The Exchanges

Q Do not worry. My ego is sufficiently inflated anyway. I will be fine. Uh, but I do want to finish on my favorite, actually. Which is, other than, you know, Evalore, what one company sales strategy have you been most impressed by recently?

A Oh, gosh. Hmm. It was a while back, but I think one of the plays that I think really helped me, even during the pandemic, so we, we bought people AI during the pandemic at TripActions.com. And it was initially to go get like contact capture so we can build our, our, our, our database to go, um, track activity and go, um, go better do marketing to those folks. And they sort of do this thing where they did the like, Hey, we know you don't want to buy this expensive analytics offering, but we think he can give you some insights. And I'm like, no, no, I got a great analytics team. CKC is the best on the planet or roll the size, like amazing. Like we got our own stack. We're good. And, and they were like, well, just, you know, we'll give it to you for free for six months. Just try it out. Like we'll help you implement it and stand it up. And if it's anything other than amazing, like you don't have to pay for it, but they built it into the contract. So it was like premium and an enterprise software sale. They sort of built a freemium thing into the contract. They worked with us to stand it up and make it successful. And sure enough, we signed, you know, we signed the check to do the, the broader sort of broader platform buy after that was done, despite A lot of skepticism on my part that it was valuable. Now that's not to say, you know, that's the, the only way to do it, but in a wor…

AI assessment note: “they sort of built a freemium thing into the contract”

Q What are the most common reasons that you don't get deals over the line?

A I think there's a few places that comes up. Number one is you never had true buy-in at the, to start with. You didn't do the deal the right way, yet you're trying to prosecute and just go through the sales stages. I'll send out contracts, you know, boss, I got 10 contracts out. All right, are any of them going to sign, right? By when, by what? Actually trying to do the contracting and the, like, operational sale without actually getting over the hump with your champion, with your economic buyer, with a business case that matters. Um, that's a huge issue, particularly right now in a changing market. Um, uh, second one is not getting to the economic buyer and actually selling to them. Right now the, oh, I got, you know, I got the EB back behind the scenes. That's not a true champion. You don't have a deal. Those are probably the things that are hurting deals the most right now in this current environment and this changing.

AI assessment note: “Number one is you never had true buy-in at the, to start with.”

Q Dale Revees. How often do you do them? What makes a good deal review versus a bad one? How do you structure them?

A Yeah. Um, yes, we do them. Bad deal review is everybody get in a room. Let's go talk about the deal. See what happened. Right. Great deal review. Um, you know, my, my, uh, my successor at the Vine, Carlos is, I think who you've met also, uh, has like this nice little simple MedPic template that I stole from him. Thank you, Carlos. Uh, which is, uh, literally like, all right, let's actually go through and, and see, use a framework, any framework, MedPic, you build your own, right? Command of the message, like, you know, what's the pain? What's the negative consequences? What are the outcomes you want? What are the, the after scenario and positive business outcomes? Use a framework, but be religious about actually using it so that you're not just getting in there. All right, what's going on with the deal? You know, and it's sometimes, uh, doing that for all the key deals that are not necessarily just going to close in a quarter, but that you need to go evolve from whether it's 10 or 25% stage to the 50, 90% stage. That's actually where the impact is driven. Like, when we're looking at the deals that are supposed to close this quarter, it's like, all right, Do you have a closed plan? Do you have access to the EB? Have you quantified the metrics? Have you done the validation steps? It's actually that cohort of deals that's like going from whatever you call it, that we've done the d…

AI assessment note: “Bad deal review is everybody get in a room... Great deal review... Use a framework”

Q Not at all. The pleasure's mine, but I want to start with a little bit on you, because you've worked with some of the most incredible orcs in, in the last kind of 10 years of business building, really, and so I want to start with how did you make your way into the world of tech and sales first?

A Yeah, yeah, it's a great question. First of all, it's, uh, it's, uh, there's a lot of luck involved. I think it's a lot easier to see things going back than looking forward. Um, but I, I started my career as a, as an engineer, biomedical engineer. My parents are both engineers, we're immigrants, and so that idea of get a technical degree, get a technical background, and then, you know, you'll always have work to do was a little bit of what I grew up with. But after finishing, I realized, oh, wow, I, Watch the movies. I, I see TV, and I really wanted to be some kind of a business executive someday. I didn't really know what that meant, uh, and I thought, okay, this was during the, uh, dot-com bubble burst, so there weren't a lot of jobs out there, and I was reading and doing my research and going, huh. You know, it looks like a lot of these, uh, these, uh, business leaders, these CEOs, they seem to have this, like, sales background. That's interesting. Maybe I should try that, and, uh, and, you know, if I, if it, if I don't, can't do it well, if I suck at it, you know, I'll go back and take one of these engineering offers that I had walked away from, and so my first job was, I was, I think the base salary was like 20,000 dollars, and so it was like, well, if I can't, Make a good commission. I won't pay my rent anyway, so why don't we give this thing a shot for a year? And that w…

AI assessment note: “I started my career as a, as an engineer, biomedical engineer.”

