The Exchanges

Q No, I totally agree. I think nail it and also kind of create repeatability in it for others to really take hold of. If we think about PLG versus Enterprise, something that I see a lot of today is founders chasing PLG and Enterprise kind of from day one. Can you do both at the same time, do you think, Kevin?

A I think you can, but I think it's extremely difficult. I think Slack was able to do it. I think they nailed PLG first, and then enterprise, but they always had an eye towards enterprise. The reason why I say it's extremely difficult is to capture the end user's imagination, capture that end user love is one thing, but to build out the enterprise security set, the feature set, and the enterprise posture, all the processes and controls that are necessary to really go big in enterprise, uh, takes many, many years. So I think, uh, it is, if I had to pick a path, it's probably more sequential. PLG first, gathering that end user love, and then adding on the enterprise layers following that.

AI assessment note: “I think you can, but I think it's extremely difficult.”

Q No, I totally agree. I think nail it and also kind of create repeatability in it for others to really take hold of. If we think about PLG versus Enterprise, something that I see a lot of today is founders chasing PLG and Enterprise kind of from day one. Can you do both at the same time, do you think, Kevin?

A I think you can, but I think it's extremely difficult. I think Slack was able to do it. I think they nailed PLG first, and then enterprise, but they always had an eye towards enterprise. The reason why I say it's extremely difficult is to capture the end user's imagination, capture that end user love is one thing, but to build out the enterprise security set, the feature set, and the enterprise posture, all the processes and controls that are necessary to really go big in enterprise, uh, takes many, many years. So I think, uh, it is, if I had to pick a path, it's probably more sequential. PLG first, gathering that end user love, and then adding on the enterprise layers following that.

AI assessment note: “I think you can, but I think it's extremely difficult.”

Q I absolutely love that, but then we come to that realization, we're getting pulled into enterprise, we're getting pulled into procurement, I think there's a maybe naivety sometimes around what needs to change when you move to enterprise. What are the biggest elements, Kevin, that need to change when you're scaling from a PLG motion to an enterprise motion?

A Well, I think number one is scale and reliability. They need to know that if they're, if this becomes business critical, that you're going to be, you know, providing the SLAs in the 99.99 uptime. There's data geography requirements around data residency. If I'm going to use this service in Japan or if I'm going to use it in Europe, I need to know that you've got local data centers. There's process controls. Tell me, you know, they want to know how your engineers control data, who has access to that data. What, what security and protocols you use around that data. They have encryption requirements, data loss prevention requirements, uh, so it gets pretty deep, and I think the one thing to emphasize there is that there's no finish line. It's not like as a PLG company, you can dip your toe into enterprise and deliver these three or four features. It's, it's a lifelong pursuit that you need to be in partnership with your customers. If you look at today, And just the changes in the, uh, data requirements around GDPR, like that's a full-time job for somebody to be looking at that and say, okay, well, how are we running our service? And is it compliant in Europe? So it is a, uh, it's naive to think it's just a few features, uh, because in fact it is a lifelong pursuit to, to make sure that you're staying up with the, the most stringent requirements that are coming out of enterprises t…

AI assessment note: “Well, I think number one is scale and reliability. They need to know”

Q I mean, we're gonna delve into that. I just have to ask, you mentioned Slack nailing PLG first there, and then moving to Enterprise. I, I just chatted to Kim before this show, and she said I had to ask, how did you know it was the right time to move into Enterprise when you did with Slack?

A If you're a product that's generating enough end user value, and it starts to spread within companies, you're going to get pulled in by those companies to enterprise, and you're going to get to user counts that are so significant. You're going to get on the radar of procurement and legal, and they say, if this many people are using this product, I want the right terms in place so that I can feel comfortable using the product. So you're going to feel a real pull. If you're getting it right and that virality is happening within companies. And I think that's what happened at Slack. They had, in some cases, tens of thousands of users within single companies that said, Hey, look, we need to come to the table and operate. You need to operate as more of a strategic partner than a rogue service that my end users love.

