How To Succeed As a First Time VP of Sales -- Updated

Hey everybody. We have talked so much over the years on Saster about how to hire a great VP of sales. It's some of our most iconic posts. Some of our best SEO is on how to hire great VP of Sales. And go to sasser.com, type it in our Algolia search box or do a Google search and you'll find great posts on how to do that, how to make sure you don't screw it up. How do you hire the right type of the 48 types of VPs to sales? I don't want to talk about that today. I want to flip it around. I want to give hints and advice to VPs and VPs to be that want to be a VP of Sales or really VP of anything. Most of this, most of this test, most of these tips we're going to talk about will work for a VP of any position. And if you're going for it, here are the mistakes that you shouldn't make because you will hit a while and you will fail as VP of Sales. And again I would say rough and tough. 70% of the VPs of sales I see hired by founders don't work out. They don't make it a year and you don't want it that to be you. So let's go through 15 things not to do as a first time VP of sales are really a VP of anything. The number one. And boy I see this so so often. Number one, don't pretend you know how to do something you don't do. Let me give you a few examples. If you come out of an S and B background, you do not know how to do field sales. Okay if you've only done inbound you do not know how to do outbound. Be honest. One I see so much these days. Everyone has figured out you have to add an Outbound playbook to inbound. And I see so many first time VP of sales, even experienced ones claiming they know how to do outbound and they don't. And they hit a wall. They hit a wall because there aren't enough leads and they've never done Outbound and they claim they do. And they struggle for a quarter or two to find this magical director of Outbound that they have to hire because they don't know how to hire SDRs and build the team cause they haven't done it. Boy those VPs of sales fail. The other one I see are VP of marketing that don't really know how to do demand gen and they claim they do but they don't and they can't generate any leads or opportunities or MQLs for sales. Be honest. Be honest. No one in sales, marketing or customer success or product has done it all. But especially in sales and marketing. And be honest about what you're good at. Focus there, be clear about it and then hire folks over time to help you do better. But claiming you know how to do things and you don't, you can fool a lot of first time CEOs because they haven't done it. But it comes crashing down on you in a quarter or two. You will lose your job if you claim you know how to do important parts of the job and you don't. Point number two, this is something where you generally crash as a VP more around quarter four, five or six. Once. Once you've kind of established yourself. But the stakes get bigger because it gets harder. Each year as a VP of Sales the numbers go up. Going from say 3 million in ARR to 6 million ARR in a year is hard enough. But then you've got to go to 12 and 24 and 48 and goodness, those numbers just get bigger and bigger. And the number one mistake I see is not hiring managers that are better than you can't as a VP. When you come as a recipe, you can hire eight, maybe 10, maybe even 12 people yourself and make it. And maybe you can take a few of those top folks on your team, those junior ICs and promote them to managers so that you can get some scale. Because really you can really only manage about 8 AES per person and maybe 10 SDRs. That's about Max. So you're going to need directors under you mid level management to scale in sales and other functional areas. And what I see again and again is only internal promotions and only hiring junior people that are not threats to stretch VPs. You'll never scale. You'll never scale. Have you, if you've never built a company yourself to a hundred million, two hundred million in ARR. If you don't bring in people better and more experienced than you, you will wash out. You do not have the skills to do that. But what the best folks do and you see it all the time in CEOs. But the best VPs of sales and other VPs too is they hire folks under them better than them. And you have to learn how to do that. How, how the. The. The Aaron Levy's and the Drew Houstons and the. And the Collision brothers at stripe. Collision Brothers type started stripe in their teens. How do they, how do they scale as leaders, well, they bring in incredible folks like Clare Johnston from, from Google that have far more experience than they do, that are amazing and you're going to have to build a whole management team like that. And as a VP, here's a rough way to think about it. 5050 in terms of internal promotions and external folks, you can promote some of the kids on your team that are pretty good, but they don't know how to do it either. You've got to bring in a couple directors from the outside that are great and that are better than you. And again and again I see hiring just inexperienced folks and everything breaks. I literally was just doing a zoom yesterday with a great up and coming leader at a SaaS company at 30 million and I asked what a stretch point is. He says none of our managers know what they're doing in sales. They're all internal promotions and we love them, but they can't really guide us from 30 to 60 million because no one's done that on the journey. So look, it's hard, but the best people find a way to recruit people better and more experienced than them. And you might ask, why