The Top 10 Mistakes I See In The VP of Sales Hiring Process These Days with Jason Lemkin

Hello! Hello, everyone! Welcome to another week of Workshop Wednesday. Thank you all so much for joining. Just giving folks a moment to get here in the room and get settled. Welcome! Welcome!

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Hello, everyone! Great to see so many familiar faces. Hello, SaaStr community. Thank you again for joining us today. We are thrilled to be back for Workshop Wednesday. It is a holiday week this week in the States, but we know people are tuning in from all over the world. But with it in the spirit of Thanksgiving, we are so grateful for this community and for everyone taking the time to join. Every week, you know, we bring along a SaaStr expert to walk us through some content and to make sure we have an interactive Q&A. And this week we are hearing from SaaStr's own Jason M. Lemkin. Jason M. Lemkin needs no introduction. His sessions are the most requested and the most popular. And today is going to be covering an always evergreen topic, the top 10 mistakes of sales hiring process that he's seeing these days. You probably know if you're in this room that he's written a few blogs about this, he's tweeted about it a bit over the years. But with ever-changing market conditions, there's always new insights, always valuable lessons. So we're really thrilled to hear Jason's take on the latest. And as always, we're going to have time for questions at the end. So please be sure to drop them in the chat. I'll be coordinating with you to get you queued up to ask Jason live, or I can help facilitate. So without further ado, Jason, I will pass it over to you to take it away so we can maximize our time with you. But welcome and thanks for hosting this week's Workshop Wednesday.

