The Exchanges

Q I can't believe I get paid for this. I mean, I'm just waiting for someone to catch me, but I want to start with your falling in love with sales. I often find that there's a moment. When did you fall in love with sales? And when was that like, aha, I really want to do this as a career.

A So I wish I had a really elegant answer. I listened to Egan's, um, conversation. It was like very intentional and similar to say, Mark, um, from Grammarly, I'm an accidental salesperson. Now I'm a son. Of a salesperson. My father, my late father was a dedicated salesperson, so I was never going to get into sales. So through undergrad and uni and graduate school, I was a bartender and it was great, right? But when all of my smarter friends were taking on internships, I was slinging cocktails. So I got my first assignment at the corporate executive board, CEB, and my job title was marketing associate. Well, it turns out that I was making 300 cold calls a day to C-suite executives in the Fortune 1000. I was what's now called a sales development rep, a sale, an SDR. And that's what I felt in love with sales. I had this moment where I said, wait a minute, if I make more phone calls and book more meetings for my account executive, you'll just give me more money. Yeah. It's like, okay, this is amazing. And it tapped into my competitive spirit, trying to be on top of the stack rankings. And I've been basically at SDR ever since it's like, 22, 23 years later, but that's when I fell in love with sales.

AI assessment note: “I had this moment where I said, wait a minute, if I make more phone calls”

Q Isn't that why content marketing is the most important thing that you can do today? And then should all sales teams not just be a team of content marketers? If you're the only final nine percent, then surely you should just have an amazing content marketing team, and fuck it, they'll tip over for the final nine percent.

A Well, there's, I've got good news for the sellers out there. I've got good news, because here's, according to Gartner, Harry, um, 43% of buyers, according to Gartner, 43% of buyers That had a digital only experience in purchasing have a 1.65 X higher regret rate, right? So the best sales cycle is when it is rep enabled. Like the rep is part of that process. In fact, you reduce buyer regret by half. If the rep is involved in the process. So what the rep does, so to your point, yeah, like content marketing, super important teaching things when no one's around. Yeah, yeah, you gotta do that. But the good news for the sellers, right. Is that we get to be there to make sense. To bring the human context to what they're buying. And so they can ask, ask, uh, actual questions.

AI assessment note: “43% of buyers that had a digital only experience in purchasing have a 1.65 X higher regret rate”

Q Yeah. What's the right OT level, do you think?

A So, uh, on the enterprise and national pay, depending on what your quota would be, It's probably the right place to start, right? So best practice is a five to one ratio. So if I'm going to pay someone 200 pounds sterling, I want them to have a million quid as a, as a goal or as a quota, right? So like thinking about what the, the, um, what that ratio that you're willing to pay now in a startup, you may have to sacrifice that a bit to maybe four to one, based on what that quote is versus what you're willing to pay. But that's considered best practice, so look at it in that type of way. Then, depending on where you're hiring, you can get plenty of data on what, like, the averages are.

AI assessment note: “best practice is a five to one ratio.”

Q just, we said it was conversational. I just think so much about the blurring between marketing and sales today, Because I think if people don't know your brand when you first speak to them, really it's on the fold of marketing and brand awareness. How do you think about the blending of sales and marketing in that way? And actually whether there is a chasm between the two today almost?

A Yes. Well, the blend couldn't be more relevant today. And I view my role right now as the head of selling when I used to be the head of sellers. So the CMO, the marketer, Must be very effective at selling and the head of sales must be very effective in marketing. And the primary reason why is because of the buyer. When on an inbound lead to your business, the seller now gets nine percent of that buyer's time to evaluate whether they're going to go with you or not. And Harry, in that nine percent, this is according to Gartner, in that nine percent, you must split that time with the other partners or vendors in that process for the buyer. So the reason why this is such a great question is that how do you grab their attention, their buyer attention? How do you teach them about your product? How do you teach them about what you do when they're not talking with you? So there's much more of a blend today than ever before.

AI assessment note: “the blend couldn't be more relevant today. And I view my role right now”

Q Isn't that why content marketing is the most important thing that you can do today? And then should all sales teams not just be a team of content marketers? If you're the only final nine percent, then surely you should just have an amazing content marketing team, and fuck it, they'll tip over for the final nine percent.

