Hiring that Great (First) VP of Sales

All right, I'll take the car with me.

Welcome back, guys. I thought the new relic in the Atlassian was pretty cool. So I wasn't as clear when we left. We're now for the rest of the day and it'll be similar on Thursday. We're split up on two stages. So if you're interested in Downstairs go. It's gonna be a really cool. The first session's really cool. It's hitting Shahoo. Probably every single person here reads and he's got illusion, reality and product market fit, which is a terrific topic. And then we'll have Sean Ellis, who a lot of you folks read on growth hackers talking about culture. So if you want to hear something more tactical, go downstairs. None of us will take anything personally. The more you can get up and leave. Right now we're okay and go do it, but just split. Split between times and events and journeys as you want to do it. And so what I want to do now with my good friends here is the most popular thing on Saster, as we probably all know, is all the content on how to hire a great VP of sales. And I've done this presentation a million times. It was all the mistakes I made working with Brendan and Sam in particular. And now we have Emmanuel Scala from Influitive Helping. And this was my 8 year old daughter's idea, which was we had one hole in the schedule. She said, well, why don't you just do whatever is most popular but with interesting people? So I said that's a good idea. So let's actually do this topic and let me find the clicker for real and take the learnings. So I literally want to just go through some of our top 10 learnings on let me how to hire a great VP of Sales. And I'll go through them, but I'd love all my colleagues and friends here to kind of challenge him. And let's go through this one first. And Emmanuel, you were talking about this, I think when we were emailing before. But let's step back. This is my classic chart that I think we all agree at in some high level, right, which is hiring a VP of sales before you have any customers. How often does that work?

Never.

Never, Right? Never. Right. There are rare exceptions. If you raise 20 million in your seed and you want your head of sales to learn about the product, that's the rep, but it never works. Right. And we make that mistake. Right. So my learning, but really I learned it from Brendan, was this thing that I think a lot of folks have Figured out too, which is one rep that's performing is nice because then. But you're not sure that it's repeatable. Right. Until you have two. I'm not even sure we had to. When Brendan joined, we had Sam that was doing SMB, but he wasn't a core rep at the time. Right.

Well, I wanted to make him an sdr, but yeah, he was.

Yeah, you're an sdr. So we maybe didn't even have two. We might have had one and a half. Well, we had two and a half. We had two and we probably had two and a half. Right. We had Joe and Adam that were doing pretty well. And we had Sam blazing the path. And then Brendan joined actually as my second VP of sales, but first VP of sales. And that's where I saw the growth. And before Brendan, actually the same rep that was really good when Brendan joined was there my first VP of sales, but I only had one. And of all the other people except for Sam, and Sam was only there for the time that none of them performed. And my problem was I learned nothing. Right. I literally learned nothing from the one rep that could close. So anyhow. But Emmanuel, you had some thoughts. So when is the perfect, absolute perfect time to make the hire?

I actually agree that the two reps performing is probably about the right time. I guess the question is how do you know it's repeatable? How do you know you actually have something repeatable? You need some kind of metric. The metric of two reps performing.

Yeah.

I think is probably a pretty good metric. Obviously you probably don't have quotas and process up until that point.

Yes.

So I think if you can look at your asp, look at what it is, and if you feel like you're on 2, 3/4 of some level of predictability, that's probably when you hire your first EPSOs.

Yeah. And so you're saying. And that's tough for a lot of founders that aren't patient. I gotta wait two to three or four quarters to see if the two reps perform. Right.

I think it's a lot of.

I think usually most folks want to do it like a day after I have 2 reps hitting quota. Right. Yeah.

I do it. When your second rep is ramped.

Second rep is ramped. I guess the variant of automatically.

It depends on the sales cycle. Right. If it's a huge enterprise software package that takes a year to sell, it's going to take longer than very transactional product. I think the caveat is that you also have to be looking to hire more. You're not going to look to bring on a VP of sales and just stick with two reps and have that VP of sales manage those two reps. The VP of sales are going to build out a team. So it's important that you're sort of at 2, but ready to scale to 8 to 10.

Yeah. And Brendan, you so LinkedIn and Echo sign and others. But since then you've helped several companies. Right. And you've literally taken what we know how to do and rinse, wash, repeated it. Right. You've done it at HackerRank, you did it at TalkDesk, you've done it. So what's any new learnings on this continuum for us?

Yeah, I'd say don't hire the same two reps. Right. I thought that was really helpful at EchoSign.

Yeah.

You had two salespeople that were dramatically different styles, different ages. And I think before you know what to scale or what to clone. Right. It's important to be able to have a couple different styles and approaches to see what really works. And I think that was helpful for us. At EchoSign, you had like the Salesforce rep, you had. Sam, 24, had never been an account executive before and then a more senior rep. And so we had different styles, different philosophies and I got to see how that played out and what worked. And obviously, you know, they all worked out in varying levels. I think Sam probably worked out the best. I think that's fair to say. Thanks.