Q What, what else are you seeing with the CRO, COO discussions that you're having? Are you seeing a complete pullback in marketing? What, what other trends are you seeing in this new market? I'm fascinated.

A Yeah. I, I think right now, um, every founder, every board member, every CFO is, is being pushed to say, okay, in this shift from grow to shift to productive growth, What is the operating envelope that we can play in right now, right? I think we're looking, you know, right now, sales leaders, COOs, CBOs, whatever the, you know, president, whatever the title is of the person that runs a go-to-market, um, is being asked to say, hey, how do you demonstrate that you are building an effective and productive go-to-market on a per rep basis, on a per C basis, whether it's my support org, my CS org, my AEs, my SDRs, my partner people. I'm trying to figure out what is, how do I actually measure the effectiveness and productivity of that org? Bookings per head rep, ops per rep, source dollars per marketing spend. If I can start to normalize those investments to metrics that actually matter, and I can start comparing to each other, then I can start making the trade-offs of, wow, is my cost per new booking customer or new booking dollar, is that actually better or worse with An SDR lead, or a marketing inbound, or an AE outbound, if I say they're going to spend a quarter of their time doing pipeline generation. That's the kind of effort that I think, even with, you don't need some, you know, crazy, expensive analyst to do that, to just start having that conversation and actually making tho…

AI assessment note: “shift from grow to shift to productive growth, What is the operating envelope”

Q What, what else are you seeing with the CRO, COO discussions that you're having? Are you seeing a complete pullback in marketing? What, what other trends are you seeing in this new market? I'm fascinated.

A Yeah. I, I think right now, um, every founder, every board member, every CFO is, is being pushed to say, okay, in this shift from grow to shift to productive growth, What is the operating envelope that we can play in right now, right? I think we're looking, you know, right now, sales leaders, COOs, CBOs, whatever the, you know, president, whatever the title is of the person that runs a go-to-market, um, is being asked to say, hey, how do you demonstrate that you are building an effective and productive go-to-market on a per rep basis, on a per C basis, whether it's my support org, my CS org, my AEs, my SDRs, my partner people. I'm trying to figure out what is, how do I actually measure the effectiveness and productivity of that org? Bookings per head rep, ops per rep, source dollars per marketing spend. If I can start to normalize those investments to metrics that actually matter, and I can start comparing to each other, then I can start making the trade-offs of, wow, is my cost per new booking customer or new booking dollar, is that actually better or worse with An SDR lead, or a marketing inbound, or an AE outbound, if I say they're going to spend a quarter of their time doing pipeline generation. That's the kind of effort that I think, even with, you don't need some, you know, crazy, expensive analyst to do that, to just start having that conversation and actually making tho…

AI assessment note: “in this shift from grow to shift to productive growth”

Q um, zoom info on the show, and he said they're actually having to change that org structure because of the challenge of renewals being so much harder. And so they're actually placing a lot more people in data and data kind of enforcement, proving out that it's a really efficient tool to use within organizations before everyone just upsold anyway. How are you seeing renewals and what's the impact there?

A Yeah, so, so a couple things I'll caveat that at Everlaw, we, you know, we sell to the government, we sell to, you know, the DOJ, for example, right? We sell to law firms, we sell to corporate legal teams, GCs. So it's different for different folks. Right now, though, the default is the same thing that happens on the pre-sale side is happening on the post-sale side, right? How am I rationalizing the use of this tool or the tool to this degree? What am I actually getting out of it? Can we clean out a bunch of this SaaS proliferation across the company? That is coming across pre and post sale. And so the impact on renewals for the success org is we need to have a pure, like true business justification if we're going to keep, expect that customer to stay with us. So think about it as the converse or the mirror image of what needs to happen in the sales side and why the sales and success side needs to be tightly intertwined. If a lot of these deals, think about how we were doing deals like early days of TripActionsNavon or early days of Everlaw. Awesome product. It's great. You sold to early days of MuleSoft, right? Sold to a developer who's using it for a project. CFO, CIO doesn't care about that, right? They want to centralize on a tool. They don't see it's valuable. Like, they don't care who bought it and what lower level, mid-level person bought it. So how do you do that in the…

AI assessment note: “the impact on renewals for the success org is we need to have a pure, like true business justification”

Q back. Uh, the question I have for you is the case. We both agree that it should actually be the founder building out that playbook. So, uh, then they kind of hire against it. Should they be hiring a sales rep to jack of all trades, dog test it, really just execute on that playbook, or should they hire a head of sales to build out a team beneath them?

