The Exchanges

Q I love that as a first step. You can tell that the buyer would resonate when someone comes in prepped. We're moving to the end of the cycle. People are slow to convert. We both know this. How do you create urgency in a sales cycle where there might not be urgency on the buyer side?

A Yeah, I think, um, I think if it starts with you as an organization and what's in the interest of the firm trying to sell it, I think it's, they're going to see through that. I don't think it's going to work. I think it's got to be to the lens of the client, like full stop. So let's take an example. I'm a customer. I'm trying to stand up a new program. Um, that's always going to require people process and tech, but tech's got to enable something to get set up and they go, Hey, we have to go live next July. We don't need it yet. This is Q four, like come back in six months. Well, We go, great. You need it in July. When do you do user testing? Well, we're going to do user testing at bay. So when do you need to administer the technology? Well, we'd probably do that in February or March.

AI assessment note: “I think it's got to be to the lens of the client”

Q totally get you in terms of not being healthy together. I'm thinking about like, you know, high alpha, high ego people. And I think about very experienced and also very high potential when I hear that as a potential conflict, how, and this was actually from one of your friends, Matt, he said, how do you rank high potential versus high experience on the spectrum of importance when hiring leaders?

A Uh, so that's, that's an easy one for me. Um, it's always hypo one experience to the, there's always an exception to that though. I think when you have like a big mature, uh, customer and a big brand with a lot of visibility, You'll always have to take experience first. You don't want someone learning on the job in a very high profile environment, because then you might be setting them up for failure, and that's like not fair to them as a sales rep. So, with the exception of that, I'll always hire for potential, um, and, and I want to take someone who's got, um, a tremendous amount of adaptability and, and, um, and future potential, give them a job they might be a year away from, watch them be a little bit nervous and stumble for a quarter, but what's going to happen is, They're gonna get there way faster, so I, I'll always go potential first.

AI assessment note: “it's always hypo one experience to”

Q I love that as a first step. You can tell that the buyer would resonate when someone comes in prepped. We're moving to the end of the cycle. People are slow to convert. We both know this. How do you create urgency in a sales cycle where there might not be urgency on the buyer side?

A Yeah, I think, um, I think if it starts with you as an organization and what's in the interest of the firm trying to sell it, I think it's, they're going to see through that. I don't think it's going to work. I think it's got to be to the lens of the client, like full stop. So let's take an example. I'm a customer. I'm trying to stand up a new program. Um, that's always going to require people process and tech, but tech's got to enable something to get set up and they go, Hey, we have to go live next July. We don't need it yet. This is Q four, like come back in six months. Well, We go, great. You need it in July. When do you do user testing? Well, we're going to do user testing at bay. So when do you need to administer the technology? Well, we'd probably do that in February or March.

AI assessment note: “I think it's got to be to the lens of the client”

Q Not at all. As I said, excited, and Xenia said the most wonderful things. So I want to start with a little bit on you. You've run some of the most incredible sales orgs. What was the entry into sales for you, Frank?

A Look, I knew I wanted to be in sales straight away. In college, I worked for a company selling knives in people's homes, like the opposite of the job you'd ever go for. I ended up running an office as a college student. I was 20 years old and had 75 people working for me in Palm Beach, Florida. It was like getting a PhD in sales. So in undergrad, I'm in finance. It's an overloaded, uh, degree everyone's getting in. So I started to pick up some programming classes just to try to Find some separation. And then IBM picked me up. They love the intersection of like, you know, sales and programming. And I'll tell you one thing, as soon as I got to sales training, I realized most people didn't have any proper sales experience. And I was really excited that I had the hustle and grind of that, of that experience. Um, and then my first role at IBM was a competitive sales rep. So every account I talked to didn't want to talk to me. So you get to kind of have this like bulletproof skin on you, which is a really, really great way to get into sales.

AI assessment note: “In college, I worked for a company selling knives in people's homes”

Q Talk to me about negotiation in that process. People often think that that comes first. Where does negotiation sit in that process of like, you know, customer discovery, customer understanding for you?