Hey, hey, thanks everybody. We'll go as long as we can with questions on hiring a VP of sales or frankly anything even vaguely related to that. Put them in the chat or otherwise and during this, or more likely at the end, I'll do as many as humanly possible. This is— I did a blog post on this topic a while ago, and I realized it was worth a deeper dive to be helpful. And, you know, we've been writing about hiring, the cheat codes to hiring a VP of Sales on SaaS, all the way, my goodness, since 2012. So for 11 years, it's some of our top-rated content. We've got a set of interview questions you can find on SaaStr. There's a great ebook which you can download, which is pretty good. We must have, we have over 100 of the top CROs having done SaaStr presentations at annual and otherwise. We just had the CRO of Toast and OpenAI and Cloudflare and so many. But when reflecting, I actually realized the last 18 months or so has seen the biggest changes in VP of sales hiring in my career in SaaS. And in fact, for a variety of reasons, I realized over the last— over this year, I've interviewed almost 100 VPs of Sales for portfolio companies, for friends, for Saastr itself, just so many more than I think in a year than I've ever interviewed. And the conversations have just been different. And that's kind of like this sub-tagline here. We're still learning what world we're in. I think some of this is the way we interview now, which is that we all interview over Zoom or whatnot first. Some of it is how we hire. Some of it is figuring out how we're gonna build these teams in the current age. Some of it is weird overhang from the crazy explosion in SaaS in the second half of 2020 to 2021, to the downturns for some of us, but not all. Some are growing like crazy, but the downturns for some of us the last 18 months to dealing with team turnover and layoffs and quiet quitting and just so much has changed. And this isn't the most profound presentation, but hopefully it'll be helpful to folks because trying to not get this hire wrong is so important. So I thought I would say, talk about the 10 mistakes I see in the VP sales hiring process these days. And just by way of caveat, I think 8.5 of them are new, are things that are different than they used to be. 2 are golden oldies, but still I wanted to have them all together in 10. So let's chat about them. And we can talk about as many questions as you guys have at the end. Now, this first one is nothing new, but boy, have I seen this issue accelerate the last 18 months. And the reason this is number 1, and you gotta trust me on this, anyone that's here today live, watches this later, listens, if you don't get to 2 through 10, if you don't, if you don't do reference checks, if you make all the other mistakes, trust me on this one, and a lot of folks challenge me on this one. A lot of VPs of sales and CROs challenge me on this one at first, but then they come back to me a week or so later and they say, you're right, you're right, Jason. And this is number 1. Never, ever, ever, never, ever hire a VP of sales who doesn't really understand your product during the interview process. I have seen this be the top mistake, and I knew this was a mistake in the old days, but if I have to look at the top reasons I've seen VP of sales hire implode over the last 24 to 30 months, it has been this. We have hired more quickly, we have hired over Zoom, and founders are attracted to folks that know sales process and can talk about recruiting and NRR and GRR and ARR and all of these things, but they never understand the product. Now, sometimes you can be lucky, you can hire a VP of sales that already knows your product, right? I was lucky, we've chatted over the years a lot about my first great VP of sales, Brendan Cassidy, who had worked at LinkedIn, but LinkedIn was a customer, an early customer of ours. So while Brendan didn't know everything about the product and he is a 10, I kind of forgot about the fact he already knew the product pretty well because he'd been using it a year and a half in production. But I can tell you, especially for non-sales products, for non-marketing products, for more complicated products, for workflow products, for technical products, for developer products, for products that in any way, shape, or form are more complicated than the last sale, I find they implode. And the simple reason is this bottom piece is you can't learn it on the fly. You come in, you join as a VP of sales, and you think it's all about process. And you, if you don't know the product, you start joining calls and you start talking about, uh, when can we get the contract? And do you need a discount? And do you need a bigger discount? And, uh, how can we get it done this month or quarter? And you go through all the mechanics, but there are so many SaaS products and it's so brutally competitive that the VP of sales that doesn't know the product is just gonna lose the deal. They're gonna go to your competitor who deeply knows how to solve your problem. These VPs of sales that don't know your product, why is that an issue? It's because they can't solve your problem. And I hear a lot of folks say, no, it's okay as long as they know the industry. No, it's not enough. It's not enough to know the industry does not mean you can solve the problems. And I hear other folks say, hey, why is it my job to, to learn before I start? It's because you can't succeed if you don't. Okay. And we have this thing called Google, and there are explainer videos on websites and there are weekly webinars like we're doing here. We do 52 a week at SaaStr. I can't even— for SaaStr itself, we— I interviewed a lot of sales candidates the last year, the majority of which never even watched a Workshop Wednesday that we're on or read anything on our website or watched a single sponsor video. You can get up to speed, you can use the demo. And so trust me on this, if you like the candidate, if they talk the talk, if they dress well, if the team loves them, but they don't know the product, they never will. There's not enough time. They all get slaughtered in most spaces. So trust me, I have seen this and I had an aha moment with a VP of sales that I've known a little bit for years that I really like that was profoundly struggling recently, joined a great startup and sales went down, sales went down. And it was the first time I'd heard the honesty. The honesty was I really should have known the product when I started. I came in, I hired reps that didn't know the product. I didn't know the product. I thought I could run a Dashboards playbook. I thought I could run a Territory playbook and a Quota playbook, and I never learned the product. And we just lost all those deals to the folks that did. So trust me, I know it sounds counterintuitive. I know you wanna give folks time to learn the product. If need be, you know, pay 'em for a few weeks before they start on day one. Look, if they don't have time, give 'em a couple weeks of quiet salary. And your job is to quietly go do research if literally that's such the issue and they're so great. But make sure they know the product, not an expert, but pretty well on day one, or they'll never have time, they'll never catch up. Okay, two, this is one that is not new, but I find people skipping this this day. So I just wanna touch on it briefly so we have it comprehensive, but never hire a VP of sales with no one lined up to follow them. Never do it. You can hire, of course, an AE, an individual contributor. You can hire maybe even a lead, maybe, But all the great VPs of sales are spending 25%, 30%, 40%, half of their time in some cases recruiting constantly, not always working with recruiters, but passively recruiting, following up with folks, relationships they built at their last company, relationships they know in the industry. If you know any great VPs of sales, you'll know they all seem to know each other, right? Or other people, and they all seem to know a few great up-and-comers, not everybody, because they know, because sales is usually half the headcount in a startup. Right? There are no efficiencies. There are no economies of scale with sales. In fact, you have diseconomies of scale, like they consume more and more of your headcount. And so any sales leader knows that half their job is building the team. And the last thing they want to do is start without a team, just like you shouldn't start without knowing your product, which is the first point. You shouldn't take a VP of Sales job unless you've already got some of your team lined up because it will take you too long. And where VPs of Sales fail is they start and they're like— and I ask them when I do interview, How are you going to get your candidates? He's like, well, after I start, I might hire a recruiter. Okay, who's your recruiter? I'm not sure yet. There's just no way. There's no way they can, they can build the team you need to have if they have no one to follow them. So just trust me on this one. You can hire them in as an individual contributor. You can hire them as an A. You can find some other role for them, but you can't be a sales leader if no one will come with you. You've already started the recruiting and in fact, you're recruiting 52 weeks a year. Okay, third one. This one is newer. It's not new, but it is newer. Now, in the old days, we wrote a classic SaaS post, which people still love and we update. It's called the 48 Types of VPs of Sales, right? Don't make the mistake and hire the wrong one. Google it, read it. It's still good today. It talks about Mr. and Ms. Dashboards when you get bigger and all they wanna do is hit reset and watch the dashboards. That was a persona 10 years ago, 5 years ago, 3 years ago, and 3 weeks ago. That is an issue. Um, but there is a related issue that I think is highlighted, that has been accentuated by two things. One is just how long we've been doing SaaS, right? We've been, we've been doing this current generation of SaaS for like 15, 16, 17 years. People get tired. Um, and I think part of, and I think people just have gotten burnt out over the last 2 and a half years with all this change since 2020. And so I find so many candidates I talk to not candidates, in many cases candidates that have only been doing this for a few years, but so many candidates that again talk the talk. They know NRR and GRR and Salesforce and HubSpot, but they just aren't willing to sell themselves anymore. They're not willing to, to close deals themselves and they will tell you it's not important. I will hire Bill and Elena and Joanna and John and Jillian and they will do the sales and