VP of sales

“One of the mistakes that we made there was not hiring a sales manager or director underneath me fast enough. And, you know, I fell into the classic we fell into this classic mistake of we needed a VP of sales from the get go. We weren't We're not ready for one…”

“At any company under a couple hundred million in ARR, your VP of sales should be someone you're very proud to fly in to meet with the CIO of Nestle to help close the deal. And if they don't want to do that, they're a bad fit.”

“Like, I have an opinion. It should be between eight to 10 in ARR. If you want a really solid VP of sales, they're gonna want to come in. They don't want it to be too scrappy, and they don't want it to be too far ahead”

“I mean, no. I would have reps first to show that your stuff works, that customers are interested, that prospects are interested. You're gonna find a couple amazing reps, and you're a startup, and you're gonna hire for aptitude at first. So, I would start with …”

“Equity, if a VP of sales candidate or a CRO wants, is passionate about the equity stake that they want, or that they want to get, I think that's a good sign, because that indicates their level of confidence that they can deliver for the company, versus maybe a…”

“Great VPs of sales and CROs, they admire the work of their peers. certainly Jennifer was somebody that I knew and respected even though she didn't even know me. When I reached, when I wrote a blog about the top five VP of sales and tech that are women, she …”

“When you're in startup mode, startup going to growth, and even growth mode going to scale, you want to find someone who knows how to actually figure things out. Not execute on a playbook that's been given to them.”

“I sort of ballpark it at about 30, 30 VPs of sales or CROs have taken their SaaS companies to fifty million in ARR plus. That's an unofficial number, so you can agree or disagree with that. But that's not a lot of people, and when you talk about hiring, ah, yo…”

“And to make sure you find someone that can do or that has done at least two of those modes before.”

“Do they have a list of people that they would hire when they came in as the, come in as the VP of sales? I'm huge on this, not everybody else is, but this is critical for me because one of my first sales jobs, I worked for a VP of sales that had this phenomena…”

“I would guess probably eight in 10 startups probably fire or lose their first VP of sales inside of a year.”

“But my real point is, if you hire someone that's two stages above where you're at and bring them in, high, high chance of failure, right? You know, I think you can risk doing one stage above. So in other words, if you're doing one million, Right? I think you c…”

“But I think, actually, of all the bad hires you can make, VP of sales is the worst because it's far worse than no hire at all, right?”

“If you're at a startup, right, for me, pipeline is a sign of failure, right? How much revenue are you going to close this month? I don't need to see the charts, and I don't need to see seven million dollars next to Comcast, or twelve million dollars next to wh…”

“And it turns out a mediocre VP of sales that's just closing the deals you would have closed otherwise, but taking 300,000 dollars out of your own pocket is clearly a cost center. It's a frustrating, painful, expensive cost center. But a great VP of sales, and …”

“If you can maximize the success for this hire for your recurring revenue business, this is probably the number one best thing you can do to accelerate your business once you have a smidge of something, right? Once you have a little bit of traction.”

“Classic mistake is hiring someone before you have a repeatable process. I don't have a repeatable process. I want to hire Linda to create it for me. Linda will not succeed nine times out of 10. You've got to have a repeatable process.”

“Whether you're doing poorly or well, if that person can't come in and increase the revenue in one sales cycle that comes out of them, it is hopeless. Right? There is no excuse, because either they're going to do a better job with what you have or not.”

“The other type of risk to take is someone that's more junior than you want, right? It's, you're gonna hire a director of sales masquerading as a VP of sales, right? And there's, the trade-offs there, I think that generally works as long as they've at least hir…”

“If this person did not successfully hire at least three to four good reps, even if they're young, they're not a VP of sales, ok? If they inherited a team that was somewhat successful, they didn't recruit any of them, They're not a VP of sales.”