Good. And on this point, let me just ask a. Because I see now that I work with more founders and the best companies are growing faster than ever in many cases. Right. What I see with founders that haven't done managed sales driven organization is they get this, they believe you, but as soon as they have one, they want to make the hire. Right. Because they're anxious and they see one kid that can do it. And if they really haven't, and the problem is they don't have the second one on deck yet. Right. And they're worried and then it's going to be like 90 days to find that second rep and scale them. And they had. And even though the one rep is doing it, the other three he hired didn't work out. So what's the advice to the founder that wants to go for it with one? Is it don't or is it just be fearful, but do it?

I think it depends on who you're looking to hire. You're not going to be able to attract, I think a true VP of Sales. When you have one sales rep that's being successful, that's true too. You're sort of marginalizing the talent that you're going to be able to get if you just have one sales rep that's selling. And so it's sort of an investment to wait, hire another sales rep. You may have to be patient to get the VP of sales that you actually want to get, but in the long run, it probably pays off.

Yeah, I agree. I think you don't want to compromise on your first VP of Sales hire. And if there's not something that's repeatable that that person feels like they can take and mold and scale, you're going to end up compromising by definition because a great VP of sales is going to feel like that's way too much risk to walk into an environment where you haven't actually proven that you can replicate beyond potentially the great personality or prowess of one guy. So I would say definitely wait until you can prove that it's not a fluke. A dot is not a line. It's kind of one of my favorite lines. And so two people that's starting to make a line now, there's a trend there. And then you'll be able to hire, maybe even hire a little bit ahead of what you need right then. But like Sam said, that's going to pay off in the long run because you'll be able to have that person on board a lot longer.

Yeah. And Brandon, let me ask you a follow up question on that. The other thing I realize I see now is driven founders that have never done a sales driven process before, but have raised at least a little bit of money, they'll take this advice and interesting. Which is they'll want to hire like seven. Right. And it's more common when they're building an SDR team, having never done it before, but they do it with AES too. And they're like, listen, I don't know. And if I got to get, if these guys say I got to get two, I'm not going to have 100% hit rate. And a lot of times first time founders don't. Right, right. So should you hire six or seven to make the two work? I mean, it sounds silly, but I see this happening.

It depends on the demand. Right. And I think demand is not just inbound, but outbound from a lead standpoint. So if you can create the requisite amount of opportunity to scale up to six or seven reps. And again, a lot of times a VP of Sales has to come in and diagnose this yourself. Right. You may actually come in ahead of a marketer. Yeah, I've done that before. And where you come in and you have to really like look back through historical data and say what is our lead velocity and all that other stuff. And then you can sort of start from there. But if you don't have any leads, then you really can't hire account executives.

No, we try to match leads for sure. It's silly. It's a rookie error to hire a bunch of closers with no leads. Right. But just. And I haven't fully thought through what this number is. Just ask. But let's say you've internalized this. I've got to get two. And I know every situation's different, but how many reps can I. Can I, can I. Should I plan to hire four to get two? Should I plan to hire two and be thoughtful and make sure to win? Like what should my loss. I think we all, I'm guessing all four of us want low loss ratios later in time. We believe in the power of a low churn sales team. But if I'm a founder, like how many should I plan for to get to the. Assuming I have enough leads for two, how many should I any gut.

What's.

I don't know the answer.

I would say hire two to get two.

Yeah, let's say that again.

Hire two to get two. Right?

Two to get to two.

I wouldn't say let's hire four to get two or eight to get two. Because again, at that point, like leads are precious.

Right.

So if you're going to say let's, you know, if you have 100 leads a month, let's split them four ways, then that's really not a good path forward and say, hey, let's get two people we really believe in. Let's invest in them. And again, that doesn't have to be over a year. It could be over a month or two months, months or three months. But just hire the two and make them successful and then scale on that.

In my opinion, the CEO also doesn't have the bandwidth to manage 6 reps appropriately. I mean there's just, I think that would fail and I think they would feel like they're not getting the support that they need. They're not getting the training that they need. When you hire that many people to.

I still see more people do it.

Today, but I do it really manageable for, you know, for an entrepreneur to, you know, to take them on ride alongs to show them the messaging and get them excited about the product and the vision. And, and plus, at that point you're hiring missionaries and it's really hard to find six missionaries at once.

It is hard to find. Yeah, that is true.

Yeah, I was going to say something really similar. It depends on the CEO. As you get to four, five, six sales reps, you're effectively becoming a sales manager as a CEO. So if you as the CEO have some sort of sales background or management background, you may be able to scale that more successfully than somebody who doesn't.

Yeah, it's a good point. So good. Let's talk about this. Let's talk about the timing. Too late and too early. Right. So I see this and you know, too late is not as bad as too early. Let's be clear. I mean, too early, too early. Best case, like Emmanuel says, you can't get anybody good. Right. Or best case, you hire a super stretch and it just happens to work out even though they've never hired anybody. Right. But if you start, if you start once you already have two scaled reps and you're not the hottest company on the planet, it's going to take more than a week. Right. So thoughts on this? How should I recruit someone like the three of you? How early? But before I have anything, it's a pointless meeting. Right. So how do I avoid being too late? Any thoughts on this?