A Head of sales has a lot of, can mean a lot of things in, in software and SaaS. It could be a person running a, you know, 500,000 person org. It could be someone who has a CRO title or president title that has no direct reports. So we'll, we'll, we'll use the version of it that we'll define as like, depends on what role, right? I think the, throw the title out the window for a moment. I think that first hire, when I'm looking to scale, I'm looking to scale me out as a founder. I'm trying to figure out how do I get someone who can continue to help me shape this message because it's not all done yet, right? We, I speak, speak about it sometimes like it's binary. It's not, uh, to help scale and continue to refine the go-to-market, um, and can give me some scale so that I'm not doing all the sales, so that I have someone who's close enough to me that's giving the feedback back so that we can iterate on that story, on the, the, the ICP, on the, on the product market fit, yet it's helping me do more of those sales. To me, that could be a player coach. Um, it could be a player who's stretching in a player coach. It could be someone who, Has that sort of creativity, but also can get out in front of the customers and help me continue to hone that message. The next role would be the person who can probably run that first line team and continue to help shape that narrative, but also manage…

AI assessment note: “To me, that could be a player coach. Um, it could be a player”

Q Dude, with the reps, should we hire two at a time? Jason Lampkin's like, hire two at a time. You'll see who's good. Do we do that, or do we hire one?

A Yeah. I'm a big fan of two at a time, right? Again, this is the engineer, me coming out. My wife can't stand it, and the towel's gonna be perfect and stuff. The two at a time thing, right, so much goodness comes out of it. First of all, if you don't have enough conviction in your business that you're hiring a rep to go hire two, get there. Like, get it to the point where you think you have enough for two versus one, because ultimately you're splitting hairs if you're like, oh, well, I think I can support one rep, not two. Fundraise, get more conviction, the product, the story, whatever. But the two point is just so valuable because cohorting in terms of ramping, the supporting each other, the ramping, the competitive elements of it, it's really hard to know, is my product market fit fundamentally wrong? Is the way I'm telling the story fundamentally wrong? Is the, you know, is the PG messaging I'm using fundamentally wrong? Or is it the rep that sucks or the rep that can't figure it out? Having two helps to at least give you the minimum viable, like, Separate the two and give you a little bit of signal about what's happening, right? Now again, if you hire two great reps, awesome, you have two bad reps, like, you know, maybe you gotta press restart and, and, uh, and do it again, but at least it helps to neutralize for that.

AI assessment note: “Yeah. I'm a big fan of two at a time, right?”

Q I want to talk about some of the art of sales though, which is a quarter kind of doing it well, and I'm going to pepper you with questions. Number one, discounting. Do you do discounting? How do you advise founders on discounting?

A Depends on what is, what is the model I'm trying to run, right? Every, every approach has trade-offs. If I'm trying to do, like, it's a crowded race, it's a knife fight, we got to capture share, I'm gonna do the lowest that I can possibly maintain from a margin standpoint to capture that share and do it efficiently, then raise the prices. Is it a, hey, we think we built, even in a crowded space, the best product, It's at a premium. I can clearly tell a story that is defensible and differentiated when I get into that room with the CFO and tell them why it should be worth more. Um, those are pretty different approaches. If I'm a lot of the founders I speak with, you know, will probably tell me, Hey, we, we, and Everlaw is the same way. We think we built the best product. We think we have the best team. We demonstrably get in the room and people say, yep, you guys are the best product. You've got built the best thing by far. Then it becomes a question of how much of a premium can I charge? And that, That premium depends on how well I can tell the story, quantify the value, have proven results for delivery, and so from that standpoint.

AI assessment note: “Depends on what is, what is the model I'm trying to run”

Q What are the most common reasons that you don't get deals over the line?

A I think there's a few places that comes up. Number one is you never had true buy-in at the, to start with. You didn't do the deal the right way, yet you're trying to prosecute and just go through the sales stages. I'll send out contracts, you know, boss, I got 10 contracts out. All right, are any of them going to sign, right? By when, by what? Actually trying to do the contracting and the, like, operational sale without actually getting over the hump with your champion, with your economic buyer, with a business case that matters. Um, that's a huge issue, particularly right now in a changing market. Um, uh, second one is not getting to the economic buyer and actually selling to them. Right now the, oh, I got, you know, I got the EB back behind the scenes. That's not a true champion. You don't have a deal. Those are probably the things that are hurting deals the most right now in this current environment and this changing.

AI assessment note: “Number one is you never had true buy-in... second one is not getting to the economic buyer”

Q nervous to do one and commit and burn the boats on PLG or just be a top-down enterprise org. For me, I think that's a big mistake. I might be totally wrong because I'm a VC. It's my prerogative to have opinions and be wrong. You're the CRO who knows. When, when doing PLG and enterprise, can you do both at the same time? And what are the thoughts here?