I'll coach them and I will help them. Great. But you will never learn the product. You will never get good at it. You will never know the specific playbook. You will never know the customer pain if you don't sell it yourself. So I used to be a little nuanced on this. I wrote an old SaaStr post, which is, I think is pretty good, but maybe misinterpreted. So I updated it, which is, you know, your VP of sales can't hold a, carry a bag forever, right? If you're gonna come in as VP of sales and then you've gotta take that company from $4 million to $8 to $16 to $32 to $64 to $128, you can't have a full quota. There's no time, right? You've gotta recruit 100 people and a RevOps team and all all these other pieces. But if you don't start carrying a little bit of a bag, you never learn how to sell. I see this again and again. Don't hire these people. Don't hire a VP of sales that at least for the first quarter not only isn't willing but wants to sell themselves. And I'll simplify this. Again, I've done like 80 VP of sales interviews this year and I listen and I do my Columbo routine and I'm trying to be really nice and friendly. That may surprise some of the SaaS team who thinks I'm very intense, but I try to be very nice and friendly on these interviews. And about 30 or 40 minutes in, I'm like, hey Taylor, So do you think you actually wanna sell the product yourself? And they're usually pretty honest. Nah, I don't, I'm not like, I'm past that point in my career. That's, don't hire that person if they're past that point. The best folks are always selling. If you watch the other, just, just last night, it's people selling, but, but people made a little bit of fun of Marc Benioff for reaching out to a leading OpenAI engineer himself and saying, wanna come work here during this OpenAI talent? That's selling, my friends. That's selling Salesforce. If it's not beneath Marc Benioff to sell, don't hire VP of sales where selling her or himself is beneath them. Trust me, you don't want this person. You don't want them at $100 million, $200 million AR, but there's no way you want them at $2 or $15 or $20 or $30 million in AR. Okay. 4, related to the prior point, it's another tell. This is another tell. I know that we're all comfortable at home. I know we're doing Workshop Wednesdays and all this fun stuff, and we're all, whether you're in the office or back, We're all running distributed teams at some, to some level. I don't know anybody that, that in my little ecosystem that's 100% back in the office. It's just because if nothing else, we hired so many great people for 2 years that aren't in your city. You've gotta have a distributed team. But this is one that just outside of SMBs, and you gotta ask is you can't hire a VP of sales that doesn't want to go visit customers in person. And I get it. Not all of us want to travel. It's tiring. And not only do we not wanna drive to the office, we certainly don't wanna fly to Vegas to meet customers at re:Invent or to fly back east or New York or this or that. But I had an aha moment earlier this year when I, when I was talking with a highly regarded VP of sales candidate, highly regarded. And it was to join a company that was in the Mid-Peninsula in Menlo Park. And this candidate lived in the East Bay, in the Bay Area. And I asked him, if he was willing to go visit customers in Palo Alto. And he said it's too far. He said he's not willing to do that anymore. It's too far. Okay. So we can laugh, but this was a highly regarded candidate who was a road warrior. And I get it. Okay. I get it. But some folks spent, you know, a ton of time on the road until March 2020, and now they want to stay home. They want to stay home with their families. Their offices are comfortable. Their lives are comfortable. Frankly, most people work about 4 hours a day as it is. We used to commute to So that felt like 6, and then we'd go to lunch. So that added up to 8. But now a lot of people just want to work their 4 and they don't want to get on a plane. Doesn't work in the enterprise, doesn't work in the mid-market. You will get demolished by competitors and others that show up to close these deals, especially these days. Again, for small businesses, $1K deals, $2K deals, 2 call closes not required. Above that, don't make the hire. Okay. 5, I think we made this point, so I'll do it briefly and go on, but they've gotta close at least some customers themselves. Okay? We made this point. So maybe I, I got it all in, in, in prior number 3, but again, too many VPs of sales just don't wanna close customers themselves. They wanna join folks on their team. They wanna help them, but they never learn. They never really learn the playbook to closing if they don't wanna close any customers themselves. So ask, ask, what do you want? Do you wanna close any customers in the first 90 days? The best ones always say, you know, I want to close a few, I want to carry half a quota, I want to, I want to learn the ropes myself, I want to get out there and start talking to prospects my first month. And the mediocre say they're just going to help Billy Bob, Elena, and Jane. Okay, 6, this is one that's new, er, newer. And it's tied to some of the other issues. But this is something that has exploded in my interviews this year, which is the cynical VP, the cynic. And you honestly, you can see this all over LinkedIn. You can see everyone on LinkedIn talking about how they got fired from their last job in a year, even though they crushed 7,000 times the quota. You can see everyone that wants to be a solopreneur or a wanderpreneur. You can see everyone that's got 8 side hustles and they're burnt out. And you can see this whole thing. If you want, hey, if you, I need founder pay for founder work. I'm not gonna work a full-time job unless I'm paid as much as the CEO. Let's have as much equity, and as much everything, this vibe, it's a vibe. It is cynical. It is cynical that these stories that I worked my ass off for this unicorn and made nothing. And you know what? There's 1,000 unicorns, and I think 700 of them are either going to fail or be worth less than what they raised. And so 700 of those VPs of sales are going to be pissed. They're going to feel like they got ripped off. They joined a unicorn. It was worth $1 billion on paper. How could I make nothing? That Lemkin CEO or whoever ripped me off. The system ripped me off. The VCs ripped me off. Sequoia ripped me off. And I get it. And even myself, I've had moments in my life when I've gotten the short end of the stick on deals or the system, such as it works in startups. And it is a system. People get equity, companies grow, valuations grow. It doesn't always bounce the way you want it to bounce. And I'm not here today to talk about why it works the way it works. We can do that in the Q&A. What I want to say is, I've got to tell you, I think 30% of the VPs of sales, maybe approaching 50, I talk to are burnt. They're cynical. They're cynical and you need pirates and romantics in a startup. You don't need someone that can tell you why their last companies were jerks or mistreated them. And you don't need someone that has 7 to 10 angry LinkedIn posts a week about how they were ripped off. I'm not saying they're wrong. Like, I have a ton of empathy, but this person will not come in and make your sales process better. They just come in and every— the world is against them when they start at your startup too. It's a quiet toxicity that then permeates your sales team. You end up with a bunch of cynical sales reps working for them. And what you want is to be exceptional. You want an exceptional startup. You want— look at the OpenAI thing, like it's crazy. But look at all everyone that came back last night to work there. We can't all completely reproduce that in our startups, but you don't wanna start out with a cynic. You don't wanna start off with a cynic or you'll never build a great sales team. And I know there's a bunch of sales and revenue leaders that disagree with me when they hear this, but then they'll think about it and come back, you're right, you're right. Like, and they'll— and the truth is And here's the real truth on this point, and it's a tough lesson. A lot of these folks that are cynical need to get out of the game. This is what one of my favorite sales leaders told me when we talked about someone we knew that kind of imploded as a VP of sales. And I said, what happened with him? And my mentor, good friend, said, you know, he just should have stepped out of the game 6 to 12 months ago. He just, you know, sales is hard. We've written about this on SaaS for years. Every month, every quarter, the dials in Salesforce or HubSpot go back to zero and the goal goes up, right? Except in the tough times, maybe people got a little bit of a pass on the bookings the last year in some minutes, but mostly each quarter the number gets bigger and bigger and harder and harder. Now you have to do it with less budget and it can burn people out. And maybe people can't be a VP of sales forever. Not everybody, even if you give them a title, even if you make them SVP of sales or CRO, whatever, maybe it, for some people, this isn't a lifelong career. Um, but you don't wanna hire someone that's actually done. That's the thing. You don't wanna hire someone that's actually done but needs a job. I feel for them. But don't hire them. Okay. Seventh one. This is number 7. This is related to the prior points. And again, I get challenged by a lot of revenue folks, but boy, trust me on this one. Trust me on this one. If you want to tell of someone that is burnt, that doesn't want to do sales, that doesn't want your job, they're just way too often on LinkedIn and social media. I, I'm not a huge fan of social selling, but I do think that promoting yourself as a leader to some extent absolutely helps with recruiting. I think it absolutely helps. And I think one or two posts a week that are very insightful, um, and that can attract folks to work for you, or at least they can research as part of the diligence process, I think that can be great if you're great at it. Um, the folks that are posting twice a day, uh, especially the cynics, um, they have decided they wanna be influencers. There are many SaaS folks, not just VPs of sales, plenty of maybe even more in marketing that just frankly want to be influencers. They, they, they— and you can see them bragging. I got to 1,000 followers, I got to 5,000, I got to 10,000 followers on LinkedIn. How much money do you make with 10,000 followers on LinkedIn versus your OTE? It's a bad ratio, but they're excited about it, whether they're burnt