The Exchanges

Q Why, what were they, what did they have? What did they not have that made them not fit in the rubric? What made them that way?

A So for one thing, they didn't come from the right companies or they didn't have the right LinkedIn profile or something about them would have canceled them out from even getting into the funnel from a hiring standpoint. But the best salespeople will, will have those four H's, but they're also going to have creativity. Can you take duct tape, chewing gum, and a Zoom link, and MacGyver a seven-figure closed one deal, right? Like, that takes creativity. I've seen people do it. It's extraordinary. Not everyone has that. Are they adaptable? The two, uh, first salespeople at RAMP. The first one now leads half the sales and SDR teams. The second one is chief of staff to our CEO. Right. They're adaptable. You're hiring people not for what they can do today, but people who have enormous growth potential. That's how you get a 10 X outcome.

AI assessment note: “they didn't come from the right companies or they didn't have the right LinkedIn profile”

Q I have to touch on that. You mentioned the time at Navon in such a transformational and kind of hyper growth time for the company. What are one to two of the biggest takeaways for you from that time and from being the first enterprise sales leader there? Uh, what have you taken with you to your time now as ramp?

A There were so many lessons across the, the four and a half years that I spent there and working with, with great mentors like Rich Lou and Carlos de la Torre. Uh, the first lesson that I really took away, and this comes from, from when I was an IC, an enterprise account executive there, I built up a massive amount of pipeline the, the first six to nine months. I had 87 opportunities in my name, Harry, and if you know anything about enterprise sales, that's way too many opportunities. Uh, but I started to, to close deals about, uh, month six, and what I recognized was, you don't need product market fit In order to sell an enterprise, especially as that first seller, what you need to find is product customer fit. And so when you have a huge amount of pipeline like that, you can really prioritize it and focus on the accounts that match best with the vision that you're building toward and where their required capabilities match with your core competencies. So when you focus on that, that's going to drive 80% of your outcome. Amazing things happen, and I closed about thirteen million dollars of revenue that first year.

AI assessment note: “The first lesson that I really took away... what you need to find is product customer fit.”

Q sold Twilio to Uber when they were a tiny startup is probably the best deal in enterprise history now, and it transformed, obviously, from a startup to an enterprise deal, um, but at the time it was a nothing deal, and it was probably stunned by a credit card, almost. Um, how, like, how relevant is deal attribution to you when determining quality of candidate? I'm just too interested there.

A It's why you need to ask those why questions, Harry. Uh, some companies are, are great at product led growth and they're selling to an organization when it's an SMB. At what point did you sell to that organization? Was it a 10 person company that grew to a 10,000 person company? Or did you sell to them net new when they were 10,000 people? Did you sell wall to wall across the entire organization? Or was it a land and expand motion? Who else was involved with you in selling that deal? But you need to dig in to understand, uh, you know, did they do all of the work? Did they generate that deal themselves? Was it self-sourced? Or did an SDR make a cold call, and that's how it happened? Or did marketing generate the lead, and it came inbound?

AI assessment note: “you need to dig in to understand, uh, you know, did they do all”

Q You said that you can get product customer fit without having product market fit. I'm really intrigued. Does the sales person need to be the one to create the sales playbook or does the founder need to be? How do you think about that question in terms of the product market fit question as well?

A Yeah. For product market fit, I think that that is driven more by, by the founder, uh, being out in the field, talking to customers, talking to prospects. Uh, really understanding their pain points and being able to, to dive in at that level. But when you think about sales and a sales playbook, I think that's originating from the salesperson. And in some businesses, the founder is that first seller. Uh, in other businesses, I would say, uh, you, you wanna hire a junior salesperson to go out there and, and figure things out. But in no circumstances do you really want to bring in a VP of sales before you have a seller, because they're gonna come in with the preconceived notions That ultimately might not mesh with, with your particular business model.

AI assessment note: “when you think about sales and a sales playbook, I think that's originating from the salesperson.”

Q when I could, uh, who worked with you. And so I have a lot of information about why you're so brilliant, Mark. So I want to dig into some of the areas where your tax, and I want to start with deal champions and multi-threading in particular. I think it's something that people universally still do badly, actually. How do you confirm you have a deal champion in a cycle?

