ways as a founder and CEO to scale yourself. And I found that people ops can be extremely helpful in that regard and in many ways. So whether it's saying goodbye to somebody, Whether it's internal communications, whether it's getting your next level of leadership, a lot of that's going to emanate from people ops team. So I found that to be incredibly helpful. I also think having strong people ops, once you start to get to scale and you have more than a hundred, a hundred people, you're going to end up with a pretty broad representation of the overall general population. And you're going to get a lot of different kinds of people. And there's going to be a point where you're just going to need experience Experienced people ops to deal with things that you might have never imagined having to deal with as a founder and a CEO. So whether it's risk mitigation or difficult conversations, especially if your turnover is spiking through that phase, there are very important legal and just human things that you need to be aware of during those transitional periods, and I find that a strong people ops team is crucial to that.

AI assessment note: “you need to find ways as a founder and CEO to scale yourself.”

Q Do you agree with the thesis that if they're surprised, those individuals being replaced, if they're surprised by the replacement, then it's clearly the fault of the manager for not kind of continuously updating them and having those checks. Would you agree with that kind of need for that continuous communication?

A Um, I would say so to some degree. I think it's sometimes difficult to predict what the org is going to need next, and it's evolving constantly. So what the org needs next is also a reflection of how well somebody's doing in that position or not, and how well they're scaling. So it's a very iterative process, because in reality, you would prefer not to have to replace anybody, and you would hope that they would all perform well. So, but when you start to see Cracks start to form in that performance. You do have to recognize it and be upfront. And that's where I think regular one-on-ones and especially performance reviews, sometimes you just need a level of formality around it to kind of point out where some of the challenges are. The more forthright you are, the better, earlier, the better. But honestly, sometimes it just doesn't become apparent until there's some major event or some, some major lapse. It could happen in a board meeting. It could happen with a major deal that doesn't close. It could be from customer feedback. There's a lot of moments that then add up to having to make a decision.

AI assessment note: “I would say so to some degree.”

Q Can I ask, that's the kind of sector that we don't hear much about in terms of kind of the boards in Integration with hiring. How is it a challenge in terms of kind of negotiating new hires with the board, and what does that communication stream look like?

A It is a bit of an art, and it is absolutely essential for senior leadership hires that the board is involved, and that I include every board member speaks with and interviews our finalist candidates, and I need buy-in from them, just like I need buy-in from our leadership team, so they are integrated into that process. I think the art part of it is sometimes you need to have your own team sign off on the person before the board does, and then in other roles, you want to get the board's buy-in before you then run that person by your own leadership team. But it's a bit of an art, and you also are herding cats in a way because, you know, there might be differing opinions on the board about somebody, and somebody may have some strengths and some weaknesses, and sometimes you need to then bring in somebody else to complement that person's skill that

AI assessment note: “every board member speaks with and interviews our finalist candidates, and I need buy-in”

Q Do you agree with the thesis that if they're surprised, those individuals being replaced, if they're surprised by the replacement, then it's clearly the fault of the manager for not kind of continuously updating them and having those checks. Would you agree with that kind of need for that continuous communication?

A Um, I would say so to some degree. I think it's sometimes difficult to predict what the org is going to need next, and it's evolving constantly. So what the org needs next is also a reflection of how well somebody's doing in that position or not, and how well they're scaling. So it's a very iterative process, because in reality, you would prefer not to have to replace anybody, and you would hope that they would all perform well. So, but when you start to see Cracks start to form in that performance. You do have to recognize it and be upfront. And that's where I think regular one-on-ones and especially performance reviews, sometimes you just need a level of formality around it to kind of point out where some of the challenges are. The more forthright you are, the better, earlier, the better. But honestly, sometimes it just doesn't become apparent until there's some major event or some, some major lapse. It could happen in a board meeting. It could happen with a major deal that doesn't close. It could be from customer feedback. There's a lot of moments that then add up to having to make a decision.