“One of the best, the biggest ways you can waste money is making someone a player coach for too long, because they gotta bring these people in. You can do it for a quarter, right? Prove them out, have them hold a quota, but if you've got this person holding a q…”

“We know that the Oracle VP doesn't work. Salesforce is the same as Oracle today, right?”

“If you've worked with a successful VP of sales in the early days, you'll realize that they're an extension of your product team, right?”

“As long as your deal size isn't like a million dollars or more, it's about a million and a half in revenue. Ok, and a million and a half in revenue, You've probably got at least a hundred customers, 50 customers, 80, you've got a statistically significant numb…”

“If you hired a VP of sales and all, he or she keeps all the reps you have, that's trouble, ok? Because they know that they're not all great. They can't, if you have three or four folks on your team, the bottom person, like, you, you're not a sales manager. The…”

“You should be meeting with as many potential VP of sales candidates as you can, because this may be a six to 12 month hire.”

“Sometimes you do need to hire this person because you're burnt out and you need leverage, but this person will be gone by a million and a half in revenue. I can tell you nine times out of 10, the person that, that's totally smart, 160 IQ, loves your product, c…”

“If your product today is, say, 300 bucks a month, ok, and that's great, but next, but you're starting to get a few bigger customers, and your goal next year is do 20 K deals, 20 K ACV deals. If this person has sold at 20 K, he or she will have developed the sk…”

“Why do 70% of folks hire the wrong VP of sales?”

“And as long as you're even at a million and a half in revenue, whatever that OT, the on target earnings, The total amount you pay him or her, as you can see in the match, he or she will pay for themselves.”

“You have to be the first VP of sales. For the simple reason that if you, first of all, well, two simple reasons. One, you can't attract anybody good when you're that early. A VP of sales wants to make money and want to make a lot of money in their stock, but t…”

“A great VP of sales always has at least a couple of people that worked in their last gig that whatever they do, they want to go with them, right?”

“One thing you'll notice here is that I've called the heads of a lot of these departments head of sales as opposed to VP of sales or chief revenue officer. The reason for that, I find this works with a lot of my series A companies, is they're not sure if that p…”

“The amount of like, you know, sort of sweat equity and intellectual capital that's been built there with that team is not replaceable most of the time.”

“If I were a founder looking for a VP of sales right now, I would be, and I didn't, you know, I didn't have, you know, a big network of sales leaders that I knew, or whatever, you know, whatever the terms of the scenario are, like, I would be meeting with peopl…”

“What does a mediocre VP of sales do if there's sixty million in the bank? They spend it all. They spend, the mediocre ones, a hundred percent of them spend it all.”

“The ones that used to join at one million, they're all waiting for a ten million ARR startup today or a unicorn, whichever comes earlier, all of them.”

“I've found that in true enterprise, like real enterprise, the founder is often the VP of sales until ten million.”

“If you don't have those two AEs and you hire a VP of sales, 80% of the time it doesn't work because there's nothing for them to work with, right?”

“How much of a revenue boost did you get from your first great VP of sales? 20% half got 20%, and about half got 40 to a hundred percent boost.”

“You're almost better off without a week, with no VP than even a mediocre VP.”

“It was interesting to me that all out of over 2000 votes, only 13% said more than 50%, although all very few had almost no variable comp.”

“A great VP of sales should make an impact in one sales cycle or less.”

“As founders, your job is spend at least 20, 20% of your time recruiting, half if you can, but meet all the great VPs, and if you think you need a VP of sales, but you find a great VP of demand gen, just hire her. If you think you need a great VP of product, bu…”

“I've never seen a single VP of sales succeed that didn't bring in one or two good people with them immediately when they joined. Never seen it. Not once.”

“It's actually a completely weak sign when a VP of sales is missing a quarter, and he says, well, you know what, I'm not going to make it, but let's raise prices so that we can make my plan. It's a cookie. You raise prices on your base once. It works once. You …”

“Don't hire a VP of sales, hire a director. And let them try and earn the job.”