A I would say it's, it's, and again, operational definition enterprise can mean a lot of things to a lot of people. It can be any company that's not an SMB. It can be large enterprises like You know, Coke or Pepsi or, or, uh, sorry, Coke or Walmart or Nike. Um, for operational definitional purposes, let's, let's say enterprise meaning, uh, the, you know, few couple 100,000, few 100,000 dollars sales rep in a long protracted, you know, six to 12 month sales cycle. Uh, and PLG will call sort of pure sort of online self-sell, self-serve. And then there's probably something in the middle of it, which is like a velocity, uh, Sales assist or sort of inside or sort of inside outside hybrid model. So again, spectrum, right? I want to make sure we don't fall into the camp of everything is binary. Um, but I would say at a high level, um, I agree that it's really hard to do both well, right? And it comes back to even how you design your product. So for example, Mule Facebook, Meta Facebook ads is inherently a self-serve platform, right? Built self-serve first. You can use it self-serve. You can now self-onboard. Everything is built such that you can do it without any handholding. And so the way that you build the people org around that naturally is, okay, well, let's make sure we can get everybody self-serving and then using that as your funnel to figure out, oh, who are the bigger spenders…

AI assessment note: “I agree that it's really hard to do both well, right?”

Q Dale Revees. How often do you do them? What makes a good deal review versus a bad one? How do you structure them?

A Yeah. Um, yes, we do them. Bad deal review is everybody get in a room. Let's go talk about the deal. See what happened. Right. Great deal review. Um, you know, my, my, uh, my successor at the Vine, Carlos is, I think who you've met also, uh, has like this nice little simple MedPic template that I stole from him. Thank you, Carlos. Uh, which is, uh, literally like, all right, let's actually go through and, and see, use a framework, any framework, MedPic, you build your own, right? Command of the message, like, you know, what's the pain? What's the negative consequences? What are the outcomes you want? What are the, the after scenario and positive business outcomes? Use a framework, but be religious about actually using it so that you're not just getting in there. All right, what's going on with the deal? You know, and it's sometimes, uh, doing that for all the key deals that are not necessarily just going to close in a quarter, but that you need to go evolve from whether it's 10 or 25% stage to the 50, 90% stage. That's actually where the impact is driven. Like, when we're looking at the deals that are supposed to close this quarter, it's like, all right, Do you have a closed plan? Do you have access to the EB? Have you quantified the metrics? Have you done the validation steps? It's actually that cohort of deals that's like going from whatever you call it, that we've done the d…

AI assessment note: “Bad deal review is everybody get in a room... Great deal review... use a framework”

Q couple of areas of your career. Cause as we said, incredible organizations, and we're going to do like a quick fire at the beginning, uh, to get to know each other. This is why I'm single. Cause I actually do this on dates too, but we're going to start with matter. Okay. What was your biggest lesson from your time with matter and how did it impact your operating mindset?

A So I, I convinced myself, I, I got a, I got a job there by, by whittling my way into Cheryl and down to David and, and Grady, uh, to do basically strategy and ops work, like this big segmentation tiering project. And I was coming from outside the industry, never done it before, but, you know, I pitched, pitched that because I did a lot of that work in my prior company. One of the things I learned most about that company, and I know that sometimes it's derided is, Move fast and break things. Like the idea that you don't have to be perfect, but sometimes, especially in a fast changing market, speed is at a 10 X premium. Um, that was a lesson that was, that was huge for me because I came out of this investment shop, high focus on compliance and regulatory and don't break the law, do things perfectly right following this process into an organization where even at the time I joined, it was over a thousand people. So I don't know, a 1002 thousand people. Going like, hey, everyone just try to do the right thing, experiment, move fast, break things, and maybe a few of these will work, and then we'll start doing more of that. And to me, that was mind-blowing, but I think that really balanced out a lot of how I think about scaling now, which is there are times when you want to really strive for, we got to do things right, we got one cut at this thing, it's a glass ball, it's not a rubber…

AI assessment note: “One of the things I learned most about that company... is Move fast and break things.”

Q What are the biggest fuck-ups that you see people make?

A Biggest fuck-ups would be, one is staying too close, right? I speak sometimes with founders who have, like, 10 sales reps reporting directly to them. That is, like, that makes no sense. Five sales reps reporting directly, makes no sense. It completely impedes And then you also build this, like, sales model where, like, you are de facto head of sales or head of revenue, and, and you're doing, you're starting to play in territory that you might not be good at in terms of coaching and developing and holding accountability, metrics, comp plans, all that stuff. So, so I think that to me is a, hey, you maybe moved a little quickly against it, or sorry, too slowly against it. Too quickly would be in a couple flavors. One is you hire someone who's, like, really large scale that Has aspirations to be an early startup, thinks it's cool to be in an early startup, maybe was in an early startup 10 years ago or 20 years ago as your first person. And again, Gokul's post on LinkedIn, you should check it out, like, talks about, like, they don't really know what to do, or they can't do it without hiring a bunch of other people to do it. That's a telltale sign of, like, okay, this person's too far, or has been too far from it for too long, and either isn't willing or able to To go step back and get their hands dirty to the degree I need done. Hey, build a comp plan from scratch. Build me a sales …

AI assessment note: “Biggest fuck-ups would be, one is staying too close, right?”

Q Dude, with the reps, should we hire two at a time? Jason Lampkin's like, hire two at a time. You'll see who's good. Do we do that, or do we hire one?