You have to start thinking about who you want early and thinking about what's the ideal profile that I want and talking to people. I mean, you have it later, but it's probably going to be a six month recruiting process.

That's what I thought.

Yeah. You want to start thinking about it before you have the repeatability and start thinking, all right, who should I be talking to? Who's in my network? What is the kind of profile I want? Talk to a bunch of other founders that have gotten to the next stage, ask them how they did it, but you definitely want to be thinking about it and start schmoozing and networking at least six months in advance.

Yeah. It's almost too late for you current founders. So just take reference for your next startup. But it's a long game, right? You're talking about Jason and I knew each other for I think two years getting to it and that, you know, obviously my comfort level with him was a huge factor. And when you're doing it cold and you're just meeting somebody for the first time, the odds are going to take, you know, I'm way, way more risk averse at this point in my career than I was, you know, six, seven years ago.

Right.

And so you're almost trying to avoid a mistake as much as much as anything else. So. So you have to have that relationship, especially if you're early and you only have a couple sales reps and maybe you have product market fit, but not a lot of brand around you. It has to start now.

And you can't be afraid to go back to someone that you spoke to who, who might have said at that time, you know, you're way too early for me. I'm just kind of not ready. All right, then prove it. You know, go get a couple more quarters under your belt and then go back to that person and say you weren't ready then, but look what we've done now.

Yeah, that's true.

In my opinion. You just wait, you know, don't stretch, don't reach for that hire. Because the reality is that's 12 months of your startup's life probably if you hire a VP of sales too early or the wrong VP of sales. And that's just the reality is with, you know, board members and, and pride and egos involved, most people are gonna give it a year. And the question is, you're never gonna get that year back. Can you survive that year? I think is the question. And that's death for a lot of startups unless you really, you know, if your company can survive that, that means you're a pretty good company.

Yeah, I was gonna say, I think Brendan and Jason talked to each other for a year longer before you actually ultimately hired Brendan. But another way to look at it, not all two sales reps, SaaS, companies are created equal. So from a revenue perspective, I think when companies cross that million dollar in ARR milestone, that's something that a true VP of sales, if you have two sales reps and a million dollars in ARR, that seems to be sort of what people are looking for for the first VP sales.

Yeah, that's a good point. So try and fast forward. When are you going to hit a million, right. And back into. And if you're going to need six months, I mean, if you're a rocket ship, you may not have the six months, but. But you're going to need the six months to time it perfectly to get there. Right? So there's enough. So let's talk about this one. I actually think this is the most important slide of all of them because you guys will laugh. This is totally non intuitive to founders, right? Totally non intuitive founders. So I've Built my company to a million or 2 million in revenue. I did it myself. I don't know sales, but I can get out, I can hustle. Right. And then I realize I don't know what I'm doing. And then I go to hire the VP of sales. Right. And sometimes I don't budget enough for it, which is an issue. Right. But let's talk about. Is there any disagreement? Then I want to ask questions that the number one job of VP sales is recruiting. Is there any? Disagree? You disagree? Good challenge.

I think number one is optimize the existing team. That's the first thing.

The short term.

Yeah. Yeah. So if you're walking into most likely a situation, whether there's two, two or five or 10 salespeople, I think evaluating that team quickly and defining who's gonna fit and who doesn't, I think is critical. That has to be first. Then recruit the team.

Well, let me ask a variant. How much? And you can change it over time. How much of the three of you, as a percentage basis you spend on recruiting of your time?

Well, for me, it was most, most, most. And my top three would be recruiting a team is definitely number one, I think six sales tactic and sales tactics. Strategy, kind of similar. Right. So sales strategy. I remember Brendan and I would lock ourselves in a conference room for hours at a time and just strategize on how to approach individual opportunities, what we want to present in our decks, all that sort of stuff. And then number three, which actually isn't up here. I think it's incredibly important to find somebody that motivates the team and maintains a really positive culture.

Yeah, that should be high on the list.

Because you'd rather have a B player that's highly motivated to be successful than an A player that doesn't care.

Yeah. As soon as I meet a VP of sales, no matter how competent they appear. But if I don't believe in them, it never works out. Right. I mean, the team has to fall in love with them. Right. But for different reasons. We have three different personalities on stage. Right.

Well, I think a good question to always ask and a question I always ask myself when I hire managers and other leaders is what? I want to work for the. This person.

Yeah. It's true. Yeah. And I think that's a great question for everybody in every role. I think, thinking about it, I think a lot of founders make that mistake with the VP of sales, we assume this is so different than me. I've got an engineering background. I've got a product background that it's okay if I wouldn't work for. Because it's a different. It's a different beast. But I don't think that's true. Right.