A Well, there's, I've got good news for the sellers out there. I've got good news, because here's, according to Gartner, Harry, um, 43% of buyers, according to Gartner, 43% of buyers That had a digital only experience in purchasing have a 1.65 X higher regret rate, right? So the best sales cycle is when it is rep enabled. Like the rep is part of that process. In fact, you reduce buyer regret by half. If the rep is involved in the process. So what the rep does, so to your point, yeah, like content marketing, super important teaching things when no one's around. Yeah, yeah, you gotta do that. But the good news for the sellers, right. Is that we get to be there to make sense. To bring the human context to what they're buying. And so they can ask, ask, uh, actual questions.

AI assessment note: “best sales cycle is when it is rep enabled. Like the rep is part”

Q Okay. Okay. So let's just take those. Sorry. I like to go. Are people honest? Everyone likes to feel important when you say, hey, you know, are you a decision maker for, for buying greenhouse? Of course I am. Yeah, yeah, yeah, yeah. It's me. You're, you're speaking to the right person. How do you, how do you know?

A That's a great call out, and you are right. That happens nine times out of 10, and frankly, they are not the person that can sign the order form, so you, you are right. Um, the question to ask maybe differently is, who should I engage early? Because Harry, role play again, ok? Harry, buyers like you, I have 7000 customers, and buyers that look and feel just like you, what happens at the end of this process is the CFO will get involved, the head of procurement will get involved, It will get involved. Harry, I don't think your company's going to be any different. So, in order to be a good steward of your time, let's get them involved now, because then I can set you up for success. Harry, you want this product, and I know you do. But in order for you to be successful, let's get these players involved.

AI assessment note: “the question to ask maybe differently is, who should I engage early?”

Q Yeah. Very powerful. How the fuck do I forecast in 2024, Sean? Like, you know, everyone's telling me it's harder than ever. Everyone's saying, oh, CFOs, they're not buying. And I'm sitting here today as a CRO or a CEO thinking, are we going to two X last year? Are we going to three X? I don't know.

A I, I wish I, yes. Um, the short answer is artificial intelligence. That's how you're going to forecast in 2024. Um, there are some, there's technology, uh, shout out to my friends at Clary. Um, there's technology today that's putting a lot more science using the machine learning into what's going to be the output, 90 days out. And frankly, on my new logo side, it's been within five percent accurate, 90 days out. So Harry, that's how you should forecast in 24. Uh, use the technology. Uh, I have wasted years of my life trying to predict the future. In forecasting. Years of my life, I'll never get back. And I still can't get it right. I still try so damn hard, but forecasting is very difficult.

AI assessment note: “the short answer is artificial intelligence. That's how you're going to forecast in 2024.”

Q Yeah, I mean, that's a very accommodating product team, to be fair, to actually engage for that long and to let you roll with it. Um, yeah, no, I'm totally short. You mentioned the sexy logos. Do they really make a difference? Like, when companies come and say, hey, we've got Slack and Dropbox and you name it, do they make a difference or not when closing?

A It's a good question. The short answer is it does make a difference. Now, every salesperson in the world pitches and they overpitch those enterprise logos, but the first problem, That I mentioned when moving up market is you lack credibility. And the reason why those logos do matter is I need to show you. So Harry, you're my enterprise customer and you're looking at me like, fuck you, you can't do half the shit that you're talking about. But what I need to be able to say is you, it's like, Harry, look, I'm going to set you up with the folks at Slack, DocuSign and Snowflake, and they're going to tell you a story of how they use my product. I need that. You need that.

AI assessment note: “The short answer is it does make a difference.”

Q Okay. Another area where they're like, not only, yes, everyone wants customization, especially now everyone wants a discount and some are like, you know what? We don't discount. We know the value of our product and others are like, of course we discount. Um, what's the right approach to discounting for founders listening, thinking about that scale into enterprise?

A Discounting is okay. It's fine. And in different environments, it's important that you adjust when you need to. We all believe that our products are the best, especially those founders that are listening, I know, but there are moments that when everyone on the block is charging 80 dollars for a beautiful steak, and then the market goes south, and then the rest of the street is selling those steaks for 20 dollars, you can't keep charging 80 dollars for your steak. You can, but you're going to lose. The worst deal is the one that takes too long. Drop your price and go get the fucking deal and move on. Just move on. Go get the next deal. So I have been a big advocate of flexibility. Maybe not discount, refaming it a little bit. It's flexibility in negotiating terms. It's not necessarily just discounting the drop of your price, but go get something different. So as an example, if my price is a hundred K, I will do this deal for 60. And then Harry, what I expect from you is a story about how you love my product. Harry, I want you on the stage of my annual conference raving about my product, and I want two social posts from you raving about my product, and then we'll do the deal for 60. So it's not a discount. It's a trade.