A Yeah. I'm a big fan of two at a time, right? Again, this is the engineer, me coming out. My wife can't stand it, and the towel's gonna be perfect and stuff. The two at a time thing, right, so much goodness comes out of it. First of all, if you don't have enough conviction in your business that you're hiring a rep to go hire two, get there. Like, get it to the point where you think you have enough for two versus one, because ultimately you're splitting hairs if you're like, oh, well, I think I can support one rep, not two. Fundraise, get more conviction, the product, the story, whatever. But the two point is just so valuable because cohorting in terms of ramping, the supporting each other, the ramping, the competitive elements of it, it's really hard to know, is my product market fit fundamentally wrong? Is the way I'm telling the story fundamentally wrong? Is the, you know, is the PG messaging I'm using fundamentally wrong? Or is it the rep that sucks or the rep that can't figure it out? Having two helps to at least give you the minimum viable, like, Separate the two and give you a little bit of signal about what's happening, right? Now again, if you hire two great reps, awesome, you have two bad reps, like, you know, maybe you gotta press restart and, and, uh, and do it again, but at least it helps to neutralize for that.

AI assessment note: “Yeah. I'm a big fan of two at a time, right?”

Q um, zoom info on the show, and he said they're actually having to change that org structure because of the challenge of renewals being so much harder. And so they're actually placing a lot more people in data and data kind of enforcement, proving out that it's a really efficient tool to use within organizations before everyone just upsold anyway. How are you seeing renewals and what's the impact there?

A Yeah, so, so a couple things I'll caveat that at Everlaw, we, you know, we sell to the government, we sell to, you know, the DOJ, for example, right? We sell to law firms, we sell to corporate legal teams, GCs. So it's different for different folks. Right now, though, the default is the same thing that happens on the pre-sale side is happening on the post-sale side, right? How am I rationalizing the use of this tool or the tool to this degree? What am I actually getting out of it? Can we clean out a bunch of this SaaS proliferation across the company? That is coming across pre and post sale. And so the impact on renewals for the success org is we need to have a pure, like true business justification if we're going to keep, expect that customer to stay with us. So think about it as the converse or the mirror image of what needs to happen in the sales side and why the sales and success side needs to be tightly intertwined. If a lot of these deals, think about how we were doing deals like early days of TripActionsNavon or early days of Everlaw. Awesome product. It's great. You sold to early days of MuleSoft, right? Sold to a developer who's using it for a project. CFO, CIO doesn't care about that, right? They want to centralize on a tool. They don't see it's valuable. Like, they don't care who bought it and what lower level, mid-level person bought it. So how do you do that in the…

AI assessment note: “the impact on renewals for the success org is we need to have a pure”

Q And how do you tell that? Do you look in Pipedrive and see, do you look in their calendars and see their email?

A Yeah, so, so I'm, I'm looking at, so there's as tactical as activity, but if we could set up basic Salesforce reporting on how many, you know, ops they're generating, how, a good rule of thumb is like an AE in my book should be generating at least a new op a week. By themselves, without SDRs, without marketing, helping them in an enterprise software sale, outbound sale. Are you at least doing one off a week? If you're not, okay, are you doing activity? How are you doing it? Do you actually know how to do it? That's the hardest part of selling. If they don't have either the appetite or the skill to do that, you better get it fast because you're not going to work here. And granted, we should be vetting for that in our hiring process, going back to what we just talked about. That's number one. Number two is when they just don't seem to grok the product. Like, If I don't, if I can't grok the, like, talk track, how to talk about it, how to, how to use the product, how to share it, yes, and we talked about not going straight to a product-led sale, a driven sale, but if they're not showing that at a pretty fundamental level and quickly grappling on, grappling onto those soundbites, talk tracks, um, that's usually a big red flag for me. So between those two, those are pretty early, because those are the precursors to, can you actually get pipe? Can you actually build late stage pipe? C…

AI assessment note: “set up basic Salesforce reporting on how many, you know, ops they're generating”

Q couple of areas of your career. Cause as we said, incredible organizations, and we're going to do like a quick fire at the beginning, uh, to get to know each other. This is why I'm single. Cause I actually do this on dates too, but we're going to start with matter. Okay. What was your biggest lesson from your time with matter and how did it impact your operating mindset?

A So I, I convinced myself, I, I got a, I got a job there by, by whittling my way into Cheryl and down to David and, and Grady, uh, to do basically strategy and ops work, like this big segmentation tiering project. And I was coming from outside the industry, never done it before, but, you know, I pitched, pitched that because I did a lot of that work in my prior company. One of the things I learned most about that company, and I know that sometimes it's derided is, Move fast and break things. Like the idea that you don't have to be perfect, but sometimes, especially in a fast changing market, speed is at a 10 X premium. Um, that was a lesson that was, that was huge for me because I came out of this investment shop, high focus on compliance and regulatory and don't break the law, do things perfectly right following this process into an organization where even at the time I joined, it was over a thousand people. So I don't know, a 1002 thousand people. Going like, hey, everyone just try to do the right thing, experiment, move fast, break things, and maybe a few of these will work, and then we'll start doing more of that. And to me, that was mind-blowing, but I think that really balanced out a lot of how I think about scaling now, which is there are times when you want to really strive for, we got to do things right, we got one cut at this thing, it's a glass ball, it's not a rubber…

AI assessment note: “One of the things I learned most about that company... is, Move fast and break things.”

