The Exchanges

Q buyer side, like multi-threading, brilliant word. I love how kind of intellectual it sounds. Um, but when we think about multi-threading, often I hear this as well. We said about slipping deal cycles. It's like, ah, our champion left. Um, and you're like, well, build multiple champions. Um, How do you think about the right way to multithread? At what stage it makes sense, and often mistakes that you see?

A Yes, it's like, um, it's like, I think this goes back to customer obsessed. If you, if you've been a rep with two accounts, or if you've got three people covering one account, the common denominator is you've got time to be completely immersed in that company, right? So, let's go through the example. Um, you're dealing with, uh, an organization that sells cell phones, right? Well, you're a consumer. Go buy the cell phone. Uh, or if it's a public firm, go buy the stock and sit in the shareholder meeting. Um, go on Like, go into the inside sales organization, put on a headset, bring them donuts, bring them some, some stuff to, like, say thank you for their time, and listen in to what their customers are challenging them with. So Harry, you were asking about multi-threading, you know, how do you do it? I think it starts with customer obsession, right? And so, if you really want to understand what the customer needs, I think, like, a traditional sales cycle of thoughtful discovery, and a few meetings, and being single-threaded into, like, one buying unit or one person, That's scary. Like, what if someone leaves the organization? Or like you said, what if the sponsor leaves? Like, that drives problematic approaches. So if you really want to get to know the account, you got to be obsessed. Buy the share. Um, if you're selling to a cell phone organization, go buy the cell phone, go in…

AI assessment note: “start threading in conversations from, like, IT professionals To data, to the line of business”

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... I like to do, like, an obsessive in-the-trenches process”

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: “generalized, it's an hour and a half a week, right?”

Q Do you have more patience with your sales team for that unknown element? Because you're also then engaging in a Process of customer education, which is just traditionally another three to six months at least. Do you have more patience with that? And how do you think about the customer education as an additional challenge to, oh, I get it. I'm replacing something on my budget.

A Yeah, so I think, like, when I think about, like, an industry playbook, right, what I do is, think about the first quarter as a sales, the sales rep. The first thing that you're asked to do is create an account plan. That's good. It gets you organized. It gets the whole squad and team organized. I would argue that you want to have an account hypothesis, and you want to go back and finish that in Q-one. So let's, let's like, let's take this apart piece by piece. First, you want to identify where the TAM is. Where is everyone going to mobilize and drive an and business, right? So where are the dollars? Known, unknown, big, small, near, far. From there, then you want to have a set of industry, um, sort of assets. So, if you want to drive client relevance, um, and you're going to show up to an insurance firm, and you're going to work with, uh, like an insurance claims adjuster, they don't want to see a demo of technology. They want to know, how do you make the life of a claims adjuster easier? How do you get to the scene of the accident faster? How do you detect fraud? How do you ensure payment comes faster? So, like Rosetta stoning everything from technology into the use case and the persona of the person, Now, boom, you have an immediate set of client relevance where they go, well, this person really understands my industry. And on the, on the rep side, they're not thinking so mu…

AI assessment note: “Rosetta stoning everything from technology into the use case and the persona”

Q very strategic large accounts takes a lot of challenges from a product perspective, whether it's SOC II or any of the security requirements. Where do you think are the biggest Not misalignments, but alignment gaps that sales faces. Is it with product? Is it with legal? Is it with, um, design? Is it with customer success? Where are the biggest misalignments that sales has with other functions within the org?

A You know, it's interesting as, as, as I've started, as my career has grown, what I've noticed is a big part of my job is, um, is dealing with all of my parallel, my peers, the extended team. Like that's in some cases, the majority of my job. By the way, the first question I always ask every time I meet with those leaders is how are you measured? What do you need from me? And this is, these are the three things I need from you. And do we have agreement and alignment on what those priorities are for both of us and what the expectations are? So every time we talk, I don't want to go through everything else. Let's start there and then we'll cover the rest of it. So I think like an area where it's, um, it's really hard right now is customer success because they're kind of like the customer might beat them up. The sales team has very different goals than they do. And what I find is a lot of time, the sales team doesn't understand how success is measured and paid. Uh, they don't appreciate the challenges of how hard it is to be a success manager because everybody wants something from you and you've got to be everywhere. But if you're measured against everything, you're measured against nothing, and so I think one way to, to make it that, um, to kind of make that problem smaller, bring success on the sales calls with you. Make sure they're client facing. Have them come in and don't do …

AI assessment note: “an area where it's, um, it's really hard right now is customer success”

Q I agree with you totally. My question is, what's a stumble, and what's a stumble too far?