would anyone join, join me as a VP if they're better and more experienced than me? Like, it seems like you're almost forced to hire folks that are a notch down at experience or skillset than you. But no, if you've been there for a year or two, you have so much institutional knowledge, you are so much more important than just the title. Become part of the fabric of the company. You become part of the management team, the key members. If you're part of the management team, that is a special place and folks will understand that as that hot company scales, if they want to join it, they may need to join folks that in theory have less years of experience than them, but have more years of experience at that company. They know it cold in and out. And if you're that person, if you know everything about your 2,000 customers, how to sell them, how to close them, and if you know why it's exciting and you know why, this is an amazing opportunity for directors and even VPs under them, you will find a way to recruit them. It's hard, but the best folks always hire folks that are better than them under them. Okay, point three mistake. And boy, I know you know this one, but I see it again and again with first time VPs of sales and even just VP of sales, taking almost any job is signing up for an impossible plan. Folks, this is, this is death. As a VP of sales and as a VP of Marketing for sure. Don't sign up for an impossible plan if you do not believe the plan that the SEO presents to you is a feasible achievable. If you haven't seen the metrics and challenge it. Make sure you see the lead flow. Make sure you see the opportunities. Make sure you see the pipeline. Make sure you know the number of reps you're allowed to hire. Make sure you believe the plan is achievable. Not easy, but achievable. At least you'll come close. But boy crazy plan set everyone up for failure. But especially VP of sales, you just, you just miss the plan almost immediately and you never dig out of a hole. So your CEO wants you to go from 3 to 20 this year. And you and you've looked at it and you know this is a good startup, it can triple this year. But 3 to 9, that's hard enough. It says 3 to 20 is insane. Do not agree to that job. You, you will lose your job.4 and this is subtle and complicated, but especially as a first time VP of sales, headcount alone will not drive revenue. Now let's break this down. At some point as you scale, you can't have fewer better reps. We all want that in the early days. We all want a handful. 2 then 4, then 8, then 10. A group of reps that can just all hit an exceed quota and make a lot of money. That's how you get off the ground in SaaS. You get two reps that really know how to do it and then you add to that and everything's great for a while. But ultimately sometime past 10 or 20 million. 30 million in revenue. Ultimately, once you have a brand established and an engine that brings in leads all the time, you need headcount to hit the plant. You could not grow from 30 to 60 million in one year without more than doubling your sales team. It just becomes impossible. One human being can, can maybe close a million in revenue, maybe a little bit more. But to go from 30 to 60, you're going to need at least 30 quota carrying reps. And really probably more like 60 because each will achieve 500k yielded. So you need headcount to hit a plan past a certain point. But what inexperienced VPs of sales do, as well as folks that have only been in big companies, is they think headcount alone will do it. And look, if you've got to go from 30 to 60 this year and you need 60 skilled reps to do it, it's not enough. To just shove a bunch of kids in that don't know what they're doing. So boil it down. What I often see is a VP of sales will come in, they'll be hired at 2, 3, 4, 5, 6 7, 8 million in revenue. Big difference between that spread but single digits and immediately they hire mediocre reps. It just doesn't work. Got to get great people and you've got to learn how to do it. Okay, so point number six, not becoming a demand gen semi expert. What do I mean is as a VP of sales, you've got to learn a little bit about marketing at least below 20, 30, 40 million in revenue to survive. First of all, you've got to become a bit of a marketer yourself because everyone's doing outbound. You're going to have to learn how to do outbound. Unless you're in the smallest of SMBs, you're going to have to learn how to add that to the sales playbook. But you're also going to have to know how to work closely with a VP of marketing, how to know what a good MQL is, what a lead is, what an opportunity commit is. You're going to have to learn a bit of the demand gen playbook. You're going to have to create your own collateral. You want to want to meet with a great VP of marketing one on one and if you don't know how to do a little bit of this yourself, you won't know what's great. So become a little bit of marketer yourself and make sure you know how to build an outbound team to get going. Next point related to this headcount one, I see this so often and just don't do it. Hiring B minus sales reps to hit the plan. Look, even though now we all can hire all across the world, hiring isn't any easier. It's a great paradox. You know before when Bay Area companies only hired in the Bay Area and New York only in New York. Now that everyone can hire sales reps and engineers and everybody all across the world, shouldn't hiring get easier? No, because we're all competing with every other startup now. So it hasn't got any easier. And as folks fall into a hole as they get behind for a port quarter