A So I, I think the biggest mistake is when you just send a price over, right? And then you end up arguing about numbers that you ever see this, you send a proposal, And whether it's like a percentage savings or the absolute number, it's like human nature in negotiation to look at that and then want that number to be smaller. And so sometimes you get lost on all the wrong details. So if it's me, my preference would always be start with a blank canvas, find your buyer and spend some quality time. And I think you'd ask questions of her like this. Number one, how are you measured? What are the metrics that you as an organization, as individual are measured by at the organization level? And you start to really unpack How they define value and values and what their priorities are. And then you go like a level deeper. What's most important? Is it cash flow? Is it TCO? Is it year one fees? Is it exit fees? And you can start to kind of profile, like, what financial levers do you have to play with that matter to them? And I think commensurately, you've got to be super transparent with your organization. Here's how we're measured. Here's how we report. These are the prioritized levers that we have. Here's what we want. And so, if you do that, and then you start to align on deal structure, right? Um, whether it's like, is it a flat, or is it a ramp? Um, when you start to, like, really categ…

AI assessment note: “my preference would always be start with a blank canvas, find your buyer”

Q So the biggest reason I'm on many boards, the biggest reason for companies not hitting targets is, hey, they loved it. They loved it. Really. They're super keen, but it just slipped into next quarter. That happens all the time. What would you say if you're on the board of that enterprise sales company?

A Yeah, I'd say two things. Number one, in this environment, I, the first question is, have you adapted a lens on the buying cycle for the CFO to review it? Like, is there a, is there a quant element of value in, inside the proposal that a CFO who's never met with you, who will never meet with you, who's never used the technology, could look at, understand, and say, I like what I'm seeing financially. Because that's like the new, we have a new buyer in the cycle that was never there. That's the CFO. And they're probably going to get personally involved in an enterprise deal that's material. And if you haven't evaluated that and, and haven't like role played that, then you're going to fail.

AI assessment note: “the first question is, have you adapted a lens on the buying cycle for the CFO”

Q As a sales leader today, and I know it's very different for different segments, different go-to-market motions, but just for you, how do you think about forecasting where it's like, I don't know, there might be war, there might be hyperinflation, Biden might remember the day of the week, might not, uh, England may have a new prime minister tomorrow, like, you know, How do you plan with such uncertainty?

A Um, I think there's three pieces. Uh, one is you need like a, a very left brain math model that looks at all the historicals and says, you know, like on an average ratio, this is our close rate to pipe. Like there's basic math that everyone should include as part of the cycle. Number two, everyone should be layering in AI to be able to, at a predictable level at, if you're a big organization at scale, understand trends because If everyone else in the organization is seeing a downfall in forecast, technology is going to pick that up, where if you've got a team of five people in a small territory, you're not. Like, you don't have a chance to pattern match, because you're not talking to a thousand reps, but the tool is. The third is, I think you need to have, like, a right brain qualitative review of everything in your cycle. So what we do is, we do a bottoms up deal by deal analysis, and then we go back and compare it to the math model, And whatever AI says, and we go, do we believe the truth of this? And I think if you're really involved in your business, if you're like out talking to customers and listening to them and asking qualifying questions, I think between those three or four dynamics, you should be able to call your business. But I think when you look at the Wall Street Journal, you can, you can tell when there's going to be more cost pressures. So like we spent a lot m…

AI assessment note: “I think there's three pieces. Uh, one is you need like a, a very left brain math model”

Q I don't know if it's okay, but I'm going to anyway. Uh, can you unpack this for me and how you feel on this one?

A Uh, look, it's about resistance and persistence. I think, you know, my job every day is to solve problems. And I think if you, if you have a problem with a problem, you're not going to persevere. If you're okay tackling something that's super difficult, how you respond to that. Is going to help define you. So like for me personally, when I was a kid, my father passed away when I was eight, my mom remarried. I picked up an incredible stepfather. And then years later, my brother passed when I was 30. But what it does is it makes you really grateful for what you do have to look for the positive, but it always kind of produced a chip on my shoulder and a feeling of being unstoppable. And it's like, Hey, I made it through that. Let's go. And that's just carried, carried on with me through my professional career.

AI assessment note: “look, it's about resistance and persistence. I think, you know, my job every day”

Q and I said, who's the best sales guy? And he was like, oh, Frank. So I know your game. I know your game. Um, but you've mentioned like hiring many, many times. We're going to get back to playbooks and accounts, but I just want to touch on it because we're so on it now. How do you advise me on the hiring process for sales reps? Let's start there.