No.

How much of your time have you spent recruiting over the last year?

At least 50%.

50?

Yeah.

I was thinking you're gonna tell me 25, 50.

50%. It is the most time consuming part of. Well, the reality is you have to kiss a lot of frogs before you actually find the good rep. And I agree with what Brendan said. I think, listen, it depends on how fast you're scaling. It also depends on if the person, if you're coming into an environment that's exactly like what you left from in terms of ACV and stage. But I think you need a quarter maybe or a couple months to assess the team and make sure you really nail the profile. Because hiring, if you're going to scale up fast and you hire five reps in the wrong profile, you're equally as screwed than if you hired the wrong VP of sales. Right. And so getting a little bit of time to assess. All right, what is the right profile that's working here? Again, you may have come from a company that had a similar trajectory or a similar space or ACV or something, but that would be what I would do first, then focus on recruiting and then. And then culture. I don't know, I kind of almost put that number one. And it's something that you actually have to spend time on. You can't just be a nice person that everyone wants to follow. I spend time crafting and like documenting what our culture is.

But I think you have to recruit. Right. To have the right culture. Right. Is that you want to recruit people in that are low drama and that constantly reinforce your values and culture. Right. I think we had that at Echo Sign. We had like some pretty experienced salespeople and the way they operate, their values sort of breathe through the company. If you don't hire the right people, you can talk about culture all day, but it doesn't really matter. On some level, you almost have to.

Define what the culture is before you can go out and start hiring.

Right? Yeah. And then I think if you're talking to a VP of sales candidate and they can't give you three to five people that they would bring with them, then to me, that's a massive red flag. I would not ever hire that person under any circumstances because A, it says, you know, that this person's not much of a recruiter, B, it says that, you know, nobody really wants to follow this person from where they've been in the past, which speaks to, you know, the type of VP I wouldn't hire.

So yeah, that's. And so let's hone on that. I don't think we guys disagree on that. Right.

Yeah.

I see this pattern so often with first time founders and, and they meet a VP of Sales that's eloquent and has a good LinkedIn and is probably smart and can talk all the things and they can never identify a person that will go with them. Right. And, or they've managed, and here's the second one. They've managed a team that may be successful, but they didn't recruit anyone on the team. I believe it's 100% a no no. No matter how tough a spot the company's in, no matter how boring, how competitive it is. I think it has to be a no no if no one will come. And you never recruited a team. But there's like any. You want to challenge that assumption. Because I'm so binary on that when I see it, I just tell founders, I don't care how much you like her.

No, I think it depends on how quickly you're growing. I think one thing that would be incredibly important is of course somebody that's worked at a startup you don't want to hire. You write about this all the time. You don't want to hire somebody from Oracle if you have two sales reps. But I do think if you're growing very quickly, it's important to hire somebody not only that's managed a team, but that's managed managers. Because it's a very different skill set to manage an individual contributor than it is to manage a manager and sort of coach them on leadership qualities than it is to coach somebody to close deals.

That's for sure. But that would be. We'd all love to have a manager of managers, but I think there's so many startups we might have to give on that one, don't we? Well, you've got to give it a great to have. Right. You've got to give on something. Right.

You mentioned three. Right. You mentioned have they recruited the team? Will anybody follow them? And then I'll add a third and that is have they managed managers?

I think that would be great to have.

Yeah. So if you add that to the mix and they maybe check one or two, but not the third box there.

Yeah, that's a good advice.

So I agree with. You know, are there people who are willing to follow them? I think you got to be A little careful though, about saying, all right, who are the next three people you're going to bring into this company? If I look at myself, the company that I worked for prior, yeah, there was people who would work for me again. I would never bring them into influitive. They're just. It's not the right profile. And there was a much more transactional, you know, it was selling to it. We're selling to line of business. We're doing much more about it. So while they say, yeah, she's a good leader and I would work for her again, if Mark said, you need to bring in three people, who are they? I just wouldn't do it. So I also think you need to be careful about that. VP of Sales doesn't have to necessarily bring people along. They just need to be the kind of person who can recruit and who will be followed.

Well, you're raising some good challenges to my overly simplistic analysis, which is good. Which is the more your VP of Sales is moving into a different ACV and a different segment. You have to cut a little bit of slack on two things, right? And the first one makes sense to me, although I still don't like it. But I agree with you. Maybe those reps that all sold a $5,000 a year product are not the right fit at 500k. I still think there might be one, but it's a good point. The second one that's interesting, which I'd love to hear folks thought on, is I believe, and I've seen this in action, but I might be wrong. When the VP of Sales comes in and you have an existing team that's two or six or eight. I think the VP of Sales knows in a week who's going to make it or who isn't going to make it. But you're saying if it's very different domain, cut the VP of Sales some slack. Give her 30 or 60 days to assess the team. And that's a challenge from knowing my experience, which is, you know, whether you raise your hand or not, you know, in a week. And I get nervous when a VP of Sales doesn't raise her hand. And 30 days goes by and Alaina's still on the team and I don't even work at the company. I know, Elena sucks, right then. I like that VP of Sales is. So you're challenging it, which I like.