AI assessment note: “It's not necessarily just discounting the drop of your price, but go get something different.”

Q So that's really interesting. I always say when you have to educate your customer, it's so much harder. It's just so much harder. It's like when you're fundraising and your VC doesn't know anything about the space you're in. Good luck. Do you agree or not given the fact that the best educate?

A I do believe the best educate. And in fact, in my sales process internally, third company in a row, the first stage of the sales process is called teaching. Teaching hypothesis based selling. I mean, look, if you are a seller today and you engage a potential buyer and you're wasting your time asking about what fucking CRM that they use or where they're located or who they do business with or how they make money, you're fucked. You just, just don't even call. Right? So the first stage is teaching. If I can teach you more about your business, if I can teach you something about your business that you might not even be thinking about. You will engage with me. And so I agree to the, to this, to your sentiment of what you're saying, but that teaching component is critical.

AI assessment note: “I do believe the best educate.”

Q just, we said it was conversational. I just think so much about the blurring between marketing and sales today, Because I think if people don't know your brand when you first speak to them, really it's on the fold of marketing and brand awareness. How do you think about the blending of sales and marketing in that way? And actually whether there is a chasm between the two today almost?

A Yes. Well, the blend couldn't be more relevant today. And I view my role right now as the head of selling when I used to be the head of sellers. So the CMO, the marketer, Must be very effective at selling and the head of sales must be very effective in marketing. And the primary reason why is because of the buyer. When on an inbound lead to your business, the seller now gets nine percent of that buyer's time to evaluate whether they're going to go with you or not. And Harry, in that nine percent, this is according to Gartner, in that nine percent, you must split that time with the other partners or vendors in that process for the buyer. So the reason why this is such a great question is that how do you grab their attention, their buyer attention? How do you teach them about your product? How do you teach them about what you do when they're not talking with you? So there's much more of a blend today than ever before.

AI assessment note: “the CMO, the marketer, Must be very effective at selling”

Q this. I mean, dude, there are so few good marketers who are good at marketing. I mean, the CMO generation is one dearth and like, yeah, very few talented people. Sorry. Um, Oh, Jesus. If we're expecting them to be good at selling as well, we're in the real minutiae. I mean, fuck. So what does it mean for a CMO to be a good seller on the flip side?

A So Karen Van Vuren is a CMO I get to work with. What Karen or what the best CMOs do that I get to work with and I have worked with, they know our buyer better than anyone else. They spend time with our customers. CMOs don't spend time with the customers, right? That's just kind of like, that's like a head fake. But the best CMOs understand deeply the pains of the buyer, what makes them tick, what drives business value and personal value for the buyer, and that's what makes the best CMOs today, because when you know that, then you become a great seller, right? Because people, they don't want to be sold to, but they do want to buy.

AI assessment note: “when you know that, then you become a great seller, right?”

Q sell to and you have sold to over your career. I mean, I'm invested in many companies and kind of the holy grail is like, well, we're going to scale into enterprise and then hundreds of thousands of dollars of ACVs will just magically open up and it doesn't happen like that. And there's this real naivety. What do you think customers or founders get wrong about moving into enterprise?

A A lot. Okay, there is a lot to get wrong. The three biggest hurdles in taking that holy grail of moving up into the enterprise, those massive ACBs, the sexy LTV to CAC, those sexy logos that you talk about, but the hardest problems. First, the credibility. No one knows who you are, especially in the enterprise and it will destroy you. Right. The second is, do you have real product market fit for those big companies? Because those big companies, they all believe that they're special snowflakes. And so they need things that are just different because you've built an SMB or mid market platform that's there to scale. Right. And third, it's somewhat related to both. But your financial and your financials, because as you move up market, they just don't trust you. Very similar to credibility, but they just don't trust that you'll be around. They don't trust that you can survive as, as a startup for that long. So I think those are the three, um, probably not so insightful insights that I've experienced in moving up.