or two, it's so tempting when hiring, it's hard to hire B minus sales reps, but it doesn't work. It doesn't work. And that's your biggest trap. Once you introduce B minus sales reps into a startup, it all falls apart. Let's be realistic. When you have a dominant brand in your space and you have great training, great training and great management, can you have some B minus sales reps? No matter what anybody says? Of course you can. If you're handing them reps and you're handing them a canned script and you already have a dominant brand. Look, an A rep is still going to be better than a B minus, but they can still maybe be mid pack. But those reps fail in a startup. So if you can't hire, B minuses will not bail you out. Okay, next mistake I see so Many first time VPs of sales make is they don't get a mentor. We all need mentors. I still need better mentors myself. A lot of the whole point of Saster is to help give you a mentor. But go find one. Ask can I have a budget? Can I have a few thousand shares for one mentor? Not 10, not 20. Maybe it could be your old boss that often a great one. If you're a first time VP of sales, you often worked at least for one great VP of sales in your career. It could be a great CEO you know who has been through the next stage of the journey. But get a mentor and unpaid mentors are nice, but they're not the same. Someone with a few shares and maybe a few nickels if they want cash. They one person to go the extra yard to really coach you to see things you don't see. It's a gift. And not enough CEOs have mentors, but absolutely not enough BPOs have formal mentors. So ask for a budget. A budget of say 5% of your stock options, whatever it is that you can give to one mentor and go out and find her and send her and bring her on the team. Okay, next mistake that first time VPs of sales make again and again and again. Ugh, blaming others. Okay, when I see this in a board meeting or an email or a presentation, I know it's all over for a VP of Sales. A great VP of Sales might grumble when marketing comes up a little short. They might complain when customer success did not pitch in as much on the renewals or the upsells as they hope. They grumble. Look, don't get me wrong, VP of Sales complain a little bit. They do complain a little bit, but they don't blame others. A great VP of Sales never says buy VP of Marketing is terrible unless they're so bad like that. Literally they have to go. Okay, but that's different than blame. That's saying we've got to make a change leaders once in a while you might have to do that every one or two years is put your foot down on a truly on a truly terrible hire in another department. But you know what if marketing comes up a little bit short? The best VP of sales find a way. They get on the phone, they do more emails, they stay later. They missed the plan by a little bit maybe, but they know it's not daisies and unicorns. As soon as it's some other department's fault and not yours. As soon as sales blames marketing or marketing blames budget or product blames engineering, that's a sign of a weak vp. A weak VP always takes responsibility even if they complain or grumble a little bit. So that that's just a terrible sign. The flip side is another death is unrealistic optimism, especially around unlaunched product features. A little bit of optimism is great, but this crazy confidence that a crazy plan will still be hit, which we chatted about before, or crazy confidence in features that have not come out yet that shows a lack of understanding of what it takes to scale sales. Right? I've seen a few times before a nervous new VP of sales comes in and just has extreme confidence in a in a roadmap that hasn't even delivered new features or in a crazy plan. And a little bit of optimism is necessary. Even a little at the edge of crazy, it's okay. But unrealistic optimism? It really doesn't help. Next flag that I see so much time is too much talking in the talk. Too many buzzwords. Great VPs of sales are not talking about their CAC ratios and the SDRAE coverage or their their angel investments or other things all the time. They're talking about deals in the pipeline. They're talking shop. You want to hear talking shop. Not talking. The talk. Buzzwords are a sign of someone that actually doesn't know what they're doing. I see it all the time in sales throwing out crazy numbers around pipeline. What are you closing? And I see it in marketers who are making up metrics around earned views and other things that are different than MQLs. No. How many opportunities did you deliver to sales and sales? What what's your commit? The only metric that really matters for sales is what they're committing to closing and what they've closing too much talking. The talk is trouble. Fire in the wrong way. No one. Look, no one wants to fire good people. But the best VP is the sales know when to and when not to because it's instantly accretive. What you want to see In a great VP of sales is when they join in the first 30 to 45 days they've they've focused on the top performers and moved out the weak performers. You've got to see this. If they keep everybody, including the weak performers, that's a really, really weak sign in a VP of sales. And if someone good or the only good people quit off, man, you're in trouble. Because what do you do as a first VP of sales? The immediately thing you want to do is you concentrate your leads on who can close the most. So you figure out who am I? What are the top resources I have today? You give them more leads and you figure out who can't close and you move them out and bring in