But there's some obvious. I mean there's. The obvious has to go.

Yeah, the obvious.

Just not hitting numbers, not a good fit, has a bad attitude. Whatever right there's obvious has to go and yeah, if your VP of sales doesn't take action pretty quickly, you have a problem. But I think when you're trying to figure out what to replicate, especially if you're going to scale really fast, you hire 10 people and you only and five out of 10 don't work out, that's a really big hit.

I think you can do it in parallel on some level. You don't have to say hey let's wait 90 days before we make any judgment. You can sort of start to the people that you like and want to keep start to give them a little bit more and the people that you're pretty sure you don't want to keep start giving them a little bit less. And granted there's somewhat of a self fulfilling prophecy but still give them a chance to try and turn it around or prove they can hit a number. But you're not betting the farm on them on any level. So I think you can do it in parallel at the same time on some level.

Well, I want to hit a few more things on this but you brought up a fun topic that challenged me and what you're thinking. A related point is ok, you come in, there's an existing team, it's a new space, a new acv. I want some time to evaluate the mid pack performers. Right. Because maybe this is as good as we're going to be able to do in the short term and then I optimize better. But let's say you've joined as a VP sales where there's never been one before and someone hired say 8 reps before I believe and I don't like to fire anybody as you guys know. I believe if one of them isn't gone in 30 days, this is not a VP of sales because there's never too many leads. Right. And the simplest thing to do is to get rid of the loser that got.

Some companies have more rigid HR processes as far as how you actually make.

Yeah but when I've seen someone not get rid of the bottom person quickly within three or four weeks then I've my and it's probably four or five situations I've never seen the VP of sales work out. Right.

So I think the exception to that might be if the team is as a whole performing pretty well and you have a ton of momentum, you may not want to disrupt that by terminating somebody that could have.

The CEO is a good VP of sales himself or herself. Right? Not great. But he knows that would make sense. Yeah. So Last one on this because we could spend our entire time on this chart. But let's do the last one because this confuses founders too. And I've said this a million times. How much should the VP of Sales carry? A bag? And this may change a little bit if IT's enterprise or seven figure deals. But if I'm hiring the VP of sales and I have 2 reps and I need 10 by the end of the year, how much quota should the VP of Sales carry? Are you smiling, Emmanuel?

I think zero.

Right, Right.

You're not going to hire a VP of Sales if they're going to carry an individual contributor quota.

Yeah, but the average founder has never done it before and I've written about it. But they see the VP of Sales as a cost center, which for a short period of time is true. There's no question. Until you have more reps and they outperform and then clearly she or he pays for herself. So there's this, well, maybe if just for 90 days, if I don't have. If I can just. If Brendan can just close a few big deals, that would really help pay for the salary. Right. It's not an irrational thing to think. Right. And what's the guidance? Should the VP of Sales agree? Should they push back? Should. What's the.

I mean, I think you're going to be pretty hands on. I mean in any scenario I would want to be sort of on the playing field side by side with whoever your AE is and contributing almost equally. But I think you can't do, you know, you can't be the person that literally has a quota attached to it for an individual deal.

You're also not teaching your reps how to do anything if you're out there closing deals by yourself. Right. So there's a difference between being a second or riding along or being really involved in closing deals versus carrying a quota and having to close your own deals. So I think every deal should be accredited to a rep, whether or not the VP of Sales help carry that ball. Okay, that's fine. That's definitely going to happen. You're going to want to be hands on, but then that reps going to learn and the next time they're going to be able to do it themselves. And that's why you hire a VP of Sales. Not to close big deals, but to teach the reps how to do it.

It's true. Yeah. Sometimes you see a variant and Sam, maybe you can give me your thoughts. Sometimes you see a middle ground on this which I haven't seen work. But I don't say I wouldn't fail, which is the VP of sales comes in and says for a quarter I just want to carry the same quota as a new ae. Like I'm not trying. I'm not going to carry a 10 million dollar quota. But if an AE can scale up and do 50k in bookings her first quarter, I want to prove that I, I've done this before. Like I just for one quarter I want to hit 50k and then I'm out of, out of a bag. Right. I see that sometimes as a way to prove myself to my boss and my team, even though it doesn't really matter in the long run. Right. Any thoughts on that when you see it?

Well, if you're making that higher, you're probably hiring somebody too junior to be a true VP of sales anyway. And if you are going to be selling for a quarter, you're going to be sacrificing on what is your number one and probably my number one also, and that's recruiting a team.

If you're spending half your time recruiting and I even have to have an AES quota, then there's no way I'll hit the recruiting quota.

I will say it is important that he or she does sell themselves because you can't do again, what's sort of my number two in that sales strategy. You can't do the sales strategy unless you're actually doing the selling also.