AI assessment note: “The three biggest hurdles in taking that holy grail of moving up into the enterprise”

Q Yeah, I mean, that's a very accommodating product team, to be fair, to actually engage for that long and to let you roll with it. Um, yeah, no, I'm totally short. You mentioned the sexy logos. Do they really make a difference? Like, when companies come and say, hey, we've got Slack and Dropbox and you name it, do they make a difference or not when closing?

A It's a good question. The short answer is it does make a difference. Now, every salesperson in the world pitches and they overpitch those enterprise logos, but the first problem, That I mentioned when moving up market is you lack credibility. And the reason why those logos do matter is I need to show you. So Harry, you're my enterprise customer and you're looking at me like, fuck you, you can't do half the shit that you're talking about. But what I need to be able to say is you, it's like, Harry, look, I'm going to set you up with the folks at Slack, DocuSign and Snowflake, and they're going to tell you a story of how they use my product. I need that. You need that.

AI assessment note: “The short answer is it does make a difference.”

Q Is there a way to try it without huge resources? Is there a way to put your foot in the water of like enterprise? With a couple of customers, see if it's what you need, or is it a full on budget reallocation?

A Yeah, the, the, the hard truth is it's a full on budget allocation. It's a full on effort. Um, however, you can test to see if your product will work with a few test cases with some few customers. So for example, to the founders out there, try and engage an enterprise and maybe do it on a house. Engage a few customers and give them your product for a year and let them use it for a year. Find out where the mistakes are. Find out what goes wrong. Learn what's wrong with your product. Before you really go big. So there's probably a little bit of both Harry, but the truth is. Yeah. You need some capital to go into the, into the enterprise and you won't get that immediate love. You won't. It takes time. It doesn't have the same return on speed as the SMB or mid market will have. That's the truth.

AI assessment note: “the hard truth is it's a full on budget allocation”

Q Huh. I love that. Well, it goes back to the teaching element. Is there any big lessons for you on, like, negotiation on comp and what that tells you about people? I find, like, specifically title and comp are two of the most revealing parts of a hiring process. Do you have any lessons on this?

A I have so many lessons on comp. So first, the biggest lessons I've learned on comp is transparency. My biggest lesson. So for those that are up to negotiate at final offer, to me, that just creates a different economics, um, bias that could come in into that process. So maybe someone's better at negotiating compensation than another, right? So maybe that filters it, but with transparency, look, I'm never going to be the highest paid shop in town. You can always go somewhere else to make more money, but I'm looking for transparency so everyone knows what they're walking into. Here's the, the variable pay. Here's the, the, the salary, right? And it's just very transparent. Everyone knows what it is. So I don't waste my time. I'll waste theirs. Transparent pay. The second lesson I've learned is I've moved to a national pay structure, right? So if I live in London, um, if I live in New York City, if I live in Cleveland, Ohio. It's still the same job, right? You're still performing the same tasks. So that transparent standard pay doesn't really matter where you live. And I pay on the higher end. I assume you live in London. I assume that you live in New York city and I will pay you on that high end, not the highest paid shop in New York city, but I'll pay you on that high end. So transparency and one pay structure.

AI assessment note: “I have so many lessons on comp. So first, the biggest lessons I've learned on comp is transparency.”

Q Okay. Another area where they're like, not only, yes, everyone wants customization, especially now everyone wants a discount and some are like, you know what? We don't discount. We know the value of our product and others are like, of course we discount. Um, what's the right approach to discounting for founders listening, thinking about that scale into enterprise?

A Discounting is okay. It's fine. And in different environments, it's important that you adjust when you need to. We all believe that our products are the best, especially those founders that are listening, I know, but there are moments that when everyone on the block is charging 80 dollars for a beautiful steak, and then the market goes south, and then the rest of the street is selling those steaks for 20 dollars, you can't keep charging 80 dollars for your steak. You can, but you're going to lose. The worst deal is the one that takes too long. Drop your price and go get the fucking deal and move on. Just move on. Go get the next deal. So I have been a big advocate of flexibility. Maybe not discount, refaming it a little bit. It's flexibility in negotiating terms. It's not necessarily just discounting the drop of your price, but go get something different. So as an example, if my price is a hundred K, I will do this deal for 60. And then Harry, what I expect from you is a story about how you love my product. Harry, I want you on the stage of my annual conference raving about my product, and I want two social posts from you raving about my product, and then we'll do the deal for 60. So it's not a discount. It's a trade.

