The Top 10 Questions to Ask Any VP of Sales

I wanted to talk a little bit about one of the most consequential and important decisions you'll make, which is how to hire that first VP of Sales. And in particular, so you don't screw it up, what are 10 great questions to ask candidates you'll hire, especially the ones you really want, that you really like? Because it's tough. If you don't make the hire, generally speaking, almost always in fact, you will stall out. Whether it's at $1 or $2 million or $4 or $5 million, which I find the most common point. Or later, most of us need a VP of Sales to scale. We'll start off finding a way to get those leads with founder-led sales, and we'll close these early customers with hyper-affinity for your feature-poor product, but then it just, it just runs out of gas. Even if you find a couple great AEs, it just never scales past 2, 3, 4, 5, 6, 7, some area without that VP to help you. So you've got to hire her, you've got to find her, But you know what's even worse than not finding her? Hiring the wrong VP of Sales. I mean, ask anyone that's done it and I would say the majority of first VPs of Sales hires are wrong. You will find they lost a year. They lost a year. That wrong VP of Sales, not only is she expensive or he expensive, but they hire the wrong person. They decelerate sales because they don't know how to close your type of customers. They make everything worse and they need time to figure it out and you just dig yourself in a deeper and deeper hole with worse sales reps than you used to have before, Worst performance, worst revenue per lead, so you can't get it wrong, but you can't wait forever. So let me give you and dust off a SaaStr classic on 10 questions that you can ask your prospective VP of Sales to see if she really knows it or if she's just a smooth talker with a great LinkedIn, because that's more common these days. The Cloud Leaders, the Boxes, the Datadogs, the LinkedIns, the Twilios, they're all growing faster than ever, so they're spinning off executives, they're spinning off stretch VPs and directors and Even more senior folks, and they're, they're scattering to the next generation of cloud companies. So you'll meet more and more folks with incredible logos and incredible experiences, at least seemingly on their LinkedIn, but you can't screw it up. So let me walk you through 10 questions, and if you don't hear the right answers to most of them and possibly even all of them, you have the wrong candidate. So the first one, um, and it's a lot of these are Columbo style. It's what I like to do. They're softballs. The first one is, how big a team do you think we need right now given what you know? The best VPs of sales, the good ones, they always know the answer. Most of them will say they don't know, I need to learn more, I need to get in there, I need to understand the metrics, but it's not that complicated folks. If you've done it before, you say, okay, how much revenue you at today, Ms. CEO? $2 million? What do you want to be at next year? $6 million. Okay, that's plus $4 million, that's $4 million in bookings, $500,000, you know, yielded per, per scale day, I'm going to need 8 folks scaled on my team. That means I need 4 within the first 90 days to hit that plan, and I need— I want to ramp up to 8 within 4 to 5 months. That's a great answer. Might be a little bit wrong, might be a little bit right, but it totally ties to really basic math of how much capacity do you need to hit a plan. But I will tell you, folks that haven't really done it, that haven't really planned on hitting a number, that haven't really managed a team that together had to hit a plan, they can't do that math. They can't do it, and they'll almost always say, "Well, I would need more time." I would need to really dig in there to learn it's not true. It's X bodies for X amount of bookings yields X amount of growth. So if they can't answer how big a team do I need to hit the plan, pass. They may be great at some things, but they're not ready to be a leader. The next one is, what deal sizes have you sold to on average? And this is important because sales is a certain playbook for sure, but especially at a given deal size. Basically all $5,000 a year deals are sold the same way, $20,000 the same way, $200,000, $1 million. There's a certain set of skills from hyper-transactional to field, and you're taught them over time. You may not even realize you have a very differentiated skill set, but you do if you've sold in a band. You can take a little bit of risk here. You can take a risk that someone's mostly sold $20K deals, and you can let them stretch up to $50K or $60K, knowing that that probably means they'll leave some money on the table but close faster, right? If you take someone that's been in a slightly lower AC environment, they probably can move more quickly because they have to close more deals per year, but they're not as great at maximizing the deal size, at turning that deal into a massive 6-figure deal. That may be okay Someone that's done $20K deals and a handful of $50K or $60K maybe can stretch to $50K or $60K, but someone that's done $2,000 deals is not going to be able to stretch to $100K deals, or vice versa, $100K to $2K. And make sure the answer you get is honest, because people will fudge it. They will have worked in heterogeneous environments of small, medium, and large deals, but the truth is they mostly worked on one type of deal. So there are exceptions, but I've almost never seen it work where someone principally sold a very different deal size could flex to a different deal size. And make sure you get an honest answer here. Share your concerns about your own ACV and deal size, and make sure you have conviction around the answer. Third one, and this one is, you know, the first three are perhaps the most important on the list, but which is, tell me about the teams you've managed and how you built them. This one is so important because there are so many folks out there that were amazing AEs that have never been managers, and you'll love them because maybe they were the number one AE at a hot startup, And there are folks that led teams because they inherited them or they were given them by their boss, but they never recruited anybody. So just ask them, "How did you get your team at your last company and how did you build it?" You gotta ask the second part. "How did you build it?" Most of the candidates you find that are stretch