A It's a tried and true method. When it comes to thinking you have a champion, there is only one way to know if they really are a champion for you. You have to test them. And the way that you test them is asking them to take you to the executive buyer. Now that can result in two things. One, they have the power and influence to be able to take you to the EB. Typically that's a CFO, especially today. If they have the power and influence to do it, and they're willing to take you there and, and, and help present with you, you need to be in that meeting on your B. On your behalf, they're selling internally. You've got a champion. If they say no to you, for whatever reason, it means one of two things. Either they don't have the power and influence to take you to the executive buyer, in which case you're dealing with a coach or just a stakeholder in the organization who, who really is not going to be meaningfully important for you, or you haven't earned the right yet to have them take you to that CFO or to that EB, in which case you have more selling to do.

AI assessment note: “You have to test them. And the way that you test them is asking them”

Q which as we said, needs more confidence and needs a lot of mentoring, but can still be brilliant in terms of like hiring it. We need to know what great looks like. And you said to me before that it's about the four H's success in sales is the four H's. I'm loving the acronyms today, Mark. Fuck it. I'm going to go for it. What are the four H's?

A The four H's is something that I came up with that really is about saying, The intangibles matter more than the tangibles. So first H, hunger. You need to want it more than anyone else. If you don't have that burning desire to succeed, that deep need to win, that insatiable yearning to compete, you probably won't win or compete or succeed. Hunger is an incredible motivator to get you through the inevitable challenges. Hustle. It's not enough to just be hungrier than everyone else. You need to be prepared to outwork them too. There's a great quote from John McMahon, who was a tremendous sales leader, and, and it sums it up well. The difference between winners and losers is that losers practice until they get it right. Winners practice until they never get it wrong. Such an incredible quote from, you know, absolute sales genius, uh, and also applies to sports. I, I always think about Tom Brady when I hear that, someone who was not the most gifted athlete of all time, but certainly the greatest professional athlete of all time, uh, because he outworked everyone else, watched more film than everyone, was in the gym earlier than everyone. No one would outwork him. And so he was able to rise when it mattered the most. Third H, humility. This is one that I will grant you a lot of salespeople don't have. They come in with bravado. Um, but I actually think humility is the approach. You …

AI assessment note: “So first H, hunger... Hustle... Third H, humility... The last H is heart.”

Q before. Um, I love any acronym, you know, as a VC, it's what feeds my soul. Um, but I do want to ask, okay, so we're going through this qualification process and I am leaning in. Okay. I'm excited for what you've got to sell, but I'm not quite converting. What do you do to create a sense of urgency in a sales cycle to get someone over the line?

A It comes down to pain, Harry. If you don't have enough pain, there's Not a world where I can get you to have the urgency you need short of discounting. And that kind of cheapens what we, what we all do. And so what I would suggest is you've got to go back to first principles. You've got to go back to discovery. And if you, Harry, don't have enough pain, I need to find someone else in the organization who has that burning pain. Uh, I need to find other people and build groundswell. Uh, again, this comes Down to multi-threading and pipeline generation. You want to get as high and as wide as you can in an organization, because the only thing better than having a champion is having multiple champions.

AI assessment note: “It comes down to pain, Harry. If you don't have enough pain,”

Q where they need to lead the case. When it is the founder leading the case, what are the signals that they need to hire the first junior sales rep? Often it's like a million in ARR is touted as kind of the number, which I think is kind of bullshit, because it means little. What are the signals that the founder needs to make that first hire, do you think?

A I, I think they should make that first hire, uh, as soon as they have a product that they really want to be testing out in the market, and so I, I think it's a lot sooner than a million ARR, to be honest. The, those first sales, I don't think about revenue as being important. The revenue or the currency that matters in those first sales are the logos. You, you need to be acquiring logos. You need to be able to say, hey, this company works with us. That gives you credibility when you're trying to make that sale for revenue. You want their feedback. You want the case study. You want them to be a reference for you. That matters a lot more than revenue in those early days.

