The Exchanges

Q so just pausing there. I'm the CEO. Do I say, Xenia, you need to go meet the head of product, the head of engineering, dah, dah, dah, and I make it happen? And do I need to give you the low-hanging fruit to go get? Or do I drop you in and say, make it happen? Should I expect you to do it, or should I give you the guidance?

A I think that, like, expecting me to do it, expecting your first sales hired to do it, it only makes sense if you're trying to test them more, but you just interviewed them. You should have tested them to the extent that possible before they joined. I think after they joined the company, it's your mutual job to make them successful. It's their job, and it's your job, and if you have any ability to help them, do it. Go introduce them to your board members, to your people who are their peers, sit down with them for like four hours, walk them through the intricacies of the product. I think investing as a hiring manager, as the CEO, as a founder, you need to invest a lot in your hires, especially in the first months, to then see the investments pay back in the next several years.

AI assessment note: “after they joined the company, it's your mutual job to make them successful.”

Q Can you give me an example just so I understand that? So a couple of criterias would be, and then what would show they don't have them?

A Sure. So here on the resume stage, I focus only on the things that I can get and can read from the resume, right? And, um, I have, I try to have a very short list, and I don't have nice-to-haves, I only have must-haves. So, for example, let's say that I'm looking for, um, head of Europe for a fifty million dollar a-hour company. So I'm looking for a person who, you know, I may have a criteria, you know, ran a team of at least a hundred people, one. Uh, I may have a criteria, uh, was, um, Uh, let's say, uh, ran, you know, was a part of a company that grew from fifty million to two hundred million. Um, you know, not necessarily led this company, but was a part of that. I may have a criteria worth the company that had a PLG motion, or maybe I don't care about this and I have a criteria worth at a company that had, you know, um, multiple different, so not only European, purely European company, but an international company that had, uh, you know, presence in several different places. So I would focus on those few things. Um, and you know, the fourth thing that I would typically look for, for example, have strong experience in the enterprise. So sold, You know, million dollar contracts to the enterprise market. And then those four criteria are fairly simple, right? But they mean that if I see somebody who has amazing experience and worked at the companies, the amazing companies, but…

AI assessment note: “if I see somebody who has amazing experience... but have only sold commercial, I'm not going to even talk”

Q sales rep, I think it was, because of the PLG motion. Um, and I spoke to Paul, um, who obviously you know very well before the show, and he told me that, you know, everything that goes wrong and everything that goes right In PLG and you've applied it to Miro. So what are the most common things to go wrong in PLG? And then we'll do what goes right.

A Common things to go wrong. So I think, you know, learned a few things from the companies that I've been a part of, but probably even more from companies that I haven't worked at, that I just tried to learn from what sort of exists in the world and what, you know, what can go right and what can go wrong. So I think I, um, I'm a big fan of OJ from Asana, right, but I would argue actually that companies like Asana or Dropbox were a little too late into enabling the enterprise motion on top of PLG. I think that's one of the reasons that OJ joined Asana was that Asana realized that they need to build, um, the sales-enabled motion and grow much faster, which then they did, right? So that to me is one, um, maybe mistake. It's the question of sequencing, right? It's the question of When do you transition from a pure PLG to a combination of PLG and enterprise? Uh, so if you are too late, you may just miss the market. On the other hand, the other thing that we, we talked about is that like doing enterprise too early and having hired a lot of salespeople without figuring out the fundamentals of your PLG motion just makes you into pure, you know, sales led company. And there sure are markets where, you know, purely sales led company is the right way to go, but many, many, many markets allow for a combination of PLG and enterprise. And if you are too early Into enterprise, you will miss the…

AI assessment note: “companies like Asana or Dropbox were a little too late into enabling the enterprise motion”

Q What do you mean optimize for the thing that they own? What does that mean? Sorry.