candidates did not build their own teams. I would not hire one of these folks. Recruiting's hard. You know this. If you're listening to this, you've recruited people. You know it never gets easier. You know we have to spend so much time. Time recruiting. It is so hard. And you don't want to be the startup where your stretch sales leader learns how to recruit for the first time. You can take risk here. And the classic risk is, look, if they've hired 2 quota-attaining AEs that did really well, and you should diligence them and go talk to those AEs. If they've done 2, they could probably figure out how to get 4 and 8 and 16 and 32 and 64. That's a risk you can take, especially in these early stages, that maybe they've only personally recruited a handful of successful AEs. But if it's none, it's beyond risky. So question number 3, tell me about the teams you've directly managed and how you built them. Number 4 is a Columbo style, a nice question, but it's also a good trick question. What sales tools have you used? And what tools do you like? And what don't you like? You'll find that a lot of folks can pretty much only say Salesforce, or Salesforce and Salesloft, or Mixmax, or Outreach, or something like that, but they won't really know the stack because they were too senior. They were too abstracted away. They didn't really use the tools themselves. And that's okay at 20, 40, 80, 100, 200, 400 million. You have— that's what dashboards are for. Dashboards are so your head of sales can hit refresh and track her empire. But I've found that at least for an initial VP of sales, a first hire, folks that don't understand sales tools very well, they're never the one you want. They're not the sales leader. They're not trying to figure out efficiency, which tools do the most, whose calls should I listen to with Gong or Chorus, how do I route my leads properly, how do I do lead scoring, how do I map, do I even do crazy things like territories, how do I handle sales compensation. We're all experts at these tools. I wouldn't hire a head of demand gen that isn't an expert in demand gen tools, that's for sure. That's a huge flag on the marketing side, and I wouldn't do it on sales either. Someone that doesn't know what a state-of-the-art tech stack is for sales Don't hire them before you're at $40 million or $30 million until you're ready to have a whole sales ops team that will answer the question for her. 5, super important. This works for any VP role, but boy, it's the most— it works the best for sales leadership, which is, "Tell me someone working for you now that would leave and join you." Tell me someone working for you now that would leave and join you. And it's okay if it's actually someone from their last job, but it should be someone on their current team. The best sales leaders in particular, marketers as well, and engineers, but especially sales leaders know that job number one is recruiting. So they're always, they're always managing talent. And the best VPs of Sales know they don't want to go into a new gig without at least 2 or 3 ringers. 2 or 3 amazing sales reps they've worked with before that they know can knock it out of the park. That's how a new VP of Sales is going to win. So they always have a few. That are going to go with her to the next role. So ask, ask who those folks are, Paul or Brittany, whoever they are. Check out their LinkedIn, see if it makes sense, and go talk to them. And if those two AEs were some of the best at some up-and-coming startup and they want to join this VP of Sales, boy, you've got something good. Okay, that's good. But I will tell you, the mediocre VPs of Sales, they don't know anybody. They say, you know what, how you gonna, Paul, how you gonna find these two great AEs? I'm going to use recruiters. Ah, look, we all have to use recruiters. I love recruiters. Pay— they're worth their weight in gold if they give you a good candidate. But a great VP of Sales always has a small group of up-and-comers that want to work for her/him again. Um, 6, super important for scaling today: how should sales and customer success work together? Um, any good candidate will have an opinion. Um, they may think sales and customer success should go into prospects together, they may want to just hand over a signed deal to customer success. It really doesn't matter, there's different ways that sales and customer success work together. There's no right answer, there's just a wrong answer to this, which is that they don't know. A sales leader in SaaS needs to know how to work with their counterpart on the lifecycle of a customer, which is customer success. And if they can't answer this question in a way that makes total sense to you, even if it's not the way you're doing things today, but how should sales and CS work together? If they don't know, they're not ready to be a leader. 7, I love this one, tell me about deals you've lost to the competition. This ferrets out so many things. First, it ferrets out if they can sell in a competitive environment. It sounds silly, but I would say there's two types of successful sales folks out there in SaaS. Folks that have worked in brand dominant markets, if you've worked at Salesforce for example, if you've worked with Adobe and Creative Cloud, if you've worked at some Some companies who in a niche, maybe not in all of the world, but in a niche they have 80, 70, 80% market share. They don't compete so much with other vendors as they compete with budget. Like why now? Why do I really need to deploy Salesforce or Workday now? And when you have 80% market share, you can hire those folks and they're good because competing for budget is hard. But if you're in a more competitive space where there's 10 vendors, 20 vendors, or even if there's just 2 or 3 incredibly competitive competitors that are in every deal. Do not hire a head of sales that has not sold in a competitive environment. They won't, they'll melt. I see them melt left and right. They don't have the toolkit to combat the FUD, to create the FUD, to hone in on the winning features versus the losing features, to listen, to win deals that maybe you should lose because you're more responsive, because you know the space better even if you're not necessarily the better vendor. There's a whole toolkit there. That is very different than competing for budget. 