The 48 Types of VP of Sales. You Gotta Get It Right.

Hey everybody, it's Saster. I wanted to take a minute to take one of our classic saster posts, the 48 types of VPs of sales, and do it live, do it together, so we can really do a deep dive. We recently refreshed this classic post and I can't think of something on Saster that's been quoted, retweeted, reposted more times than this quote that the article is. The 48 types of VP of Sales make deadly sure you hire the right one. And it's as true today as it was when it was first written and updated. And the point is that, look, there are, look, there's Certainly, some terrible VPs of sales out there. You'll meet a few, but you'll hopefully not hire them. The much bigger risk is that you hire the wrong type. And there are more types than you think. And if you learn these 48 types, and I'm going to simplify it, it's really four types plus three additional questions to ask. But if you believe in someone and they're the right type, the right type, they likely will succeed. But most of us set our VPs of sales, our first ones especially up to fail from day one. Not because they didn't have a good run at their last company, not because they're not smart, not because they don't care and want to win. Of course they do, but they're just the wrong type for your startup. So let's start by stage. And the first mistake a lot of us folks make, make, especially in the early days, up to maybe even 3 or 4 or 5 million in revenue. But certainly the beginning is hiring what I call the evangelist. And what is an evangelist? Evangelist is someone that has some sales, but often more in their background. Business development, partnerships, other things. They haven't really been a VP of sales traditionally, but you love them because they're smart, they get your product. They may also have a product background or some other background. They may actually be some of the smartest folks you ever meet for this role. And they already know your product. In fact, the evangelist sometimes will find you. They'll find you off some press or some product hunt or a friend or a friend. And they'll come in and they'll say, your product is amazing. Here's why I love it. I want to help you. I want to help sell it. And you will be bowled over, as will your team, often, because they're great, they are great, they are smart, you will like them. Everyone will like this evangelist. But you know what the Problem with the evangelist is they've never sold for real. And certainly even if they have, they've never built a sales team. This super smart person that inbounds, ask them how many reps have you hired before how many hit quota? It's almost always zero. Okay, it's almost always zero. They may have worked at some company or a startup and hustled and done business development or big deals or partnerships, but they never built a sales team. So the problem is, even if you love the evangelist, if you have any revenue at all, you're going to outgrow them so quickly when you have to build up your sales team. The only time I've ever seen the evangelist work, and I have seen it work occasionally, is if you're way early, like the first employee, let's say you're just shipping code and you're getting your first beta users, you're not, you're almost pre revenue. And if the founders aren't sales driven, sometimes this evangelist can come in almost as a late co founder and just work with the leads you do have and the customers you have, almost as the CEO would. But they almost never know how to build a team. So the evangelists, almost always as smart as they are as engaging, almost always their hires are just terrible and don't work out and you need to bring in a real VP of sales and people wait too long and, and they end up with a bunch of crummy AES under this wonderfully engaging evangelist because they've never done it. They've never built their own sales team, even a small one. So beware of the evangelist unless you have no other choice and it's super early. And if you do hire the evangelist, understand that even at a million in revenue or so, you may need to bring in a real head of sales and transition the evangelist into like your VP of Biz dev, your VP of partnership, or VP of strategy, or maybe they just handle your big accounts or something like that, but almost never can they can they help you even build a small sales team. Okay, the next phase, which is the Goldilocks phase, it's what most of you need to find is what I call Mr. Or Ms. Make It Repeatable. Okay, this is a unicorn. This is what you all want. And what Mr. Or Ms. Make It Repeatable does is they take something that's sort of working maybe typically at 1 to 2 million in revenue, because the good ones don't want to come in too early, typically with one or two reps already hitting quota, so that you have the beginning, beginnings of an engine. It's the flywheel starting to come together. And Mr. Or Ms. Make It Repeatable hires Reps 3 through 