Yes.

So it's important that that exists, but it's not to drive revenue, it's to drive strategy.

Yeah. And so how does. So that's a great insight. If I'm a founder that sold myself but hasn't managed a sales team, how do I know that's happening? Like how do I know? I just need to see to the numbers. How do I know that when that VP of sales is working with the team that he or she is selling even without a quota? I mean, you're right. But how do I rock that in this anxious period when I've hired my first VP of sales? How do I know that's happening? Right.

Well, you're probably sitting like 10ft from him on some level.

He'll have one version of the VP of sales that doesn't work out as we know is the great guy at a Salesforce or box, which are great companies but it's too late stage and they come in and they can do all the strategy in the world and they say all the right things and the pipeline looks great, but they're not actually co selling with the reps. They're actually not. They're just managing. That's the downside of your third prong is those guys. Sometimes they're great, but they're literally. And you think they're selling because you're hoping because he's so tall and handsome or she's so eloquent and then. But you turn out three months later, they didn't sell anything. Right. So how do you know?

I think you'll see. At that point, you're probably not gonna have a. There's two salespeople. Your VP of sales, you're gonna see your VP of sales, him or her constantly, like jumping on a call or going into an office or like there's like 35, 101s a day. Right. There's a lot of time spread spent between them. Whereas a bigger company person will go retreat to a conference room, get on a whiteboard and start mapping out how we're going to scale to a billion dollars in revenue when really what they need to be is on the field with your salespeople, figuring out, hey, what works, what doesn't work, that's a good sign.

Or flag. Is he or she's spending a lot of time with the reps when she starts, or is she spending a lot of time in a conference room or working in Salesforce?

How much do they know about the deals? How much do they know about actually what's going on and what stage it's at and who are we talking to and who the decision makers are and how much do they know? Because if they're riding along, they know. And then eventually, not right away, but within a quarter or so, you should see the revenue per rep increase. And that's another metric that says that the VP of sales is actually doing that assist job and teaching them.

Yeah. I was at an e staff meeting of a startup that's doing pretty good with the new VP of sales not that long ago. And she was asked about a big account and the answer was, well, I don't know. Someone else is working on it. So, I mean, really, does that. Is that fatal immediately? I said there's no hope like, like this she's never going to work out.

Depends on the stage.

Four million in revenue.

Yeah.

That's bad.

Probably no chance.

Like zero percent chances I'd make something up. Just we're really, really well, discovery phase. Yeah. Yeah.

All right.

It's a good one.

Probably.

Let me come back to this one. I want to see if I have. Let's talk about this one because I want to run out of time. And I wrote this a long time ago and Brendan, I remember you hated it. You didn't disagree with it, but you thought it was brutal.

I thought yours said 30 days, but.

I think this, yeah, this might have changed.

I thought 30 days seemed a little extreme, but.

Well, it was one sales cycle and I wrote this and you're amazing, but you didn't like it and other people didn't like it. But I think over time I haven't been brutally challenged, which is if you come in, you cull the ones that don't work or just improve the process as you coach them. Even if you don't carry a bag, can't you make things 5% better than they were before you started? Right. So I don't know what the I call it materially. I don't know if it's 10 or with Brendan it was 160 days. 100%. 10% might be just as good. Right. But when I see nothing in my data set, it's a 0% chance this person's going to make it. Right. And often they're really great at talking the talk with the CEO. Right.

We should definitely see something in a cycle's amount of time, whether it be one sales cycle.

But you agree one sales cycle.

One sales cycle. And it doesn't necessarily have to be that you double revenue, but it could be that you've decreased cycle times by 20% or something. That's a win.

But that alone will increase sales. If you do nothing else but you decrease sales cycles, that will increase the short term win rates. Even if you're. Which you're not, you're sacrificing long term revenue, you'll see a bump. Yeah, right. If you do one thing, you'll see a bump. Right. The related thing that I see get, I think as founders we kind of know this. Even though we haven't done it, we grock it. And then what I see a lot of times for founders, especially if you're venture backed, is you'll have VCs that have not. They're really smart, but they haven't done this. They always want to give Bob another quarter. Right. Strapping bob, strapping 6 foot 8, handsome bob that talks like this and has the pipeline chart. Look, it was a rough quarter, but the pipeline is 28 million. And the VC who is smarter than me always wants. I mean I just see this all the time. Gives him an extra quarter. Right. And because it's only one, it's only one. But if the sales cycle's 1/4 and Bob's done nothing, I've never seen it recover. Right. And I just think founders get this opposite advice, like give it another. Give it another quarter. But even though it's harsh, one sales cycle, you are agreeing with me on this one, right? Emmanuel, you disagree?

No, I don't disagree. It is harsh. So when I joined and you had.

To work for Mark Oregon, who I love but is driven, what was that first sales cycle like? Tell us the experience of having to inflect sales.