AI assessment note: “It's not a discount. It's a trade.”

Q Okay. So, so we realized that the words matter in terms of how they impact our funnel of applicants on the talent side. So we use gender neutral words. We use Uh, I don't know, personality neutral words. And then what? Then, and then we have like a talent pool. How do we then hire?

A The next step after you've attracted all this talent to your company, right? You're an advantage because you've got this massive pool to choose from, right? So then what happens next is your proper kickoff and agreeing on what are the right competencies that we are seeking. What are the right attributes that we are seeking? And then who is going to do what? So setting up the structured process to ensure you have consistency through the entire, for the follow through on the interview process. So for example, the high performing reps, they have similar competencies, drive for results, um, persuasion, negotiation, intellectual curiosity. So you incorporate that in your structured process. And you only get so much time with a candidate. Candidates only going to give you as a hirer so much time. And what companies fuck up so often is that let's say there are three or four people that interview that candidate. They all ask the same damn questions. So you're not getting enough data from that candidate in the short time allowance that you do have.

AI assessment note: “So then what happens next is your proper kickoff and agreeing on what are the right competencies”

Q Okay. I got you. So we have that as that structure for those core pillars. You said about a sales task and a take home task. I'm intrigued on this one. What do you ask them to do? Is it one on you? Is it one on another company? How do you structure that?

A Yeah, it, it really depends, Harry. It depends if it's my first sales rep or my first sales manager. Um, if it's a first sales rep, it might not be a take-home test. Instead, it could be a CCAT test that you would take. It could be a personality test that you could take. It could be different types of tests, but when I do take-home tests, it could be something as simple as what would be your 30, 60, and 90 day plan when you start with me. That could be it. So then you can grasp their intellectual curiosity. You can grasp their drive, their, their, their passion about your product and the problem that you're solving. It can really be a choose your own adventure on what that take home test could be.

AI assessment note: “what would be your 30, 60, and 90 day plan when you start with me”

Q Okay. So, so we realized that the words matter in terms of how they impact our funnel of applicants on the talent side. So we use gender neutral words. We use Uh, I don't know, personality neutral words. And then what? Then, and then we have like a talent pool. How do we then hire?

A The next step after you've attracted all this talent to your company, right? You're an advantage because you've got this massive pool to choose from, right? So then what happens next is your proper kickoff and agreeing on what are the right competencies that we are seeking. What are the right attributes that we are seeking? And then who is going to do what? So setting up the structured process to ensure you have consistency through the entire, for the follow through on the interview process. So for example, the high performing reps, they have similar competencies, drive for results, um, persuasion, negotiation, intellectual curiosity. So you incorporate that in your structured process. And you only get so much time with a candidate. Candidates only going to give you as a hirer so much time. And what companies fuck up so often is that let's say there are three or four people that interview that candidate. They all ask the same damn questions. So you're not getting enough data from that candidate in the short time allowance that you do have.

AI assessment note: “setting up the structured process to ensure you have consistency through the entire”

Q this. I mean, dude, there are so few good marketers who are good at marketing. I mean, the CMO generation is one dearth and like, yeah, very few talented people. Sorry. Um, Oh, Jesus. If we're expecting them to be good at selling as well, we're in the real minutiae. I mean, fuck. So what does it mean for a CMO to be a good seller on the flip side?

A So Karen Van Vuren is a CMO I get to work with. What Karen or what the best CMOs do that I get to work with and I have worked with, they know our buyer better than anyone else. They spend time with our customers. CMOs don't spend time with the customers, right? That's just kind of like, that's like a head fake. But the best CMOs understand deeply the pains of the buyer, what makes them tick, what drives business value and personal value for the buyer, and that's what makes the best CMOs today, because when you know that, then you become a great seller, right? Because people, they don't want to be sold to, but they do want to buy.

AI assessment note: “when you know that, then you become a great seller, right?”

Q How, how are they adjusting? Everyone says all budgets are going back to CFOs and CFOs aren't buying technology. That's what everyone says. How are they adjusting? And do you agree with that?