AI assessment note: “as soon as they have a product that they really want to be testing out”

Q not be terrified. Cause I think often it's fear that makes happy is multiply. Um, I, I do want to ask you, I think kind of sales qualification is a big problem and people still suck at it. When you look at sales qualification today, how do you coach and train young sales reps? And what do you see as the biggest mistakes that people make in sales qualification today?

A I think the biggest mistake that people make from sales qualification standpoint is really not going deep enough. They'll ask discovery questions and then that first level of discovery question has, has been completed and they're already selling their solution. You need to go deep. You need to do some significant discovery where you get to secondary third level pain and really let someone stew in that pain. I'll give you an example, Harry. Uh, you know, maybe you, uh, you're on a run this weekend and, uh, you scratched your arm, right? So I ask you about that and find out, hey, you know, yeah, it kind of stings. Um, maybe you need a Band-Aid. I don't know. Um, did, you know, is there blood there, right? We start to dig in and find out, hey, you, you, you've got some serious pain. What happens if you don't address that pain right now? Well, maybe it'll get infected. And now instead of a Band-Aid, maybe you need antibiotics. And, you know, if you don't do that, what, what's the risk to you? Well, shit, maybe my arm's gonna fall off or, or, uh, you know, I'm gonna have to get it amputated. Well, now this little scratch that, you know, you weren't really thinking about is a painful, festering wound that you really need to address. Hey, turns out I've got a Band-Aid, Harry, and I can, I can solve this for you right now. You have to be able to go deep on that pain and qualify what is…

AI assessment note: “biggest mistake that people make from sales qualification standpoint is really not going deep”

Q fuck. Thirteen million dollars of revenue for one rep alone. I wish you'd work in some of my portfolio companies. Um, my, my question to you is, you said there about kind of product customer fit. I love it, I get it, but we have those 86 companies. What do we do then? What does product customer fit actually mean? Help me and help sales leaders and reps understand that.

A Yeah. So it, it goes down to, to something that I, that I built later on a, a qualification methodology I called lean pivot walk. And essentially what you're trying to do is understand, Hey, if the boxes that they're looking to check are the boxes that we check really well, you should lean in. You should be going after that opportunity, uh, full force. If what they're looking for is something that is not even on your roadmap and, and wouldn't be on your roadmap for the next five years, you need to be honest with yourself. So many reps out there have happy ears, and just because someone wants to meet with them, they think, hey, they've got an opportunity. You need to be honest and, and be able to walk away and qualify that deal out. And then there are other opportunities where maybe you check some of the boxes and not others. And is there a world where they're willing to have two different solutions? One for the rest of the world and maybe one for North America. And so you start to understand these dynamics and you can play off of them and ultimately close a lot of business that way.

AI assessment note: “if the boxes that they're looking to check are the boxes that we check”

Q terrible question. God. Silly. Um, no, I, I thank you for clarifying that. And by the way, do ridicule any questions. I love this. Um, you mentioned kind of the importance of multi-threading there and bringing in the executive buyer. It's important that sales reps and sales teams see around corners. Um, what are some ways that sales reps can get better at seeing around corners during a deal cycle?

A I think that A lot of people tend to wear rose colored glasses. They get happy ears. As I mentioned before, uh, people are meeting with them. They're excited. Rose colored glasses. People are great fun at parties, but they make for shit sellers. You need someone who, who is a lot more skeptical, who questions everything. The way that you see around corners is you ask the hard questions. You run toward the danger and what scares you not away from it. So Harry, what are the reasons why you're going to lose this deal? What happens if your champion leaves? What happens if the CFO says this, that, or the other? If you ask yourself all of these questions and, and any possible way you could potentially lose this deal. Well, now you have a map of all of the things that you potentially need to overcome. And in a worst case, you're overcoming objections that, that might not actually take place. And in the best case, you're really prepared for when that punch inevitably comes.

AI assessment note: “The way that you see around corners is you ask the hard questions.”

Q What should you provide your champion to make sure that they're equipped to sell your case best to the executive buyer on, on your behalf, but when you're not there?

