5 Steps to Make Sure You're Hiring the Right VP of Sales

Everybody. We've talked so much on Saster over the years on how important a great VP of Sales is, where to find one, how to know if you have one, how long to give them, the fact that they should inflect the curve in one sales cycle or less, that they shouldn't be great at anything, they should just be great at some things. And I wanted to summarize maybe 100 or a thousand blog posts and answers and Saster annual sessions into five points. A five part test to tell if you have the right VP of sales. This isn't a test to tell if someone you've met is great. There may be many great leaders out there, but they're just not great for your startup, for your company. Okay? So once you found someone that you love, that you believe in, and you have to believe in them, do not hire a VP of sales just because their LinkedIn is great, just because they worked at Slack or Twilio or Atlassian or wherever. You have to believe. If you don't believe whatever you do, don't hire them, no matter how else how good it looks. But assuming you believe, assuming you've been through the conversations and the team likes them and it's looking good, let me give you a five part test to make sure that the ZP of sales that you love is actually going to fit in and work at your startup at your particular company. So number one, we've been through these points before on Sastor, but I see people missing them all the time. So I want to go just through five. Number one, your VP of sales should have lots of experience at your acv, your deal size for this year or next year. What I mean by that is there is a certain cadence for 1k deals, 10k deals, 100k deals, $1 million deals, and they're different. A VP of sales can be great at high transactional deals, 2000 $3000 deals in a very high velocity environment, handling hundreds and hundreds and thousands of lead a month, but doesn't have the skill set to sell to power, okay, kind of comes up short on $500,000 million dollars deals. That that one makes sense. On the flip side, folks that are good at those 500k million dollar deals, they don't have thousands of them a month. Even at ServiceNow that has a thousand $1 million customers, it didn't happen overnight. So folks that are good at big deals are mostly good at managing a relatively small number of transactions over a lot of time and throw them 1000 leads a month and they can implode have them manage 2020 SDRs and 100 AES rapidly closing tons and tons of deals. And they just don't lack, they lack the skill set. So it almost doesn't matter what type of SaaS product you've sold. If you hire an experienced sales leader that has sold at your price point, they'll know the basic flow, they'll know how to get what type of leads, they'll know how much time to spend on them, they'll know who to talk to and how many folks to talk to in the organization, how much time to spend on each deal. And if they don't, they'll probably fall apart. I see so many times folks that are beloved but sold bigger deals melt with the velocity of smaller deals and folks that were good at little SMB deals melt in the enterprise. So again, one, make sure your VP has lots of experience at your acv, your average acv, your core acv. Number two, and we've talked about this so many times and still I see people not listening. Your VP of sales must have hired themselves at least two to three reps that hit quota and did well. And make sure this is true. You will talk to VP of sales candidates that will say they built a great team and perhaps they did. But you'll find a couple things may have happened. One, they may have inherited the team like their boss may have left and they got a game day promotion. They inherited team but they didn't really hire any of the good folks. That happens all the time. Or they're given a pod to manage as a manager or they worked as part of a great team but they didn't hire any of them. And you'll hear a lot of VPs, sales candidates up and comers stretch VPs, kind of fudge this a little bit that they managed a great team and just ask them, okay, of that great team, how many did you hire yourself? And then ask them questions. How did you find them? How did you source them? See if it sounds right? Because if they can find a way. And hiring and recruiting is hard and it's the number one job for a VP of sales which is to get you from a small sales team to a large sales team that scales that sells just as well with 5 reps and 100 reps and 500 reps as they did with 2 or 3. So if they found, if they've learned how to recruit, which is not a skill set you learn as a individual contributor, SDR or a But if they've learned that they can keep doing it. And they can get better and better at it and hone their craft. But I found a double stretch. Vp. Folks who have never built their at least a tiny sales team of two or three that you don't want them learning that on your nickel. It's too risky and takes too long. So ask them, of the folks on your team, did you hire them yourself for real? How did you find them? Learn how did they source them? And then at the very end, say, great. Ask two questions and one will hit next. Which of those two to three will come with you? Hopefully one or two will. That's. That's almost a requirement. And then go talk to them. Talk to a couple of these reps whether they're recruitable or not, and just