“Get two AEs that hit quota. One's not enough. If it's one, you don't know why. If it's one, the VP of sales doesn't know why. If it's two, the VP of sales is a hiring job mainly. If you have two hitting quota and the VP of sales is good, even if they're new, e…”

“When you hire a VP of sales or director or whatever, head of sales, this is how many minutes you get back in your day. Zero. Now. Now. What does happen is if they're any good, they re, they rework your calendar. Instead of the CEO being the opener, and the mid…”

“If they don't have anyone good in 30 days, realize by day 60 you may need to move them out, as painful as it is, right?”

“Even if they're a stretch VP, even if they're, this might be their first VP role, if they don't have one or two queued up, zero approaching zero percent chance they make it.”

“The most common mistake is you hired a VP of sales, they've cranked up your team, you have all these sales accountants, but your growth is slow. And the root cause of that is not that the sales motion isn't working, your product is not appealing enough.”

“What makes the CRO role different than the VP of sales is the fact that this allegiance to growing the overall company and an understanding that there's gotta be a marketing strategy that's in lockstep with the product strategy that then when it rubber hits th…”

“Someone that's seen it, seen the journey from the early, early millions to hundreds of millions, but they weren't in the seat. They were close to the seat. They were the second in command or third in command. And so is that level the one you want or is it, you…”

“Before March, 2020, there was zero percent chance a great, okay, less than one percent chance a great CEO in Singapore could convince a US VP of sales to join them. They just wouldn't do it.”

“If you have a VP of sales that's got, you know, 25 SKUs that they're selling, they're gonna pick, like, the three or four that are the easiest to sort of help them get to quota, and inevitably you get products that are just not gonna be as material An input to…”

“What you usually find is if you get rid of the good but not great VP of sales, And don't have a plan. Don't have someone to replace her or him. Don't have a strategy. I see companies go into a spiral they often struggle to recover from.”

“The answer is always be 90% transparent, and do what the business needs to be done, and be open about it. And sometimes they will quit, but it's ok. Like, it sucks, but it's ok. You, don't hide the ball, don't try to do a stealth search”

“A great VP of sales is in one quarter you're selling more, ok? Whether you're selling 10% more or a hundred percent more, that's a sign of a great, that in one quarter or less or one sales cycle, it's materially better.”

“And the sign of, another sign of a bad VP of sales is it gets immediately better when they leave. Because the rest of the team steps up.”

“And it's actually a really common mistake to believe that a really successful account executive is gonna make a good VP of sales, ah, or a sales manager. Ah, these are two extremely different things. Ah, one is coaching, and one is, ah, being an independent co…”

“You should probably call this a head of sales. Don't hire a VP of sales. You want to find somebody that actually has done something quite a bit like this stage recently and was successful. This is exploratory motion, and you want someone that's going to roll u…”

“Some people shy away from that because they think it'll sort of drive, have them sort of unfocused off of like, well, I don't want somebody dreaming about being a VP of sales when they're an account executive today. But in my experience people with that kind o…”

“Sometimes when I see companies like, oh, we need software experience. It's like, you don't need software experience. You need somebody that, like, has the ambition and the drive and the will, and like, you can train. It's your responsibility as a VP of sales t…”

“If you're a VP of sales and a, you know, you go to a startup or a growth company, you should have a good idea about who the people that you want to hire before you actually take the job. And if you don't, then you probably did something wrong.”

“I would say most companies are probably higher, like a marketing leader, right? Like, you know, before sales leader, I mean, obviously in a startup, being able to hire a marketing leader, that's, that is an expert in driving sort of like top of the funnel, rig…”

“I think there's some statistic that like, 90 plus percent of first VPs of sales hired at a startup turnover inside of 12 months or less than 12 months.”

“If in a sales cycle, things are not improving on several core metrics and sales, they never will.”

“If you can, the right, the perfect time to hire the VP of sales is when you have two scaled reps.”