A The phrasing of that question scares the shit out of me, Harry. Uh, and the reason why is that you need to be in that meeting. There is not a world that I would ever be comfortable living in where I want to outsource my job to a champion at a, at a prospect. That is, that is living very dangerously on the edge. I know a lot of salespeople who will take, uh, uh, you know, completely wholesale. What a champion says, Hey, my CFO doesn't meet with anybody. My CFO is too busy. I will be the one to talk to them on your behalf. No, no, no, no, no. We, we, we can't have that because what happens when the CFO asks you that question, Mr. Or Mrs. Champion that you don't know the answer to what happens when they question these numbers or they ask about Implementation, or have you talked to these different stakeholders, and you don't know the answer. We have to be in that room with you.

AI assessment note: “you need to be in that meeting. There is not a world”

Q Can I ask a lot of people say like, you know, hey, we'll give you the discount or, you know, we'd love for you to give us a customer referral and allow you to use your logo. How do you, as a startup, ask a prestigious company Hey, can we use your logo for validity? What's the right way to do that without sounding kind of needy and startup-y?

A Yeah. So one, I don't, I don't ask for it. It's something that's a requirement. So I, I think just the, the assumed close there is really important. You know, as part of working with us, we we're excited by, um, we want to support our customers. Uh, we love to show off the great companies that are working with us. Uh, and so we're going to have your logo on our sales materials, On our website. That's, that's part of what we do. Um, oh, well, we don't, we don't, we don't allow companies to do that. Okay. Well, it was, it was great chatting with you. Uh, you know, good luck finding a solution that, that, that, uh, is going to solve for the pain that you have today. You have to have confidence around it, Harry.

AI assessment note: “I don't, I don't ask for it. It's something that's a requirement.”

Q before. Um, I love any acronym, you know, as a VC, it's what feeds my soul. Um, but I do want to ask, okay, so we're going through this qualification process and I am leaning in. Okay. I'm excited for what you've got to sell, but I'm not quite converting. What do you do to create a sense of urgency in a sales cycle to get someone over the line?

A It comes down to pain, Harry. If you don't have enough pain, there's Not a world where I can get you to have the urgency you need short of discounting. And that kind of cheapens what we, what we all do. And so what I would suggest is you've got to go back to first principles. You've got to go back to discovery. And if you, Harry, don't have enough pain, I need to find someone else in the organization who has that burning pain. Uh, I need to find other people and build groundswell. Uh, again, this comes Down to multi-threading and pipeline generation. You want to get as high and as wide as you can in an organization, because the only thing better than having a champion is having multiple champions.

AI assessment note: “If you don't have enough pain, there's Not a world where I can get you”

Q Okay. So I, I love that in terms of the focus on 10 X and thinking outside the horse, but how do we determine whether they're 10 X? If we go to the interview process, say we've let them into the interview process, despite not being the traditional fit, but they're in, we're sitting down with them. What questions do we ask? How do we know if they're 10 X's?

A Yeah, you, you need to get really intimate. You need to go deep in your interview questions. Get at the why, not just the what. So many, so many interview questions are, what did you do next? Why, you know, what were you doing at that company? What deals did you close? I want to know the why. I want to know the how. I want to know and, and get, I want to know them and get really deep, uh, to understand what makes them tick. What was the reasoning behind decisions they made? Not just the performance. And a great way to test this is, is with a challenge. So I know different organizations think about this differently. I want them to sell to me, not what they're selling today, but I want them to sell my solution back to me because it shows if they can do research. It shows if they can synthesize that information. Uh, I know if, uh, if what they're saying is correct or not, uh, I can see, uh, all of the gears turning and I can test them as well in that Setting and say, Hey, I'm a CFO. We scheduled this for 45 minutes. I actually only have 10. Go. Are you adaptable? Right? Can you take a punch? Can you pivot really quickly?

AI assessment note: “I want them to sell my solution back to me because it shows if they can”

Q which as we said, needs more confidence and needs a lot of mentoring, but can still be brilliant in terms of like hiring it. We need to know what great looks like. And you said to me before that it's about the four H's success in sales is the four H's. I'm loving the acronyms today, Mark. Fuck it. I'm going to go for it. What are the four H's?