A I think fit. It's like, how do you, how do you buy a suit? It doesn't really matter like the color or the fat. It's like, does it fit you? Was it bespoke? Was it made for your frame? Right? So for me, it depends on the account. And so you look at a spectrum of like SMB to strategic sales. The answer is going to be wildly different. I'll probably talk about the enterprise component, which is top in a commercial to, to strategic. So for me, it's about fit. So if I've got, if I've got an account that has multiple reps on it, um, the team chemistry is really difficult, but I always want the closer upfront. Because they have to carry it all the way from one end of the field all the way down. But I'm also going to want to bring in like a visionary. Sometimes they're more academic. They're super right brain, very creative. They can build a vision and bring the organization along. They may not be as comfortable closing. And then the third profile of people I want to pick up is the person that wants to go hunt and take down every deal. Let's like see a bear, shoot a bear. And that's on, that's on something that I was like super talented at. I wanted to go kind of big game hunting, but you, If you're going to run an and business, you need a collection of those different skills, and you put them all together. So like, I, you want to find those people, and then at a chemistry level, figure…

AI assessment note: “I think fit... you need a collection of those different skills”

Q a win looks like for you. I've had founders say to me before, I never want to tell the customer what a win is for me, because I, I almost want them to feel I'm, I'm in hardship, almost. I don't want them to think that I'm profiting. Um, How does one communicate what a win is for them in a way that's beneficial for the progression of the deal?

A Well, it's like, you know, we talked a little bit about what sales tactics have changed over the last 20 years. Protectionism. I think, like, things are a lot more transparent. Customers have access to all kinds of data about your organization, about products, about negotiation. So, like, the idea of being closed-ended, like, you have all the information and you don't want to share it, that's just evolved. Like, we're 20 years past that, and so for me, it's about being really transparent. But if it starts with you, It's, I don't think it's really authentic. It's got to always start with them. So like I was reading a book called The Go-Giver, and it's like, how do I serve, how do I serve the person I'm working with and working for genuinely as the priority, and then you back into what's good for you. So I start with, what are your priorities? What, like, what are the mistakes? What do you not want to see? What's really going to irritate you? Um, if you're going to try to sell this internally, where are you going to catch a lot of flack? And then I say, great, now that I understand this, Here's how we are generally measured, and here's some overlap, and then what I want to do immediately up front, Harry is say like, what are the friction points that we could acknowledge? We're probably going to bump heads here, so let's just identify it. We'll try to work through those with a ver…

AI assessment note: “now that I understand this, Here's how we are generally measured”

Q totally get you in terms of not being healthy together. I'm thinking about like, you know, high alpha, high ego people. And I think about very experienced and also very high potential when I hear that as a potential conflict, how, and this was actually from one of your friends, Matt, he said, how do you rank high potential versus high experience on the spectrum of importance when hiring leaders?

A Uh, so that's, that's an easy one for me. Um, it's always hypo one experience to the, there's always an exception to that though. I think when you have like a big mature, uh, customer and a big brand with a lot of visibility, You'll always have to take experience first. You don't want someone learning on the job in a very high profile environment, because then you might be setting them up for failure, and that's like not fair to them as a sales rep. So, with the exception of that, I'll always hire for potential, um, and, and I want to take someone who's got, um, a tremendous amount of adaptability and, and, um, and future potential, give them a job they might be a year away from, watch them be a little bit nervous and stumble for a quarter, but what's going to happen is, They're gonna get there way faster, so I, I'll always go potential first.

AI assessment note: “it's always hypo one experience to the, there's always an exception to that”

Q That's what we're sorry. So we do it at the time. What do we need to do that, right? Create a doc specially for the CFO that says, I love you CFO.

A Yeah, no, that's, that's a good one. So I, here's the way I would do it. You know, after you go through, what are your value and values? What is the problem we're solving? What is the solution? What is the success and roadmap? What is the value, and then what is the pricing, and what is the next step? Like, that's the logical process. Before you get to pricing, is the value. And I think the value slide has a few different pieces to it. And yeah, like, if you're being, like, really specific, Harry, it's a Google slide, right? Um, but you've got to think through a few lenses. One is the economic value of buying. Are they getting a good deal? Are they avoiding cost? Are they saving money? And part of that is fee reduction, right? As an example, another part is, how do you consolidate and do cost reduction in this cycle where, hey, I have 15 vendors, how do I standardize on one? So, cost reduction or cost savings has a lot of different, uh, pieces. The other piece of that is value. How do they drive value to the organization? Now, if you've done your homework right and you've asked the questions, you know how they're measured, you've read the 10 K, you know what, um, what is important to that organization financially, and you've built a value framework that either says, Time to value is faster. ROI is there. This is going to drive shareholder value in these meaningful ways. And the…

AI assessment note: “Before you get to pricing, is the value. And I think the value slide”

Q As a sales leader today, and I know it's very different for different segments, different go-to-market motions, but just for you, how do you think about forecasting where it's like, I don't know, there might be war, there might be hyperinflation, Biden might remember the day of the week, might not, uh, England may have a new prime minister tomorrow, like, you know, How do you plan with such uncertainty?