A I do agree with that. The CFO in different personas, there are functions people have never even heard of that are getting involved in the sale right now. Right? So I agree with that sentiment. And I also agree that it is hard, hard stuff. But what the best sellers are doing now, and I geek out with a lot of other sellers, and what I'm finding that the best sellers are doing right now, they're revisiting their ideal customer profile. They're revisiting their target accounts, who they want to go and pursue and engage with. They're adjusting their messaging. Right? Like Harry, you and I both know growing up that there was a monster under the bed, right? We both knew that, right? And that's how many sellers talk about their problem is like, oh, there's a monster of the bed. But you know what? The better sellers, they're talking about the monster that's down the hall, Through the other door and hiding in the closet. They're teaching. They're teaching their buyer about that monster, not about the obvious monster that's under the bed. So I think the better sellers are adjusting.

AI assessment note: “they're revisiting their ideal customer profile. They're revisiting their target accounts”

Q So that's really interesting. I always say when you have to educate your customer, it's so much harder. It's just so much harder. It's like when you're fundraising and your VC doesn't know anything about the space you're in. Good luck. Do you agree or not given the fact that the best educate?

A I do believe the best educate. And in fact, in my sales process internally, third company in a row, the first stage of the sales process is called teaching. Teaching hypothesis based selling. I mean, look, if you are a seller today and you engage a potential buyer and you're wasting your time asking about what fucking CRM that they use or where they're located or who they do business with or how they make money, you're fucked. You just, just don't even call. Right? So the first stage is teaching. If I can teach you more about your business, if I can teach you something about your business that you might not even be thinking about. You will engage with me. And so I agree to the, to this, to your sentiment of what you're saying, but that teaching component is critical.

AI assessment note: “I do believe the best educate. And in fact, in my sales process internally”

Q Do you think you need specialization on a vertical playbook basis then? Because if you can teach me more about my business, Sean, I'm either incredibly stupid or you should be leading fucking Microsoft. So, so how are you going to get smarter than me on my business?

A And it might not be about your specific business, but it could be about the investor world. And the key word that we try and use Is reframing the problem. Reframing. Right? So in your world, whether you're investing, you're looking for certain types of companies before you make an investment, whether it be LTV to CAC, whatever metrics that you're looking in. But we want to reframe it to be about something different, something you might not be thinking about. And that could be your voice internal survey results from their employees. Do they have happy employees? It could be what their customers are saying about the company you might invest in. Now I'm not, I'm not giving you an insight right now. But if I'm selling to VC firms, I talk to three VC firms in a month. And fuck me if I don't have some insight about the VC community that you might not be exposed to in the last month.

AI assessment note: “insight about the VC community that you might not be exposed to in the last month.”

Q That's too good. So wait, you have someone to secure new logos. What does that mean? Like, they go out and they pull together a list of names that could be good targets, and just help me understand how that works.

A Yes. Ok, let's slow down. Uh, you have the new logo organization, and their, their, their only purpose in life is to go get more new customers. Right? So when they get an order form signed, by the way, no one's signing order forms anymore. Uh, it's digital. But when you get that order form signed, you pass it off to a customer facing team, whether that be called account management, customer success, customer support, whatever you want to call them. But these are two distinct different teams. Harry, when you have those, those roles combined, the research is profound. When you combine those roles, it doesn't work very well. So long as you have the TAM, the total addressable market, and you have, you have the green field available where you can go and secure new logos. You've got that runway. Those roles should be separated.

AI assessment note: “their only purpose in life is to go get more new customers”

Q sell to and you have sold to over your career. I mean, I'm invested in many companies and kind of the holy grail is like, well, we're going to scale into enterprise and then hundreds of thousands of dollars of ACVs will just magically open up and it doesn't happen like that. And there's this real naivety. What do you think customers or founders get wrong about moving into enterprise?

A A lot. Okay, there is a lot to get wrong. The three biggest hurdles in taking that holy grail of moving up into the enterprise, those massive ACBs, the sexy LTV to CAC, those sexy logos that you talk about, but the hardest problems. First, the credibility. No one knows who you are, especially in the enterprise and it will destroy you. Right. The second is, do you have real product market fit for those big companies? Because those big companies, they all believe that they're special snowflakes. And so they need things that are just different because you've built an SMB or mid market platform that's there to scale. Right. And third, it's somewhat related to both. But your financial and your financials, because as you move up market, they just don't trust you. Very similar to credibility, but they just don't trust that you'll be around. They don't trust that you can survive as, as a startup for that long. So I think those are the three, um, probably not so insightful insights that I've experienced in moving up.