AI assessment note: “They had, in some cases, tens of thousands of users within single companies”

Q Kevin, I'm on many boards, and very often they say, ah, you know, it just slipped to next quarter. Just slipped to next quarter. And I never quite know what to say. I'm like, well, you know, why? You know, well, we're not really sure, blah, blah, blah. How do you respond when you hear the classic, oh, it slipped to next quarter?

A When I hear it slipped to next quarter, what I'm looking for is, did you commit it to this quarter? Was, and did you tell the company that it was absolutely coming in and it's actually slipped? Or was it something that you were pursuing that potentially you could pull into this quarter? Those are two very different things. If it was committed to the quarter, uh, and did not come in, then I would, if I'm a startup, I would do a full deal review and understand why it didn't come in. And is it something around our pricing and our, our product, or is it something around the sales execution? And I would be looking at those, you know, different sides of the equation to really dig into where do I have the problem?

AI assessment note: “When I hear it slipped to next quarter, what I'm looking for is”

Q I absolutely love that, but then we come to that realization, we're getting pulled into enterprise, we're getting pulled into procurement, I think there's a maybe naivety sometimes around what needs to change when you move to enterprise. What are the biggest elements, Kevin, that need to change when you're scaling from a PLG motion to an enterprise motion?

A Well, I think number one is scale and reliability. They need to know that if they're, if this becomes business critical, that you're going to be, you know, providing the SLAs in the 99.99 uptime. There's data geography requirements around data residency. If I'm going to use this service in Japan or if I'm going to use it in Europe, I need to know that you've got local data centers. There's process controls. Tell me, you know, they want to know how your engineers control data, who has access to that data. What, what security and protocols you use around that data. They have encryption requirements, data loss prevention requirements, uh, so it gets pretty deep, and I think the one thing to emphasize there is that there's no finish line. It's not like as a PLG company, you can dip your toe into enterprise and deliver these three or four features. It's, it's a lifelong pursuit that you need to be in partnership with your customers. If you look at today, And just the changes in the, uh, data requirements around GDPR, like that's a full-time job for somebody to be looking at that and say, okay, well, how are we running our service? And is it compliant in Europe? So it is a, uh, it's naive to think it's just a few features, uh, because in fact it is a lifelong pursuit to, to make sure that you're staying up with the, the most stringent requirements that are coming out of enterprises t…

AI assessment note: “Well, I think number one is scale and reliability.”

Q Do you know what I mean? Like if I want to get it over the line, I don't want to seem desperate. I don't want to give away too much, but how do I do discounting well? And do I need approvals to do discounting? I'm a rapper on your team. Can I give a 20% discount? Can I give a 30% discount? Like what stage is acceptable versus unacceptable?

A Good discounting should originate from the office of the CFO. Meaning, the CFO knows the margins. They know what they're willing to, uh, what margins they're willing to give away on products at what volumes. What should happen in most companies is the CFO should provide a discount matrix that the rep might have a few points to give, the ref's manager might have a few more points to give based on volume, and then all the way up to the sales VP, and then at some level the exception would come from the CFO. So it should be very well organized, and it should be with an eye towards What can the company afford to give, uh, based on certain volumes? If it's, if it's distinct or not tied into CFO's office, then I think you're gonna run in circles and have a lot of problems.

AI assessment note: “CFO should provide a discount matrix that the rep might have a few points”

Q Capitalize, do you think it's a fair description that sales reps are coin-operated? And is that a bad thing even? I hear founders sometimes say, oh, I'm a bit worried about how focused they are on the comp, on the OTE, on the bonus. Is that a bad thing?

A Again, going back to timing, it does not pay to have coin-operated sales reps in the early days. They're going to be overly focused on quotas and crushing their number to get to a certain outcome. The early days are really about who is creating the best connection between my developing product and my potential customer. But I think in the later years, or as you build out your sales organization, while I don't like the term coin-operated, people do become more specialized as you get bigger as a company. And the specialization sales rep is to bring in customers and grow revenue, and they need to make a living, and so, um, I would be concerned about going to operate in early days, but not later.

AI assessment note: “I would be concerned about going to operate in early days, but not later.”

Q where you've been a central part of their sales teams and often led them. Salesforce, Dropbox, and Slack, and I thought there's gonna be, like, one or two lessons from each that have really shaped how you think, and so I wanted to delve into each in a quickfire round. So if we take Salesforce, what was the biggest takeaway for you, and how did that shape how you think?