A Um, I think there's three pieces. Uh, one is you need like a, a very left brain math model that looks at all the historicals and says, you know, like on an average ratio, this is our close rate to pipe. Like there's basic math that everyone should include as part of the cycle. Number two, everyone should be layering in AI to be able to, at a predictable level at, if you're a big organization at scale, understand trends because If everyone else in the organization is seeing a downfall in forecast, technology is going to pick that up, where if you've got a team of five people in a small territory, you're not. Like, you don't have a chance to pattern match, because you're not talking to a thousand reps, but the tool is. The third is, I think you need to have, like, a right brain qualitative review of everything in your cycle. So what we do is, we do a bottoms up deal by deal analysis, and then we go back and compare it to the math model, And whatever AI says, and we go, do we believe the truth of this? And I think if you're really involved in your business, if you're like out talking to customers and listening to them and asking qualifying questions, I think between those three or four dynamics, you should be able to call your business. But I think when you look at the Wall Street Journal, you can, you can tell when there's going to be more cost pressures. So like we spent a lot m…

AI assessment note: “I think there's three pieces. Uh, one is you need like a, a very left brain math model”

Q You said about the weekly review that I really want to dig in on this. When do you do it? How long does it last? Who sets the agenda? Who's invited? Just walk me through it again. I'm an angel investment of yours. I have no idea about weekly reviews.

A Yeah. So, you know, every team's probably dependent. I think if I were like generalized, it's an hour and a half a week, right? Um, the 1:30 minutes is free form, which is, you know, maybe it's because there's an urgent deal and we just need to like pivot into whatever senior leadership might need that week, or I have, you know, a house on fire we need to solve. Great. Let's identify it and swarm. Uh, the second hour is very structured and it's a little bit more looking forward. So I might have an hour And broken into 20 minute slots, and I've got three reviews, right? Maybe that's this quarter or next quarter. And what they're going to do very programmatically is show me two slides. One is the Y slide, and one is the big deal review slide. In the Y slide, what I'm going to do is say, I want you to tell me exactly through the lens of the CEO's long range priorities. Maybe it's a CIO or a CDO or a chief operating officer, but let's take the CEO for the example and say, what are the long range plans? And then you say, great. What's going to inhibit them from hitting that? What would be the value of, of accomplishing those goals? How would you quantify the value of solving that problem? And you kind of go left to right where what's important to them is paramount and far off on the right, you know, if you have, if you use your binoculars is the technology that solves the problem, b…

AI assessment note: “it's an hour and a half a week, right? Um, the 1:30 minutes is free form”

Q schedules. I don't know why I literally bother anymore, but anyway, I think it informs my mindset or some bullshit. Um, compensation wise, how do you think about constructing the right sales comp plans? I have a lot of early first time founders that are like, I hit like five to one, like, I don't know. How do I think about the right sales comp plan for my sales team?

A I think the biggest challenge you want to solve is alignment with how the company, um, reports to their shareholders, whether that's a private or a public company. How is the company measured? And then make sure there's alignment all the way down to how the sales rep is paid. I think in the absence of that, there's going to be a tension point where what the customer wants and what the rep wants is wildly different from what leadership wants. And then you take the salespeople, whether it's a, a first or second line manager, they're in the middle of getting squeezed. Where the people above and below them want wildly different things, and that creates a lot of tension in the cycle. If you've got full alignment that this is how the organization's being measured, this is how the reps being paid, you're driving aligned incentives and then everything starts to work a lot better. So I think if that, like, fundamental principle is there, um, the other problems start to work themselves out.

AI assessment note: “I think the biggest challenge you want to solve is alignment”

Q Can I ask, do you think that you should hire two reps at the same time? Jason Lampkin always says that you need to understand, like, you need to have two at the same time. Otherwise it could just be a shit rap. Is that true?