A Yeah, I think when you, um, it's almost like when you outsource to someone to say, hey, I think you're really good, you've got good potential, there's a big meeting coming up, you've got this. That's crazy. So like for me, what I want to do, whether it's me or one of my leaders, it doesn't matter who in the stack does this, someone who's more experienced, get in the trenches with that person and say, look, you've never had a CEO meeting before, let's figure out how they're going to operate and run the meeting. First off, they might run the meeting, and you're just going to have to go along with it. So whenever you're going to plan for it, You can just toss right out the window, and you don't know that until you go through it, and so for me, it's like during the preparation and the role playing, um, having that senior leader step by step with them to say, here's an experience I went through, but also, ideally, you have a senior leader go with them on that meeting, and they play the role, right? So maybe they're teeing them up with a softball question that they can hit out of the park, or they're there in case it goes off the rails, they can hop in, but I think having sort of like Someone riding shotgun with you in the car, uh, and then, and then giving the freedom to go take the wheel a little bit is really important. But, um, once you get through that handholding process, you g…

AI assessment note: “they're there in case it goes off the rails, they can hop in”

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 I mean by that is, what problems does a customer have”

Q I agree. I think sales is a fucking brutal job. Um, well done. Um, final one for you, Frank. I love this. What one company sales strategy have you been most impressed by recently?

A Uh, I, for me, it's Miro. So now that everything's been remote, of course, we're trying to like ramp that back. Um, I'm super right brain, super creative. I like to grab a whiteboard in an office and like work through stuff. I'm super visual. It's really hard to do remote. I put like a whiteboard up my office. My wife throws it away. Um, and so Miro's like the technology that enables the ability to feel connected as a team, have a, have a connected sort of set of tools and bring all these disparate ideas together. And all that allow the team to rally when you're remote. And then that's now a digital format that you can bring into the office and extend it when you're in person. So that's really been something that's, that's helped us, um, in the last couple of years.

AI assessment note: “Miro's like the technology that enables the ability to feel connected as a team”

Q Do you have more patience with your sales team for that unknown element? Because you're also then engaging in a Process of customer education, which is just traditionally another three to six months at least. Do you have more patience with that? And how do you think about the customer education as an additional challenge to, oh, I get it. I'm replacing something on my budget.

A Yeah, so I think, like, when I think about, like, an industry playbook, right, what I do is, think about the first quarter as a sales, the sales rep. The first thing that you're asked to do is create an account plan. That's good. It gets you organized. It gets the whole squad and team organized. I would argue that you want to have an account hypothesis, and you want to go back and finish that in Q-one. So let's, let's like, let's take this apart piece by piece. First, you want to identify where the TAM is. Where is everyone going to mobilize and drive an and business, right? So where are the dollars? Known, unknown, big, small, near, far. From there, then you want to have a set of industry, um, sort of assets. So, if you want to drive client relevance, um, and you're going to show up to an insurance firm, and you're going to work with, uh, like an insurance claims adjuster, they don't want to see a demo of technology. They want to know, how do you make the life of a claims adjuster easier? How do you get to the scene of the accident faster? How do you detect fraud? How do you ensure payment comes faster? So, like Rosetta stoning everything from technology into the use case and the persona of the person, Now, boom, you have an immediate set of client relevance where they go, well, this person really understands my industry. And on the, on the rep side, they're not thinking so mu…

AI assessment note: “ramping them in weeks instead of months and quarters.”

Q So I totally get you. What is required there is the specialization of sales teams, the verticalization into industry specific. So they are able to get up to speed with the customer, the customer problems, demands. How do you think about advising founders on how to specialize sales teams? When's enough customer demand? And if you were them, what would you advise them?

A Yeah, I think it's about, like, assembling a good team is really, really hard. Like, you know, chemistry and talent, and is this person with this experience going to do really well? So you ask the word patience, yeah, that's a big part of it, and like, stepping them through it, working with them, but I think the fastest and easiest way to do it is, let's say you're going to have an established team that has two or three people on it. You're going to get someone up front leading, like the quarterback that owns the whole process that's been there, done that. You're going to take the high potentials, put them inside that team, And then over time, they're naturally going to learn that process because they're following the leader, and they're going to get there a whole lot faster. So doing it one by one as a sales leader would be really hard to, like, literally teach every seller, but if you selectively build teams in the right way, then you're having the team teach the team, and that starts to drive scalability and repeatability, and you're not doing everything yourself, right? So I think that's the way that, that, that you do that at scale. And also, if you get really good people that care about each other and they're competitive, even if they're not on the same team, they want to help each other, And you want to reward that and incent that and ask people to step up and help you. …

AI assessment note: “if you selectively build teams in the right way, then you're having the team teach the team”

Q buyer side, like multi-threading, brilliant word. I love how kind of intellectual it sounds. Um, but when we think about multi-threading, often I hear this as well. We said about slipping deal cycles. It's like, ah, our champion left. Um, and you're like, well, build multiple champions. Um, How do you think about the right way to multithread? At what stage it makes sense, and often mistakes that you see?