A The four H's is something that I came up with that really is about saying, The intangibles matter more than the tangibles. So first H, hunger. You need to want it more than anyone else. If you don't have that burning desire to succeed, that deep need to win, that insatiable yearning to compete, you probably won't win or compete or succeed. Hunger is an incredible motivator to get you through the inevitable challenges. Hustle. It's not enough to just be hungrier than everyone else. You need to be prepared to outwork them too. There's a great quote from John McMahon, who was a tremendous sales leader, and, and it sums it up well. The difference between winners and losers is that losers practice until they get it right. Winners practice until they never get it wrong. Such an incredible quote from, you know, absolute sales genius, uh, and also applies to sports. I, I always think about Tom Brady when I hear that, someone who was not the most gifted athlete of all time, but certainly the greatest professional athlete of all time, uh, because he outworked everyone else, watched more film than everyone, was in the gym earlier than everyone. No one would outwork him. And so he was able to rise when it mattered the most. Third H, humility. This is one that I will grant you a lot of salespeople don't have. They come in with bravado. Um, but I actually think humility is the approach. You …

AI assessment note: “first H, hunger. You need to want it more than anyone else.”

Q before to me, you need to think outside the horse when it comes to hiring sales teams. Think outside the horse. I kind of repeated this to myself and it didn't become clear to me. So can you help me out here? What did you mean by this? And how does that impact how you think about what you look for in the people you add to your sales teams?

A Yeah, I, I, I love this. Um, it's a little bit of a mixed metaphor, but, but let me tell you. So from a product standpoint at ramp, we think of the legacy state as a horse and buggy. And do we want to build a faster horse and buggy, or are we going to build an automobile on a slightly different vein? I've heard guests of yours talk about the expression in sales recruiting that fast horses run together. Right? A players attract A players. But if you want 10 X productivity, you need to think outside the horse. You need a race car, not a race horse. Let me give you an example here. If you have a 10 X better product, and I hope you're investing in companies with 10 X better products because they're amazing. But if you have a 10 X better product and a good traditional sales rep, the best you can achieve is a 10 X outcome. It's a pretty good outcome. But if you have a 10 X better product and a 10 X better sales rep, you can achieve a hundred X outcome. And the best salespeople in my experience rarely fit the mold of what great salespeople should look like. And I'm not even talking about myself and my challenge getting into Silicon Valley. The best salespeople I've seen in the last several companies I've been in, none of them would be hired today based on the rubric that sales leaders have. You need to think outside the horse.

AI assessment note: “The best salespeople in my experience rarely fit the mold of what great salespeople should look like.”

Q Before we dive into kind of that integration with the existing team, which is so important doing the onboarding right, I do just want to kind of close. We go through that process and we get to the deal itself of kind of the package. What are some of your biggest lessons and pieces of advice to founders on giving the right comp structure for those early sales rep hires?

A I think when it comes, especially to early sales hires, there's not enough, uh, emphasis placed on, on equity in sales. They give out equity for, for other roles. And I think equity is, is often something that, uh, founders don't really think of when it comes to salespeople. They, they really only think about cash compensation. And I think that's the wrong approach. If you're hiring a 10 X salesperson, someone who's going to be with you for a long time and drive an inordinate amount of Impact in the organization. You should want to keep them for a long time. And they're going to be able to see the impact of, uh, their revenue generating activities on the company all the way up to, uh, raising funds. I'll give you an example of this. Uh, in my last company, uh, in May of 20, 20, uh, there was something called the COVID-nineteen pandemic that had started a couple months earlier.

AI assessment note: “there's not enough, uh, emphasis placed on, on equity in sales.”

Q And so I think it's nice to stay in the warm and cozy environment that is, you know, warm inbound. Uh, so I, I totally agree with you there. Going back to the kind of integration into the team, I think onboarding is just chronically poorly done. How do you think about the right way to onboard new sales reps into your team and how do you do it today?