A So let's say that, you know, one bad way to organize this is to have two people. One is responsible for self-serve revenue. Another one is responsible for high-tech revenue and they're only responsible for their own portion of revenue. And Uh, there is, you know, in a couple of months after that, the high-tech person will go and figure out, well, I can launch an SMB, um, motion here and sell to small companies through a salesperson, and a self-serve person will come to the CEO and say, well, you, those guys are cannibalizing my self-serve revenue, and actually they are deploying people resources where we should not deploy people resources, where the customer eventually will grow, you know, maybe it will take them additional couple of months, but will grow to the same level that it would grow with a salesperson with no costs, uh, Spent. Right. And this creates, um, a room for conflict and people are starting to spend time on things that are not productive for the whole company, but that would optimize for, you know, for either self-serve or high touch.

AI assessment note: “people are starting to spend time on things... that would optimize for... either self-serve or high touch”

Q How do you structure the actual process itself? I often see people have one meeting and offer a role or others who have 20 and still haven't made a decision. How do you think about structuring the right and efficient hiring process for sales and revenue teams?

A Yeah, I think that a good hiring process is frankly similar most places, right? So you have your hiring manager screen, your, um, interview panel, then you have some final interviews and then you, you close the candidate. Um, I will share a few kind of an orthodox design choices that, uh, worked very well for me. Uh, we started with the first one that I may try to make sure always happens, which is you need to, if I don't understand what role that I'm hiring for, I don't open the role until I do. Um, and I will go and research the role before Um, I want to fill it. The second step is as a hiring manager, I try to have very clear must have criterias. Three to five must have criterias for the role. And I ruthlessly decline candidates who don't meet at least one of those criterias on the resume stage. I don't talk to them. I look at the resume. There are five criterias I have. If one is not met, it's out. I don't have.

AI assessment note: “you have your hiring manager screen, your, um, interview panel, then you have some final interviews”

Q I feel quite naive here, Xenia, but when you say hiring panel, do you have an individual hiring panel for each hire? Is it like a hiring panel across the company? Can you just walk me through this? Cause I've never actually heard of like a hiring panel, so to speak.

A Yeah, I do have individual hiring panel for each role. Um, so what I'm looking for, I look for maybe three to five people who will talk to the person I'm trying to hire, who will be The most likely to, um, understand well what I'm hiring, like what I'm trying to hire, and who will maybe work closely with this person. Uh, and if sometimes I don't have, sometimes I don't have those people inside the company, sometimes I may ask my board member to interview, or I will ask my advisor who is, you know, head of sales at a much larger company to interview my first head of sales hire to understand, uh, you know, what to do with them. Uh, but I also will have people from within the company, uh, interview the hire as well. And so the panel I think is tailor made and I basically, I tried to make the panel as hard for the candidate as possible, because if they pass that, I want them, they're much more likely to succeed when they join the company.

AI assessment note: “Yeah, I do have individual hiring panel for each role.”

Q so just pausing there. I'm the CEO. Do I say, Xenia, you need to go meet the head of product, the head of engineering, dah, dah, dah, and I make it happen? And do I need to give you the low-hanging fruit to go get? Or do I drop you in and say, make it happen? Should I expect you to do it, or should I give you the guidance?

A I think that, like, expecting me to do it, expecting your first sales hired to do it, it only makes sense if you're trying to test them more, but you just interviewed them. You should have tested them to the extent that possible before they joined. I think after they joined the company, it's your mutual job to make them successful. It's their job, and it's your job, and if you have any ability to help them, do it. Go introduce them to your board members, to your people who are their peers, sit down with them for like four hours, walk them through the intricacies of the product. I think investing as a hiring manager, as the CEO, as a founder, you need to invest a lot in your hires, especially in the first months, to then see the investments pay back in the next several years.

AI assessment note: “if you have any ability to help them, do it. Go introduce them”

Q How do you structure the actual process itself? I often see people have one meeting and offer a role or others who have 20 and still haven't made a decision. How do you think about structuring the right and efficient hiring process for sales and revenue teams?

A Yeah, I think that a good hiring process is frankly similar most places, right? So you have your hiring manager screen, your, um, interview panel, then you have some final interviews and then you, you close the candidate. Um, I will share a few kind of an orthodox design choices that, uh, worked very well for me. Uh, we started with the first one that I may try to make sure always happens, which is you need to, if I don't understand what role that I'm hiring for, I don't open the role until I do. Um, and I will go and research the role before Um, I want to fill it. The second step is as a hiring manager, I try to have very clear must have criterias. Three to five must have criterias for the role. And I ruthlessly decline candidates who don't meet at least one of those criterias on the resume stage. I don't talk to them. I look at the resume. There are five criterias I have. If one is not met, it's out. I don't have.