A I don't know. It's like, uh, it's like a, it's a, I guess we go back to the football analogy. Do you have like two quarterbacks that compete every, I, here's a challenge. If you want the environment where people perform at their best, you need safety. If you want safety, they have to know that you're trusting them, that you've got their back. And if you have two different people kind of competing in the same environment, I don't know if that creates the right environment. I would prefer to go all in and have their back. And if need be, I'll go on sales calls. I'll do all the work with them until the They're ready to go out on their own, and that takes a lot of effort, but if you get the right person with the right potential, absolutely, I'll invest in that person for a few quarters or a year, and then they're off on their own. So, I, I would probably just go with one. That's my, that's just my gut.

AI assessment note: “So, I, I would probably just go with one.”

Q Boom. We've gone for an early sports analogy. Good to, good to get the different demographics in there, Frank. Well done. Um, I want to start though on one of my favorites because I, I go back and forth on this. People tell me I'm wrong. People tell me I'm right. Um, I want to first understand how do you define a sales playbook?

A Uh, repeatable and relevant. Maybe if I'm just gonna like boil down, there's a lot of process and MBA words that, that get lost in there sometimes. Repeatable and relevant. So I think first it's client relevance. So clients don't care about you, your gear, your product, your organization. They care about them, their metrics, their firm. And so it's gotta be client oriented. And then for the rep, it's really hard to ramp in a new firm. Like probably 50% of reps out there, there's something new. It's a new company. It's a new team. It's a new client. It's a new industry. And so It takes six to 12 months to ramp up. If you can have something that's super relevant, it allows the client to get immediate interest in the firm, and it allows the rep to, um, to ramp way faster. So like, for me, I always start with the money, and I work backward, and I focus on TAM, and then I start to build the playbook back from there. So at least I know if I'm on a treasure hunt, and I've got a shovel, and we've got people digging, are they digging in the right spot? And I think that's the question that a lot of, um, sales teams miss. They find it later in the year when it's a bit too late. Does that make sense?

AI assessment note: “Repeatable and relevant. So I think first it's client relevance.”

Q If only I had that in dating. Um, um, I wanted to start there. And again, we said, we said off schedule, I'm going straight for it. You said it was like a PhD in sales. What did you learn in that PhD of sales very early on?

A Uh, if I were to stack rank, uh, recruiting, like the art and science of recruiting, a big part of it is how do you recruit a college student to go sell knives? You sell them to your mom, your aunt, their friend. And then at some point they end up guzzling out. But The, the ability to, to recruit people to go do it. If you can recruit good people, you're going to have a lot of success. And that that's carried on with me my entire career, which is if I get the best people and I treat them great by definition, they hit their goals. I'm hitting my goals and the company's happy. So I think like the idea of recruiting the best people and it stuck with me. And then I was an intern, uh, for a recruiting firm and I enjoyed that a lot. So it's like, that's kind of the bedrock of my whole approach as a sales leader.

AI assessment note: “If you can recruit good people, you're going to have a lot of success.”

Q How, how did your sales approach change remote with COVID?

A I'd say there's two things that I learned during COVID. One is if you're, if you're a hunter rep, if you're like an SMB, it's really, really hard. You're trying to build a relationship from scratch. Fortunately, we were in the enterprise space, so we didn't have that. But in the enterprise space, I think like one thing that we would do is we build like a big executive briefing and we would send Uber Eats gift cards to everyone who would be a part of that briefing. And we would have like a really nice digital experience. And we were trying to sort of like bring in the events team and get really kind of Uh, clever and crafty and make it fun and exciting for the customer. Um, and then on the internal side, we would do a lot of virtual happy hours, like right at the very, very beginning when people were scared, just like, how do you kind of bring morale up, but people get people connected. Um, but I think now that we're on the back end of COVID, um, I think the value of face-to-face when you can do it and it's safe, I think we need to bring that back.

AI assessment note: “we would build like a big executive briefing and we would send Uber Eats”

Q You said about setting them up for success there. It's one thing that I find a lot of founders really struggle with, which is like new rep onboarding, especially when they haven't really done it before. I'm joining your team today. What does my rep onboarding look like for you in an ideal fashion?