A I think it needs to be a mix of structured learning and unstructured learning. So asynchronous learning. I think there needs to be a fair amount where they're going to be shadowing the best reps on calls. I think you need to dig in with them and, and go deep on a daily and weekly basis. So one-on-one coaching as well. And you need to make them drink from the fire hose. I know we try to, to limit that as, as companies get larger. Where, hey, we're going to give them this nice cushy ramp up period, but you're going to find out a lot those first few weeks about their ability to run at pace if they can drink from the fire hose and start to synthesize that information. So I, I'm a big believer that the training wheels need to come off quickly. I do think there's benefit as well to giving them what I'd call t-ball opportunities. So if you're an enterprise, you don't want to risk some massive Deal by giving it to the to the guy who just or the woman who just started. You need to be able to give them a smaller opportunity that's safe. That's a safe place for them to iterate and figure out the motion before they're getting into these really large complex deals.

AI assessment note: “I think it needs to be a mix of structured learning and unstructured learning.”

Q And I absolutely love that in terms of the focus on logos. In terms of kind of going back to that single sales rep hire, Jason Lampkin says about the importance of hiring two at a time. So you can really determine quality and compare. Do you agree with that? Or do you think one works just as well?

A The way that I think about it Is I'm looking for salespeople who can provide 10 X growth, not one X or 1.5 X. And when you find someone who can provide that 10 X level of growth, they're a rare find. To find two at the exact same time and to be able to recruit them and have them join at the same time is an exceptionally rare opportunity. If you do find them by all means, you should hire them. You should hire them as fast as you can, whenever you can. But ultimately, I, I think if you are at scale, uh, it's easier to hire, hey, two salespeople at a time. You're going from 20 reps to 30 reps to 40 reps. Great. Hire an incoming class. But in those early days where each additional player is going to have so much impact, you need to be grabbing the best talent when you can.

AI assessment note: “To find two at the exact same time and to be able to recruit them”

Q Why, what were they, what did they have? What did they not have that made them not fit in the rubric? What made them that way?

A So for one thing, they didn't come from the right companies or they didn't have the right LinkedIn profile or something about them would have canceled them out from even getting into the funnel from a hiring standpoint. But the best salespeople will, will have those four H's, but they're also going to have creativity. Can you take duct tape, chewing gum, and a Zoom link, and MacGyver a seven-figure closed one deal, right? Like, that takes creativity. I've seen people do it. It's extraordinary. Not everyone has that. Are they adaptable? The two, uh, first salespeople at RAMP. The first one now leads half the sales and SDR teams. The second one is chief of staff to our CEO. Right. They're adaptable. You're hiring people not for what they can do today, but people who have enormous growth potential. That's how you get a 10 X outcome.

AI assessment note: “they didn't come from the right companies or they didn't have the right LinkedIn profile”

Q fuck. Thirteen million dollars of revenue for one rep alone. I wish you'd work in some of my portfolio companies. Um, my, my question to you is, you said there about kind of product customer fit. I love it, I get it, but we have those 86 companies. What do we do then? What does product customer fit actually mean? Help me and help sales leaders and reps understand that.

A Yeah. So it, it goes down to, to something that I, that I built later on a, a qualification methodology I called lean pivot walk. And essentially what you're trying to do is understand, Hey, if the boxes that they're looking to check are the boxes that we check really well, you should lean in. You should be going after that opportunity, uh, full force. If what they're looking for is something that is not even on your roadmap and, and wouldn't be on your roadmap for the next five years, you need to be honest with yourself. So many reps out there have happy ears, and just because someone wants to meet with them, they think, hey, they've got an opportunity. You need to be honest and, and be able to walk away and qualify that deal out. And then there are other opportunities where maybe you check some of the boxes and not others. And is there a world where they're willing to have two different solutions? One for the rest of the world and maybe one for North America. And so you start to understand these dynamics and you can play off of them and ultimately close a lot of business that way.

AI assessment note: “a qualification methodology I called lean pivot walk”

Q where they need to lead the case. When it is the founder leading the case, what are the signals that they need to hire the first junior sales rep? Often it's like a million in ARR is touted as kind of the number, which I think is kind of bullshit, because it means little. What are the signals that the founder needs to make that first hire, do you think?