100 for you. They take something that's just starting to work, that has some leads, that has maybe almost a mini brand something going on, something that you as a CEO got, often with one or two reps you hired on your own and scales it from the CEO plus one or two reps to three to three to 100. And those are great. If you hire someone that is appropriate for this stage. And we'll talk about that next. It almost always works because as a founder like you run out of gas after one or two reps, they just bring in another two reps, three or four and all of a sudden revenue goes up and this Mr. Ms. Repeatable moves out a rep that isn't going to scale. Right. And they decrease sales cycles cause they spend more time talking to customers and they just run the basic playbook. And, and Mr. Ms. Makes it repeatable instantly, has an impact. Okay. And that works. In fact, you'll almost know in one sales cycle or less. But you got to find this person. And the key is, the key is this for the sales VP, that's Mr. And Ms. Make It Repeatable. They have to have done it at the stage you're at or at least where you'll be within a year. Okay. And this is where people cut corners and why the hire doesn't work out. Let's say you're at 2 million ARR and your goal is 6 in 12 months. Pretty good tripling. It'd be great if the candidate you bring in had worked in that 2 to 3 million AR environment where you are today. Then they'll know what to do. They'll know the playbook, they'll know the trade offs, they'll know the challenges. You don't have to have 2 to 3 million AR experience in their career, but you better at least have 5 to 6 million AR because you'll be there in a year. You can backfill them, you can help them. But I see so many times a company at 2 million AR goes and hires their first set of sales that has only worked at a 10 or 20 million AR environment. That's the smallest startup they ever worked with. And once in a while it works. But generally only if you're verily heavily funded and can burn through a lot of extra capital so they can learn how to work in an earlier stage. It just doesn't work. So again they don't have to have worked at a startup at exactly your stage, but at least a stage you're going to be at in the next 12 months. That is the Goldilocks hire. Try to find that in your head of sales and your life is going to be much, much better. Okay? What most of you end up hiring is what I call Mr. Ms. Go Big. Okay? And this is a great hire too. But this is something as you hit 10 million ARR and maybe raise a ton of capital and they just start to run a playbook, okay? They're really good at the playbook. They start to thinking about number of heads to revenue and that's of course always true, but it doesn't really matter in the early days when you're bigger, when you're at 20 million going to 40 million, you start doing a calculation, look, I need to hire 30 more AES or I'll never hit the number. Okay, that does happen. But that math totally falls down and breaks down in the early days. All that matters in the early days is that you have a handful of great reps. You're not just trying to check the box with heads. And so this go big hire, you'll see this all the time. I see this constantly. They immediately in their first 30 days, they don't go talk to customers, they don't hop on sales calls, which is really all that they should be doing, right? The Mr. Ms. Repeatable immediately gets on sales calls their first day. But Mr. Go Big @ the next stage. No, no, no. I don't go on sales calls myself. I do process. I'm going to fix salesforce, I'm going to get everything running. I'm going to start spooling up our recruiters, I'm already behind on recru and they're recruiting, recruiting, recruiting, recruiting. And recruiting is one of the top jobs of a VP of sales. But if it's all you're doing and you're not understanding the product in the process in the early days, you're going to drive off a cliff. So be careful. This is what happens when you hire someone for your startup that's only worked at somewhere north of 20 million is they're running the operations playbook without running the hands on sales playbook and it just crashes and burns. Okay? And there are statistically there's more of the go big candidates out there than the ones that really have operated. You know what the ARR you're at now or will be within 12 months. So most of you end up hiring Mr. Ms. Go Big and you look back and you're like, yeah, I know, I know. They worked at a startup that was at 50 million, but they were in a group or a division that was smaller. It doesn't matter. They had too much sales op support, too much brand support, too much marketing support that just does not exist at a few million in ARR. So that's probably the number one mistake. I see this even more often than the evangelist. Okay? And then the next phase, the one mistake most of you don't make, but a few of you will is hiring what I call Mr. Dashboards, okay? And