A It's a little bit contrarian, and we talked, we've talked about a couple pieces, but like, let's take Humpty Dumpty apart and look at Q-one. The first thing I want to do is, I want to build an account plan, but let's call that a hypothesis. That way, we're immediately starting to take action. We're mobilizing both the sales team and the extended team, but immediately from there, I'm going to pause and say, great, let's go do the TAM analysis, and we've talked about that. We broke that down already. Like, where's the money? Where's the opportunity? From there, I'm then going to align the sales process To where that revenue opportunity is. And if I'm doing my job right, I'm running an and business. I'm going to pick off some of the small deals along the way. I'm going to go for the big bet. And ideally there's a path to hit my quota both ways. So at the end of the year, if I intersect and both hit, I'm going to have a monster year. If one of the two hit, I'm going to have a pretty good year. From there, the third step is we're going to create like an industry playbook. I think playbook, it's sort of like this ambiguous term. So I don't mean like the PhD version of a playbook. What I mean is I'm a sales rep. I'm about to go on a call. Um, what I don't want to do is go prepare all the materials. I just want to go out and make the sales call. So let's say you're walking out, like I'…

AI assessment note: “The first thing I want to do is, I want to build an account plan”

Q Boom. We've gone for an early sports analogy. Good to, good to get the different demographics in there, Frank. Well done. Um, I want to start though on one of my favorites because I, I go back and forth on this. People tell me I'm wrong. People tell me I'm right. Um, I want to first understand how do you define a sales playbook?

A Uh, repeatable and relevant. Maybe if I'm just gonna like boil down, there's a lot of process and MBA words that, that get lost in there sometimes. Repeatable and relevant. So I think first it's client relevance. So clients don't care about you, your gear, your product, your organization. They care about them, their metrics, their firm. And so it's gotta be client oriented. And then for the rep, it's really hard to ramp in a new firm. Like probably 50% of reps out there, there's something new. It's a new company. It's a new team. It's a new client. It's a new industry. And so It takes six to 12 months to ramp up. If you can have something that's super relevant, it allows the client to get immediate interest in the firm, and it allows the rep to, um, to ramp way faster. So like, for me, I always start with the money, and I work backward, and I focus on TAM, and then I start to build the playbook back from there. So at least I know if I'm on a treasure hunt, and I've got a shovel, and we've got people digging, are they digging in the right spot? And I think that's the question that a lot of, um, sales teams miss. They find it later in the year when it's a bit too late. Does that make sense?

AI assessment note: “repeatable and relevant. Maybe if I'm just gonna like boil down”

Q You said about setting them up for success there. It's one thing that I find a lot of founders really struggle with, which is like new rep onboarding, especially when they haven't really done it before. I'm joining your team today. What does my rep onboarding look like for you in an ideal fashion?

A It's a little bit contrarian, and we talked, we've talked about a couple pieces, but like, let's take Humpty Dumpty apart and look at Q-one. The first thing I want to do is, I want to build an account plan, but let's call that a hypothesis. That way, we're immediately starting to take action. We're mobilizing both the sales team and the extended team, but immediately from there, I'm going to pause and say, great, let's go do the TAM analysis, and we've talked about that. We broke that down already. Like, where's the money? Where's the opportunity? From there, I'm then going to align the sales process To where that revenue opportunity is. And if I'm doing my job right, I'm running an and business. I'm going to pick off some of the small deals along the way. I'm going to go for the big bet. And ideally there's a path to hit my quota both ways. So at the end of the year, if I intersect and both hit, I'm going to have a monster year. If one of the two hit, I'm going to have a pretty good year. From there, the third step is we're going to create like an industry playbook. I think playbook, it's sort of like this ambiguous term. So I don't mean like the PhD version of a playbook. What I mean is I'm a sales rep. I'm about to go on a call. Um, what I don't want to do is go prepare all the materials. I just want to go out and make the sales call. So let's say you're walking out, like I'…

AI assessment note: “The first thing I want to do is, I want to build an account plan”

Q and I said, who's the best sales guy? And he was like, oh, Frank. So I know your game. I know your game. Um, but you've mentioned like hiring many, many times. We're going to get back to playbooks and accounts, but I just want to touch on it because we're so on it now. How do you advise me on the hiring process for sales reps? Let's start there.