AI assessment note: “I would say so to some degree. I think it's sometimes difficult to predict”

Q Can I ask, do you believe that certain individuals are destined for certain stages of the business? Often people say, I'm a seed to series A person, or I'm a late stage pre-IPO person. Do you believe that there is that kind of flexibility to be progressive through stage, or do you think it is very much segmented to a specific stage?

A I found that to be absolutely the case. That people are good at different stages of the business, and as a founder, and as a CEO, and as a leader, you need to be very thoughtful about people getting them in the right roles, not only now, but putting them in roles and giving them titles that will give the flexibility for them to be able to stay with the company long-term. So a very common thing that I've seen happen, and I've done it too in each of my three companies, is title inflation. Giving somebody a title that they want now is Which will then sometimes box them out of being able to progress with the company longer term. And unfortunately, if you do that, it's very hard to give somebody a lesser title. You have to say goodbye to them and replace them with somebody else with the same title. So I think there's many, many ways that you can mess this up. And I think there's also a number of ways where you can make it possible for somebody to stay with the company.

AI assessment note: “I found that to be absolutely the case. That people are good at different stages”

Q Well, I mean, now we've got David Hasselhoff in our mind, uh, we can finally talk about internal processes, which is such a smooth transition. You've said before that, that HR and people ops are of the most importance during this stage. So what leads the thinking around kind of the centrality of HR and people ops at this scaling phase?

A Yeah. So I think a lot of it comes down to the fact that what worked as a founder and a CEO early on, which is being able to interact with almost your entire team on a daily basis, that's no longer possible. You need to find ways as a founder and CEO to scale yourself. And I found that people ops can be extremely helpful in that regard and in many ways. So whether it's saying goodbye to somebody, Whether it's internal communications, whether it's getting your next level of leadership, a lot of that's going to emanate from people ops team. So I found that to be incredibly helpful. I also think having strong people ops, once you start to get to scale and you have more than a hundred, a hundred people, you're going to end up with a pretty broad representation of the overall general population. And you're going to get a lot of different kinds of people. And there's going to be a point where you're just going to need experience Experienced people ops to deal with things that you might have never imagined having to deal with as a founder and a CEO. So whether it's risk mitigation or difficult conversations, especially if your turnover is spiking through that phase, there are very important legal and just human things that you need to be aware of during those transitional periods, and I find that a strong people ops team is crucial to that.

AI assessment note: “what worked as a founder and a CEO early on... that's no longer possible”

Q he said, Matt's done an incredible job of making hard decisions when people start to top out, and then consistently upgrading the team across different points of scale. So, so many things to unpack here, my friend, but let's Start with the core and hiring that world-class team, and maybe even before the hiring, when is the inflection point from hiring that startup team to requiring the world-class leadership team?

A Well, I should give a lot of credit for this to Pat Grady at Sequoia and to my entire board, because they've seen this movie before. They've seen companies go from being small startups to awkward teenager startups in between, and then mature adult startups and mature companies, and so they've been really helpful because they've Been typically kind of six to eight months out ahead of me. So I think most founders love their team. And so to change that team is a pretty hard thing to do. If you have a heart and a pulse, you grow to love the people that you're working with. But when you scale really fast, you have to change your team and you have to uplevel your team. And sometimes you have to say goodbye to people. And it is said that by the time a software company goes public, on average, they will go through 4.1 complete leadership teams. Wow. Which means that they will have to cycle through an entirely new team about every 24 months or so. So that's how that process started.

AI assessment note: “they will have to cycle through an entirely new team about every 24 months”

Q What bit of advice really stands out to you in the scaling journey that's been given by one of the board members or advisors or mentors? Is there one element that always rings true for you?