A Salesforce does not get enough credit for being one of the original product-led growth companies. If you look at Salesforce and what Benioff did in the early days, we were one of the first companies to ever allow companies or our potential clients to use a trial of our service at no charge for 30 days. And during that trial, the sales team was obsessed with what are the business problems that this customer is trying to solve? How do I help configure the Salesforce service to help solve those business problems? And it led to incredible conversion rates. So the idea that if we're going to put the product in our customers hands, we got to give them help in terms of how they solve their problems, uh, as a, as a key accelerator. So that was an amazing element of Salesforce. And, and one, I just don't think they got enough credit for Salesforce remains an incredibly customer centric company. Uh, so lots to learn.

AI assessment note: “if we're going to put the product in our customers hands, we got to give them help”

Q it. I think it's a very, very good way to tell effectiveness. If we dive into that hiring process, I heard that you were incredible when it came to identifying talent. Um, how do you structure the hiring process for new sales hires? And if I'm a founder that you've angel invested in, how would you advise me? I've never done it before and I need that help and guidance.

A I think hiring great salespeople is about process. It's about discipline and process. When I was at Salesforce, I had the benefit of being a part of a process that came together that we really invested in. As Mark Benioff said, he, he wanted to see everybody have hiring fatigue. Everybody should be interviewing it all the time, whether it be for a job opening that you have today or one that you might have down the line. To hire well, you really need to put a multi-step process in to get to know the, the, the candidate To get to know how they approach a customer, understand business problems, and then present to those business problems in a differentiated way. No hire that I've made at my past companies have gotten the job until they've presented a mock scenario around a fictitious company and a business problem that they're trying to solve. So we really put the rep on the, on the spot, so to speak, to show how they deliver in the moment. Uh, we're talking to a customer about how they'll uniquely solve their business problem. So this is, again, we're, by the time a rep gets a job with one of these companies, they should have met with five or six different people in five or six different steps. And, uh, that stand and deliver moment, I think, is important and tells you who can really, uh, command the conversation.

AI assessment note: “they should have met with five or six different people in five or six different steps”

Q Kevin, I'm on many boards, and very often they say, ah, you know, it just slipped to next quarter. Just slipped to next quarter. And I never quite know what to say. I'm like, well, you know, why? You know, well, we're not really sure, blah, blah, blah. How do you respond when you hear the classic, oh, it slipped to next quarter?

A When I hear it slipped to next quarter, what I'm looking for is, did you commit it to this quarter? Was, and did you tell the company that it was absolutely coming in and it's actually slipped? Or was it something that you were pursuing that potentially you could pull into this quarter? Those are two very different things. If it was committed to the quarter, uh, and did not come in, then I would, if I'm a startup, I would do a full deal review and understand why it didn't come in. And is it something around our pricing and our, our product, or is it something around the sales execution? And I would be looking at those, you know, different sides of the equation to really dig into where do I have the problem?

AI assessment note: “I would do a full deal review and understand why it didn't come in.”

Q How do you think about CFOs being in every deal now? The deal cycles have changed so significantly in my mind. The buyers have changed so significantly. Everything about the way that we used to sell has changed with the complexity that now is inherent within cycles. Do you agree? And how does that change your process?

A I think when the CFO is involved, we welcome it. I think if the CFO is involved in your deal and they're spending time on that deal, that tells you that you are strategic to them. So your responsibility to respond to that is giving them the, you know, the financial or the value engineering as it's called on the ROI. And that is the job of the sales team to do that. Maybe they have resources in a value engineering team. Maybe they don't, but really giving the CFO a crystal clear picture of what's the return. Um, I think it's table stakes these days. And again, we don't, Uh, I, I welcome it because it tells you that they're willing to lean in and work with you as a partner.

AI assessment note: “I think when the CFO is involved, we welcome it.”

Q Let's move to Dropbox. You then spent four years, a little over four years at Dropbox. What was the biggest takeaway for you from your time there, and how did it shape your mindset?