AI assessment note: “So you have your hiring manager screen, your interview panel, then you have some final interviews”

Q What were your biggest lessons from international expansion at Segment?

A Um, I made a couple of mistakes at Segment that I tried to fix at Miro. It's not really a fire round. It's a huge topic that I can spend a lot of time on. Um, I think the biggest one for me was, well, first of all, it takes an entire village to win this thing. Like, you need to open local legal entities and have bank accounts and insurance and figure out local contracts and, like, localize your product to a language and maybe even localize the residency. It takes the entire company to open presence somewhere else, you know, in Australia, or in Europe, or in the US, um, and you need to be ready for it, and as just a go-to-market leader, you cannot succeed in it without the support of your CEO and CFO and the operational organization, so that's big. It's, that's a big learning. Um, the second one is that, kind of, is as big of a journey as it is, uh, it's, if you can do it, Uh, you should do it rather early and rather fast. I think at Dropbox we launched the first region outside of the US when we were over a hundred million in ERR, and I think that frankly was too late. I think you can start doing this when you are at about 20, thirty million, um, because it just takes a very long time to build reputation in the market, to build strengths in the market, and you want to give yourself plenty of time to build strong and ideally cash flow positive business, um, before you go public.

AI assessment note: “I think the biggest one for me was, well, first of all, it takes an entire village”

Q Yeah, I, I totally agree. Do you think you can do them both at the same time at an early stage, given it's expensive to do enterprise, and actually PLG is expensive too, it's a big investment in product teams. Do you think it's possible for early stage companies to do PLG and enterprise alongside each other in the early days?

A Yeah, I think in the long run, I think the best business model that you can have is PLG plus enterprise. Um, but in the early days, I agree with you that if your resources are scarce, you need to, you need to focus on one. And if you have any opportunity to build a PLG business in your market, I would advise like first figure out PLG. Uh, I think that's a lot bigger adds to your valuation, a lot bigger add to your, you know, future success. If you figured out PLG, uh, go to market, you will also, you will always Have the time for it. Um, if your PLG motion is figured out, but, um, but the PLG, if you miss it, and if you build the sales teams too early, it's very hard to build later.

AI assessment note: “if your resources are scarce, you need to, you need to focus on one”

Q sales rep, I think it was, because of the PLG motion. Um, and I spoke to Paul, um, who obviously you know very well before the show, and he told me that, you know, everything that goes wrong and everything that goes right In PLG and you've applied it to Miro. So what are the most common things to go wrong in PLG? And then we'll do what goes right.

A Common things to go wrong. So I think, you know, learned a few things from the companies that I've been a part of, but probably even more from companies that I haven't worked at, that I just tried to learn from what sort of exists in the world and what, you know, what can go right and what can go wrong. So I think I, um, I'm a big fan of OJ from Asana, right, but I would argue actually that companies like Asana or Dropbox were a little too late into enabling the enterprise motion on top of PLG. I think that's one of the reasons that OJ joined Asana was that Asana realized that they need to build, um, the sales-enabled motion and grow much faster, which then they did, right? So that to me is one, um, maybe mistake. It's the question of sequencing, right? It's the question of When do you transition from a pure PLG to a combination of PLG and enterprise? Uh, so if you are too late, you may just miss the market. On the other hand, the other thing that we, we talked about is that like doing enterprise too early and having hired a lot of salespeople without figuring out the fundamentals of your PLG motion just makes you into pure, you know, sales led company. And there sure are markets where, you know, purely sales led company is the right way to go, but many, many, many markets allow for a combination of PLG and enterprise. And if you are too early Into enterprise, you will miss the…

AI assessment note: “It's the question of sequencing, right? It's the question of When do you transition”

Q If you analyze Dropbox, you said there about not winning it. Why do you think you didn't win it?