A I think that there's always lots of good advice, but I think that this realization, particularly over the last year or so, that the leadership That you have today will need to evolve and change, and I remember when it happened, it was last year at this time, we have a board dinner that usually follows our board meeting, and we talk a lot about the talent that we have and the talent that we need, and I remember coming out of that dinner thinking, wow, like, we have a lot of work to do in terms of the leadership that we need, and I think just being open to that kind of feedback and then acting upon it is really, really important, so that was feedback That came from the board that really opened my eyes to what it was going to take to create the size and the scale of the company that we're hoping to create, and so that that was probably one of the most important pieces of feedback that I've received about scaling over the last six years since I started the company.

AI assessment note: “the leadership That you have today will need to evolve and change”

Q Can I ask, do you believe that certain individuals are destined for certain stages of the business? Often people say, I'm a seed to series A person, or I'm a late stage pre-IPO person. Do you believe that there is that kind of flexibility to be progressive through stage, or do you think it is very much segmented to a specific stage?

A I found that to be absolutely the case. That people are good at different stages of the business, and as a founder, and as a CEO, and as a leader, you need to be very thoughtful about people getting them in the right roles, not only now, but putting them in roles and giving them titles that will give the flexibility for them to be able to stay with the company long-term. So a very common thing that I've seen happen, and I've done it too in each of my three companies, is title inflation. Giving somebody a title that they want now is Which will then sometimes box them out of being able to progress with the company longer term. And unfortunately, if you do that, it's very hard to give somebody a lesser title. You have to say goodbye to them and replace them with somebody else with the same title. So I think there's many, many ways that you can mess this up. And I think there's also a number of ways where you can make it possible for somebody to stay with the company.

AI assessment note: “I found that to be absolutely the case. That people are good at different stages”

Q In terms of an unavoidable element of the transition, you did touch on it being kind of the firing. I'm intrigued to hear, how do you determine between promoting those within and then hiring externally, not in the case of firing, that is. So when you've got a really talented individual internally, between promoting them or bringing in an outsider, and then also how do you communicate that?

A Yeah, I think it's definitely a balancing act. You don't want to be seen as just going out and hiring mercenaries or outsiders for every single position in the company. At the same time, you're growing so fast that it's quite difficult for somebody to scale internally and move up as fast as the company is scaling. So I think you need to be really, really thoughtful about it. Some of the things that we've done is actually creating intermediate titles. So for example, we used to just have maybe manager, director, VP. Now we have senior managers, senior directors. So there's a path for people to move up Within the company. I'd also say that as much as possible, maybe not at the leadership level, but in the mid levels of the company, I think for every person you bring in from the outside, you want to try to promote somebody from within. And I think Google subscribed to that approach, and I think they did it pretty well, so we've tried to do the same thing.

AI assessment note: “for every person you bring in from the outside, you want to try to promote somebody”

Q Final question before the quickfire, I'm kind of latching onto that importance of mission vision values. I'm always really intrigued as to the balance between handling the immediacy of kind of current Product and current ops and structure, and then also keeping in mind the importance of having that innovative mindset and the future roadmap. How do you balance between the immediacy of now and that kind of future, Matt?

A So one of the things that I found, especially as we've scaled, is that you can actually become not innovative. You can get so focused on up-leveling your leadership team and getting process in place and building a roadmap through using data based on Customer requests that you can actually sometimes deemphasize what got you there in the first place. And so at scale, you need to actually find ways similar to building out a defined mission, vision, values that everyone can get around actually building out teams or opportunities to be innovative again. And I think it's just like everything else. You have to define it and you have to articulate that it's important. And then you have to put some resources against it. It's not going to just happen by itself like it did in the early days. I think that's been a big learning for us over the last year or so is that if we want to be innovative, we've got to be really thoughtful about it and put resources against it.

AI assessment note: “You have to define it and you have to articulate that it's important.”

Q In terms of an unavoidable element of the transition, you did touch on it being kind of the firing. I'm intrigued to hear, how do you determine between promoting those within and then hiring externally, not in the case of firing, that is. So when you've got a really talented individual internally, between promoting them or bringing in an outsider, and then also how do you communicate that?