two or three people you know. So you've got to see the right people moved out and the right people retained or you're in trouble. Okay, next point. Carrying a bag too long. Let's see this. With two too many first time VPs of sales. And there's a flip side if you I love to see a a stretch VP of sales carry a bag for a little while at least a quarter close a few deals themselves. It really helps. It helps to learn the product, not just be a coach or someone that, that, that turns the knobs and the dials. But if you carry a bag for too long, you'll never hit the the plan cannot be a player coach more than two quarters. If you've got to hire eight A's under you, that's a full time job just managing them to success. So here's my rough quarter. Carrying a bag for a quarter is great, two quarters is okay. But after that is too long and you're setting seven everyone up for failure and it probably means you're not a good enough recruiter. K penultimate point on the mistakes that first time VPs of sales make are all penultimate point. And I know a lot of people are going to challenge me on this, but I am so right. The best VPs of sales do not own anything other than sales. Okay? The best VPs of sales do not want to be head of sales and customer success. They certainly don't want to be own sales and marketing. They don't want to own sales and something else. Because the best bps of sales are closers. Trust me, you're going to hear challenges and, and but the folks that don't like this, the folks that frankly don't want to be a VP of sales anymore, it's a hard Job sales is a very, very hard job and it's tiring. And not everyone can do it for year after year and even decade after decade. So they want more. They want to become a Chief Revenue officer or a Chief Marketing and Sales officer or Chief Customer Officer. And look at some point as you scale, there are, there are, there are roles for those folks. If you have three VPs of sales, yeah, you need a CRO to manage them and when you get very large, you'll, you'll, you'll, you'll, you'll need a CMO to manage all these VPs of marketing. But in the earliest days and not just early, but early ish. Someone that doesn't just want to do sales is not a great VP of sales. It's, it's a full time job. Closing the leads we have and finding new ones. And look, if you're closing customers that are going to last 5, 10 years for life, that's a full time job. How can you do both? How can you manage closing and then the next 10 year journey? It's overwhelming. So huge flag for me frankly, almost a fatal flag. And I know again people will challenge me. Almost a fatal flag. When you go to hire vp Sales and sales isn't enough. They want to own sales plus something else. Okay, last flag. Don't do this. And it's related to a few of the points we just made. If you're, if you're joining this a first time VP of sales or VP of anything, don't be non transparent. Don't play games. A miss is a miss. The number one sign I know a VP of sales will never make it is when they don't own up to a miss. Okay, I know it. There's a couple startups I'm working with right now that had a challenging last quarter. So be it. We're all going to have a rough quarter. Almost none of us never did. And I can already see in their board decks and their presentation who's positioning it is not a mission and who's owning up to it. No one expects perfection in a startup. Now if you miss every quarter, obviously you know the startup's in trouble and you can't make it as a VP of sales. But a miss is a miss and you've got to own up, own up to it. And you've got to own up to whether it's a hard miss, I. E. It's down from the prior quarter, or a soft miss, which is growth from the prior quarter but not the growth we'd hoped A soft miss is not great. It hurts. Like if we wanted to go from 1 to 11 million and bookings last quarter to 13 this quarter, we only went to 1 1. That's weak growth. But hey, it's still growth. Going from 1 million last quarter to half million this year. That's a flag. That's a flag. That's the case. To have a repeatable process. That's a hard miss. But whatever it is, a miss is a miss. You sign up for a goal. I really hope you achieve it. I hope you had a realistic plan with your CEO. But be honest about each month. Be honest about why you missed it. Don't blame others. Transparency builds trust. Okay? All the best successful execs know this. First timers try to hide the ball way too often. First time CEOs hide investor updates. When things aren't going well, they stop sending them. And VPs of sales don't. Don't own up to a miss. Own up to a miss. Own up to a miss. In fact, here's what the best VPs of sales do. They own up to a miss. As soon as they can't do anything about it, they end up to a miss. On the. Maybe it's at 11:59 on the last day of the quarter. That's a good time because they're still trying to make the quarter. Maybe it's a couple days before the end of the quarter if you're enterprise because it's just too late. But they own up to the miss. When it happens, they take responsibility and they tell you the two to three things they're going to do better, they're going to do to fix it. That's what the best VPs of sales do. Look, I'm sorry. I know I committed to a million this quarter. I'm not. I could tell you deals just slipped. But the truth is we didn't make it happen. We only did 800k. I'm doing three things. I'm promoting Bobby, I'm promoting Julie. I'm bringing in a new resource and I'm going to focus my time here. And we're going to. And we're going to do A, B and C. That's what the best folks do. The rest of the.