A I think it's, um, I think what I learned, I guess, from Dropbox is that going into the enterprise is a commitment for the entire company that starts with the CEO and, um, that needs to take the entire, not just the go-to-market teams and sales teams, but the entire like marketing and engineering and product and the entire culture of the company needs to change a bit. Um, and the whole company needs to believe that, you know, the enterprise is good fundamentally, that it's not, uh, you know, An evil and that salespeople are not evil, but that's, uh, that it's great for your customers. It's great for building, bringing your product into the market. And I think this lack of that level of commitment, uh, early on, I think at Dropbox was what plagued us. You know, we had wonderful, fantastic go-to-market leaders, uh, at the company, but we just had them, like each one came for, you know, a couple of years and then left and You know, we never had the full, full commitment to go full on and win the enterprise no matter what.

AI assessment note: “lack of that level of commitment, uh, early on, I think at Dropbox”

Q Do you have the high touch sales team going, Hey, we need these products. We need these features for these customers, and it's going to drive revenue and that product, you know, PLG team are not doing it fast enough. Xenia, come on, help me. Do you get that?

A I don't think we do actually. Uh, so I think the way that, that we build collaboration between the two teams, we, I think the entire sort of high touch side of the company realizes that, um, the PLG side is not about small customers. It's not about self-serve alone. It's about PLG motion for all of our customers. So within the PLG team, we actually have enterprise girls team, which is a product team that sits within our self-serve organization, self-serve product organization, and that helps Mature customers to the enterprise level, and it helps expand customers in the enterprise. So, um, generally, you know, when I joined Miro, the thing that I saw as maybe mission or thing that I wanted to do most is kind of build the next iteration of the best in breed combination of PLG and enterprise and how the more they are connected everywhere, the better I think the overall motion is.

AI assessment note: “I don't think we do actually.”

Q I feel quite naive here, Xenia, but when you say hiring panel, do you have an individual hiring panel for each hire? Is it like a hiring panel across the company? Can you just walk me through this? Cause I've never actually heard of like a hiring panel, so to speak.

A Yeah, I do have individual hiring panel for each role. Um, so what I'm looking for, I look for maybe three to five people who will talk to the person I'm trying to hire, who will be The most likely to, um, understand well what I'm hiring, like what I'm trying to hire, and who will maybe work closely with this person. Uh, and if sometimes I don't have, sometimes I don't have those people inside the company, sometimes I may ask my board member to interview, or I will ask my advisor who is, you know, head of sales at a much larger company to interview my first head of sales hire to understand, uh, you know, what to do with them. Uh, but I also will have people from within the company, uh, interview the hire as well. And so the panel I think is tailor made and I basically, I tried to make the panel as hard for the candidate as possible, because if they pass that, I want them, they're much more likely to succeed when they join the company.

AI assessment note: “Yeah, I do have individual hiring panel for each role.”

Q to take this because now we've been through the process. We've got this amazing candidate. Onboarding is notoriously difficult in every company. When we think about kind of the right onboarding process, how, what does that look like for this head of sales that we've just hired? Thank you, by the way, for helping me. Um, what, what does that onboarding process look like for this first head of sales?

A So what I try to do for every leadership hire that I make, um, I Try to free up their first months as much as possible. Like, I try to create a situation where they don't need to deliver anything in the first one months. Um, I want them to, I'm hiring them not for the next six months or 12 months, I'm hiring them for the next, like, five years plus with the company, and I want them to build the foundation of being able to succeed in the company. And for that, for me, that's understand the product, get to meet everybody in the company who you will need to work with, and ideally you start from people Who you will need to work with like a year from now, not a month from now. So if you're a head of sales, you don't go and talk to your sales people first. You go and talk to your head of engineering or key engineering and product leaders, because eventually as a head of sales, you are going to need to work with them for the company to be successful. And if you miss the opportunity to build this personal connection in the first months, it's going to be very hard to do like when you're six months into the role. So the first months I tried to give them as much kind of direction to learn broadly about the company into You know, see them sales calls to just, you know, ingest, um, everything that the company has built before they joined as possible. So that's step one. And then second, I'd…

AI assessment note: “I try to free up their first months as much as possible”

Q I, I do want to ask, say they're rejected by the organism, or they're not delivering value, how do we communicate that first concern? Do we take them aside and say, hey, we're concerned by X, Y, and Z, you're on warning, just help me understand the right communication pathways after identifying a concern?