A I think fit. It's like, how do you, how do you buy a suit? It doesn't really matter like the color or the fat. It's like, does it fit you? Was it bespoke? Was it made for your frame? Right? So for me, it depends on the account. And so you look at a spectrum of like SMB to strategic sales. The answer is going to be wildly different. I'll probably talk about the enterprise component, which is top in a commercial to, to strategic. So for me, it's about fit. So if I've got, if I've got an account that has multiple reps on it, um, the team chemistry is really difficult, but I always want the closer upfront. Because they have to carry it all the way from one end of the field all the way down. But I'm also going to want to bring in like a visionary. Sometimes they're more academic. They're super right brain, very creative. They can build a vision and bring the organization along. They may not be as comfortable closing. And then the third profile of people I want to pick up is the person that wants to go hunt and take down every deal. Let's like see a bear, shoot a bear. And that's on, that's on something that I was like super talented at. I wanted to go kind of big game hunting, but you, If you're going to run an and business, you need a collection of those different skills, and you put them all together. So like, I, you want to find those people, and then at a chemistry level, figure…

AI assessment note: “you need a collection of those different skills, and you put them all together”

Q So many people on the show have said before about the importance of like recording sales calls for training purposes. How do you think about the importance of that whilst also retaining the humanity and the, the truth elements, which often people will feel less comfortable sharing when there's a recording?

A I guess that's probably predicated on the fact that we do a lot of video calls. I mean, here we are, you know, you're in London, I'm in the States, we're doing a video call. Um, I, I really miss face-to-face sales. I'm glad that we're getting back there, by the way, but, like, that's a, that's a different topic. Um, for me, I think, like, the feedback loop, which is, I think, where you're going, um, it's less about recording and dissecting. Um, it's also less about waiting a whole quarter and giving feedback, which I think it's really hard, and it never lands well. I, I like to do, like, an obsessive in-the-trenches process with my team, where we spend a lot of time prepping, we do a lot of time role-playing, We go to the meeting together, and the first thing we do when we're done is we go debrief. And the first thing is like, all right, give me some criticism. What did I do wrong? So it's not like me as a leader talking down to someone, like all of us have an opportunity to learn. And then it's like, all right, we're all, we're all in this thing together versus like, you know, how am I being evaluated or critiqued? Because like you go back to safety. If I feel like I'm being critiqued, I'm going to get defensive and I'm not going to get the best output. So I don't like the formal Process. I like just to say, like, how do we get better at our craft? So next time it's going to l…

AI assessment note: “it's less about recording and dissecting. Um, it's also less about waiting”

Q know, the reps. I remember before the show when we chatted, you said even the best sales leaders want to be super reps. And I thought it was kind of confusing because I thought the point was that reps wanted to be sales leaders and sales leaders didn't want to go back down to being super reps. So why do the best sales leaders want to be super reps, Frank?

A Well, there's two kinds of super reps, right? There's the good and the bad, right? So just go in here. So I think like if you're a control oriented leader where you've always got to be, you know, the person in the meeting or like Hey, I did this, or, you know, I'm going to get overly involved, or I'm going to, like, micro this person. That's not great, um, but, but I do think, like, if you want to understand how to drive success in the field, I think if you look at your job as internal, and, and the sales rep is external, and you're, and you're, uh, and you're too far removed from the customer, that's terrifying to me, so I want to be, like, all of our big deals, we do a weekly review, Um, full stop every single week. What are the biggest deals in the week or the quarter of the month or the year? And what I'm going to do is I'm going to get really, really involved, and the second I see something go off the rails, great, I have a two-hour block of my calendar. Cancel whatever you got. Let's get on the phone, and we're going to spend time rebuilding your entire, entire value prop. And then next week, I want to see how that goes. And so I think, like, that's, that's the way that, that I get sort of micro, but it's in the interest of the, of the rep. And the first question, the first question I ask on a big deal review is, what's your goal? Not your quota. What's your goal? What do…

AI assessment note: “if you want to understand how to drive success in the field”

Q What would you say is the biggest mistake that founders make when hiring sales teams today?

A Um, I, I think there's got, there's a maturity curve of an organization going from a few customers to really, really big in scale. And I think, um, as you start to hire the sales team, you're going to get to a maturity point where you want to move up market. Customers have a different expectation. And I think trying to train folks that don't have the enterprise experience and convert them over, I don't think it's setting them up for success. I think you need to be able to find folks that have done this before that bring in the top end of the game and then having really, really good segmentation. SMB, commercial, enterprise, and then alignment by industry. I think you need to hire the proven team that's got experience doing that. Your customers expect it. Um, but you still want the other team to be able to manage the lower end of the business because they really know the organization and the product. So I think it's, it's a compliment to those two things.

AI assessment note: “trying to train folks that don't have the enterprise experience and convert them over”

Q You said create demand that's never existed before. When we chatted before, you said this was one of the most important skills you look for. Can you just explain what that means to me and how I should look for it?