out or don't want to do it or have done the journey. But trust me, I got to tell you, the folks that are constantly posting on LinkedIn They're bad for a VP because they don't want to do the job. And actually, I think they're pretty terrible for the SDR and AE that spends their whole day posting on LinkedIn. Like, after 3 weeks being an SDR, they're the world's biggest outbound expert. I'm not sure I'd hire them either, although a little bit of that helps them get a job. But just a little is good. But the 14 posts a day to be— you don't, you don't need an influencer at your company. You don't need it. Point 8. And this is not new. This is not new, but it has accelerated the last couple of years. And it may be related to VP of sales burnout. It may be related to how long some of us are doing this, but this VP of sales that doesn't really want to be VP of sales, they want to be COO or CRO or whatever. Here's the thing, let me simplify it and then let me just dig in on a little bit more and talk about exceptions because it's not, completely a bright line rule, but it's close. This is the sub point on the slide. A VP of sales has to love closing. They have to be closers. They have to be closers. I've never— I don't know any great VPs of sales that don't love closing deals, that don't love bringing them in early, that don't love exceeding the plan, that don't love crushing quota, that don't love building a great team that goes out and beats quota and beats the quarter, that doesn't love the game, the hunt, the hunt of beating the competitors, of figuring out the playbook that wins versus losing. You want closers, want to close. And if I had to simplify a VP of sales job, half of it's recruiting and half of it is doing everything you can to close. You don't want them in operations, you don't want them in customer success, you don't want them in onboarding, you don't want them in renewals. If your product is good, someone else should renew it. It should not require massive amounts of sales efforts to renew it. And sometimes now here, there's a couple of exceptions here. Sometimes their— the VP of sales is one of your top executives and they just have to fill a hole, right? There's a great startup I'm working with right now that's probably the fastest growing company that I've invested in. And right now they don't have anybody to do onboarding. So the head of sales is taking over onboarding, but not because it's— it's not a fiefdom. It's not because he doesn't want to do sales. It's because there's a gap. It's so closely connected to sales. If you don't onboard your customers, you're not going to keep them right, that they've taken it on. But the one that wants a bigger title, this one just doesn't work. They end up hiring a VP of Sales under them, and then neither of them really want to do sales. You need 3 to 4 times the budget and it just becomes a mess. Hire a VP of Sales that wants to close. The second small exception is title inflation. And here is where, as the years have gone by, I've actually gotten more mellow and nuanced than some. You'll see a lot of folks saying be very careful, you can't take titles back, blah, blah, blah, blah, blah. It's all true, right? If you overtitle somebody and you make them a VP and then they're really a director, it's a pain in the— pain in the neck— pain in the rear to level them if they want this and that. However, folks, the best folks have egos, they have confidence, they want drive. And I think if someone's been a head of sales or VP of sales for a while and they're not really a CRO, but it's not about a fiefdom and it's not about owning customer success and onboarding and renewals all this other stuff. It's just about getting that ring and getting that recognition. A little title inflation is not the end of the world. My new rule is an inflated title is okay if you think they'll earn it in the next 12 months. So if they're not really your VP of Marketing, they're really a director, but they're so good and you think they'll get there in a year, just give them the title if they ask for it. Don't force them to be Director of Marketing or even Head of Marketing. Same thing, a lot of salespeople, when I started in SaaS, everyone wanted to be VP of Sales, every hot AE. Now every hot AE wants to be a CRO. It's not worth fighting. At some point you're going to have to give them the title because that's just, that's just the way they grew up. But again, that nominal CRO title is very different than wanting to do more than sales. Be very, very, very wary. Personally, I would never hire someone that wants to do more than sales. Okay. 9. This one's going to be triggering to some people. Okay. And I want to make sure it's taken the right way, but it's correct. Hiring a VP of sales that hasn't been in sales for quite a while. This should say quite a while, but wants to get back in sales. Now, a little bit of a break is good for all of us after 5, 8, 10 years. Okay. Someone, a great person that maybe stepped out of the workforce for a while for their family, that actually you should have one of those on your team always. This is my hack. Always have someone that is great, that's, that maybe stepped out for a little while to help raise their family, but that's a rock star. Those are, those are gifts. I think you should always have one. But the ones that just futzed around, they golfed or they backpacked or they just spent like a year and a half on LinkedIn, or I know this is going to be triggering, or have just been a fractional CRO for 4 years, they don't want it. It's too hard. Again, sales is a hard game and the boss is even harder. At least if you're a great AE, you can just hit your quota again and again and again and sometimes even get better at it. Right. The best AEs get— sometimes the best AEs can just dial it in and close $1 million or more a year. But VP of Sales is always harder. So nothing wrong with someone that took 3 or 4 or 5 or 6 months off and took a break. You want that. You want someone refreshed. But— and definitely hire someone on your team that took some time off for family. But someone that went off and did product for a while or went off and built sailboats for a while, they're not going to get back in the game. They think they want to because they need a job. But if they really wanted to go for the brass ring, they wouldn't have stepped off. They wouldn't have stepped off the stage. Okay. So a lot of that stuff is new or accelerated. A lot of that stepping off the stage is accelerated because a lot of the folks last couple of years just decided to not work for a year or two. Fine. You might have a role for them, but it ain't as your VP. This last one is the other one that isn't new. But boy, this is— this mistake has accelerated the last couple of years. Because the number of SaaS and cloud leaders have accelerated. So many great IPOs, so many, you know, 5 years ago, 6 years ago, Datadog wasn't huge and no one had heard of HashiCorp and Cloudflare was tiny. And but now there's like so many great logos you can hire from, like they're everywhere, right? So this is the mistake that founders are reluctant to admit, but you got to take your hand. And if someone last worked at a top company that you love, you got to put your hand over their LinkedIn and be honest. Would you hire them if they hadn't worked there? Would you hire them if they had not worked at Notion or whatever your dream company is? Would you hire them if they hadn't worked there? And almost always when I get an email, hey Jason, would you interview Elena? She, she's so great. She's a senior director at Shopify or a senior director at Datadog. When that's the intro, I mean, the majority of the time it ain't gonna work. It ain't gonna work. And it's not that there's anything wrong with working at Datadog or Shopify. I'm picking two of our most iconic leaders. But it's because you're being blind. They're being blinded. They're being blinded, right? They're in e-commerce, they're a developer, or they worked at Gong or wherever, pick your hero tool, or Salesloft or Outreach. They work there. And I interview them and again, they don't really know the product. They don't really want to be a sales leader anymore. They don't want to sell themselves. They're breaking a lot of these 10 rules. And so, I'm like, ah, and I don't share all that feedback with the founders. I'm a little careful, but I ask them one question. If you put your hand over that resume, If they hadn't worked at Gong or Salesloft or wherever, would you still hire them? For sure. And they're like, I'm not sure. Don't make the hire. We've all been blinded by logos our whole careers. It's just, there's so many veterans out there. There's so many logos you can recruit. It used to be impossible. Like back when I started in SaaS, the only logo was Salesforce. Everyone wanted to hire from Salesforce because it was the only multi-billion dollar SaaS company. Now there's, even with the market down, there's dozens and dozens and dozens of billion dollar SaaS companies to hire from. So if you keep at it, you will convince. Many people from a fancy logo to join you. And if nothing else for you and for folks on your team, do this. Act this. I know it sounds dumb, but put your hand on their LinkedIn, on their— where they work there, and ask Jeff, would you still hire her or him? And if no, don't make the hire. So you can use this if you want. Use this as to challenge yourself when you find a great sales leader. Dust off this blog post, dust off this presentation, ask yourself these 10 questions. At least you'll know, at least you'll know you're making a mistake intentionally. And or maybe the best outcome from this, and I know it's hard, I know it's hard, is that it will challenge you to do one more interview because really that's— if I had to ask one and then we can take some questions after this. The biggest mistake we all make is we get tired, we settle. I've been out there looking for 4 months, 5 months, 6 months for my VP of Sales or VP of Marketing or VP of Customer Success. And I settle. And it, and it feel— it doesn't feel good to settle, but you get a sense of relief and you introduce them to your team and the org chart looks good and your investors get excited. And then 30 days in, they're not signing up for their number, they're not meeting anything. And 90 days in, it's worse, right? So at least use these 10 points to challenge yourself in hiring, especially because some of it's triggering. A lot of folks will disagree with it. But thanks everybody for for listening, and maybe we can try some of the questions here.