A My biggest takeaway from Dropbox was the importance of getting it right. The, that being, how do we provide a product that end users really love, but that large enterprises can trust from a security and operation standpoint. So the balance between end user love and enterprise security posture is a really difficult one to strike. And I think Dropbox was one of the first companies to go from a B to C company into the B to B realm and really work hard to get the enterprise posture and the security and controls right. Which is no small task. It's a somewhat of an unsexy pursuit, but it's much necessary in order for large companies to trust you and to bring you in and allow you to expand within their domain.

AI assessment note: “My biggest takeaway from Dropbox was the importance of getting it right.”

Q It did, and also, that's where I heard so many great stories, as I said, from Maggie, Kim, and Renu. Now, I do want to start at the core crux of a lot of the discussions I have with founders, which is the sales playbook, and I just want to get some nomenclature right. How do you define sales playbook, Kevin?

A Well, that's an interesting question, Harry. I don't typically use the word playbook. I know a lot of people do, and I don't have a problem with it, but playbook to me seems like just a simple one, two, three, and you follow these steps, and you're going to close the deal. When I think of a playbook, I actually just think of sales motions. I prefer the term sales motions and understanding really who is the buyer? What's the user persona that we're selling to? What's the industry that they're in? What are the business problems that they're faced with? And how does our product and our service uniquely solve that problem? And talking in terms of the unique solution to that problem is where I think strong sellers Really shine, um, and, and not talking about product features, but really the solution that, uh, overall driving business value. So that's a motion more than is a one, two, three playbook in my mind.

AI assessment note: “When I think of a playbook, I actually just think of sales motions.”

Q I mean, we're gonna delve into that. I just have to ask, you mentioned Slack nailing PLG first there, and then moving to Enterprise. I, I just chatted to Kim before this show, and she said I had to ask, how did you know it was the right time to move into Enterprise when you did with Slack?

A If you're a product that's generating enough end user value, and it starts to spread within companies, you're going to get pulled in by those companies to enterprise, and you're going to get to user counts that are so significant. You're going to get on the radar of procurement and legal, and they say, if this many people are using this product, I want the right terms in place so that I can feel comfortable using the product. So you're going to feel a real pull. If you're getting it right and that virality is happening within companies. And I think that's what happened at Slack. They had, in some cases, tens of thousands of users within single companies that said, Hey, look, we need to come to the table and operate. You need to operate as more of a strategic partner than a rogue service that my end users love.

AI assessment note: “you're going to get pulled in by those companies to enterprise”

Q Does the type of person that you need change, dependent on whether you're running a PLG or an enterprise motion, Kevin?

A I'm not sure I differentiate so much on enterprise versus PLG. To me, it's a little bit more about the timing of the company. How old is the company and where are they in their journey? Uh, early days of hiring reps, you're going to need Renaissance reps that have a very wide breadth of, of skill sets, uh, who enjoy the building process. And as things go on and you start to sell, scale your sales team, you're going to see reps that are there for really to make a living and are more concerned with what's the paycheck and what's the quota. Uh, and that is, that's a different rep. So I think it's, to me, it's a little bit over time how the reps change, a little bit less PLG versus enterprise. But, uh, certainly as you go into enterprise and you've been there longer, that rep that is going to be successful there has more experience and is more focused on what, what are my set of accounts and how do I crush my number.

AI assessment note: “I'm not sure I differentiate so much on enterprise versus PLG.”

Q So like, what do we think about good versus great? How do the best do in these mock scenarios? And are there any red flags that you look for?

A The most curious part of the interview process is when they get through final interviews, And you're assuming that they're just going to crush the mock scenario. And sometimes they'll just come in and it'll be a flop. And you'll say, wow, I just never saw that coming. And that comes down to what's their comfort level being in front of a room, being in front of an audience that's going to throw up real objections. So sometimes you're surprised. Uh, good versus great comes down to are they consistent throughout the whole process, right? Do they, do they crush the interviews and then just come in with a level of confidence, uh, during the mock scenario that just wins you over and makes a ton of sense. So I, I'd say overall it's consistency. When you start to see inconsistency across the different steps of the process, ah, that's definitely a red flag.

AI assessment note: “inconsistency across the different steps of the process, ah, that's definitely a red flag.”

