How to Hire a Great VP of Sales Today with SaaStr CEO Jason Lemkin

I thought I could update some of the earliest things we've been doing for 12 years on SaaStr on hiring a great VP of sales. This is some of our earliest content from the early days. It, it really took off. And so I wanted to take a pause and think, what are the 10 mistakes that founders are making today at 2024 when they make the classic VP of sales hire? And in the old days of SaaStr, I made up a statistic. I said 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. And you might think 12 years on, we would be getting better at this. We would be getting better at making this critical hire, right? As founders. But I can tell you across my portfolio, across CEOs I talked to, we're not. We're just as bad as it, as, as ever. And I'm going to walk through 10 mistakes founders are still making and some things we're getting worse. My only hope is that 1 or 2 of these stick and you make less of a mistake. But the meta point, it took me 11 years to figure out 1 thing on this. 11 years. I'm embarrassed. I knew a lot of this 12 years ago. It took me 11 years to figure this out. It might be one of the 10 points, so it might be redundant. But if you make a critical hire in VP of sales or any role at your startup, VP of anything, it's your fault. It's your fault. I blamed my first mis-hire as VP of sales. I blamed him for not doing the job, for hiring terrible people, for writing a letter to my board saying I was incompetent. I blamed him for that. Okay. I did until about last year. It took me 11 years or 12 years to realize it's my fault. I hired him. Your VPs, your executives, anyone on your team can never do enough due diligence. They can never understand what your go-to-market motion is like, what your metrics are like, what your business is. When I do investments, I interview a lot of VPs for the founders at $1 million, $10 million, $20 million, $60 million in ARR. And I try to go last. I try to be the last one for them to interview. And I always ask them like a basic question. I'm like, do you know how much revenue the company has? Do you know how fast they're growing? Do you know how many sales folks are on the sales team? 9 out of 10 of the executives have no idea. And we can mock them and we can say, how could you have spent 8 hours, 2 meeting, 2 hours with the CEO, 1 with the CTO, 1 with, how could you not know these things? And yeah, the best ones do know, but all of a sudden it clicked on me. We don't, it's our fault. We don't qualify candidates out enough. We move too quickly. We don't do reference checks since March 2020. We want to get it done and it's always our fault. The candidate can never do enough diligence. So it's always your fault. That's my meta-learning that I want to talk through But okay, what are the 10 mistakes or 10 points now? This one is newer. This has become a vibe. What did Paul Graham call it? Founder mode. Did anybody read this? Anyone hear of this founder mode thing? I think a few people saw it. Great. Be you. Founder mode does not work for sales. It does not work for inside sales. It does not work for— there are elements of it that work, which we'll talk about. There are elements that don't work, but you need a sales team to scale sales. You do. Founder mode in sales means not exiting sales. And we'll talk about that a bit. Even if we don't, let me hit it. The number one mistake that CEOs, founders make when they hire a VP of sales is they exit sales. We've talked about this on SaaS-ter. They're tired. They've been doing founder-led sales. They hire Linda, they hire Bob, they hire Amelia, they hire Jason, and they're outta here. They leave sales and they disappear for 6 months and sales goes in the toilet because the VP of sales doesn't know the product. They don't know the customers. They don't know what happened. They were never trading. They were never onboarding. Again and again, founders exit sales when they hire VP of sales. You cannot do that. You have to spend just as much time in sales after you hire someone as you did before. It's just your time should change. You should be more a middler. A great VP of sales will grab you and bring you into 10 deals a month. Instead of you having to do it, but you'll never get the time back. But what I see founders doing, which is newer, is they're either staying founder-led too long or they're reverting to founder-led. They're reverting. And look, if you've got, you're closing million-dollar deals and you have 2 reps working for you, it's $500K, $400K deals. You could probably even get to $8 to $10 million being founder-led. You don't need that many people. But even there, you, there's too much time, there's too much to do. And so I see founders not even thinking about hiring a real VP of sales until 8, 10, 12 millionaire, or it's too late. There's too many people. And I see a new thing with some of the best founders I know who got burned. They've had a mishire for their first head of sales and then their second, sometimes their third. And they're like, frack it, frack it. I'm going back. I'm rolling up my sleeves like Paul Graham said, and we're going back to founder-led. We're at $17 million ARR. I'm gonna do it all myself. I know we have 4 products and 80 people at the company, and I got 11 VCs, but I'm gonna be the VP. I was never that good at it, but I'm gonna be the VP of sales now. I tried to do that myself as a founder. I lasted 4 days. I couldn't handle the 12 folks on our team. I couldn't handle it. Maybe you can. Okay. But when you get big, it's too much. You can't run outbound yourself. You can't do, you can't spend your entire week doing an ABM strategy. You can't be in every single deal. It doesn't work. So if you make a mis-hire or two and you go back, founder, because you got no choice because it's your fault, but