Yeah, thanks, Jason. Um, my question to you was, how do you ask people, um, how do you evaluate if a VP of sales actually wants to sell? I just love that you ask directly and that people answer you honestly, but I guess maybe they read—

you gotta ask like 30 minutes into the interview. Okay, if it's the first question, they're going to be, they're going to be thinking, right? But once they talked about their, their philosophy, it's First of all, someone tells you their philosophy of sales, don't hire them in a startup. But they've gotten deep into it and then you just ask them about half an hour in and I don't think it's that important. I think all products are kind of the same. They're all kind of the same, Taylor. It's more about my patented methodology for selling, but it doesn't really matter which product it is.

Okay. We do have some questions as expected. A lot of comments too, Jason. People are super appreciative as always. We're going to get started first up with Nassim. She has a couple questions for us. Naseem, are you still on to ask your questions for Jason?

I am, and I have more than a couple, but I'll try to keep it to one to start at least. So Jason, really appreciate the knowledge that you shared and everything. My first question actually goes to your very first point about hiring someone that knows the product. Obviously, full knowledge of the product comes when they're fully ramped. They've been in the role, they've worked with it, they've had the customer feedback. So if you would say, you know, 6 months to a year ramp, they know 100% of the product. What percent would you want them to have when you're hiring them?

I want them to be 90% as fluent as whoever did the last webinar, whoever did the last sales demo. A good VP of sales should ask you for 10 gongs. A good VP of sales should watch the last 10 webinar— customer webinars you do. If you've listened to 10 gongs and watched 10 webinars, I'm not expecting you to actually know how the webhooks work or how to configure the API, but I'm expecting you after 20 20 interactions to be able to sell me this pen.

Okay.

And I used to think sell me this pen was the dumbest thing in the world, right? Sell me this pen. Sales folks love selling. I'm like, I'm not actually a sales folk, but there's some truth to it. If you can't listen to 10 gongs and watch 10 YouTube videos about the company and watch the explainer videos and you can't sell me this pen, don't make the hire. Yep. We're scared these days. People used to always do sell me this pen in the old days as part of an interview process. And we've definitely backed away with it from AEs, which I think is a mistake. Not all everyone has, but I don't see it ever happen with VP of Sales, right? Ever. Right. And I'll give you just— I'll give everyone just a shocking example. I recently went through a CRO interview process helping out, and I was the 9th interview for this CRO. And this company had 50% of its revenue from direct sales, 50% from the channel. And that was the 9th interview. And I asked him, since your experience is only in direct sales, how are you going to get up to speed on the channel, right? I assumed he'd watched some talks. People— he's like, I actually— I didn't know that half our revenue was from the channel. This is someone that passed all the interviews.

Wow.

There's no excuse, right? So I don't expect them to know everything, but like, you—

if you—

again, if you do the 10 and 10, you're going to be able— if you can't sell the pen, you can't sell.

That makes sense. And if I'm understanding correctly, you're also saying basically they need to have consumed all the knowledge that you have out there. That's a huge part of kind of what you're evaluating. If there's webinars, if there is testimonials, if there's kind of client examples, anything on the website, they need to have consumed it and they need to know it.

Yeah. And I think we might debate, and I will even go even further, I will say If they haven't done a little of that before the first interview, don't hire them. I have yet to see a VP of sales, or frankly any senior candidate work out. And this is the problem with Zoom interviews because no one puts any work into a Zoom interview. They pop on a Zoom interview and they just wanna have coffee and they're all, "Naseem, so what do you guys do?" I'm like, "Did you go to my homepage? Did you have a chance to look at—" So many candidates actually don't even go to the product tab on the homepage and ask the dumbest questions. I've just never seen one of those people work out. So that's like the pre-interview one. But in the old days, when we'd interview in the office, everyone would have done a little homework. They'd come with notes, they'd be like, notes, I saw on your— I was watching, I saw on your homepage, you talked about how this— your customer was Clorox and this happened. Now people show up with a Zoom and they, they're all friendly, but they've done— they haven't even done 5 seconds of work, right? I've never seen those work out. And maybe that doesn't directly answer your question, but you've got to get smarter and smarter as the process goes on in the product. Putting 15 minutes in before an interview with the CEO is not a huge ask, is it? It feels like it is in 2023 because no one does it, but it's not a huge ask. And if you're going to take a VP of sales job, not with both a high OT, but a lot of career risk, a lot of career risk, you can't learn the product a little bit by the end of the interviewing process? Yeah, you can't. Why wouldn't anyone that's in— that is going to be on this journey with you, that is a Pirate or a Mac, that cares that's gonna knock it out of the park, why wouldn't you do it? As if, I mean, any founder would do it. On the other, you would, you know, I mean, the one of the dumbest things is start a company and never do any interview or talk to any customers. It happens sometimes, but it always bites you. Yeah. So, yeah, so I see this, I gotta say, and I see this comment from here, hard to believe this case. I gotta tell you, it's the majority. It's the majority, um, and especially— and it's the case with a lot of folks with good logos that are coming out of good places because they're going to get a lot of interviews. And instead of having to schlep across the Bay Area or fly to an interview, now they can do 30 on Zoom. So they don't put in the time, right? Um, yeah, so that definitely makes sense. Thank you for that. You want it— so the last point I'll just say to everybody, I know you— the biggest mistake in all of this is kind of what you're teasing at. Is cutting people slack. Cut them slack that, that they're, they have, that they're a little young. Cut them slack that they didn't work at the hottest company. Cut them slack that they made one mistake earlier in their career, they got fired once, right? But don't cut them slack that they don't even put in the effort to learn your product. That's the slack everybody's cutting. Don't, don't cut it.

Yeah, that definitely makes sense. Thank you so much for sharing that. And one more question, and I promise it'll be the last question I have for you, but you talk a lot about having the VP of Sales having the ability to close the deal themselves. Wanting to and having the ability to. So how do you weigh their leadership skills? Because at the end of the day, they also need to have the ability to inspire and hire and onboard and grow a team. So how do you kind of in tandem weigh the leadership skills alongside the closing skills?

You don't need any leadership skills. You need— and I know that sounds silly because it's not true, but you need to be able to recruit good people. So here's the You do not want the handsome strapping sales leader that talks in a baritone about how we're gonna charge the hill. Like, that's great at Adobe or Microsoft. We, you don't need that at a startup. What you need is someone that is a talent magnet. So all you need to do to assess a VP of sales leadership skills is use your own assessment, right? You, you know, are, are they above the bar? Yeah. And talk to 2 folks that they're gonna bring with them. If those two folks are good and they're passionate and they believe in her, then if she can find two, she'll find another two and then another two and then another two. That's all the leadership that matters. And I will tell you, to be clear, some of the, the best first-time VPs of sales I've ever known, you absolutely would not think that like leadership skills are their top criteria, but recruiting is right. And they always have great people, but they may seem different. They may dress different, they may talk different, they may, they may seem younger or less experienced than you'd expect. Not, I don't even mean this in an age way, but they may not seem to have that leadership package, say, for your COO. Yeah. Yeah.

Cool. That's very helpful. Thank you so much.

I appreciate it. For sure.