A Yeah, I think it's definitely a balancing act. You don't want to be seen as just going out and hiring mercenaries or outsiders for every single position in the company. At the same time, you're growing so fast that it's quite difficult for somebody to scale internally and move up as fast as the company is scaling. So I think you need to be really, really thoughtful about it. Some of the things that we've done is actually creating intermediate titles. So for example, we used to just have maybe manager, director, VP. Now we have senior managers, senior directors. So there's a path for people to move up Within the company. I'd also say that as much as possible, maybe not at the leadership level, but in the mid levels of the company, I think for every person you bring in from the outside, you want to try to promote somebody from within. And I think Google subscribed to that approach, and I think they did it pretty well, so we've tried to do the same thing.

AI assessment note: “for every person you bring in from the outside, you want to try to promote”

Q And in the case of kind of the complete paradox of hiring that brilliant all-star at the scaling phase, there is the unfortunate element of releasing people from their positions or firing them, so to speak. I'd love to hear how you think about this, and especially with the scaling, how maybe you've seen your firing process and thought process change with the scaling?

A So I think it needs to be handled extremely carefully and with a lot of finesse. The more senior the person, the more delicately it needs to be handled, and I think the company can never disclose why somebody left, but the individual who leaves, that's a lot of times, especially at a senior level, will leave it up to them as to how they describe why they're leaving. The conversation itself can be very quick, or it can be drawn out over a series of weeks and months, but to some degree, you know, the role of the CEO founder is to be playing this game of three-dimensional chess and In their heads and kind of seeing where all the pieces are going to move over a period of months and years. So I think on the part of the founder, they will start to get an idea of what might be the next position that needs to be kind of upleveled or changed. And then strategically over a period of time, you need to have those discussions with the people that might not be with the company long-term.

AI assessment note: “I think it needs to be handled extremely carefully and with a lot of finesse.”

Q What bit of advice really stands out to you in the scaling journey that's been given by one of the board members or advisors or mentors? Is there one element that always rings true for you?

A I think that there's always lots of good advice, but I think that this realization, particularly over the last year or so, that the leadership That you have today will need to evolve and change, and I remember when it happened, it was last year at this time, we have a board dinner that usually follows our board meeting, and we talk a lot about the talent that we have and the talent that we need, and I remember coming out of that dinner thinking, wow, like, we have a lot of work to do in terms of the leadership that we need, and I think just being open to that kind of feedback and then acting upon it is really, really important, so that was feedback That came from the board that really opened my eyes to what it was going to take to create the size and the scale of the company that we're hoping to create, and so that that was probably one of the most important pieces of feedback that I've received about scaling over the last six years since I started the company.

AI assessment note: “realization, particularly over the last year or so, that the leadership That you have”

Q Can I ask, that's the kind of sector that we don't hear much about in terms of kind of the boards in Integration with hiring. How is it a challenge in terms of kind of negotiating new hires with the board, and what does that communication stream look like?

A It is a bit of an art, and it is absolutely essential for senior leadership hires that the board is involved, and that I include every board member speaks with and interviews our finalist candidates, and I need buy-in from them, just like I need buy-in from our leadership team, so they are integrated into that process. I think the art part of it is sometimes you need to have your own team sign off on the person before the board does, and then in other roles, you want to get the board's buy-in before you then run that person by your own leadership team. But it's a bit of an art, and you also are herding cats in a way because, you know, there might be differing opinions on the board about somebody, and somebody may have some strengths and some weaknesses, and sometimes you need to then bring in somebody else to complement that person's skill that

AI assessment note: “every board member speaks with and interviews our finalist candidates, and I need buy-in”

Q Final question before the quickfire, I'm kind of latching onto that importance of mission vision values. I'm always really intrigued as to the balance between handling the immediacy of kind of current Product and current ops and structure, and then also keeping in mind the importance of having that innovative mindset and the future roadmap. How do you balance between the immediacy of now and that kind of future, Matt?