A Yeah, I think my philosophy here is that anybody in the leadership role, their role is just too important, a lot more important than, you know, person's feelings or the process that you need to follow. And, um, I try to lean as direct as possible. So like radical candor to the extreme, right? So you care about the person, but you need to deliver that message very clearly. Uh, so the moment that you know that there is something to deliver, You take the person aside, you sit down, and you're brutally honest in what you're seeing, and in what consequences follow if those things are not fixed. And I've seen the best reaction when it's super clear, when people also need to feel that you care about them, that you're in their camp, that you need them to succeed in the company, and you need the company to succeed together with them, right? But they need to also be clear on what are they doing right, or what are they doing wrong, and what do they need to fix to be successful.

AI assessment note: “You take the person aside, you sit down, and you're brutally honest in what you're seeing”

Q You said about, like, the many hours you spend with candidates before putting them in front of the hiring panel. Do you use case studies? Do you use data? How do you strategically test them in a more tangible way?

A Yeah, you know, I probably, I think that I interviewed maybe like thousands of people at this point, and I think early on in my career, I lean heavily on case studies, and now I barely ever use a case study. Um, I think that what I found is that, uh, especially when I'm hiring leaders, I don't want them to solve an artificial puzzle or be a thought partner for me for a given topic. I find that, you know, Their ability to succeed there very much depends on whether they were exposed to something like this before or not. I really want to talk to them about their own experiences. So all I do is all about give me a situation when you did this and that, and then I dive into it and ask like 10 follow-up questions to understand how you solved the problem. What did they think about? How did they work with other people? Like, why did they make this decision or another decision? Um, so I, I focus primarily on experiences.

AI assessment note: “now I barely ever use a case study. Um, I think that what I found is”

Q just want to pause there. I'm too interested, because I most often see founders, and they say, we need to move into enterprise, and I always say to them, listen, SMB is deeper than you think it is, and you can build a bigger business than you think you can staying there. Don't move there too soon. How do you think about that, given the need to also win enterprise?

A Yeah, I think the markets are different, right? So it really depends on where you are, how much competition you have, and where, how do you see your market developing over the years? So if you have significant competition, or, you know, if you see other people potentially jumping into the enterprise market for you, you have to try to win it and not miss the boat. If you have the time, if you are, you know, alone in your market, like there, there are a few companies that are in this lucky position. Uh, then yes, figuring out first the PLG motion, SMB motion, mid-market motion, uh, is a great thing to do. It's just one thing to know that enterprise takes multiple years to build. So even if you start today, it's not going to be until, you know, maybe three years, four years from now that you really figured out how to be a PLG plus enterprise company. Uh, so it's just, you kind of need to plan for way ahead of time.

AI assessment note: “it really depends on where you are, how much competition you have”

Q What were your biggest lessons from international expansion at Segment?

A Um, I made a couple of mistakes at Segment that I tried to fix at Miro. It's not really a fire round. It's a huge topic that I can spend a lot of time on. Um, I think the biggest one for me was, well, first of all, it takes an entire village to win this thing. Like, you need to open local legal entities and have bank accounts and insurance and figure out local contracts and, like, localize your product to a language and maybe even localize the residency. It takes the entire company to open presence somewhere else, you know, in Australia, or in Europe, or in the US, um, and you need to be ready for it, and as just a go-to-market leader, you cannot succeed in it without the support of your CEO and CFO and the operational organization, so that's big. It's, that's a big learning. Um, the second one is that, kind of, is as big of a journey as it is, uh, it's, if you can do it, Uh, you should do it rather early and rather fast. I think at Dropbox we launched the first region outside of the US when we were over a hundred million in ERR, and I think that frankly was too late. I think you can start doing this when you are at about 20, thirty million, um, because it just takes a very long time to build reputation in the market, to build strengths in the market, and you want to give yourself plenty of time to build strong and ideally cash flow positive business, um, before you go public.