Jason, I just realized you're still sharing your screen, so if you wanted to drop down, you may be able to see a few more folks. And then while you're doing that, Addie, I think you have a question or a couple of questions if you would like to.

Yeah, I'm gonna, I had a similar question to Naseem, so I'm not, I'm gonna skip that one and maybe rephrase it slightly differently, Jason. So the first, thank you for sharing and thank you for pushing some buttons. I appreciate that. I think it's useful, especially coming from you where, you know, you're not doing it to get likes on Twitter in this case. So full transparency, I'm fractional, not in sales, and I agree 100%. If you've decided to go fractional, you've done it for a while, you've I've lost the hunger to do it for one place for a really long time. And I'm fairly honest with people who tell me that, and it helps because it also clears my lane as to where I'm gonna play. That being said, I was curious, would you— I always think to have a lot of information, which is super critical to show you care about the company and learn it, you need to get almost get signed. Say, I say to clients when I was, I'll sign your NDA, can I get a couple more pieces of information? Yes. And therefore prove that I'm actually doing some research stuff I can't get off your website. Would you encourage CEOs to do that? Because I would.

This is another top mistake. It's not in the deck. Oh my God. From these 80 interviews I've done, right? I can't tell you. Now, they should have asked. I can't tell you how many candidates also don't know fundamental metrics of the company. Do you know? And so I always, I'm shocked when I'm sharing them. Do you know what your plan would be for next year? Do you know your plan for next year is to go from 20 to 30. I don't know. Do you know how big the sales team is? I don't know. At a minimum, what I encourage everyone to do is share the gongs in sales. Just share that. If someone is curious about the role, if nothing else, they're going to listen to 3 or 4 gongs. So, I like to get like, and I ask the team to assemble 3 good ones and 3 bad ones, 3 deals where we won and 3 deals where we lost, which is great. Have them listen and folks don't share those. And they don't share enough metrics. And it's just you're wasting people's time. And I don't know why folks do it, but all I can tell you is far less stuff is confidential than you think it is. Some stuff is confidential and you should, but it's about 10% of what you think is confidential. You got to share a little bit. You got to share a few numbers. You got to share a few lost deals or you'll never get there with the great people. So share more to founders, right? Just figure out what's really secret, like about your product or something. But, you know, even your revenue, I can go on LinkedIn, see how many employees you have, see how you're growing and make some rough guesses. I can figure out roughly where your revenue is. Like if you're claiming you have $100 million in revenue and you have 18 employees, unless you're Craigslist, it just ain't true. Yeah.

And I back into burn rate using number of employees.

You can do that too. It's just like, you know, just share it.

Just share it, right? Thanks so much. Thanks, Adi. Next up is David Nelson. David, you want to come off mute and ask Jason live?

Sure. Yeah. Thanks, guys. Hey, everybody. First off, thank you guys for this community. It's incredible. I've been following for several years and it's been a huge help. Unfortunately, I wish I'd gone through this conversation about 2 years ago. So I run a company. It's about 55 people. We're about $7 million ARR. Hired a VP of sales, did not work, uh, sold less with them, unfortunately.

So terrible but common. Yeah.

Um, so now we're back in this hunt again. So this is a huge help. Um, I'm noticing a ton of people want the CRO title. They don't want VP. And it feels like at our size, we don't necessarily need that, but I don't know, any suggestions there?

Well, that I did hint to that. It's something that I've given on over the years. Um, I just think that, look, you're right. At your size as founders, anyone you're hiring, you're hiring a VP of sales, you're not hiring a CRO, right? That's a fact. But I think it is seared in people's brains. Like, again, 10 years ago, every up-and-comer wanted to be a VP of sales. And folks were so desperate for those 3 initials or letters, VPS, VP sales, that they would move too quickly and they would fail by being so desperate as they used to do it. Now everyone wants to be a CRO. It's just whether it's ego or drive. And so I know many people will disagree out there, but I would give it to somebody again if you think they can grow into the title, right? It's just not worth fighting over. It's not worth fighting over. And yeah, then you're thinking, oh my God, what if I have to hire a real CRO later? Well, people will give this advice that there's nothing harder than leveling someone later. You know what's harder? Not hiring someone great. It's much harder than leveling someone later. Okay, you can either have the really tough conversation, say, hey, now you're going to be a VP or an SVP. Or you can hire a CCRRO, or like, I know it's pain, but it's fixed. It is more fixable than people on the internet think it is. Okay. And I just don't want to fight. You can't fight that every AE wants to be a CRO someday. And you can also even fight that a lot of folks that should just be VPs of marketing really want to be a CMO today. They really do. And I don't think these are battles. I think it's okay to stretch one title. Um, stretching too is the flag.

Yeah, fair, totally fair. Uh, one more question if that's okay. So right now we have a fantastic director sales, kind of moved up, started as BDR, went to account executive, moved up once we had to move out the VP that didn't work, and doing fantastic. But the board wants someone with more experience, right? It's a tough one where we want to level up. We want— you want a promoter. It's fantastic work. Yeah, but the board wants just someone who's been there, done that kind of thing. I got it. So it's a bit of a risk.

And she's both your best closer and best manager. Yeah. Yeah. Look, I don't— you— when it's very interesting when you have turnover on the team, especially like a VP of sales turnover, it's very interesting because you get to watch how the team responds and you think it's terrible. And it was terrible because your sales went down. And it happened to me back in the day with my first VP of sales. Sales went down. Despite hiring 14 AEs. And it's— the story is as old as the history of software as a service. But what is interesting is watching what happens, right? And sometimes your whole team implodes, and that's terrible. But some— but more often than not, the best people rise up, right? The cream rises to the top. And you got to either promote her or be willing to let her go. The truth is, right? And I think It's, I understand the board's perspective and don't do an OpenAI. Talk with them, get them engaged on the discussion, explain your thinking. And you may need to bring in a few, like you may need to bring in a few candidates over 60 days and really interview 10 to convince the board that this is the right risk to take, right? If you haven't done it. But then if that's the right decision, just do it. But don't force it down their throats, right? Because I get it. They want the person that, you know, the, the, the, the, with the great logo and they, they probably put a bunch of money into you and you're doing okay, but growth decelerated over this. And I think that the answer is, is, is, uh, you know, Mr. Paratrooper from, from big company, right? Um, and you know it's not today, right? Right. So interview 10 more. I know it sounds annoying. Treat them with respect. Take it seriously because maybe one of those 10 is good, right? And give it 60 days and include her in the process one way or another, either directly or matter or inherently, and then tell the— do with your investors, pull up the slide, here are the 10 folks I talked to, here are pros and cons, and here's Linda. And of today, like, I don't know where we're gonna be in a year, and we can hire a CRO in a year or two, but right now this is our best way to get back to growth. And they're at the end of the day, they're gonna back you if you show them that thought process. Love it.