A So one of the things that I found, especially as we've scaled, is that you can actually become not innovative. You can get so focused on up-leveling your leadership team and getting process in place and building a roadmap through using data based on Customer requests that you can actually sometimes deemphasize what got you there in the first place. And so at scale, you need to actually find ways similar to building out a defined mission, vision, values that everyone can get around actually building out teams or opportunities to be innovative again. And I think it's just like everything else. You have to define it and you have to articulate that it's important. And then you have to put some resources against it. It's not going to just happen by itself like it did in the early days. I think that's been a big learning for us over the last year or so is that if we want to be innovative, we've got to be really thoughtful about it and put resources against it.

AI assessment note: “You have to define it and you have to articulate that it's important.”

Q Incredible. But I do want to finish on, we spoke about kind of the transition through stages. What's the next stage and what's the future five years for Namely, do you think, and are you planning for now, Matt?

A Well, I think there's a lot of different ways to answer that. We can answer it in terms of revenue, of course. We can answer it in terms of potentially being a public company. But ultimately, I think it's about creating a company at scale with high levels of internal employee satisfaction, which then leads to high levels of client or customer satisfaction on a global basis. So those are the really the two things that I'm, I'm focused on. If we create a great Culture at scale, which is a lot different than creating a great culture as a, as a smaller startup. If we can do that, then that will lead to a lot of great things down the road. So I think building a great company culture with what will by then surely be thousands of employees. That's the number one goal that I have over the next five years and everything else will flow from that. If we get employee satisfaction and get to a great place with culture as a scaled business, Then there's nothing that stops us from having a great run for another five to 10 years after that.

AI assessment note: “building a great company culture with what will by then surely be thousands of employees.”

Q he said, Matt's done an incredible job of making hard decisions when people start to top out, and then consistently upgrading the team across different points of scale. So, so many things to unpack here, my friend, but let's Start with the core and hiring that world-class team, and maybe even before the hiring, when is the inflection point from hiring that startup team to requiring the world-class leadership team?

A Well, I should give a lot of credit for this to Pat Grady at Sequoia and to my entire board, because they've seen this movie before. They've seen companies go from being small startups to awkward teenager startups in between, and then mature adult startups and mature companies, and so they've been really helpful because they've Been typically kind of six to eight months out ahead of me. So I think most founders love their team. And so to change that team is a pretty hard thing to do. If you have a heart and a pulse, you grow to love the people that you're working with. But when you scale really fast, you have to change your team and you have to uplevel your team. And sometimes you have to say goodbye to people. And it is said that by the time a software company goes public, on average, they will go through 4.1 complete leadership teams. Wow. Which means that they will have to cycle through an entirely new team about every 24 months or so. So that's how that process started.

AI assessment note: “when you scale really fast, you have to change your team and you have to”

Q And in the case of kind of the complete paradox of hiring that brilliant all-star at the scaling phase, there is the unfortunate element of releasing people from their positions or firing them, so to speak. I'd love to hear how you think about this, and especially with the scaling, how maybe you've seen your firing process and thought process change with the scaling?

A So I think it needs to be handled extremely carefully and with a lot of finesse. The more senior the person, the more delicately it needs to be handled, and I think the company can never disclose why somebody left, but the individual who leaves, that's a lot of times, especially at a senior level, will leave it up to them as to how they describe why they're leaving. The conversation itself can be very quick, or it can be drawn out over a series of weeks and months, but to some degree, you know, the role of the CEO founder is to be playing this game of three-dimensional chess and In their heads and kind of seeing where all the pieces are going to move over a period of months and years. So I think on the part of the founder, they will start to get an idea of what might be the next position that needs to be kind of upleveled or changed. And then strategically over a period of time, you need to have those discussions with the people that might not be with the company long-term.

AI assessment note: “the role of the CEO founder is to be playing this game of three-dimensional chess”