AI assessment note: “I think the biggest one for me was, well, first of all, it takes an entire village”

Q Yeah, I, I totally agree. Do you think you can do them both at the same time at an early stage, given it's expensive to do enterprise, and actually PLG is expensive too, it's a big investment in product teams. Do you think it's possible for early stage companies to do PLG and enterprise alongside each other in the early days?

A Yeah, I think in the long run, I think the best business model that you can have is PLG plus enterprise. Um, but in the early days, I agree with you that if your resources are scarce, you need to, you need to focus on one. And if you have any opportunity to build a PLG business in your market, I would advise like first figure out PLG. Uh, I think that's a lot bigger adds to your valuation, a lot bigger add to your, you know, future success. If you figured out PLG, uh, go to market, you will also, you will always Have the time for it. Um, if your PLG motion is figured out, but, um, but the PLG, if you miss it, and if you build the sales teams too early, it's very hard to build later.

AI assessment note: “in the early days, I agree with you that if your resources are scarce, you need to focus on one”

Q If you analyze Dropbox, you said there about not winning it. Why do you think you didn't win it?

A I think it's, um, I think what I learned, I guess, from Dropbox is that going into the enterprise is a commitment for the entire company that starts with the CEO and, um, that needs to take the entire, not just the go-to-market teams and sales teams, but the entire like marketing and engineering and product and the entire culture of the company needs to change a bit. Um, and the whole company needs to believe that, you know, the enterprise is good fundamentally, that it's not, uh, you know, An evil and that salespeople are not evil, but that's, uh, that it's great for your customers. It's great for building, bringing your product into the market. And I think this lack of that level of commitment, uh, early on, I think at Dropbox was what plagued us. You know, we had wonderful, fantastic go-to-market leaders, uh, at the company, but we just had them, like each one came for, you know, a couple of years and then left and You know, we never had the full, full commitment to go full on and win the enterprise no matter what.

AI assessment note: “lack of that level of commitment, uh, early on, I think at Dropbox was what plagued us.”

Q I totally get you in terms of the commitment top down. What, what would you say was a big takeaway for you from Segment? It was an incredible journey there. What would you say is a big takeaway that impacted you from Segment?

A So like Segment for me, Segment was really the first place where I ran the sales teams, right? So I started about six years ago and, um, I started as a head of customer success team at Segment. And then about a month in Peter, the CEO, um, asked me to run sales and I told him, Hey, you know, there's so many people who know how to do this way better than I do. You can go and hire them and, you know, do you really want to do it? He said, well, yeah, like you seem to be, to understand how the go-to-market thing may work and go and try to run the sales team. And if you fail, we will hire somebody. And so I've been, um, at segment ever since, like every six months increment is like, okay, let's trust another six months to Genia and let's trust another six months, um, to see how he can run sales team. So I think the biggest learning from segment for me was this kind of pass of an outsider into the sales team in learning about the sales world and like Um, you know, I'm kind of a mathematics nerd and an operations geek. Um, and I think that I saw initially sales as maybe nothing other than building relationships and maybe knowing your product well. And over three years of segments, I came to realize how, um, fantastic and how deep the world of sales is, how much it has to, you know, to master and to learn. Um, and that it's sort of a separate, um, Field of knowledge, even like several,…

AI assessment note: “biggest learning from segment for me was this kind of pass of an outsider”

Q Do you have the high touch sales team going, Hey, we need these products. We need these features for these customers, and it's going to drive revenue and that product, you know, PLG team are not doing it fast enough. Xenia, come on, help me. Do you get that?

A I don't think we do actually. Uh, so I think the way that, that we build collaboration between the two teams, we, I think the entire sort of high touch side of the company realizes that, um, the PLG side is not about small customers. It's not about self-serve alone. It's about PLG motion for all of our customers. So within the PLG team, we actually have enterprise girls team, which is a product team that sits within our self-serve organization, self-serve product organization, and that helps Mature customers to the enterprise level, and it helps expand customers in the enterprise. So, um, generally, you know, when I joined Miro, the thing that I saw as maybe mission or thing that I wanted to do most is kind of build the next iteration of the best in breed combination of PLG and enterprise and how the more they are connected everywhere, the better I think the overall motion is.