8 is a related point, but it's how do you deal with FUD in the market? This will tell you how they compete and win. How do you— what is FUD? Fear, uncertainty, and doubt. When your competitors say things that are lies, that are half true, that used to be true but are no longer true because you've closed that feature gap, you've fixed that security hole, you don't go down any longer, how do you deal with that? Because FUD is so stressful and annoying when you think you're going to close this big prospect and the competition says something about you that's not true and the prospect believes it. Boy, it's frustrating because you've done all the other things right to win the deal, you've been ethical, you've told the truth, and they're saying some half-truth that scares the prospect. There's no perfect answers to this, but I love to hear how a VP of Sales that wants to win deals with FUD, and you'll learn how she thinks in her head. And you'll learn if she can, again, if she can compete or win. Next one is, how do you work with sales engineers and support? How much help does the team need to close deals? Just learn. There's no wrong answer, I think, to this one, but there are vendors where sales gets a lot of support. They'll have sales ops, and sales engineers, and solution architects, and forward engineers, and customer success in the deal from day one. There are folks who work with lots of support. And often actually don't need to know the product as well. And there are environments where, boy, the AEs have to be pretty good. They have to be almost engineers themselves. At least they have to be product managers themselves, because they get no help. So find out. A sales leader will fail if she's worked in an environment with tons of help on the architect, sales engineer, support side, and she's not going to get it at your, in your company. And then 10, and then there's a bonus 11th. 10 is, what will my revenue look like in 120 days? I like this question. You want to ask it last once you've gotten through these ones that are all about strategy. And it is a trick question because there's no right answer, but I love to hear it. What is my revenue going to look like in 120 days? And if you've spent enough time with the VP of Sales, they should know. How much ARR do you have today? What's your goal for next year? How have you grown the last 4 months? How much does she think she can inflect that curve? She should have a sense. She should have a sense, and you should listen to this answer very carefully. You may hear, "It's too early to say," and I don't like that answer. I think that if they're too conservative, it's never going to work out. And at the other end of the spectrum, you may hear a crazy answer. When I hear a crazy answer, not aggressive, not confident, but simply insane, that one never works out either because they're a yes person. You do not want— a yes person in sales is dangerous. You want to hear a lot of You want a positive person, someone that can take the hill and take the bridge, but boy, there's nothing scarier than a VP of Sales that won't tell you the truth, that's always yes. Like, "Oh, we're at $2 million ARR today, we're growing 5% a month, so we're not even doubling. In 120 days I want to be at $4 to $5 million ARR." Ugh. Phil, it's not possible, man. Do the math in your head. I don't care how good you are. There's not enough time in SaaS to add that many bookings in 120 days. And 120 days is a good number because it's It's just past that 90-day threshold. It's just at the edge of it becoming hers, right? After 90 days you own it. After 90 days you inherit whatever bad hires were there before, whatever feature gaps, whatever issues. You can't, you're not the new guy after 100 days. You're not. So 120 days is the perfect time to ask them, you know, where do you think our revenues will be after you join? And you'll just learn so much from that. And the last one, the last one. That there's no perfect answer to, but boy, you'll learn a lot about what you're getting at leadership level is the bonus 11th question is, "How should sales and marketing work together?" And this, you will learn so many things. You will learn how much marketing support they've gotten before, and as you know if you read anything or listen to anything or watch anything on SaaS, I believe that marketing and sales should be joined at the hip. Right? Marketing, there should be almost a transparent overlap between The top of the funnel and the bottom of the funnel. They should work in sync. There's going to be frictions between marketing and sales. Marketing is going to blame sales for not closing their leads, and sales is going to blame marketing for not giving them good enough leads, but at the end of the day, it needs to be teamwork. So I really want to hear how a sales leader has worked with marketing before, and sometimes they haven't. Sometimes they've gotten a, you know, a raw deal where they never got any help from marketing, and that's okay to learn. That actually means if you go find her a great VP of demand gen to help, Wow, then watch what happens when you take someone that's never had any Dimension help and give them that help. Boy, that, that's magic. That is magic. That is just helping someone that did it the hard way do it the slightly less hard way, and that's when I actually see the best performance. You'll also hear opinions and how they want to work with marketing and how they want to get leads, and maybe if you've never hired a VP of marketing in Dimension, you don't have one yet, maybe this VP of sales can help you. But you really want to learn how they work together with marketing to see how sophisticated they are. And how much they can drive your overall revenue strategy, not just closing. So these are my 10+1 questions. They're not magic, but ask them. Ask these ones, and I'll link to the blog post here with the URL, but ask these questions. Ask them. And some of them have right answers, most of them don't, but you will find out if they're a leader that can lead at your startup, and if they're a stretch candidate. Most of you will hire stretch, someone that hasn't exactly done it before, but They've built a small team. They've hired a few great AEs. They have some good experience 'cause those folks are ambitious. They can get a lot out of a startup. You may hire a stretch VP, but these 10+1 questions will make sure it's not a stretch too far. You have to, you have to get great answers and they have to be, on whole, better answers than you've already figured out yourself. Good luck everybody.