Q What do you mean by intellectual range, Kevin?

A What I mean by intellectual range is this person, this initial sales leader is going to have a lot on their plate. Uh, they're not going to have a big marketing team that's, that they can outsource all of the, uh, the writing and the messaging to. They're not going to have all the resourcing from product management and so forth. So they're going to need to do a lot of different things. And so they're going to need to have energy and range to do everything from writing to messaging to closing and, uh, providing that customer feedback and the voice of the customer back into product. So that range, as we, as the companies become bigger and more specialized, uh, starts to narrow, if you will, but in early days, it's really about how much stuff are you willing to take on, and that's, that's what I'm referring to when I talk about range.

AI assessment note: “What I mean by intellectual range is this person, this initial sales leader”

Q Do you know what I mean? Like if I want to get it over the line, I don't want to seem desperate. I don't want to give away too much, but how do I do discounting well? And do I need approvals to do discounting? I'm a rapper on your team. Can I give a 20% discount? Can I give a 30% discount? Like what stage is acceptable versus unacceptable?

A Good discounting should originate from the office of the CFO. Meaning, the CFO knows the margins. They know what they're willing to, uh, what margins they're willing to give away on products at what volumes. What should happen in most companies is the CFO should provide a discount matrix that the rep might have a few points to give, the ref's manager might have a few more points to give based on volume, and then all the way up to the sales VP, and then at some level the exception would come from the CFO. So it should be very well organized, and it should be with an eye towards What can the company afford to give, uh, based on certain volumes? If it's, if it's distinct or not tied into CFO's office, then I think you're gonna run in circles and have a lot of problems.

AI assessment note: “CFO should provide a discount matrix that the rep might have a few points to give”

Q Let's move to Dropbox. You then spent four years, a little over four years at Dropbox. What was the biggest takeaway for you from your time there, and how did it shape your mindset?

A My biggest takeaway from Dropbox was the importance of getting it right. The, that being, how do we provide a product that end users really love, but that large enterprises can trust from a security and operation standpoint. So the balance between end user love and enterprise security posture is a really difficult one to strike. And I think Dropbox was one of the first companies to go from a B to C company into the B to B realm and really work hard to get the enterprise posture and the security and controls right. Which is no small task. It's a somewhat of an unsexy pursuit, but it's much necessary in order for large companies to trust you and to bring you in and allow you to expand within their domain.

AI assessment note: “My biggest takeaway from Dropbox was the importance of getting it right.”

Q So like, what do we think about good versus great? How do the best do in these mock scenarios? And are there any red flags that you look for?

A The most curious part of the interview process is when they get through final interviews, And you're assuming that they're just going to crush the mock scenario. And sometimes they'll just come in and it'll be a flop. And you'll say, wow, I just never saw that coming. And that comes down to what's their comfort level being in front of a room, being in front of an audience that's going to throw up real objections. So sometimes you're surprised. Uh, good versus great comes down to are they consistent throughout the whole process, right? Do they, do they crush the interviews and then just come in with a level of confidence, uh, during the mock scenario that just wins you over and makes a ton of sense. So I, I'd say overall it's consistency. When you start to see inconsistency across the different steps of the process, ah, that's definitely a red flag.

AI assessment note: “good versus great comes down to are they consistent throughout the whole process”

Q Can I ask you, Kevin, you've hired some of the best across many different organizations. Comp packages are pretty hard to understand if it's your first time, and to know what's good, what's fair. What have been some of your biggest lessons on effective comp package giving when rearing?

A Well, first, your comp plan needs to be fair, and there's plenty of market data out there that you can get to understand in my end range of market to provide a fair comp plan. I think when I'm closing a candidate, I'm, I'm interested, if I'm giving them a fair comp plan, Are they really interested in about the long-term journey of this company? Because this comp plan only represents this moment in time for the next year or two. Um, if we're both successful, the company will, um, increase in size. Our jobs will be different. Our jobs will be bigger. So what, how do they view the, the long-term journey at this company? And are they excited about the company and the journey, or is it about the comp plan? Sometimes if it becomes too much about the comp plan, then that's a red flag because it is It's really about a total rewards element, which is you're, you're joining a rocket ship, uh, you're gonna love this job, and it's gonna, you know, really benefit your career overall. So that's kind of what I'm looking for, but comp plans certainly need to be fair. If you're not providing a fair comp plan, you, you can't, uh, expect to hire the best.