you had to let Jason or Amelia go, it's fine for a month, a quarter, but start recruiting the next day, the next week when it doesn't work out. You cannot go without a head of sales for a year and get from 10 to 20 to 40 to 80. There is too much human capital required. Sales has no efficiencies whatsoever in it. You need even more people the bigger you get. It has dis-efficiencies of scale. Software is wonderful in theory. You write it once, it can be read everywhere. This has worked great since the days of floppy disks and DVD-ROMs. It has never worked in sales and never will. You will need to hire headcount infinitely, linearly with revenue, and you can't do it without help. So this is my advice. Even if you're not sure. Buy $2 million in ARR, be hiring your first head of sales, and we'll chat about the mistakes. If it doesn't work out, hire another. And if you go back to founder-led, don't stay at whatever you do, don't stay there. Paul Graham may or may not be, he's much smarter than me, I am much richer, much better investor, but he never ran a founder-led sales company. Okay. He didn't do it. And he didn't mean founder, maybe he did, but in my mind, he did not mean founder mode or whatever it's called to mean you be the VP of sales at $23 million in ARR or even $6. Don't go back. This is a big mistake. Okay, next one. And this one is new too. Maybe this was true before that little bug went around in 2020. Maybe it was always true, but friggin' A, it is the truest thing in hiring any VP today. Whether it was being locked up in our backyards for 8 months, whether it was the markets exploded in 2021, coming down in '22, crashing in There's been so much change in 4 years. We are full of executives that are the jaded, the broken, and the done. The jaded, the broken, and the done. They need a job. Okay. That side hustle as a fractional CXO didn't work out. Their clients dried up. They need a job again. They're back out on the market. Sometimes that can work. Don't get me wrong. Or the 11 side hustles they were running. I don't know, but we've all been through so much. Here's the issue. When we started SaaStr, you couldn't find any VPs. There weren't any VPs that had come outta Datadog or Mongo or Klaviyo or Bill that are here, the CEOs here, or any of these great companies. They just, there were only so many executives when we started SaaStr. Today, there's 100 public SaaS companies that are all turning over directors and VPs and senior directors and senior managers, hundreds of them every year. And you will want to hire one of them. Even folks that are here at Duplo Cloud, at Notion, whoever. We can read them here at G2, folks. Great folks will leave G2 or whomever, and you'll want to hire some of them. And these are great companies, but you got to be careful. Too many folks are jaded, broken, or done. And I guess they're the same thing, but I'll give you a few tells. Don't hire these people. If they're— we need pirates and romantics in your startup. You need folks that want to go on this crazy journey with you, not phone it in from home, not phone it in working 18 hours at home and just managing people. You don't need that. So number 1, don't hire the jaded. The one literally 4 minutes into your interview, they're telling you how the CEO or the VC screwed them over. I can't tell you how many times I heard it. I crushed it at my last startup that didn't make it and sales went down when I was there, but it wasn't my fault. It was that stupid CEO who didn't know sales, that dumb CEO, that idiotic meddling CEO. I'm sure there's truth in that. Anyone that says that, I'm sure there's truth. Don't hire them. They're going to think the same thing of you about 3 weeks in. Okay. They're going to think the same thing of you. Okay. They may be right, but they're broken. The next one. I crushed it. Okay. I took the company from $1 million to $800 million single-handedly myself, but I made nothing because the VC screwed me over. The VC screwed me over. We raised $500 million and sold for $80 million. Okay. I don't think the VC screwed you over. Okay. You sold. This is called life. I don't know if the Christophe got into this last presentation. You sell for less than you raise. No one makes any money. Okay. I'm sorry. Cry me a river, but this isn't charity. There are no best efforts points. There's no participation points, folks. This could be half the presentation. There's no participation points in SaaS. I'm sorry. You busted your ass and the company sold for less than it raised and no one made any money. That's life. You didn't crush it. Okay. So anyone that tells you the VC screwed them, it didn't work that way. There's, there is no magical deal out there where the VCs 10x their money and this great executive you're meeting made nothing. It's just the map venture. I can explain venture map doesn't work that way. Okay. There, there are times when the VCs get their money back 1x and employees make nothing. That does happen. And maybe that's not fair at some level, but that's not crushing it. Making 1x money in 10 years as a VC is not exactly crushing it, is it? That's a 0% return, like IRR, it's not, it's not that great. So you gotta let these folks go. Their related cousin is the broken. They don't want to sell anymore. So many sales leaders I talk to don't want to sell. This is going to be a theme. Don't confuse what they did and the beautiful PowerPoints they have and their endless discussion of their brilliant process and how they do process and how great they are at process. And how great they are at managing process. They don't want to sell anymore, but they need the job. They don't want to do it. You got to— do they want to sell? Ask. Here's the simple way you can figure out if they're broken. What do you want to do, Jason M. Lemkin, your first 2 weeks on the