That's awesome. Thank you. Thank you. Appreciate that. Okay, last question. I kind of raised earlier in the chat, but for the sharing gongs, do you wait to see who proactively reaches out and says, hey, can I look at some gongs? Or do you say, hey, go watch these 3 good, 3 bad, 10 total?

You know, it's a good question. I don't know. Maybe this is one way I'm passive-aggressive personally, which is I wait for them to ask because the good ones always ask for something. Like, they may not know, they may not always ask for gong, but they ask for something. And then you can say, well, would it help to listen to a few gongs? And they're like, oh, thank goodness. So I'd like to think I'm not passive-aggressive, but I do wait for people to act because the ones that don't is a bad sign, right? But having said that, if I think someone's really, really good, right? And I've spent a bunch of time with them and they don't ask, I also just give them the gongs. Okay. Okay. Right. But I do ask, I do want to see some engagement first.

Right? Absolutely. Right. You want to see that proactivity. But if you're just not getting it from any of these candidates, then do you keep hunting or do you force feed them a little bit?

It's a tough— it's even tougher these days. There's, you know, there's a meta question of how long do you have to sell a candidate before it flips back and they need to sell you, right? And it's always hard, right? I mean, Mark Benioff, again, reaching out to OpenAI engineers or Elon Musk. I forget the CTO at OpenAI that, I mean, he might have been the one that pushed Sam out, but Elon Musk personally recruited him for Google over 6 months and lost his relationship with Larry. It's a big deal, right? I mean, so you got to wine and dine the best candidates, but at some point it's got to flip around, doesn't it? You want the hunger. You want the hunger. It's tough. Yeah, it's tough. And I guess, but that's why I think you got to sell, but there's got to be some point where they, they learn more, right? They do become more engaged in the process. And that's— maybe that's when I would share the, the gongs and such.

Okay, awesome. And we're up in Canada, 100% of our staff are Canadian, but almost all of our customers in the US, 95%, I would say. How do you feel about hiring a leader that's remote, who'd be down in the US versus up in Canada that can see all of the team? What's your deal size? About 50K, 40, 40.

Well, you're at the edge of risk, right? You're selling mid-market to the low end of enterprise, but you're not in your native market, right? So that's the risk you're identifying, right? Yeah. So look, I think selling it is getting on jets, airplanes from Canada to the US is hard. It's a tax and people don't visit customers as often. The Canadian— I work with a lot of folks with great Canadian teams, but the truth is they don't visit as many customers. That's the truth. That's really the issue. They don't visit as many customers. And so you have to decide, no matter what anybody says, is that the right trade-off, right? Because, um, just like the, the seasoned candidate that didn't want to go from Pleasanton to Palo Alto, that was bad enough because this was traffic. Um, but yeah, I mean, you got to go through customs and it's a headache, and there are other reasons, and I work with some incredible Canadian executives, but they don't meet the big customers as often. They'll say the opposite, but it ain't true. It ain't true. The folks in the Bay Area and the folks in New York meet the most customers. Gotcha.

And so better trade-off to do that than to see the team, see the teams over Zoom once in a while kind of thing, but see the customer.

I think the question is really, well, look, here's the thing. The reality is it's so hard to find someone great that you have to make some tradeoff. So true. So I think that's the simple answer. I think that— I think that if you found a beloved sales leader that was local, that would work hand in hand with the sales team together in the office, such as they come to the office and my trade-off was they would visit customers, but fewer customers, I'd take that. I would personally take that trade-off. Okay. I think, I think the honest truth is so many, some, some folks are great at these distributed sales teams, but it's usually for smaller deal sizes. And so many sales teams have, have deteriorated in this current world. And I don't have all the answers, but I can tell you when I was backstage at SaaS this year talking with the best CROs in the industry, the number one thing they wanted was their teams back in the office. That's the main thing they wanted. And they wanted customer success to do any work at all. A different topic. These were the top, the best CROs, but they just, they didn't need people back 5 days a week, but, and they didn't need their number 1 rep back, but they needed everyone back 3 days a week. So how are you gonna do that remote? Like you just need someone even better, right? So I would probably take that trade-off.

Okay. Thank you. Appreciate it.

I'll stop asking questions now. Thanks so much for the great questions, David. Jason, we're getting a couple folks that are asking questions and making some comments just about budgeting. So someone is commenting, I'm scared to hire a VP of sales without having the budget to build the AE and SDR team. Any thoughts or advice in that situation?

Yeah, look, it's, it's an interesting paradox. First of all, step back. I wrote a post that needs a little more— I'll update it because it needs a little inflation added to it, which is you need at least $3 to $4 million to hire your first sales team. Okay? I think that's true today too. You need $3 to $4 million. It doesn't— now you don't need it all on day one and you can fund it from bookings and you can fund it from revenue. So you don't literally need to spend $4 million in one hour to build a sales team. But if you think about what the OTs are and everything, they've— some one or another $4 million of incremental revenue is gonna have to be generated or $4 million of incremental venture capital to fund this team. right? So, and that's daunting, right? And so I think for, especially for bootstrap startups before a few million in ARR, you cannot hire a lot of VPs of sales. They just need too many people. I'm gonna give you an asterisk and a dagger and a caveat in a minute, but you can't, you really can't, if you're bootstrapped, hire a lot of traditional VPs of sales until you're approaching $8 or $10 million, until you have real money. You really can't. Can you hire a true up-and-comer, right? Can you hire someone that David was talking about, which is your best AE that becomes a director, that becomes a VP? Yeah, you can always find money for that person because they're always— here's the point— they're always accretive. So no matter how bootstrapped you are, the best sales folks are always accretive. The best sales folks take 100 leads and instead of turning them into $500,000, they turn it into a million. Every single time, the best people turn the same amount of leads into more revenue. And the best ones, that delta is almost always far exceeds the additional compensation or compensation. So, the mistake we really make is that we hire non-accretive people. We hire non-accretive people. That's the thing. And you have to have worked with a great sales team and in a sales team, probably to appreciate just how accretive the best ones are, right? You know, there are— I know it became a toxic term, but there are 10x engineers. All us founders know there are 10x engineers, and there's not necessarily 10x sales reps, but there's definitely 5x ones. There's definitely ones that do 5 times as much revenue with the same leads. And so they're accretive. So look, it's going to take you $3 to $4 million, and you either have to hire Hire a sales leader and be honest with her or him and say, this is what you got. Like, you're going to have to build up to it. You're going to get one hire a quarter for— and then as you prove it out and as we hit more, I'll give you more budget. It's not that complicated. And you're going to have to find someone that's willing to sign up to live, to work in that environment. And it's going to be a stretch. It's going to be a stretch hire. And that's okay. But yeah, you cannot hire the person that's also interviewing at Notion or Deal or whatever, or OpenAI. You just, you just don't, don't, don't even interview that person.