A I, I think they should make that first hire, uh, as soon as they have a product that they really want to be testing out in the market, and so I, I think it's a lot sooner than a million ARR, to be honest. The, those first sales, I don't think about revenue as being important. The revenue or the currency that matters in those first sales are the logos. You, you need to be acquiring logos. You need to be able to say, hey, this company works with us. That gives you credibility when you're trying to make that sale for revenue. You want their feedback. You want the case study. You want them to be a reference for you. That matters a lot more than revenue in those early days.

AI assessment note: “as soon as they have a product that they really want to be testing out”

Q What should you provide your champion to make sure that they're equipped to sell your case best to the executive buyer on, on your behalf, but when you're not there?

A The phrasing of that question scares the shit out of me, Harry. Uh, and the reason why is that you need to be in that meeting. There is not a world that I would ever be comfortable living in where I want to outsource my job to a champion at a, at a prospect. That is, that is living very dangerously on the edge. I know a lot of salespeople who will take, uh, uh, you know, completely wholesale. What a champion says, Hey, my CFO doesn't meet with anybody. My CFO is too busy. I will be the one to talk to them on your behalf. No, no, no, no, no. We, we, we can't have that because what happens when the CFO asks you that question, Mr. Or Mrs. Champion that you don't know the answer to what happens when they question these numbers or they ask about Implementation, or have you talked to these different stakeholders, and you don't know the answer. We have to be in that room with you.

AI assessment note: “the reason why is that you need to be in that meeting”

Q not be terrified. Cause I think often it's fear that makes happy is multiply. Um, I, I do want to ask you, I think kind of sales qualification is a big problem and people still suck at it. When you look at sales qualification today, how do you coach and train young sales reps? And what do you see as the biggest mistakes that people make in sales qualification today?

A I think the biggest mistake that people make from sales qualification standpoint is really not going deep enough. They'll ask discovery questions and then that first level of discovery question has, has been completed and they're already selling their solution. You need to go deep. You need to do some significant discovery where you get to secondary third level pain and really let someone stew in that pain. I'll give you an example, Harry. Uh, you know, maybe you, uh, you're on a run this weekend and, uh, you scratched your arm, right? So I ask you about that and find out, hey, you know, yeah, it kind of stings. Um, maybe you need a Band-Aid. I don't know. Um, did, you know, is there blood there, right? We start to dig in and find out, hey, you, you, you've got some serious pain. What happens if you don't address that pain right now? Well, maybe it'll get infected. And now instead of a Band-Aid, maybe you need antibiotics. And, you know, if you don't do that, what, what's the risk to you? Well, shit, maybe my arm's gonna fall off or, or, uh, you know, I'm gonna have to get it amputated. Well, now this little scratch that, you know, you weren't really thinking about is a painful, festering wound that you really need to address. Hey, turns out I've got a Band-Aid, Harry, and I can, I can solve this for you right now. You have to be able to go deep on that pain and qualify what is…

AI assessment note: “biggest mistake that people make from sales qualification standpoint is really not going deep enough”

Q You mentioned your mentor there being Carlos. What do you think sales leaders can do to better mentor this younger, less confident cohort to be their best selves? I spoke to some of your mentees who said amazing things. What does great sales mentorship look like and require today, do you think?

A I think the key to mentorship is helping people see their blind spots. Right. So I'll give you an example. I, I know you spoke to, uh, to a founder of a YC company who, who I mentor. Uh, he actually reached out to me in a cold LinkedIn message and, and it cut through the noise and I responded to him and, uh, I've been excited to, to work with him and, and, and his team. Um, but he's not a sales professional. And so he's going through this deal cycle. Uh, and, and, you know, I shared with him what, what are his blind spots? Well, he thinks he's got an opportunity here. What happens if, you know, it doesn't work out? Well, does he want to have all of his eggs in that basket? No, you got to build more pipeline, right? So I'm, I'm helping him as an example to see around his blind spots and ultimately, uh, to, to be able to, to close more opportunities with other reps, with other people, uh, the dynamics can change. The buttons you need to push will change, but ultimately You're helping to make them more well-rounded, and I've, again, been fortunate with Rich Liu, with Carlos Del Torre to have some great mentors who helped me to see my blind spots before they, before I got into a wreck, and ultimately, it's allowed me to be a better manager as well.