job? Amelia, what do you want to do your first 2 weeks on the job? Brendan? Oh, I need to set up processes. Don't make the hire. If they don't say go meet friggin customers the first 2 weeks, do not make the hire. Anyone that wants to sell wants to be in deals. The first day, the first week, I want to go, I'm going to get on the road my first week and go meet your top 10 customers. And then my second week, I'm going to start closing them. That's what you want to hear. That's what you want to hear. And it's probably true, but too many folks worked from that EDU in their backyard, got bitter, stock went up, stock went down, thought they were millionaires, weren't millionaires. And now they just want to manage a team and not sell. There's too many folks out there that just want to manage a team and not sell. Do not hire them. They're broken. And the last ones which are related to it, they're just done. They're really nice. They've been a fractional CRO for now 4 years. They went fractional in June when it was easy. Now we're in September. They've been fractional for more than 4 years and they're nice. And they, and again, they have great strategy slides. They have great triangles and squares and arrows going everywhere and how you onboard 700 reps and their patented onboarding strategy, but they're done. They're done again. Simple test for all this. What do you want to do your first 2 weeks? Christophe? Jane? You don't hear them, customers. Don't, not even sell, but that's good. You want to hear, I'm going to go meet customers. I'm going to get on the road. I'm going to go talk to prospects. That's what you want to hear. And I'm going to bring Brendan and Sam with me. I'm going to bring these 2 guys with me. But that, that used to be enough, but there's too many folks that just want to manage and not work that think they have a couple of folks to bring with them, which we'll talk about. It's not enough, but you want to hear, go meet customers. Okay, we hit this one. I'm not going to be redundant because I guess I got it, but I'm going to be redundant anyway. Because you're all so many, this was not a mistake that I think we made before March 2020. I got to say 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. Again, process slides. Oh, I have my 2 weeks right here. Process, not meeting customers. Trust me, it's 80%. You gotta listen. Just because they talk the talk about what, how it was so great at Datadog and how it was so terrific does not mean they will do it anymore. They gotta do sales themselves. How long? Probably once you hit $100 million ARR, they can get out of deals a little bit. But I think most of you are under $200 million ARR and maybe not. Maybe not, right? There's this classic story that I've told before. If you're old OG SaaS-er, And then there's a newer version of it, but the classic story was one of, one of our first 10 in the old days biggest customers was Groupon. When Groupon was exploding, they went from 0 to 1,500 sales reps in a year and a half. They're all using Adobe Sign, EchoSign. Great, almost 7-figure deal. So we flew out there in the middle of a terrible Chicago winter. It was like January or February. I had a really thin, like track sweatshirts that used to be in back then. They're that a millimeter thick from Zazzle. Wind was ripping through me at 20 degrees in Chicago. Go up there to Groupon, hanging out, doing our pitch. And next door is friggin' Marc Benioff, who flew in from Hawaii on his jet to meet with then 24-year-old Andrew Mason, one of his new $50 million a year customers. Because you got to be in sales. He's still doing it. Marc Benioff said he still goes to Davos every year because he sits at the top of the one staircase there and he meets with 200 customers and prospects in Davos flying there. Now we can't all fly private. It is convenient. It is convenient, but there's a point here, right? You gotta meet the customer. So is it even at $200 million? Salesforce is coming up on $30 billion and Marc Benioff's still out there hustling and meeting with customers. If you're a VP of sales and gonna, or CRO, pass. Don't matter what else you like them. Okay. This one, a lot of you are gonna want to give on. You're going to want to challenge me on. You're going to want to cut a corner here. You finally found someone that's actually willing to leave their home. Okay, that's willing to actually go meet a customer in person, that's willing to actually sell and not just manage a team. You finally found that. It took you 4 months, but they don't— it's not clear they really understand your product. It's a little complicated. It's environmental SaaS. It's a deep type of compliance. It's a new type of SOC 7 or 11 or 82, and they've never really done security before, but they worked at a sales— half these folks worked at a sales-led company, which their salespeople, like, how hard is it to sell an e-signature or Salesloft or Outreach? I'm not saying it's, it's easy, but if you've already used the tool for the last 5 years, you probably have an intuitive sense of the product. Going in to sell a complicated piece of regulated software in a new industry, most people can't make the jump. Okay. That's an issue in and of itself. Number one most important thing, do not give on this. Everyone has, this is, no one does reference checks since March 2020. No one asks sales reps to do demos before they hire them anymore. Horrific error. And everyone hires a VP of sales that never learns the product until after they start. Never. There's a company I invested in. I love this company. They got to $10 million, hired their third VP of sales. Great guy. Came in, 6 months in, sales were down, way down, but honest, most honest guy in the world. Gets up in the board meeting and he says, I gotta be honest. I didn't actually learn the product when I started. I thought