A Yeah, so when we talked about the TAM example, where demand is known or unknown, I think, like, how do you create money that doesn't exist? You go look at the demand that's inbound, and then you look at the latent demand that doesn't exist. That's an immediate way to increase the TAM that you're pursuing without hiring any more people. And so, like, when I think of, um, creating demand that doesn't exist, and you ask someone that, what I mean by that is, what problems does a customer have that they don't understand how to solve, where you've created An answer to them. So go back to like the Frank Slootman example, right? Uh, he works with, he worked with different firms where he'd ask clients what they thought about the product and they were using it in very diverse ways that surprised the organization. So at a product level, they're like, Hey, we didn't design it that way, but customers are using it here. Well, like lean in on that and ask them, well, how are you using it? Why are you using it that way? You go back and align that to the long range plans of the organization. Chances are there's a big gap in execution where they've got a big vision and a big target. They don't know how to get there. So how do you take a malleable platform and create a vision around them that says, oh, you're trying to align and move up market? What if you had better insight into the customer pro…

AI assessment note: “what problems does a customer have that they don't understand how to solve”

Q What advice would you give to a sales leader starting a new role today?

A It's not about you. It's about your team. So I always think that you want to put the customer first. I think you got to put the employee first before the customer. It's always been kind of wild to me that, um, that folks would, would, would be self-focused as a, as a sales manager, because by definition you're as successful as your team is. And so like, I was just reading the book, the go-giver. Um, I want my team to be more successful than I ever Have been. I want them to be able to create wealth for their families. Uh, and so I think the more that I work for them, I serve them, and they know that, and I'll do anything they need for me to do. Um, so I think just like running a very flat organization, uh, being very selfless, um, and driving their success, what I found is not only do they end up producing, it creates a level of incredible loyalty that you really weren't planning on, where sometimes they don't want to leave the nest even when they need to. So it's, it's kind of simple, but I don't see it enough.

AI assessment note: “It's not about you. It's about your team.”

Q sent the schedule and you're like, yeah, whatever. Um, do you see why I was like, don't bother preparing. It's fascinating you said about safety there though, because especially in sales, I get it, but you also want a bit of Well, a lot of healthy competition. You want real quarters ending efficiency drive urgency. How do you create safety with a little bit of fear of not hitting targets?

A Well, look, if you hire the right people that are, um, that are just super competitive, right? It's like athletes on the field. You don't have to worry about that. Like they're, they have the inner drive and the competitiveness that's going to far exceed any pressure that you could ever apply full stop. That's just the way that I operate. I think it goes back to some of the things we started this conversation with. And so like for me, if you get the right people involved, a lot of those problems go away. So how do you find fast horses? You hire a fast horse and guess who they run with? They run with fast horses. Go find the best sales rep that you're going to go find and see who they hang out with in the office and socially. They hang out with top performers. They hang out with winners. And so whenever you're on the interview cycle, the first question I always ask full stop is, hey, top rep, who are your friends? And should I have an opportunity to meet them? Because they're always going to know the best talent. And I think when you bring them in and you drive that competitiveness, all those problems go away.

AI assessment note: “they have the inner drive and the competitiveness that's going to far exceed any pressure”

Q But six months in, I haven't closed a dollar. Are you going, shit, Harry's not great. How do we know whether I'm good or not? Because the sales cycles are so long.

A Yeah, I guess, you know, that's a really good point, especially, you know, if you think about what the, you know, I wonder what the enterprise sales cycle is, probably what, 12 months? Six to 24? 12 to 18 months? Um, I, I think, like, first off, you gotta set them up for success. If it's a big account, and, and they're gonna do a big buy every couple years, you can cyclically understand what the odds are of that person coming in, and I think if it's a one to two year sales cycle and you have someone new, maybe it's more of an 18 to 24 month sales cycle, So if you put them in with the hope that they're going to land it in the first year, you're setting them up for failure. So I think you can prohibit some of that. Um, so I think you either give that account to them in year two, um, or you don't give that account to them at all. So I think, I think that what I think measuring the effectiveness along the way is predicated on setting them up for success at the beginning of the year. But I also think that if you're a team and you're going on sales calls together, you know, if they're doing the job or not, right? Like there's no escape. From, from that. If you're actually giving them ample time to prep, to go on a meeting with them and to debrief, like your job as a leader is to spot that it shouldn't be hard.

AI assessment note: “if you're a team and you're going on sales calls together, you know”