you can make fun of Mr. Dashboards. If you've ever worked at a big tech company, you know the Persona. They're literally looking at their dashboards, okay? Because after 50 million, 60 million, 100 million, a huge amount of what a CRO does is look at dashboards, look at efficiencies, look at, look at how everything's trending, look at how much pipeline's been created and how his or her 8 or 10 or 20 RVPs and managers are doing okay. It really does become a dashboard. And this is one of the reasons Salesforce is so powerful. You don't really understand Salesforce when you have two reps. It seems like a tax, but boy, once you can see all your data and all of your pipeline flowing through your organization, it's super powerful for the managers. But beware of Mr. Dashboards. And here's where you get into trouble with Mr. Dashboards. Most founders know we don't really want Mr. Dashboards early. We know that he or she doesn't really seem to understand what sales is at our startup. But here's where I see the number One issue where Mr. Dashboards gets hired is your board. Okay, a lot of times, if you have a fancy or successful board of directors, they don't know sales. They don't know what sales is, but they know you need to do it. And they're willing to write a check. These are the best of times and sets. They're willing to write you a 10 million, 20 million, 40, $50 million check. And of course, they want you to hire an ex head of sales from Dropbox or Salesforce or Slack or it really doesn't matter where, and they have no idea what it does. And this Mr. Dashboards is very appealing to your board. The board loves to talk to them about strategy, about the future, about grandiose ideas of go to market and scaling. And so your board will often like the Mr. Dashboards most of all. This turns out to be true for Every position, sometimes a board that doesn't know how to what an engineer does, loves these types of VP of engineering, never works out, et cetera, et cetera. But be careful, be careful. If your board falls in love with Mr. Dashboards and you're not north of 20 million because you're getting, you're getting bad advice from your board, we can kind of all distill these phases. The evangelist, the ideal, make it repeatable, the go big and then the Dashboards. We can distill it all almost down to one question that we touched on earlier. Has this VP of sales that you love, that's in your recruiting process, have at some point in her career, has she sold at either where your ARR is today or where it will be in 12 months from now? If they haven't, just pass. Unless you have 100 million in the bank, just pass. Because they won't be able to do what you need to do in the next year. Right. If it's more than a year out, it's just a stretch too far. Okay, so now let's assume they've sold at your current ARR. If you're at 2 million, they worked at a startup at 2 million or at least 4 or 5 million. Okay, now, and so at some point they've been in a startup at your size or within the next 12 years, and you like them and you believe in them when you would buy from them, like you're checking the boxes. Now let's ask three questions to make sure that they are the right fit for your type of startup. No matter how great they are, they've worked in a similar environment. You like them, you trust them, but it doesn't mean for your specific type of sale, they're right. So the first one is this one sounds basic, but it's not. Make sure if they can do competitive sales if you need them to. And your laugh. What do you mean competitive sales? Well, what I mean is there's always competition in sales. If it's not sort of a sales off versus outreach or, you know, whatever, I don't know, a Monday versus Asana or something, I'm not sure where that exactly is in the productivity space, but there's certainly spaces where there's two vendors duking it out, both with market share north of 20%. That happens. It happened to me at Adobe Sign and Echo Sign with Docusign, it's very competitive. And what I've learned is that folks that haven't been in very competitive environments, they melt. They melt because they don't know the playbook. They don't know fud, fear, uncertainty, and doubt. They don't know how to pick on the one feature that wins. They don't know how to be limber and how to react to the situation. Folks that have not worked in competitive environments, as soon as the deal gets tough, they quit. They lose the deal. They lose like all the deals. But the folks that have worked in competitive environments actually love it. They get really good at it. They know it's a game. They know it's a game where you have to listen to the customer, hear what their concerns are, tweak the rfp, tweak the discussion, figure out where their weak spots are and your strong spots are because each of you in your competition will have relative strengths and weaknesses. And the great sales teams get really good at it, and they just win at it. So folks