Thanks, Jason. Another kind of budget-related question from Huben. Um, they're asking, um, let me just find it really quick, I just lost it. They're asking, for Series A company, did not raise a lot and don't plan to raise a lot but want to be capital efficient, how can you attract candidates?

Um, well, there's, there's some complexity here. The real complexity is What's the bookings to OT ratio? What's the bookings to OT ratio? So, a lot of founders freak out about an OT, okay? Like, oh my God, we can only afford $120K OT at our company, but this candidate wants a $130K OT, okay? And let's simplify that half is base and half is bonus. If you don't earn your bonus, you don't make your bonus. Yes. Like we obsess way too much about OTEs and not enough about attainment and what it takes. So, uh, I'm gonna break that up into two very different points. You can probably, even if you don't have a lot of money, you may be able to, you don't have to have like bottom quartile OTEs, but you may need to have top quartile attainment. You may need to have high attainment to make the math work. So let's go back to basics before the boom of 2019 to mid-2022, there were basic fundamental numbers in SaaS. An enterprise rep would need to close 5 times what they took home, a mid-market 4 times, and an SMB rep in a high-velocity inbound environment, sometimes 3 times. Okay, 3, 4, 5. Some folks do much better than this actually, which is magical. And what's under discussed is that what we did with all this venture capital and unicorn money is these numbers went way down. Okay. They went way down and they went way down on two axes. They went way down because we didn't really make you close 5 times what you brought in, in the enterprise. And they also went way down because we hired a ton of folks and a ton of attainment and a ton of people around them and a ton of tools. So, on a blended basis, their efficiency was wretched, right? So, if you just step back for a minute and if you have 1 or 2 reps, that can close 4 to 5 times what they bring in, they can make a lot of money at your company and you can attract other folks because they will make a lot of money, right? So, on the one hand, you can't compete with bloat. The numbers have to work. But at the— but OTs themselves are not the enemy and work your tail off so that 1 or 2 people can work in your system profitably. And make a lot of money. If they see 1 or 2 people are making $300,000, $400,000, $500,000 a year, and maybe to make $300,000, they've got to close $1.2 million, right? Or maybe to make $500,000, they've got to close $2.5 million. Like, that's hard. But once they do it, everyone will believe it can be done, right? And you don't have to fear the high OT. Those are my best, best inputs.

Awesome. Thank you so much, Jason M. Lemkin. Okay. Thanks everyone for joining. We have one question to close us out. Julie Iscal from Workiva is on the line with us. Julie, we'll dive into your question and we'll probably be—

Thanks, Jason and all.

Hey, thanks for joining.

What do you disagree with? No, quick question. I noticed the Flowcast head of sales came at $3 million and is still there at $100 million ARR. And I'm wondering what your perspective is or so I'm told he's told me that if you hire a great VP of sales at, you know, say $10 million or $3 or $20, you know, how long, how long in dollars can you expect they'll stay great for you and your, your company? Is it to $50 million to $100 million? When do you need to?

It's really interesting.

Some will last longer, but what do you, what can we all expect when we hire one at $10 million on average?

Yeah, we actually had a, you had a great session at SaaS Trainer. We had another one with the CRO of Gong together with my with Sam Blonde, who was CRO at Brex, and Jameson M. Lemkin, who is the CRO of Gong, was the first sales leader today, and he's still head of sales today. And they had a— if you really want, for folks in general, watch that session. We haven't promoted it on SaaStr, but it's on YouTube. It's so good. And they talk about— this is one of the top topics they talk about. And I think at a high level, what we learned over the last X years in SaaS, you know, in the old days, we're like, oh, it's tough. You're gonna have to top everybody. Right? That's the way we thought. I think the nuance that we've learned today is for, especially for SMB or mid-market, you get so many at-bats so quickly, like the amount of dog years or sales years you get if you're an SMB is so high that folks like Jameson can go the distance, right? And, you know, Brendan and I, my VP of sales, we watched because we used to compete with DocuSign and we watched one of their early sales leaders be there to $100 million and then $200 million and then $1 billion. I think he was VP of commercial or SVP of commercial. And often these folks are not the CRO, they're the head of sales or the SVP, but they're there forever, these commercial or SMB folks, because unlike the enterprise folks where the sales cycle, like you don't get enough turns, that 9-month sales cycle. And if you're a VP of sales and you miss a quarter or two with a 9-month sales cycle, you never get a chance to recover. But with a 2-week sales cycle, you can get like 30 years of experience in 3 years. So that's my nuance. So when I see a great high-velocity sales leader, my advice to founders is bet on her forever. You never— my advice now is you never want them to leave. And if you're going to bring in a CRO later or whatever, you better darn well make sure they're better than her and that she's in this process. Because these mid-market commercial folks, we're seeing them go from a couple million to hundreds of millions. I think Flowcast seems an aberration like 10 years ago. Now I think it's becoming the norm. Great.

It's a great, it's a great—

We appreciate it. Yeah. And so lean in, right? I think with the enterprise, it's complicated, right? But boy, and the last thing you want is that incredible SMB mid-market leader walking out the door with all that domain expertise. You never get it back, right? It's just, it's just a tragedy. And so I'm heartened when I see those folks. And the last, so that's the simple answer. And the other one, even the more nuanced next level one is at some point they're done. If at some point it's not working, find another role for them. Chief Strategy Officer, Chief Business Officer, some kind of like thing because those folks that took you from 1 to 50, like the folks that join at 50 never understand the product. They never understand the customer the same way. Maybe it's okay because you get a brand, right? And you get other, but never, never let them go. Find some role for them no matter what. Never. And my last ramble, I did write this post. Tell them, tell them when you have this person that, you know, like you don't know where the future is gonna go, right? But you know, they're so good at this first VP of sales level. Just tell them at the end of the year or when you're having a calm conversation that, look, you don't know where everything's gonna be at $100 million or $200 million. Or— but whatever happens, Jane or Jim, or I want you here, like you're not allowed to leave. Like if you do need to leave, I'll support you and I'll help you. But until that moment, you're banned. You're not allowed to leave. You have a job forever. No one says this to sales executives. And I find that when that happens, it's miraculous because everyone feels like their job is constantly— no matter what they say, they're at risk or something's going to happen or some dumb VC is going to fire me or something. And if you— they've never been told I want you forever. And it's just, it's, it's a magical thought. So thanks for joining.

Thanks for closing us out with a great question, Julie. And thanks so much, Jason, for the amazing content as always, and everyone in the community for your amazing questions. Um, we will be back next week. And as Jason said, the enterprise is complicated. So we have Noé Callen, managing director at Salesforce Ventures. He's gonna be talking about moving up market and nailing enterprise sales. So super timely. He was a great session in Europa, and we'll have plenty of time for Q&A. So we will see you next week at 10 AM Pacific time, and see you then. Thanks so much, everyone. Happy Thanksgiving. Thanks, Taylor.