Q What are the biggest fuck-ups that you see people make?

A Biggest fuck-ups would be, one is staying too close, right? I speak sometimes with founders who have, like, 10 sales reps reporting directly to them. That is, like, that makes no sense. Five sales reps reporting directly, makes no sense. It completely impedes And then you also build this, like, sales model where, like, you are de facto head of sales or head of revenue, and, and you're doing, you're starting to play in territory that you might not be good at in terms of coaching and developing and holding accountability, metrics, comp plans, all that stuff. So, so I think that to me is a, hey, you maybe moved a little quickly against it, or sorry, too slowly against it. Too quickly would be in a couple flavors. One is you hire someone who's, like, really large scale that Has aspirations to be an early startup, thinks it's cool to be in an early startup, maybe was in an early startup 10 years ago or 20 years ago as your first person. And again, Gokul's post on LinkedIn, you should check it out, like, talks about, like, they don't really know what to do, or they can't do it without hiring a bunch of other people to do it. That's a telltale sign of, like, okay, this person's too far, or has been too far from it for too long, and either isn't willing or able to To go step back and get their hands dirty to the degree I need done. Hey, build a comp plan from scratch. Build me a sales …

AI assessment note: “Biggest fuck-ups would be, one is staying too close, right?”

Q What would you most like to change about the world of sales?

A I would love to see more people get into it instead of feeling like, you know, when I got into sales, that was a, that was a gangly, Engineering student from Yale, and I had this understanding that it was for like, you know, slick, well-spoken, um, white guys that could tell the story the right way, and I sort of had that chip on my shoulder, um, and I would say that I would love to see more people consider it as a career coming out of any major with any background, um, uh, because it's an amazing career. I've learned a ton. I've met some really cool people doing it, and the reason I'm still doing it is because I keep learning, and I keep figuring out ways to Um, to do it differently, and in an environment where maybe AI is going to take our jobs, The ability to go connect with people in a real way, the ability to go show value, the ability to go do deep discovery, um, I think that's at a premium.

AI assessment note: “I would love to see more people get into it”

Q big company, baby. We are big players. You got too much cash with that. Okay. So I'm going before we used to rock up, show you the product and you go, Ooh, shiny. And now it's like sell to our CFO, sell to procurement. What does that mean? We need to change. Doc wise, team structure wise, should we not invest in product or growth? Should we invest in sales?

A If I'm a founder, and that's the environment I'm in right now, and I advise and invest in a number of companies who are going through this exact same thing right now, right? The sale is real different for sales automation or, you know, whatever the technology is just six or 12 months ago. Um, right now, I'm not necessarily saying it's, it's a person, but what I need to figure out in the jobs to be done model is like, I need to figure out What is the problem my product solves and for whom, right? By getting back to that exact, okay, what is the problem I solve and for whom and how do I quantify that thing and how do I make sure that that problem I solve is actually something that the CFO, the CEO, the COO actually cares about right now, right? Cutting costs, running an efficient business, sales productivity, you know, margin. I need to be able to make sure I can map back my narrative of what my product does and To that big thing. And unless I can do that, I'm not going to get in the room. That can be a, you need a big, bad enterprise sales leader to do it. You could be, you need some marketer to do it, but fundamentally it could be sitting down with your advisors or your investors to say, hey, how do I map that back right now? So I'm sitting with Jonathan Friedman at demo stack a couple of weeks ago, and he's like, hey, we're trying to work on this thing. Great. Okay. You have a…

AI assessment note: “I need to be able to make sure I can map back my narrative”

Q Okay, so a quick one before we talk about hiring, which I can't wait for. Which one's easier to start in?

A It's a good question. As, as a go-to-market leader, I'm, I'm a bit of a, an orthodox person who's done consumer, B to B, B to B to C, Large enterprise, velocity, PLG. Uh, so I've seen a lot of different businesses through a lot of different stages of different motions and different sort of spaces. The intellectual answer would be, it depends on which one, which space you're in and what your DNA is, right? If I'm a large enterprise seller to come out or large enterprise sales leader to come out and say, Hey, now we'll do a velocity motion. That shit's hard, right? Cause you, you know, you don't have a lot to go off of. If I'm an SMB velocity sales leader that runs 300 person inside sales teams, then I'll try to figure out an enterprise sales motion. Like that might be hard for other reasons. So I think a lot of it depends on what space you're in and which business you should build. Like if I'm building a security company doing enterprise security, I should probably start at the top of the market and then go down because that's where the inherent need is biggest. And if I'm building, you know, like an ads business, right? It's an online ads business publisher, like Facebook going bottoms up was absolutely right. So if I were trip actions, a B to B to C, That's done sort of a mid-market down and then mid-market up. Like, that was interesting because they started where there was a …

AI assessment note: “The intellectual answer would be, it depends on which one, which space you're in”

Q I have to ask, do you do it on your company, and so you have the domain knowledge that you can judge and value them against, or do you do it on their company where they're operating from a situation of safety and domain experience?