AI assessment note: “The three biggest hurdles in taking that holy grail of moving up into the enterprise”

Q Is there a way to try it without huge resources? Is there a way to put your foot in the water of like enterprise? With a couple of customers, see if it's what you need, or is it a full on budget reallocation?

A Yeah, the, the, the hard truth is it's a full on budget allocation. It's a full on effort. Um, however, you can test to see if your product will work with a few test cases with some few customers. So for example, to the founders out there, try and engage an enterprise and maybe do it on a house. Engage a few customers and give them your product for a year and let them use it for a year. Find out where the mistakes are. Find out what goes wrong. Learn what's wrong with your product. Before you really go big. So there's probably a little bit of both Harry, but the truth is. Yeah. You need some capital to go into the, into the enterprise and you won't get that immediate love. You won't. It takes time. It doesn't have the same return on speed as the SMB or mid market will have. That's the truth.

AI assessment note: “the hard truth is it's a full on budget allocation. It's a full on effort.”

Q Okay. I got you. So we have that as that structure for those core pillars. You said about a sales task and a take home task. I'm intrigued on this one. What do you ask them to do? Is it one on you? Is it one on another company? How do you structure that?

A Yeah, it, it really depends, Harry. It depends if it's my first sales rep or my first sales manager. Um, if it's a first sales rep, it might not be a take-home test. Instead, it could be a CCAT test that you would take. It could be a personality test that you could take. It could be different types of tests, but when I do take-home tests, it could be something as simple as what would be your 30, 60, and 90 day plan when you start with me. That could be it. So then you can grasp their intellectual curiosity. You can grasp their drive, their, their, their passion about your product and the problem that you're solving. It can really be a choose your own adventure on what that take home test could be.

AI assessment note: “when I do take-home tests, it could be something as simple as what would be”

Q Huh. I love that. Well, it goes back to the teaching element. Is there any big lessons for you on, like, negotiation on comp and what that tells you about people? I find, like, specifically title and comp are two of the most revealing parts of a hiring process. Do you have any lessons on this?

A I have so many lessons on comp. So first, the biggest lessons I've learned on comp is transparency. My biggest lesson. So for those that are up to negotiate at final offer, to me, that just creates a different economics, um, bias that could come in into that process. So maybe someone's better at negotiating compensation than another, right? So maybe that filters it, but with transparency, look, I'm never going to be the highest paid shop in town. You can always go somewhere else to make more money, but I'm looking for transparency so everyone knows what they're walking into. Here's the, the variable pay. Here's the, the, the salary, right? And it's just very transparent. Everyone knows what it is. So I don't waste my time. I'll waste theirs. Transparent pay. The second lesson I've learned is I've moved to a national pay structure, right? So if I live in London, um, if I live in New York City, if I live in Cleveland, Ohio. It's still the same job, right? You're still performing the same tasks. So that transparent standard pay doesn't really matter where you live. And I pay on the higher end. I assume you live in London. I assume that you live in New York city and I will pay you on that high end, not the highest paid shop in New York city, but I'll pay you on that high end. So transparency and one pay structure.

AI assessment note: “the biggest lessons I've learned on comp is transparency.”

Q Okay. Okay. So let's just take those. Sorry. I like to go. Are people honest? Everyone likes to feel important when you say, hey, you know, are you a decision maker for, for buying greenhouse? Of course I am. Yeah, yeah, yeah, yeah. It's me. You're, you're speaking to the right person. How do you, how do you know?

A That's a great call out, and you are right. That happens nine times out of 10, and frankly, they are not the person that can sign the order form, so you, you are right. Um, the question to ask maybe differently is, who should I engage early? Because Harry, role play again, ok? Harry, buyers like you, I have 7000 customers, and buyers that look and feel just like you, what happens at the end of this process is the CFO will get involved, the head of procurement will get involved, It will get involved. Harry, I don't think your company's going to be any different. So, in order to be a good steward of your time, let's get them involved now, because then I can set you up for success. Harry, you want this product, and I know you do. But in order for you to be successful, let's get these players involved.

AI assessment note: “the question to ask maybe differently is, who should I engage early?”