AI assessment note: “if it becomes too much about the comp plan, then that's a red flag”

Q How do you think about CFOs being in every deal now? The deal cycles have changed so significantly in my mind. The buyers have changed so significantly. Everything about the way that we used to sell has changed with the complexity that now is inherent within cycles. Do you agree? And how does that change your process?

A I think when the CFO is involved, we welcome it. I think if the CFO is involved in your deal and they're spending time on that deal, that tells you that you are strategic to them. So your responsibility to respond to that is giving them the, you know, the financial or the value engineering as it's called on the ROI. And that is the job of the sales team to do that. Maybe they have resources in a value engineering team. Maybe they don't, but really giving the CFO a crystal clear picture of what's the return. Um, I think it's table stakes these days. And again, we don't, Uh, I, I welcome it because it tells you that they're willing to lean in and work with you as a partner.

AI assessment note: “responsibility to respond to that is giving them the, you know, the financial or the value engineering”

Q It did, and also, that's where I heard so many great stories, as I said, from Maggie, Kim, and Renu. Now, I do want to start at the core crux of a lot of the discussions I have with founders, which is the sales playbook, and I just want to get some nomenclature right. How do you define sales playbook, Kevin?

A Well, that's an interesting question, Harry. I don't typically use the word playbook. I know a lot of people do, and I don't have a problem with it, but playbook to me seems like just a simple one, two, three, and you follow these steps, and you're going to close the deal. When I think of a playbook, I actually just think of sales motions. I prefer the term sales motions and understanding really who is the buyer? What's the user persona that we're selling to? What's the industry that they're in? What are the business problems that they're faced with? And how does our product and our service uniquely solve that problem? And talking in terms of the unique solution to that problem is where I think strong sellers Really shine, um, and, and not talking about product features, but really the solution that, uh, overall driving business value. So that's a motion more than is a one, two, three playbook in my mind.

AI assessment note: “I prefer the term sales motions and understanding really who is the buyer?”

Q be done. There's also just the actual ability to move there in the first place. When you think about structuring your sales team as well, does the sales team carbon copy from PLG to Enterprise? Should we change the structure? Should it be, you know, more formal from AE to SDR to you name it? Like, how does the structure of sales teams change when moving from PLG to Enterprise?

A Well, I think at first the sales team is, is obviously there for revenue growth, but almost even more importantly, providing customer feedback into the product group, giving the product team that they're working with a sense for why do these people gravitate to the service? What business problem is it solving? How would you down the line translate this into ROI for the end user? And once they start doing that, so it's, it's kind of at the early days, It's creating a major feedback loop, which you can build that repeatability on. Once you have that repeatability, then you can start to build sales teams that are more traditional with the EDR. Um, core sellers focus on just revenue numbers, uh, supported by sales engineers and so forth.

AI assessment note: “Once you have that repeatability, then you can start to build sales teams”

Q it. I think it's a very, very good way to tell effectiveness. If we dive into that hiring process, I heard that you were incredible when it came to identifying talent. Um, how do you structure the hiring process for new sales hires? And if I'm a founder that you've angel invested in, how would you advise me? I've never done it before and I need that help and guidance.

A I think hiring great salespeople is about process. It's about discipline and process. When I was at Salesforce, I had the benefit of being a part of a process that came together that we really invested in. As Mark Benioff said, he, he wanted to see everybody have hiring fatigue. Everybody should be interviewing it all the time, whether it be for a job opening that you have today or one that you might have down the line. To hire well, you really need to put a multi-step process in to get to know the, the, the candidate To get to know how they approach a customer, understand business problems, and then present to those business problems in a differentiated way. No hire that I've made at my past companies have gotten the job until they've presented a mock scenario around a fictitious company and a business problem that they're trying to solve. So we really put the rep on the, on the spot, so to speak, to show how they deliver in the moment. Uh, we're talking to a customer about how they'll uniquely solve their business problem. So this is, again, we're, by the time a rep gets a job with one of these companies, they should have met with five or six different people in five or six different steps. And, uh, that stand and deliver moment, I think, is important and tells you who can really, uh, command the conversation.