A I've done both. Obviously, with your company, you can see if they can quickly do the research, assimilate all the information they get with how to pitch it, figure out the product, and pitch it back to you. If you do their product, you can demonstrate more about how they would run the meeting, how they would do the discovery, how they would, um, How they would sort of practice these core sales skills. So it really depends on what you would want to get out of it more. And actually I might do either one depending on, you know, do I have, do I have questions of if this person's either smart enough to do my sale or motivated enough to go do the research or is putting together the pieces or it can actually help tell my story in a way that's better that I haven't thought about yet. If it's like a new product, like, can they give me some ideas? If I have questions on like core salesmanship or salespersonship, um, I might have them do theirs and I can sort of play, you know, play into their role. Or I might do a little bit of both, but we're going to spend 15 minutes on a meeting here, and then we're going to do, like, a quick five minute, like, if you're prospecting and doing PG, how would you help PG me, uh, to take a meeting and go do, you know, our product, right? Um, but that exercise is super important. And then finally, like, references and back channels. Um, I know sometimes pe…

AI assessment note: “I've done both. Obviously, with your company, you can see if they can quickly”

Q And how do you tell that? Do you look in Pipedrive and see, do you look in their calendars and see their email?

A Yeah, so, so I'm, I'm looking at, so there's as tactical as activity, but if we could set up basic Salesforce reporting on how many, you know, ops they're generating, how, a good rule of thumb is like an AE in my book should be generating at least a new op a week. By themselves, without SDRs, without marketing, helping them in an enterprise software sale, outbound sale. Are you at least doing one off a week? If you're not, okay, are you doing activity? How are you doing it? Do you actually know how to do it? That's the hardest part of selling. If they don't have either the appetite or the skill to do that, you better get it fast because you're not going to work here. And granted, we should be vetting for that in our hiring process, going back to what we just talked about. That's number one. Number two is when they just don't seem to grok the product. Like, If I don't, if I can't grok the, like, talk track, how to talk about it, how to, how to use the product, how to share it, yes, and we talked about not going straight to a product-led sale, a driven sale, but if they're not showing that at a pretty fundamental level and quickly grappling on, grappling onto those soundbites, talk tracks, um, that's usually a big red flag for me. So between those two, those are pretty early, because those are the precursors to, can you actually get pipe? Can you actually build late stage pipe? C…

AI assessment note: “basic Salesforce reporting on how many, you know, ops they're generating”

Q What, what would you advise sales leaders in terms of accurate forecasting in 2023? What will be a hard year?

A Yeah. Um, now is the time more than ever to go inspect what is real and what is not, because things that might have been a deal that you could feel 50%, 75, 90% confident in a year ago might not close at all this year or might get delayed this year. So, like, the difference between deals pushing, deals not closing at all, or deals coming in way smaller is, in my opinion, Do I have direct access to an EB? Do I have a real business case, or am I selling it off of a cool, you know, this is a nice product we'd love to have? Um, if I'm doing that kind of inspection for true business case, direct access to EB, you know, do I have a closed plan in front of them, or an evaluation plan that we've talked about? By this date, we will do this. By this date, we will do that. You are looking for these three things to go make a decision. These are who the people are who are going to make the decision by this date, and this is what we will show them. If we don't have that, even if it was a good deal last year, it's probably not going to close this year and it's definitely not going to close on time. Like, so that level of inspection of your mid-stage pipe and, and what are the things in your sale you need to have a deal right now and take a fresh look at it. That is what I think everyone should be doing in your entire sort of mid-stage pipe and building into your early qualification deal proce…

AI assessment note: “now is the time more than ever to go inspect what is real and what is not”

Q nervous to do one and commit and burn the boats on PLG or just be a top-down enterprise org. For me, I think that's a big mistake. I might be totally wrong because I'm a VC. It's my prerogative to have opinions and be wrong. You're the CRO who knows. When, when doing PLG and enterprise, can you do both at the same time? And what are the thoughts here?

A I would say it's, it's, and again, operational definition enterprise can mean a lot of things to a lot of people. It can be any company that's not an SMB. It can be large enterprises like You know, Coke or Pepsi or, or, uh, sorry, Coke or Walmart or Nike. Um, for operational definitional purposes, let's, let's say enterprise meaning, uh, the, you know, few couple 100,000, few 100,000 dollars sales rep in a long protracted, you know, six to 12 month sales cycle. Uh, and PLG will call sort of pure sort of online self-sell, self-serve. And then there's probably something in the middle of it, which is like a velocity, uh, Sales assist or sort of inside or sort of inside outside hybrid model. So again, spectrum, right? I want to make sure we don't fall into the camp of everything is binary. Um, but I would say at a high level, um, I agree that it's really hard to do both well, right? And it comes back to even how you design your product. So for example, Mule Facebook, Meta Facebook ads is inherently a self-serve platform, right? Built self-serve first. You can use it self-serve. You can now self-onboard. Everything is built such that you can do it without any handholding. And so the way that you build the people org around that naturally is, okay, well, let's make sure we can get everybody self-serving and then using that as your funnel to figure out, oh, who are the bigger spenders…

AI assessment note: “I agree that it's really hard to do both well, right?”