AI assessment note: “I don't think we do actually.”

Q Let's just pause that because I'm too interested here. So, okay, so we, how many candidates do you go through this extensive process with? Is it three to five?

A So it really depends on the role. I had roles where I would do three to five, but I also had roles where I would do like maybe 20. Um, but it doesn't mean that I spend four or five hours with every candidate. I usually start those, um, interviews with the topics that are hardest, that I think will be the hardest for the candidate to succeed in. And then if on the, after the first interview, the candidate is not succeeding, I will, you know, move on to, to other ones. So the thing for me here is that Um, I don't want them to go to the interview panel until I'm sure that they are actually good, and that I am calibrated, and I, I know what I'm hiring for. I have, I, they passed my bar. Um, what I find with interview panels is several things. Like, one is, I will lose everybody's time if I pass candidates who I'm, like, half sure about, and, you know, then that, that's what lead to, you know, half a year, a year, 18 months long, Um, hiring cycles where, you know, all of your exec team have interviewed 25 people and are, you know, bored to death from this role. I only need, I only want them to talk to maybe three to five people and then say, okay, like, all of them, all three of them are good, and this one is better than the two others. That's one thing, but also I find that it's only the hiring manager who really, really sets the hiring bar, um, and your panel will not be able, you…

AI assessment note: “I had roles where I would do three to five, but I also had roles”

Q kind of constructing individualized hiring panels for each role. I think that's awesome. When we think about going back to like the actual like candidates themselves, you know, PLG enterprise labs we spent time on, how does what we need in each change when we're thinking about sales leaders, if we're a PLG sales leader versus an enterprise sales leader, how are they different in terms of what we need?

A So frankly, I think the fundamentals are the same and I think create Enterprise seller and enterprise sales leader at a PLG company should be also a great one in a pure play enterprise company. I think to me the only difference is kind of that people, those people should have the appreciation for the importance of end user experience and appreciation for teams like product or customer experience. So, um, they don't necessarily need to have PLG experience at a PLG company, but I want to See them sort of respect and value perspective of other people and ability to learn new things. And if they can learn new things, then they can easily learn the PLG motion as well. I don't think that there is a special breed of, you know, PLG salespeople. I think that, you know, say a great salesperson is a great salesperson. Uh, they just need to be open-minded about changing their motion, their sales motion to, to benefit from the PLG.

AI assessment note: “I think to me the only difference is kind of that people, those people should”

Q Tough question and not one in the schedule. What are the biggest ways you fucked up in our hiring process? Like what are the biggest hiring mistakes you've made?

A Oh yeah, I made quite a few. Um, right. So I had like people who reported to me who had to leave companies and every company that I've been a part of. Um, Frankly, the biggest ones were when I, I think that I knew that I'm not doing the right step, but I did the step anyway, where I had the criteria for myself at the beginning of the process, and either I ignored them or, um, I didn't pay enough attention to them. So like an example was, you know, for a given role, I hired a person who had no experience working at similar companies at all, and they worked, you know, they had a third year career at, um, in technology, but have never worked. You know, at a similar company that will have an international presence, and it was just extremely hard to change the mindset, um, and, and we had to part ways, and I knew that it would likely be extremely hard that just for some reason I thought that I would be able to, you know, because of all the other strengths that the person had that, um, I'd be able to, um, you know, to, to take care of this. Uh, the other experience was, uh, when I I looked at the candidates, I trusted the interview panel too much, and I trusted the candidates resume too much. So I looked, they had like a wonderful, fantastic resume, and my interview panel was very fond of them. And I think the problem with this is, you know, you're on your interview panel, everybody …

AI assessment note: “Frankly, the biggest ones were when I, I think that I knew”

Q to take this because now we've been through the process. We've got this amazing candidate. Onboarding is notoriously difficult in every company. When we think about kind of the right onboarding process, how, what does that look like for this head of sales that we've just hired? Thank you, by the way, for helping me. Um, what, what does that onboarding process look like for this first head of sales?