AI assessment note: “I think the key to mentorship is helping people see their blind spots.”

Q Okay. So I, I love that in terms of the focus on 10 X and thinking outside the horse, but how do we determine whether they're 10 X? If we go to the interview process, say we've let them into the interview process, despite not being the traditional fit, but they're in, we're sitting down with them. What questions do we ask? How do we know if they're 10 X's?

A Yeah, you, you need to get really intimate. You need to go deep in your interview questions. Get at the why, not just the what. So many, so many interview questions are, what did you do next? Why, you know, what were you doing at that company? What deals did you close? I want to know the why. I want to know the how. I want to know and, and get, I want to know them and get really deep, uh, to understand what makes them tick. What was the reasoning behind decisions they made? Not just the performance. And a great way to test this is, is with a challenge. So I know different organizations think about this differently. I want them to sell to me, not what they're selling today, but I want them to sell my solution back to me because it shows if they can do research. It shows if they can synthesize that information. Uh, I know if, uh, if what they're saying is correct or not, uh, I can see, uh, all of the gears turning and I can test them as well in that Setting and say, Hey, I'm a CFO. We scheduled this for 45 minutes. I actually only have 10. Go. Are you adaptable? Right? Can you take a punch? Can you pivot really quickly?

AI assessment note: “I want them to sell my solution back to me because it shows if they can”

Q Can I ask, should we, if we're a startup hiring, what does that process look like? Is it like first interview, get to know you, the why, second a case study, So what does that process look like step by step, do you think?

A So for me, I want to be able to qualify quickly. Is this person of the right caliber? Have they closed the right level of deals? Do they have the right experience? Do they have the right gravitas to be able to hold themselves in an executive meeting? That, you know, is a, is usually like a 30 minute sort of getting to know you call. Um, assuming that goes well, you want to go deeper. You want to spend an hour with them. You want to really go deep. You want to ask those why questions, those how questions. Really get to understand what makes them tick. You want to have other stakeholders meet with them as well. Uh, typically in enterprise, you're a quarterback. You're, you're working with other people internally and externally. So how do those relationships form? Uh, are you able to play off those dynamics? And then ultimately, yeah, you want to do a challenge with a panel of, of, of interviewees all the way up to your C-suite leadership.

AI assessment note: “30 minute sort of getting to know you call... spend an hour... challenge with a panel”

Q I think we all learn a lot from making mistakes. I know I've made many, uh, in my time. Um, what are the biggest mistakes you've made in terms of hiring for enterprise sales teams and how did that change how you think?

A I've certainly made mistakes. I think sometimes when you assume their experience, Uh, if you assume their fit, uh, based on where they've been or what they've accomplished in their career, uh, you, you put yourself in a, in a very risky situation where when they come in, if you haven't tested for that, they may fail. Uh, I've seen people who are extremely accomplished join organizations I've been a part of, and within six months, they're no longer in the company because they weren't able to cut it. The fit was wrong. And so you really need to test for that because the last thing you want is to Waste six months of their career, of their time, and six months of, of your runway and six months of your time on someone who, who isn't a fit.

AI assessment note: “when you assume their experience, Uh, if you assume their fit”

Q Do you think traditional sales outbound is dead? And why does no one in sales want to do traditional outbound anymore?

A Traditional outbound is the most important thing, Harry, and if you're not doing it, uh, you are doing sales wrong, and the reason why is because pipeline is the most important thing if you want to hit your quota, as we just established, and the way that you build pipeline is through outreach. Uh, the founder that I mentor, he PG'd into me. He, he cold messaged me. Without that, I wouldn't be mentoring him. Uh, we have so many opportunities that are in our pipeline Because we did the hard thing. We picked up the phone. We sent out an email. We were persistent with it because usually it takes about five messages before someone is going to respond. Uh, and ultimately we feel good about it because we're providing a solution for them that helps them. We're not trying to, you know, to sell them something that they don't need. We're actually helping them. And so if you think of it from that standpoint, uh, what you're doing when you're picking up the phone is something that's good for you and it's good for the people that you're calling.

AI assessment note: “Traditional outbound is the most important thing, Harry”