Q much kind of, uh, by the book and driven in numbers way operation. And you're like, okay, you've just told me that Rich is not operational, but he's very creative. It's a really good one. Tell me, man, uh, we need to give these guys an offer and girls an offer now. How, what's been some big lessons on comp, comp packages for sales teams? How should I do it?

A Sometimes I hear founders say, oh, that person's like, You know, getting an offer from so-and-so or they're competing with so-and-so. I got to compete with this. Uh, and, and to get over anchored into like throwing the kitchen sink and, you know, giving half the company to go get them. There are some good benchmarks out there for any role, AE, CSM, marketer, you know, partnerships person, ops person, strategy person. So, so, so trust that any, all the VCs, all the talent folks and recruiter will give you, give you that. The bigger question is also trying to figure out Um, is the person actually at that level and with that experience that you are comfortable making that offer to them, right? I think a lot of the call it offer inflation out there that we had seen the last few years was like, okay, anybody can be a VP sales, CRO, CRO at a series A, whatever company. And so the whole titling thing got sort of thrown out of whack because the inflation is out there. Um, another thing is like, okay, do the job for a year. Does that make me a great COO? Does that make me a mark, you know, because I got the title now at one place at a company that may or may not be similar at similar scale, similar problems to solve, that doesn't necessarily qualify me for the job. So I would be really clear around like, let's make sure what you need in the job is like based on, I need to solve this end…

AI assessment note: “There are some good benchmarks out there for any role, AE, CSM, marketer”

Q big company, baby. We are big players. You got too much cash with that. Okay. So I'm going before we used to rock up, show you the product and you go, Ooh, shiny. And now it's like sell to our CFO, sell to procurement. What does that mean? We need to change. Doc wise, team structure wise, should we not invest in product or growth? Should we invest in sales?

A If I'm a founder, and that's the environment I'm in right now, and I advise and invest in a number of companies who are going through this exact same thing right now, right? The sale is real different for sales automation or, you know, whatever the technology is just six or 12 months ago. Um, right now, I'm not necessarily saying it's, it's a person, but what I need to figure out in the jobs to be done model is like, I need to figure out What is the problem my product solves and for whom, right? By getting back to that exact, okay, what is the problem I solve and for whom and how do I quantify that thing and how do I make sure that that problem I solve is actually something that the CFO, the CEO, the COO actually cares about right now, right? Cutting costs, running an efficient business, sales productivity, you know, margin. I need to be able to make sure I can map back my narrative of what my product does and To that big thing. And unless I can do that, I'm not going to get in the room. That can be a, you need a big, bad enterprise sales leader to do it. You could be, you need some marketer to do it, but fundamentally it could be sitting down with your advisors or your investors to say, hey, how do I map that back right now? So I'm sitting with Jonathan Friedman at demo stack a couple of weeks ago, and he's like, hey, we're trying to work on this thing. Great. Okay. You have a…

AI assessment note: “I need to be able to make sure I can map back my narrative”

Q back. Uh, the question I have for you is the case. We both agree that it should actually be the founder building out that playbook. So, uh, then they kind of hire against it. Should they be hiring a sales rep to jack of all trades, dog test it, really just execute on that playbook, or should they hire a head of sales to build out a team beneath them?

A Head of sales has a lot of, can mean a lot of things in, in software and SaaS. It could be a person running a, you know, 500,000 person org. It could be someone who has a CRO title or president title that has no direct reports. So we'll, we'll, we'll use the version of it that we'll define as like, depends on what role, right? I think the, throw the title out the window for a moment. I think that first hire, when I'm looking to scale, I'm looking to scale me out as a founder. I'm trying to figure out how do I get someone who can continue to help me shape this message because it's not all done yet, right? We, I speak, speak about it sometimes like it's binary. It's not, uh, to help scale and continue to refine the go-to-market, um, and can give me some scale so that I'm not doing all the sales, so that I have someone who's close enough to me that's giving the feedback back so that we can iterate on that story, on the, the, the ICP, on the, on the product market fit, yet it's helping me do more of those sales. To me, that could be a player coach. Um, it could be a player who's stretching in a player coach. It could be someone who, Has that sort of creativity, but also can get out in front of the customers and help me continue to hone that message. The next role would be the person who can probably run that first line team and continue to help shape that narrative, but also manage…

AI assessment note: “To me, that could be a player coach. Um, it could be a player who's stretching”