I could do it. I thought I could do it. I thought the simple tagline of this company, which is great, the tagline's great. It turns out you go in, the customers just cut his head off. They wanted to know the deep ways this integrated with 28 leaders, how the workflows worked, why, and importantly for sales today, why you would win when they have 10 competitors. You cannot walk into a meeting in this world when it is, when some areas are in a Downturn. I don't believe we're overall in a downturn, but everything's harder. You can't walk in there and think you're going to be a people person when whomever, Duplo Cloud or Drata or Justworks walks in there and they know the friggin market cold. They know where you're weak. They know how to fix, they know how to solve your problem as a customer. And Mr. Backslapping Lunch Guy comes in and just wants to talk about, oh, where do your kids go to school? Oh really? My kids go to Nueva, which is right over there. That's great. Next. Okay. I got 99 problems to solve and us talking about sports or the Olympics or the Tour de Italy ain't solving one of my problems. And it just does not work. I see folks just get slaughtered in sales when they're not product experts, from the bottom to the top, from the bottom to the top. We are all such, we are all, every year we are smarter buyers, all of us up and down the stack. And you cannot go into that meeting and not know the product. It is embarrassing. It is embarrassing. Whatever you do, you can't hire a VP of sales that is not willing, and I know many will challenge me on this, sales leaders. They'll think about this and then they'll come, they're going to come back to me 3 or 4 months later and say, you're right. I wouldn't let them start until they know the product holds. 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 take a month before you even show up and go learn the pro— I don't even want you starting. Go to all of our webinars. Go do it. Do it every— you be you. You show up October, Halloween, not tomorrow, and you show up an expert, right? And a related point, I remember in the early days of Gusto, Josh Reeves, a very distinctive CEO, but I remember he had this thing that at the time I thought was crazy, which is when Josh would hire a new executive, I think he wouldn't let them work for 60 days. And I think at this time we can ask them, I think we more wanted to make sure they knew the, the Gusto culture. Like you have to wear slippers in the office, not shoes. And there's a certain way of doing business. And maybe that was the goal, but there's something to really knowing the company and the product as a leader before you start. And I just see train wrecks. You come into a complicated space and you don't know the product. One of my favorite companies I've ever invested in They just broke up with their second VP of sales after over a year, and they closed their first 7-figure deal the other day. 7-figure deal a year. The VP of sales allegedly was an expert in the industry. He had worked at a competitive company before, but always had a team of SEs, sales engineers and solution architects with him. Never learned the product in a year. For this 7-figure deal, they left him outside in the lobby. They left him outside because the last big deal He embarrassed them, not because he's not smart or a good person, but he could not go in front of a Fortune 500 CTO and talk API and security with the Fortune— he embarrassed them. He embarrassed the founders. So for the next 7-figure deal, they left first. They left him in the lobby. They flew out and they left him in the lobby. And that was the right call because he never learned. He had— maybe you can make this work with 10,000 SEs, but most of us don't have enough around. So. I, this is just me. Maybe you could wing this pre-2020. Maybe you could wing it in 2021 when people would buy anything with a pulse in some categories. Okay. Maybe you literally could. I don't think this works today. Either make sure they're a product expert before you start, force them to do a demo that you believe that you would hire, or give them a vacation until they start. But don't let them start up thinking that they will learn your product on day one. We don't have, they'll close nothing. Okay. Related point. This one seems so obvious, my friends, but it's maybe the most important. I know I put it on 5, not 1 or 10, but it's probably the most important point in here. Whenever a VP of sales doesn't work out with, and I talk to the CEO and I talk to the founders, the other 4 things are true. Were they a product expert? No. Okay. Did they really want to sell? Meh. Well, all these issues came up. Were they checked out? Yeah. Did they bash their last? Did they blame the VCs? Sure. Yeah. All these things. Then I asked them at the very end, did you 100% believe in Jason? 100%? Did you know in your heart and soul that she or he would be successful? And they always say, no, I never, I got tired. I'd been looking for 6 months. I needed an answer. He was the best. Lemkin was the best one I could find. And we all have to settle at some level, like Mr. Perfect, Ms. Dashboards is not the right call. But they never believed, they never believed. And the ones that fly, when I hired Brendan Cassidy, who we've talked about, and he's probably here, who had been the first head of sales at LinkedIn, I had disagreement with one of my VCs who thought he would, wanted someone more senior, whatever. This was years ago. I knew 100 fricking percent in my heart he was the guy. I knew it for a couple reasons. I knew because I'd done a reference check with him about a year prior, and he gave me the best insights of any sales leader I'd ever talked to, just in a reference check for you at recruiting. I knew I wanted him, but most importantly, even if I was wrong, I knew I want