that haven't worked in competitive sales, you know, they often have different competition, which is budget. Competing for budget is hard, and it's often true in the enterprise, it's salesforce. Like, people want to deploy salesforce, but do you really have to do it this month or this quarter, this year? Often you don't, right? Yes, Zoom has competition, but not really. Okay, Zoom has pulled away so far from the market that I'm not saying sales at Zoom is totally easy, although it's been pretty easy the last year. But it's not a competitive sale. So be careful of folks and ask, ask who they competed with. And even better, this is a better trick. It's even better if you're in competitive sale that they did. And then it's even better if they come from a number two or number three player because then they really had to learn how to compete. But never hire someone that hasn't done competitive sales if you're in a competitive, a directly competitive market. Okay, number two, when you find someone that's at the right stage to believe in, do they have experience with similar deal sizes? This will control for so many issues. Broadly speaking, there's three types of deal sizes. Okay, we could slice it finer, but there's really three types. Four figure, like a couple thousand dollars a year deals, five figure, 10, 20, $30,000 years, and six figure and up. And this doesn't mean that your startup might not have customers of all different sizes. Zoom does Slack does. Most of us have small, medium. And you have to decide what's your core, what's the biggest, the thickest part of your customer base, the small, medium, and large. And then make sure they've Sold that way a lot. If they have almost no matter what the product is, there's a certain way of selling. If the deal size is very small, a couple thousand dollars a year, it has to be very high velocity. Okay, tons of 50, 60, 100, 150 leads per rep. If the deal size is six figures, the reps may only have a couple leads a month. But the reps will have time. They'll get time to know all the stakeholders, to manage long sales cycles. To invest a lot of time in a large commission in tiny deals, you got to move fast. You're hoping for one or two call closes and you can do a lot of discussion with the customers, but you can't do discovery across 11 vps. It doesn't work in a 3k deal. So it normalizes for so many things, the deal size. And I see so many VPs of sales crash and burn when they're so great. But your products, $5,000 a year and they've only sold 50k your products, it doesn't work. They sell nothing because they're overwhelmed with the lead velocity. And the folks that have done 5k deals and not 50k deals, that's easier. It's like going up market. But they leave a lot of money on the table because that insta close playbook, they don't know how to slow down and sell to power and sell to multiple stakeholders and bigger deals. So ideally they have spent a significant amount of their career at your core, at your target acv. That's. That's point number two and last one. And this one is a little bit less important than the others because the ACV controls it. But inbound versus outbound, Just be thoughtful about this. What's your cadence going to be? Is it going to be inbound mainly or entirely like your brands bringing in tons of leads, you just don't know what to do with them. That's too many leads. And that's not all good. It's a problem. Is it outbound? Are you doing well? But it's all through hustle and going out and getting it, or is it a mix? And what you'll find is, you know, almost all sales professionals have not done both and they haven't done both well. It's very different, it's very specialized. So if you're mostly inbound, find someone that's dealt with a highly inbound environment. If you're mostly outbound, make sure that they've spent a lot of their current outbound or both will struggle because the skill sets are very different. So again, four stages of VP of sales, from the evangelist to the go big rather to Mr. Repeatable than to go big. And then the dashboards make sure that they're, that they have this experience roughly at the stage at least you're going to be at next year. Okay, that's four categories. And then you add these other factors. Have they sold competitive sales if you need it? Do they have experience with similar deal sizes? And have they done whatever type of sales you do inbound versus outbound? If you can check the boxes on the stage and those three factors, it turns out to be 48 combinations. If it really works and you believe in the VP of sales and they've hired anyone great in their career, it's going to work out. But most of you will hire someone from the wrong stage. Don't do it. Don't do it. No matter how matter desperate you get, no matter how far behind you fall in your search, because you're not doing yourself or the candidate any sort of service. If you hire someone into an environment in which they just can't thrive.