“If you hire someone that was already a VP of sales here, why are they going to join you at two million? Probably only because they're terrible. It doesn't make any sense. It's illogical. They're probably not good.”

“There's a million things a VP of sales will do to bring, to cut your sales cycles on the order of 20 to 30%, but not half. It's not possible. You can't accelerate procurement. You can't accelerate discovery past a certain point. If you need to do five discover…”

“What I have learned is if they already know the product, if they're already a customer, if they've already sold it, sure, like they could just be a manager. But I think 80% of VPs of sales today should close when they start. 80 to 90%, they gotta close.”

“The only way you get time back when you hire a VP of sales is if the last product they sold was truly harder to sell. If it's truly, they go into an environment that in every way is easier, right? Then you get some time back because they already did it. They a…”

“The first executives today, the VP of sales, VP of marketing, even VP of CS, VP of product. They got to carry it back today for real. They got to, and it doesn't, it's if they don't, they never will. They'll never, they'll, we changed too much. They needed too…”

“When fear sets in sales, it, it's almost unrecoverable. It's the one symptom where if you're ever deciding, should I give my VP of sales more time? We've talked about this for years since after. The numbers aren't improving, but things look okay, or this or th…”

“The number one reason I see startups struggle at your stage. In today's world is they hire a VP of sales that either doesn't want to sell. Or doesn't ever want to learn the product.”

“I used to not be sure. Now I think it's a hundred percent required. They've got to sell themselves. And if you hear hesitation in their voice, they ain't gonna do it. If you hear a maybe, don't make the hire.”

“Salesforce is coming up on thirty billion, and Mark Benioff's still out there hustling and meeting with customers. If you're a VP of sales and gunner or CRO, pass. Don't matter what else you like them.”

“The number one mistake that CEOs founders make when they hire a VP of sales is they exit sales.”

“If your model is like, 20%, 50%, 80% outbound, and you want it to go up and you love this head of sales, But they've only done inbound, zero percent chance of success.”

“I wouldn't let them start until they know the product folds. I wouldn't let them start. Now, best of all is literally give them the, if you really think they're so great, give them the offer, agree on the comp, agree on the equity and say, you know what? Now t…”

“I interviewed almost. VPs of sales last year, early last year, only two were actually willing to travel. You can laugh only two out of 40.”

“80% of the VPs of sales candidates that founders that I know invest in work with ask me to meet. 80%, bring me this guy, gal, whenever, no gender. They just, they won't do the sales themselves.”

“If you guys have investors, they're, listen, they're right on many things. They're almost always wrong on a VP of sales.”

“If you make a critical hire and VP of sales or any role at your startup, VP of anything, it's your fault.”

“70% of first VP of sales don't work out. I think I surveyed 11 people and I think 7.8 of them said it. So I think I coined 70%. I've done surveys on LinkedIn for thousands of people. They've confirmed it.”

“Make sure, even in a stretch candidate, that they have hired two to three salespeople that hit quota before. Not 20, not 200, but it's not enough if they inherited a team. It's not enough if they were on a sales team. It's not enough if they were an SDR that g…”

“A mishire in a VP of sales sets you back a year.”

“The number of companies that say they want one, but what they actually want is a VP of sales is wild.”

“That's where almost everyone fails on the way to a true VP of sales is they never learned to hire. They never learned to hire and they're a great IC.”

“Hire a VP of sales before you have two reps hitting quota, hyper risky. And so typically that doesn't happen between one and two million in revenue.”

“Where the VP of sales role is a little bit different is they need to be able to take and work within Where the organization is at today... They are actively in the trenches and engaged in a majority of the key deals. They should be taking a look at the assessm…”

“And I think if you totally trust them and you have a good relationship with them, I think they are a soft veto because the challenge is. They can look for cultural and ability to maybe understand the product or market, but that's likely where their experience …”