him. So I backed him on anything, wherever he needed help. And most importantly, your job as leaders with your VPs is not to tell them what to do. It's to backfill them. This is where the founder mode comes in, not to do their job, but to back— not everyone can be great at everything. So you got to backfill them. If you 100% believe in them and they need you in Chicago at Groupon in the middle of the winter with a jacket on, you're going to be there. If you don't believe in them. You're going to give up on them. They're going to fail. Don't hire any VP, doesn't even ask, that you don't 100% believe in. It doesn't mean you need to be 100% right, but you have to say in my gut, I love Jason. I love Amelia. I love Brendan. I love Sam. No matter what anyone, no matter what anyone on my board or any of my, even the rest of my team, the best ones, often your team will be split on because they may be a threat to the way things are, the way things are. But this is the number one, I always ask, do you really believe in them? No. Founders know we have that spider sense. Of even if we haven't made the hire, we know who we think is that, that your jaw drops, the best of the best, and don't make the hire. It's not gonna work out if you don't believe. Okay. Point 6, this seems minor, but again, this is a new one over the last couple years. This mythical full-stack salesperson, mythical full-stack. We talked a lot about this with Sam Buan, who was ex-CEO of Brex in our Miami meetup. Earliest year, and I'm going to come back to that in a second. This does exist, but it's rare and it has to exist at birth. Okay. And what do I mean is today everyone wants, there's this meme, there's this myth, there's founder mode, but there's also this full stack AE and full stack VP of sales and CRO where you know how to do everything. You're great at out, you do, you, I do my own outbound. I do my own qualification. I do, I do my own training. I do my own onboarding. I'm my own SE. I close everything. I go from SDR to close to everything. And I get what these want this. There's nothing more frustrating than a founder than when half your sales team just waits for the inbound lead to come. And that's all they do. They just want the inbound lead to come in and say, I want to buy today. And then send them a document to e-signature. That's half of sales in SaaS. And I'll share data on this tomorrow. I'm not making it up. And it drives us nuts and we want this and we think we want this full stack person, but they're really rare folks that haven't done outbound. They can't learn on your dime. Folks that haven't done partnerships, channels, technical buyers, in-person. Price point, the points I put at. And it doesn't exist for a sales rep unless you train them from day zero, in which case it's possible. But you have to only hire folks that have been full stack, that have earned their own soup, that have earned their own keep. Most importantly for VPs of sales, do not expect a full stack VP of sales or CRO to magically happen. Ask them. If outbound, here's a perfect example. If out, and this is my real point, and I can give you so many stories. If you're, if outbound is not part of your model, if it's 100% inbound, then you don't need an outbound expert today. Maybe you want to add it. Okay. If your model's 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, 0% chance of success. What are they going to spend a year learning outbound? They're going to go buy Nuxt or some other tool here and magically turn it on. These are great products. That alone is not enough if you've never done it before. Another huge flag is direct versus indirect revenue. How much revenue you get direct or versus partners. I just talked with the VP of sales I've known for over a decade that flamed out at a SaaS company at $40 million, got fired. Okay. At $40 million. And I said, what happened to this guy? He's like, it took me a year to realize half our revenue came from partners in the channel. I'd never done that before, he said. So not only did it take him a year to figure something out he should have figured out the first week, but he never leaned in on this indirect selling because he was only a direct selling guy. Okay. He didn't get it. He couldn't be full stack. Partnerships, channels? Can they sell to a technical buyer? Like we talked about where they left the VP of sales in the lobby, right? Are they willing to sell in person or only on the phone? This sounds, this was a big, this was still a big deal before 2020. Today, it's a huge deal. If you've only sold again from your ADU or from home and your motion and you sell more when you go visit customers, and it's true of 96.842% of us, and they're not willing to travel. They're not going to start traveling when they magically join you. I interviewed almost 40 VPs of sales last year, early last year. Only 2 were actually willing to travel. You can laugh. Only 2 out of 40. My point, there's a lot to read into that, but my point is don't expect your VP of sales to do these things, outbound, partnership, indirect, technical selling, travel, that you, if you know you need them, if they're already part of your motion, ask if they've done it before. Just be kind. How much outbound have you done? How much partnership sales have you done? How much channel sales have you done? How much traveling did you do at your last job? Do you mind? Oh, I love it. Like, I can't stand being at home. My husband drives me nuts. Great. Okay. But you got to ask these. Don't assume— the meta point is don't assume they will do all of it. Most VPs of sales zeros either won't, haven't, or don't want to. Okay. The next couple ones, and then we can take questions with our remaining time. This one's an oldie. This one hasn't changed. Some of this stuff is new, is I think new vibes since 2020, especially since 