Yeah, I mean, that was exactly the. Our first quarter that I was there, you know, was the best quarter the company had had to date. And we only had two reps and the revenue per rep increased.

So that's good. We've talked a little bit about your colleagues inside. Tell us what you did. Right. Because you didn't do anything magical. You just did things that were right.

No, it was honestly the basic blocking, attacking, like low hanging fruit kind of thing. So you're looking at where. Looking at your funnel and looking at where they're, you know, where's the bottleneck and, you know, attacking that and doing. Spending a lot of time with your two reps. I mean, I had two. Right. So I spent a lot of time with them, helping them take deals over the finish line because that was where.

Their bottleneck was pushing over the finish line.

I think two caveats to that. One is if that VP of Sales, that's 6 foot 8 with a really deep voice, tall, dark and handsome, if he's recruited an excellent team and that's what he spent most of his time on during that first sales cycle, and you're really confident in the ability of the team that that person's recruited, maybe do give them a little bit of extra time.

No. Good to challenge me. Yeah. I mean, it's a great excuse. There's no doubt. I've been team building. Right. I know the quarter was worse than before I started, but I've been out there. But even Emmanuelle said only 50% of her time is recruiting. What are you doing the other 50%. Right.

Well, the other thing I was going to say is if there are external forces that have an impact. So if the site's been down for half the time and you have an exact impact, it's not necessarily the VP of sales fault.

Yeah. But okay, just to finish that, because I do think this is such a profound point and challenge me. I get it. If the site's down half the quarter, that the VP of Sales gets a pass. But let's assume things are awful. But they were awful the last quarter before. But we have two reps performing. You really think even if he's out recruiting half his time, he can't at least find bottlenecks in the funnel, at least coach them how to. I mean, Brendan was great at herding the cats at the end of the month in the quarter, wasn't he? Right. You can't at least spend 10% of your time making these crazy but successful kids more focused and at least grow 10% more in that first quarter. You don't think so?

I'm not saying that they've done a great job. I guess what I'm suggesting is you gotta compare what you have today to the alternative. And if you get rid of that.

Person, that's why he gets another quarter. That's why the board always says give him another quarter. Because the alternative.

But what if he takes the team that he's recruited that you think is actually really good with him anyway? I'm just challenging, but.

No, no, it's good. But has a mediocre VP of sales ever recruited a great team in the history of sales organizations? I'm just having a little. I mean, I think it's good to give. I just, it's. I mean, I say this always one sales cycle, there's good exceptions, right. But they often lead into this excuse cycle of.

I agree with the premise. I think that most people don't agree with you. I agree with you. But I think most startups, most founders, most boards ignore that advice. And I think it's potentially fatal for a lot of these companies.

Yeah.

So I think if, you know, once, you know, even if it's a quarter and you want to give them another quarter, you should at least see them sleeves rolled up in deals, coaching, reps. Right. If they're off, you know, like creating another forecasting module or you know, whatever on the whiteboard, creating another plan to a trillion dollars, then, you know, I think it's, you know, just that whiteboard.

It's funny, but you see it a lot, don't you?

So by definition, right, if the first thing in the first quarter a VP of sales is doing is recruiting and then also trying to figure out what can they optimize and getting their hands dirty and they're out in the field. If some metric isn't going up and to the right in a quarter, ish, Then I agree. I don't think you actually have the right. It may not be the holy grail metric because maybe possibly the bottleneck in the funnel is really early. Right. So maybe the metric is. All I did was convert more leads into ops. Yeah, okay. But at least some metric that will result in revenue is up and to the right after one quarter.

Yeah. And so. Okay, we hit this one. Let's talk about the last one on this bullet point for just a minute because I think it's interesting is just to make. Maybe you don't. If the VP of sales comes in and actually makes a few changes and things are better, but the next hires aren't an upgrade to the team, is that as big a flag as I think?

Well, it is. I think what all of us agreed was the number one priority for a VP of sales is recruiting.

So he's recruiting. Right.

They're not affecting it.

It brings in people, which is great because it's hard if the bar doesn't. I guess my question is it's hard because sometimes those first couple reps are great. They're quirky, they're missionaries, but they're good. But does the. And eventually we might agree that the bar in some ways has to go down because at least it has to get broader. Right. You have to have a village. But from 2 to 10 or 2 to 20 rep. Does great VPC sales bring in some good reps, really good reps after that, shouldn't the quality bar go up until it goes down in some sense? Or do you disagree? This is what I look for because when I see the guy come in and he's built a team, but those first two reps, I'm like, I don't see it. It seems to me to never work out. Right.

Yeah. I think if you bring in somebody with two reps, they bring in two people that are great. It actually should continue to improve.

Okay, so you're agreeing with me.

Even more becoming more attractive for hires 6, 7, and 8, because hires 1 through 5 are killing it. So if you can point to all this success that the rest of the team is having, you should be able to hire really strategically.