ask, did Lauren or Bob recruit you? How did they? And make sure it happened and make sure it makes sense. And again, if they can find two or three great folks that hit quota, they'll find you 20 over time. But if they've never really done it, don't, don't take that risk. Maybe if it's super early, but I would never take that risk. VPs need to know how to recruit. It's number one job for VP of Sales. Okay, the third point out of, out of five, and really we're going to do six. There's going to be a bonus one, so let's call it six. The third one we just hit which is a great VP of Sales, should always have at least one or two reps from their last company or maybe their, their prior company before that, but from one of the last gigs that want to come with them. Why? It's not that complicated. Sales teams that make a lot of money and have fun and, and hit and exceed the plan, they like to stay together. It's rare. It's rare for, for a sales professional that you can work with a magical team. It's so special. And there's so many sales teams and so many VPs of sales that know that lightning only strikes a couple times. So if you're an AE and you worked for Brittany at her last company and you made a ton of money and it was fun and you hit the plan and you had a great journey and you find out Brittany's going to an even better startup, you're going to want to go with her. You're going to want to go with her. Maybe not all of your team, but a couple good ones. So always ask. And I got to tell you, there are exceptions, but nine times out of 10, even an up and coming VP of sales. They've always got a couple folks from their last team that want to join them. And as part of that, a great VP of Sales is always recruiting, whether they're in the market or not. So not only are they bringing a couple, not only a couple folks want to join them, but they always have a few folks because they know they may need them for their next gig. So net net, don't hire a VP of Sales that doesn't know where to get reps. Don't hire VP of Sales. When you ask them where are you going to find your first couple reps? And they say, you know, angel list, recruiters, recruiting boards. No, all that stuff is good. And you've got to do everything to top talent these days. But the Vespa sales have a couple great folks that already want to come with them, generally that work for them. Okay, point four. Your VP of Sales has to have experience, at least at the stage you're at next year. So let's say you're at 5 million ARR and you're growing like a weed. And next year you want to be at 12. Okay? Your VP of Sales does not know, have to know how to thrive at your current size, 4 to 5 million, because you'll be past that soon enough. You actually don't need that skill set. You already have it. But. But they have to have worked at say 12 or 15 million ARR where you'll be next year. Or you're just too many steps away from what they know. I see this so many times. There's a hot startup and a VP of sales at a 50 million, 60 million, $80 million SaaS company who got topped or they brought in a new CRO or things changed, so they're out looking for the next role and they want to join a hot startup. Everyone does. Don't get me wrong, you should make your startup hot so people want to join it, but if they never had experience below 30 or 40 or 50 million ARR, which is common, they'll kind of crash and burn at your 4 to 5 million ARR startup. So it's okay if they have experience where you're skating to where you're going to be in eight months or 10 months or 12 months, but much beyond that, it's just too different. Okay, so make sure they have experience. If not at where you're at today, at least where you'll be by next year. Otherwise they're too big company. And point five. And we hit this one actually in the very beginning, you have to believe. I know we talked about this in the beginning, but do not hire a VP of sales. You don't 100% believe in just because your board thinks it's great that they worked at wherever, at some hot tech company, but you don't believe, don't hire them. If something's off in the interview process and you don't believe, don't hire them. You have to believe and, and that means you have to be thoughtful about this and you have to know which shortcomings and gaps to overlook in which to lean in on. And it means you need to spend maybe more time with candidates. And as you spend more time with these VP of Sales candidates, you should either. It's like investment. You should either get more excited or less excited. And after three or four interactions, you should be excited. You should trust them. You should be ready to go on this journey together. You should, you should believe this is the right choice. And if everything else, if the references are good and that LinkedIn's are good, but you don't believe, you'll. It'll never work out because you'll never have their back. And sales is so hard. A VP of sales really can only thrive if the CEO has her back. So you've got, you've just got to believe. And no matter how stressful it is, no matter how hard it is to find someone great, and this is why people do it, it's three, four months in and they haven't found the right person. They're stressed about hitting the plan and they don't really believe in this candidate. But it checks all. They check all the boxes. It just never works out. Okay, so let's go through the.