2023. This one slide, I think I wrote in 2012, 2013, 2014, 2024, 2025. But man, this is brutal, my friends. This is brutal. A, a mis-hire in a VP of sales sets you back a year. The only thing that's changed in my learning as we started it, is it's your fault, not theirs. It is your fault if you make a mis-hire. You did not do enough diligence. You did not spend enough time in person. You did it over Zoom. You did not understand that actually they've never done channel sales. They've actually never done outbound. You did not understand that they are not, they're, they've never sold to a technical buyer before. They've never sold in your industry before. You skip too many steps. It's your fault, but it will set you back a year. Why? A couple of things. The first one is when you make a true mishire, sales always goes down. It happened to me. It happened to half the people here this week or more. You go in, in the product-led stage, you're not a great seller. You're not a perfect closer. You do the product cold. The customers love you. And then you disappear from sales and you bring in someone that doesn't know your product. What do you think happens? Sales goes down. Those deals don't close. Even worse, she brings in or he brings in 2 reps that don't know the product either. Now you've got 3 new sellers on your team that don't know the product or the industry. Throwing them at deals where if just you and Linda did it together, they all would've closed. They all would've closed. So it gets worse. And then they hire 3 and then they hire 10 and all your money's gone. Okay. And then what, after a month? And, and then Safter says only give them 30 days, but no one believes it. Even though I wrote that post and you give them 60 days and 90 days, and then your inv— if you have any investors, they say, Jim's a nice guy. He's pretty good. The, the board who's talked to him twice. Give Jim another quarter. So now you're 6 months in, 7 months in, and then you go to let Jim go in month 7 and he changes your mind because he's a good sales guy and it's 9 months and he's hired 10 people. And then you finally move on from Jim and you start your search for 6 months. You've lost a year and millions of dollars. This avoidable story is again and again. So look, there are certain mishires or mistakes you're going to make that are very— there's the old saying, push down or do the mistakes that are irreversible, slow down the big ones that are irreversible. This one's in the middle. It's not irreversible, but boy, it's damaging. So when you're tired, when you've been looking for 6 months, when you've honestly interviewed 30, you're not pretending you've interviewed 30 candidates like we do, but you've really interviewed 30 and you meet with Jason and you, you, you're not 100% all in. Just realize, push on and find someone you love in life. In hiring, as a co-founder, find the one you love because you're going to lose a year when you settle. It's not worth it. You think settling is good. You think, look, I'm, I know I'm tired. I know Jason's not the greatest VP of sales, but at least I'll have somebody. There is a little bit of rarefied air between very good and great. Don't get me wrong. That's taking risk. But when you settle, sales will go down. All the money will be gone and they'll hire 10 terrible reps. It's not worth it to buy yourself 2 weeks. Of mental relief of having made the hire. It's not worth it. You'll lose the year. Okay. And these ones are updated versions of older points, but I gotta tie it all together so we've all done it. This mistake we actually, we used to make in the early days of SaaS for All Time, 'cause we didn't have all the veterans. We didn't have all the folks that had come outta Mongo and Salesforce. And actually we had folks from Salesforce who started SaaS for All Time, but there wasn't, there wasn't enough others. Now again, there's 100 public SaaS companies to recruit from. So in the old days, we would hire folks that were too junior to do the role. Now we're hiring hundreds of folks that are broke and burnt, but certainly have the title on their LinkedIn. But still, what are you going to do? So you can't hire the SVP from Salesforce or Mongo or Twilio that doesn't want to sell anymore. You can't make that hire. So you can go for that perfect Goldilocks person that has everything at the right moment in time and the right hour in their career. And yeah, they have an offer from OpenAI and Cohere and Glean and Notion, but they still want to join your startup they've never heard of. Of course they do. Of course they do, because you're such a great founder. But so that Goldilocks person probably doesn't exist. So when you've decided the SVP from Datadog is wrong, that got fired because he never left the ADU, and you've decided Mr. Goldilocks doesn't exist, then you realize you got to hire a stretch. You got to hire a kid. Now this kid may be 60 or maybe 26. I don't know. But what I mean is you got to hire someone on their journey with energy that's going on the way up because this is their shot to be your head of sales. Of course you do. Of course you need to stretch higher, but there's just one thing you have to do when you stretch higher. They're not going to have the full package. They may not have worked at the right place. They probably even got fired once if they were pyro-dramatic and passionate. It's okay. Getting fired from every job in sales is probably bad. Getting fired just once, a good sign, just once. But you cannot, the whole point, going back to the first point of revert, why you can't stay in founder-led. At the end of the day, if you can actually sell and you can learn the product, you can get out on the road and you can talk to customers, you can do the sales process yourself as a VP of sales, not skip it because you want to be a manager, but do