AI assessment note: “To hire well, you really need to put a multi-step process in”

Q Does the type of person that you need change, dependent on whether you're running a PLG or an enterprise motion, Kevin?

A I'm not sure I differentiate so much on enterprise versus PLG. To me, it's a little bit more about the timing of the company. How old is the company and where are they in their journey? Uh, early days of hiring reps, you're going to need Renaissance reps that have a very wide breadth of, of skill sets, uh, who enjoy the building process. And as things go on and you start to sell, scale your sales team, you're going to see reps that are there for really to make a living and are more concerned with what's the paycheck and what's the quota. Uh, and that is, that's a different rep. So I think it's, to me, it's a little bit over time how the reps change, a little bit less PLG versus enterprise. But, uh, certainly as you go into enterprise and you've been there longer, that rep that is going to be successful there has more experience and is more focused on what, what are my set of accounts and how do I crush my number.

AI assessment note: “I'm not sure I differentiate so much on enterprise versus PLG.”

Q What do you mean by intellectual range, Kevin?

A What I mean by intellectual range is this person, this initial sales leader is going to have a lot on their plate. Uh, they're not going to have a big marketing team that's, that they can outsource all of the, uh, the writing and the messaging to. They're not going to have all the resourcing from product management and so forth. So they're going to need to do a lot of different things. And so they're going to need to have energy and range to do everything from writing to messaging to closing and, uh, providing that customer feedback and the voice of the customer back into product. So that range, as we, as the companies become bigger and more specialized, uh, starts to narrow, if you will, but in early days, it's really about how much stuff are you willing to take on, and that's, that's what I'm referring to when I talk about range.

AI assessment note: “What I mean by intellectual range is this person, this initial sales leader”

Q lovely one. Can I ask you though, you know, again, we mentioned, like, working with amazing people. Again, spoke to so many that worked with you, and they said once you hired them, you were incredible when it came to trust building, and I wanted to ask you, How do you think about building trust with new Marais, and then building trust in you, both ways? What works? For you?

A Well, I think on the journey of people joining a company in the early days, they, they want to have clear expectations and you as a leader need to be a little bit more directive on what are the expectations and how the, how, how you're going to get there. And then as they become competent and ramped up in their job, it's a little bit more of a partnership and here's about, here's what we're going to do. I want to hear more ideas from them on what they see. Uh, as the next steps for the organization. So it goes from directive to more of a partnership. So I think that's an important element. Um, the job and the manager employee relationship changes over time. Uh, so that's one thing I try to focus on.

AI assessment note: “goes from directive to more of a partnership. So I think that's an important element”

Q Speaking of kind of leaning in and working with you as a partner, when you think about like driving them home to actually closing, how do you think about quite a challenging element, which is balancing hitting quarterly revenue targets with longer term pipeline and sales strategy? How do you think about that balance?

A I think the balance between hitting the quarterly number and building long-term pipeline For the, if it's an early stage company who absolutely needs that, that deal, You're probably going to need your leadership and executive support as a seller on your side to make it clear in the right tone to the prospect that this is an opportunity that would really help the company at that time. Uh, but it needs to be done in a tone that works for the customer. Uh, jamming deals at the end of the quarter is always kind of obnoxious, but, uh, it happens. Uh, it does work, but sometimes there is a detrimental effect to kind of Cramming deals at the end of the quarter, uh, from a brand standpoint and from a relationship standpoint. So, uh, you know, the magic in all this is the best reps are creating ample pipeline throughout the year, and they somehow have so much, you know, they create enough pipeline that they're able to hit their quarterly numbers without doing any, anything unnatural to get those deals in, because if one falls out, they've got another that comes in. So it's around really generating enough pipeline throughout the year so that you don't put yourself in that position. Um, now is that possible every time? Probably not, but, uh, for the most part over the long run, uh, pipeline covers all soon.

AI assessment note: “the best reps are creating ample pipeline throughout the year”