I think it's more challenging once you get outside your network on some level though. Right. So for me, having five or 10 people on a list always that I know can come in and crush it. Once you move beyond that list, I think just naturally the quality can go down a little bit. I think it's hard to keep that quality up unless you're just like a rocket ship in the press every other day and it sort of just feeds on top of itself. But I think once you move beyond. Once you move beyond your network, if that list of five or ten people that you want to bring on are that good, yeah, you'll see a decline.

But Emmanuel, let me just ask you a very. Just because I see this happen all the time. I'm a great founder, but I've never done sales before. I do it right. I get someone great. I already have two reps. She's managed a good team before. It all checks out. Maybe it wasn't a manager of manager. I gave a little bit that and it all looks good and I actually trust her and I come in and the next two reps I just don't believe in right now. I'm not sales driven and so Reps 50 to 51 cannot be like me, I'm an engineer. But when the next two. When I don't believe in the next two, is that a big flag for a founder to think or do you disagree with me on this? Because I see this happen a lot on a borderline candidate.

I think it depends on the founder. I mean I don't believe in. There's a founder who's never actually seen what a successful company.

No. But she closed the first half million revenue herself. So she does know what the customer is like.

Right. Then I think there's a red flag there that I would definitely watch out for. I mean it also depends on how quickly you're looking to scale and how much you're going to. If you're trying two more. If you're going from two and you're hiring two more. Yeah. Those two better be rock stars. If you're going from two AND then hiring 20 or 30 all at once. There may be a few in there that aren't going to be as good, but the whole entire team should definitely be a step function up.

Yeah.

I think you've also got to be careful about giving the person that you've just hired autonomy to do what they think is best with the sales organization. You just mentioned that you have to.

Have to give them autonomy.

Right.

That you.

You don't know. You haven't been a sales founder. So let the person that you've hired as the expert try and be successful rather than doing it your way because hopefully they are better than you.

Yeah. What are them just. And maybe that there's about a hundred things I'll let's chat about that because we do see that sometimes too. Right.

How do you.

What's the advice for founders here and for maybe VP sales and to be here when you have a Great CEO that is a micromanager that hasn't done sales. Right. Because you have to let the VP of Sales run with it, don't you? This cannot work if you're micro. So what? Any Zen learnings from this or advice or thoughts on it?

Yeah, I think you have to. If you want an A plus vpa, sales, on some level, you have to be willing to step aside or set up, subjugate your ego a little bit.

Yeah.

And just let that person make decisions. And some of those will be the right decisions, some will be wrong, but on some level, you just have to let them go and be willing to step back a little bit. I think that's. If you look at VPs of sales like us, if you're gonna recruit us in this early stage, that's pretty appealing aspect of it.

Right?

Which is, hey, I'm not the expert. I want you to come in, I want you to recruit, run the show. It's your ship. I think that's what we're all looking for versus coming into a situation where somebody's like, hey, I've got all the answers. Right. They're right here. Yeah, you can interject your opinion every now and then, but this is the way it's done. I don't think any of us want to walk into that situation.

I think that's the downside. If that's what you want, you're not going to be able to recruit somebody like us. A great VP of sales wants to be given the autonomy to learn the market and crush it and not be told exactly what to do. And if that's what we sound like.

Prima donnas, but yeah, a little bit. But that's what I think. The more experience you have, the more control you have over whatever step you're going to take. And I think that's, for me, it's critical.

And it's usually not the founder's subject matter expertise. It's not their domain usually. So usually they need to trust that while it might look different or it might feel different than what I would do. As an example, I often see good VPs of sales help with the messaging because sometimes the messaging early days can be really up here and not necessarily resonate with the market. But a good VP of Sales is going to take that, maybe dumb it down a little bit and be able to eventually, obviously sell more. And that might not sit well with a founder, but if it's working.

Yeah. Let me ask Sam, since we're running out of time, but let me ask you a variant of that question. So one scenario I see is great founder, that's a micromanager, remains micromanager. I see another scenario with a lot of first time founders, which is they actually built the couple reps themselves and do everything and the minute they hire the VP of sales, they check out of sales. They're like, I don't want to be. I don't really even like sales. They're like, I hired you because I don't want to have any involvement. And it sounds silly, but I've seen this happen as often as the micromanager. So any counsel or advice like what is the minimum that the CEO should remain involved if he or she hasn't done it before? Any thoughts on that?

Yeah, it's a really good question. I think it's going to work differently for different CEOs. I don't know that there's necessarily one size fits all here because you can be successful doing it different ways. Of course, I do think there's an easy way around putting yourself in a situation where you have a micromanaging CEO that makes you unsuccessful as a VP of sales. Just define the relationship before you come on board. And as long as you set really clear expectations with each person and that's sort of how you want to work and the type of environment you want to be in, then I think you mitigate your risk on that one.

That's good.

Any last guys? We're over, but this is amazing. It goes by. Any last insights or comments on this stuff? All right, let's thank our panel. This was epic. Thank you very much.