it yourself. Then it all becomes about human capital. I've got to grow the sales team from 2 to 4 to 8 to 16, 32, 64, 128, because our revenue is doubling each year. Whatever it's growing, you have to roughly grow headcount with your revenue and sales. You can't avoid it. $500K quota, $800K, $400K, it doesn't matter. You can't increase it to $4 million. It don't work that way. So if your yielded quotas for an AE is $500,000. And you want to add $5 million of bookings, you need 10, 10 scaled reps. And if you want to add $50 million, you need 100. You can't get around the math. So at the end of the day, if they know the product and they can sell, the most important thing is recruiting. VPs of sales are the best recruiters on your management team because they're constantly recruiting. So make sure even in a stretch candidate that they have hired 2 to 3 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 got promoted to manager, but never hired any of the SDRs that reported to her. They have to have found, hired 2 people and made them successful. If they can figure out how the hell to find 2 people in this crazy world where everyone really wants to work 10 hours a week from home, if they can find 2 people that can get quoted, they can eventually find 200 for you. 'Cause it's hard to find 2. So ask them who the two are nicely and then say, hey, can I go talk with Pooey and Robbie? Just ask. And if they're any good, they'll connect you on the meeting. You call them up and just ask the question, how is it working? How was it working with Brendan? What was it like? How did he find you? Oh, he hunted me down, right? He hunted me down at this event. Here it is, great thing. He lured me out of this company and I closed $600K with him the next, in the next 12 months. Great story. How'd you do it with Ravi? Hear those stories. No one does this anymore. You don't want to do this because you want to believe that LinkedIn's going to work out because you're tired. You don't want to do this because you're worried what you're going to hear. You're worried that they'd never really hired 2 reps before, that they don't actually know how to recruit. Because the folks that don't, you know what they do? They show up. First, they work on their process slides for a couple weeks. Then they spool, then they tell you they're going to spool up a few recruiters they worked with before, that they never really worked with before. And so 3, 4 months later, they've hired 2 bottom of the barrel reps from some recruiter they don't know. Great. That gets you nowhere. I've said it before, but it's worth saying again, any great sales leader always has a couple folks ready to go with her the next day. They, and I know you got to be careful with this word, this day, but it's true, this word, they groom them. They groom them. The best sales leaders are meeting with tons of folks up and down from SDR to AE. To senior, and they're asking, they're, they're, I want to work with them. I want to work with them again. Or they're meeting with VPs of sales that leave a hot startup. Who is the best person on your team? Linda, Amelia, and Stacy. And they go meet with them because it's half the job at scale. Half the job is recruiting. So if they can't bring 2 good people with them, they'll never do it. And I just go talk to them. Just, it's, and I, I asked so many CEOs this question. Okay, you hired Jim. Does he have any to bring with him? Yeah, Jim's got a couple of great folks to bring with him. Did you talk to them? No. 80% chance those folks aren't coming with Jim or they don't exist or they were somebody worked with. It's not true. You got to talk to the two. If they can hire two great folks, they can hire 200. Think about it. It's true. Okay. Penultimate point. I'm forgetting what the ultimate point is, but this one's so important. This one is so important. If you guys have investors, They're, listen, they're right on many things. They're almost always wrong on a VP of sales. I can't tell you how many boards I've been on, how many startups I've been on, where every single VC is wrong. They're all wrong. All of them. They're all wrong. They all love the handsome 6'4" paratrooper that talks the talk in a deep voice and looks good in a button-down. They love him. And he talks quota attainment. And, and quota metrics and funnel management. And he talks the talk and he's got a, I can't, I don't know what a baritone is, but he talks all the great, I had 111.6% and I was at 11 President's Circles. I was at the, and I love them. And I was at, I knew Reid back when at LinkedIn and I knew whoever, I knew them all. I knew Tiago at Talkdesk and I knew them all. Then your board falls in love with the name dropper, paratrooper. They love them. They don't know. They don't know. And why? One, most of VCs have never done sales. They've never done it and they don't know. So they give you terrible advice. The subtler one is there's more and more VCs that were CEOs and were founders back in the day. And those are great. All things being equal, pick one of them. Not, not, not that big a deal. We could talk about it, but it's nice to have a VC who was a founder, a successful founder. There's a lot of reasons that's comforting. There's only so many slices of your cap table you can give up. It's nice to have a successful CEO. The problem is the company they founded 12 years ago with a million dollar ACV in a different industry is not yours. It's not the same product as selling to restaurants at $2K a year. It's not the same. And just because they know sales doesn't mean they know your sales. So they give you bad advice too. They're mapping it. That's so common. So again, just listen to your VCs and investors. And it's not that they won't have a few good ideas, but I just think 87.2% of the time, they just give you the wrong advice for