A Yes, it's like, um, it's like, I think this goes back to customer obsessed. If you, if you've been a rep with two accounts, or if you've got three people covering one account, the common denominator is you've got time to be completely immersed in that company, right? So, let's go through the example. Um, you're dealing with, uh, an organization that sells cell phones, right? Well, you're a consumer. Go buy the cell phone. Uh, or if it's a public firm, go buy the stock and sit in the shareholder meeting. Um, go on Like, go into the inside sales organization, put on a headset, bring them donuts, bring them some, some stuff to, like, say thank you for their time, and listen in to what their customers are challenging them with. So Harry, you were asking about multi-threading, you know, how do you do it? I think it starts with customer obsession, right? And so, if you really want to understand what the customer needs, I think, like, a traditional sales cycle of thoughtful discovery, and a few meetings, and being single-threaded into, like, one buying unit or one person, That's scary. Like, what if someone leaves the organization? Or like you said, what if the sponsor leaves? Like, that drives problematic approaches. So if you really want to get to know the account, you got to be obsessed. Buy the share. Um, if you're selling to a cell phone organization, go buy the cell phone, go in…

AI assessment note: “threading in conversations from, like, IT professionals To data, to the line of business”

Q Can I ask, you know, speaking of like high potential, but maybe not quite there yet. One thing I do struggle with often in enterprises, I enterprise sales cycles along and measuring rep effectiveness is naturally harder. How do you think about measuring rep effectiveness in strategic sales with much longer sales cycles?

A Let's take two examples. One, one example is you've got a big account that you're pursuing, um, and you've got two or three reps. The first thing I do is grab the hypo and put them inside of that organization, right? So they're, they're, they're teaming along with it. Uh, if not, I think there's a, there's a level of, uh, babysitting, and I say that as a positive term, not a negative term, where I'm gonna sit side by side with that rep. And so, like, a big part of my day is I clear two to three hours that I have no plans for, specifically so a rep says, hey, I've got a big account meeting coming up, and I feel stuck, or I have an account meeting coming up, and I want you to join, I can immediately, I will immediately clear my calendar and say, let's get in the, let's get in the trenches. So I'm literally personally teaching them and bringing them along, um, and never letting them out on their own until they're ready to go. So like that, and, and so there, I don't think there's any substitute for on like handholding on the ground training. And so the only way that you do that is personally getting involved. And so that's why we just run a super flat organization. I could care less what my title is or what yours is. We all have the client's interest in mind. Let's get together and go. So like I'm a rep, put me to work and that's my mentality. And I think the team appreciates that…

AI assessment note: “The first thing I do is grab the hypo and put them inside of that organization”

Q How do you create the slides? I know it sounds stupid, but is this like Google slides? And then how do you share them across the team? Because I love that in terms of a way to run people efficiently. It's fantastic. But what do you use in practice?

A Um, so, so first off, I drive people crazy. So like I did this personality test a few years ago with my coach. And what I found out is I'm, I'm off. I'm, I'm full blown left brain and right brain at the same time. Normally someone's very dominant on one side or the other. And I'm both. Which means I drive people crazy. I have a lot of ideas that I want to execute. And so in the absence of focus, I'm everywhere. Like I'm the absent-minded professor. And so what I have to do is get really, really focused on, um, what's the idea? How do we prioritize, stay on message, and then execute with focus? So that's one of those learnings as a leader that I've, that I've tried to get better at over time. So a big part of what we do as a team is we want to bring the creative energy in. We want to bring the right people, not to conform to our group, but bring in a lot of diverse set of Uh, of experiences and personalities and, and perspectives. So we do like a lot of right brain, creative, whiteboardy stuff to, to come together on, hey, we tried these five different points with a customer, three fail, two work. Let's go in on those two. So it's very much trial and error. So like mistakes, very encouraged in our group. So if you screwed up and the client meeting went poorly, great, like tell us so we don't go do that again. And so whenever we build the playbook, they'll end up in slides. But t…

AI assessment note: “And so whenever we build the playbook, they'll end up in slides.”