A So what I try to do for every leadership hire that I make, um, I Try to free up their first months as much as possible. Like, I try to create a situation where they don't need to deliver anything in the first one months. Um, I want them to, I'm hiring them not for the next six months or 12 months, I'm hiring them for the next, like, five years plus with the company, and I want them to build the foundation of being able to succeed in the company. And for that, for me, that's understand the product, get to meet everybody in the company who you will need to work with, and ideally you start from people Who you will need to work with like a year from now, not a month from now. So if you're a head of sales, you don't go and talk to your sales people first. You go and talk to your head of engineering or key engineering and product leaders, because eventually as a head of sales, you are going to need to work with them for the company to be successful. And if you miss the opportunity to build this personal connection in the first months, it's going to be very hard to do like when you're six months into the role. So the first months I tried to give them as much kind of direction to learn broadly about the company into You know, see them sales calls to just, you know, ingest, um, everything that the company has built before they joined as possible. So that's step one. And then second, I'd…

AI assessment note: “I Try to free up their first months as much as possible.”

Q This head of sales hire, what are the biggest signs in the first three months that I've fucked up this hire?

A If you don't see any results delivered in the first three months, if you see the person sitting and, um, figuring out quote unquote strategy and drawing charts and not meeting customers and, um, you know, not delivering anybody for the early sales team in the first three months, um, that's a big red flag for me. So, um, Uh, when we were, when we had, um, exact new exact team or new leadership team, uh, members joined segment and they asked, how do I, how am I successful in this company? Like the biggest beginning of the answer was you need to start delivering value on your month's number two or number three, and you need to ship something. Uh, and so that, you know, it's a small company. There's no time to like wait and, you know, build plans. You need to deliver fast. You, you have this maybe beginning one month to, Um, where you are invested in, but then you need to start paying back very quick. Uh, so I think that's the first one. The second one for me, which I've seen a couple of times was when your initial team starts to reject, uh, the person you just hired. You know, you maybe have, you know, five salespeople and you are now hiring the head of sales, or maybe you have, you know, customer success folks or somebody else. And on months two or months three, somebody from the team comes to you and says, Hmm, I didn't know about this new guy. Uh, And your job as the CEO is act…

AI assessment note: “If you don't see any results delivered in the first three months”

Q This is assessment and monitoring on a kind of per person level. I'm intrigued when we think about on a deal level. Do you do post mortems on deals? Do you do deal reviews? And how do you structure them internally? I'm fascinated.

A We do, um, and we did, um, both segmented, you know, the, um, I think the purpose of the deal reviews is primarily for your sales team to learn what to do well and what not to do well. I think your audience for the deal review is not the person who did the deal, but all the people around. Um, and I think the best, you know, one of the worst way to do a deal review is when one person is listening and nobody else pays attention. And, you know, only the person who, who was there in the room, like gets any input from your head of sales on how to do the deal better. Um, I think the best deal review is basically Clinic for the entire team on, you know, here are the things that we did really well. That's what resonated. How do we do it in every deal? Or here's the thing that we didn't do well. And you know, how do we do things differently?

AI assessment note: “We do... the best deal review is basically Clinic for the entire team”

Q because you can't bring in, bluntly, low-level sales reps and expect them to manage, create, and execute on a new sales Playbook. That would be a lot to expect a young sales rep. Do you agree then that it's head of sales next? And if so, do any heads of sales want to join as the first sales person in an org? And if they do, are they any good?

A Yeah, I think I agree that the head of sales is the best role to hire for instead of just reps. I think that if you can at all afford it, and then I think go and hire your first head of sales. I think the stage is important, right? So if you don't know where your initial product market fit is, you should hire any salespeople, either reps or head of sales. They are not going to figure it out for you. Like, The founder is a lot more likely to figure out the initial product market fit. But after you close to either several deals, or maybe you are up to maybe one million in revenue, it is time to hire your first head of sales. I think that the junior rep will consume bandwidth from the founder, and the founder will need to spend time on those first few reps to enable them, to support them, to show them what to do. And the head of sales will instead create bandwidth that the founder can use to go solve other problems, to go like build a product, to go hire a finance person, to go do something else. So I'm a big believer in Scaling yourself through hiring people who can do things independently of you.

AI assessment note: “Yeah, I think I agree that the head of sales is the best role”