VP00. So be nice, nod your head, say thank you. But if your gut is, if your gut isn't 100%, don't make the hire. And again, if your gut is 100% and they tell you it's the wrong hire, tell them thank you, I'd still make the hire. Okay. Last one. And then with whatever time we have left, I think we have time. I'll take any questions you guys want. This is new. It's old. This is old, but it's new because in that earlier slide I talked to so many founders have given up and gone back to founder-led sales. They've given up. They've given up. They, it's not just they made one bad VP of sales hire. They made two and they're burned and they're tired and they lost, they burnt half the money and they lost a year and they did it twice and they realized, shoot, I'll just do the million-dollar deal myself. I'll just go up to the customer and close it myself. I've been doing this for 5 years. I'm tired of it. Was just emailing with the CEO I invested in this morning. Got the company to $20 million, 2015, 2020. So from 2015 to 2020, got it to $20 million. And then it, and then he went to $20 million and then $20 million. Went through 3 CEOs, then went to founder that finally found his guy. Got back to 40% growth, not 100%, but back to 40% growth and sold his company for $300 million. Was that third VP of sales. Gave up for a couple years, gave up, went into founder-led sales at $20 million in the desert, did it all himself. But there was churn and there were industry issues. So for every new customer he brought in, he lost one and he was bailing out the boat, but he didn't have the help and he couldn't, he for those two bad VPs of sales and the terrible CEO, he couldn't get over it. And then he finally found the one he loved and going from 0 to 40%. And having a company that had no value to $300 million, pretty big change. So my point is she is out there. She is out there. There are, even in today's world, there are ambitious folks. Sales doesn't breed ambition the way it did before March 2020, but it still breeds ambition. It's competitive. The best folks want, in sales, want their shot. They want their chance. They want the chance. They want the bar. They want the big equity. They want the chance. To put that VP of sales on their resume. They want their shot, time in the sun, especially if they worked under a great one. What you'll find is the really charismatic, successful VPs of sales, like on my own team, Sam Blonde, Brendan Cassidy, why are those folks the heads of revenue at Rippling and Brex and so many other companies? They're all our team and so many leaders. Gong. Why did our team? Yeah, they were great. They were very good, but they also were bred to want to be Brendan or Sam. They wanted it and they went out and they've become The CROs at 10 iconic leaders from Rippling to Gong to Brex and others, they wanted it. So these ambitious folks are out there, even if, and give them their shot, keep interviewing 100. And if you don't think there's a great VP of sales out there, it's because you've never worked with one. This is maybe the last point I'll make and take a break. This was an old, maybe one of the best blog posts I ever read in my entire life was years ago, a guy named Joe Krause, who you won't know, but he founded Excite, which was an early Google competitor that got bought for billions. And then he founded an early collaboration company bought by Google. And one of the first things he wrote when he was at Google is, if you don't think you need a general coun— a great general counsel, it's because you've never worked with one. You think legal is stupid. You don't see the point. It's wasting your time. But when you've worked with a great— when you're growing and you have a million contracts and risks and you've worked with a great lawyer, you're like, Jesus, that's great. Turns out it, I've rewritten this for, for us. It's true of everything. So many great CTOs today think they don't need a VP of engineering. I'm tired. I don't want, I don't want someone that just does process and wears a blazer. You don't need that. But if you've worked with someone that is amazing, you will never go back. When you've worked with a great VP of engineering, you will never go back. So many folks today are like, oh, I'll be the VP of product forever. I don't need someone that like is working on a pixel in Gmail. Understood. Have you ever worked with a great VP of product that could walk into an enterprise customer and make that workflow work and close that 6-figure deal with you? Once you have, you've worked with an amazing one. Have you worked with a VP of product that went out and in his first 2 weeks met with 50 customers and came back with 10 insights you didn't know about your customers? You probably have, and I have. Then you'll want that VP of product. Same with marketing, and it is true with VP of sales. If you are burnt, if you made 2 mishires and you're a little bit broken like Andy in that story, like many of us are. And you don't want to, you don't want to get off the floor and you want to stay in founder mode. Trust me, there are the ambitious out there. Go find them. You will find them. There are the ambitious. Your product. Yeah. Okay. Maybe you do some weird regulatory thing for wastewater management, or maybe you do some weird, really weird part of, of defense security or really weird part of the tech stack that people aren't interested. Maybe you're doing advanced Fortran integrations and you think you can't find anybody to do this. You will find somebody. You will find somebody if you're tenacious that loves it. Your product is, you're not that special. Your product isn't that special. Your moment, the way you're bringing these elements together, very few things in software are new. You will find your person. Keep hunting. So those are my 10. Thank you. Appreciate it.