7 Things The Best Sales Reps Get Right. And 10 Ways The Rest … Make Things Worse

In this SaaStr Workshop Wednesday session, Jason Lemkin answers audience questions about how founders and sales leaders can spot future top‑performing sales reps during the ramp period and how to structure sales and marketing functions for sustainable growth. He contrasts founder‑led sales hiring—where speed and cultural fit dominate—with the more measured approach of a trusted VP of Sales who can tolerate diverse personalities and give reps time to prove themselves. Lemkin stresses the need for heterogeneous sales teams, the importance of trusting and backing up hires, and taking full responsibility for mis‑hires through rigorous diligence, even extending the offer‑letter period to ensure fit. He then shifts to pipeline generation, explaining that the split between marketing‑sourced and sales‑sourced leads varies widely, and that many founders mistakenly hire brand or product marketers instead of demand‑generation experts, leading to weak pipeline. He outlines how to use a simple “pie‑chart” of revenue sources to set realistic KPI expectations for marketing, and warns that moving a sales leader from a 100 % inbound environment into an outbound or mixed model leads to a high failure rate. Throughout, Lemkin offers practical, experience‑based advice on hiring, team composition, and aligning sales and marketing to drive growth.
Chapters
Come all, come all ye SASTR faithful. Come, come, come, come. Okay, everybody, welcome to Workshop Wednesday. We did have a last-minute cancellation, so they brought in me again, but I'm here. Hopefully I can help having a little bit of fun. But we are here for Workshop Wednesday. First of all, I hope everybody can make it to SASTR Annual September 10th to 12th in the SF Bay Area. If you need a secret code, the very best one on all of planet Earth is Jason30. So you can get 30% off at least until the end of the month until they turn off my codes. So SaaStr Annual in the Bay Area, we're on track. It is kind of interesting. We have— we're at— what is the world like today? We're at— right now we're at 99% of last year in terms of attendance. Hopefully we'll be over 100% last year. Founders are up, VCs are down. That's probably the world we're in. VCs aren't hunting as much. Founders are looking to do even better.
Little bit of data.
We'll share more. But anyhow, we'll have a about 10,000 or so of the, of the best of the best in SaaS and cloud there and hundreds and hundreds of workshops and brain dates and more. So it's going to be pretty good. So hopefully you guys are there. So what I wanted to do today was and just kind of take a piece of content I did and do a deep dive on it on telling the best reps from the rest. For some of you, maybe some of this will be redundant, but I think the most valuable thing is when you're doing hiring today, when you're looking at your team, when you're trying to figure out what's going on in your company, Here are some tells. Is someone on your sales team above the fold or below the fold? Does it really make sense to keep them? Ironically, in tougher times, we often default to keeping our sales team more than in good times. In good times, we feel like, hey, we can get some more folks in. We have this. If Bob or Lemkin or Amelia isn't cutting it, we just let them go in better times. In tougher times, sometimes we don't know what the root cause is, and we worry we won't be able to get anyone to replace even an underperforming sales exec. So I thought I'd go through 7 things that the best reps get right and more quickly a few things they get wrong. And then let's use the extra time. I'll try to do this in less than 30 minutes and let's use the extra time to do some open Q&A on anything that's sort of sales or revenue or revenue related. So hopefully this will just help you see whether it's you or them when you're struggling a little bit on the sales side. Okay. Quick look. And this, this one, this one sounds so basic. But if you really wanna understand if someone on your sales team, including your VP of sales, including your CRO, including everyone, is really doing what you need to do in 2024, is are they solving your problem? Look, there's some spaces that are on fire. I'm sure if you are at the OpenAI sales team today, it's order taking to some extent. To some extent, probably not for their biggest customers. When you, when you are doing so well that you are in order-taking mode, sales reps don't have to solve a problem. They literally, there are times and places where order takers work in sales. For 90% of you, they won't work today. The reason someone wants to talk to sales and the reason sales isn't yucky, the reason sales isn't sleazy, the reason sales isn't selling you a '92 Camaro with one of the hubcaps off or a broken Trans Am that you know isn't gonna make it down the block. Is because the best sales reps solve your problems. They solve your problems. They ask you, you demo what you're doing, you talk about how you're doing a workflow, and they show you exactly why they can solve one of your top 10 problems. They don't immediately go into discounting and pricing and all that. They solve your problem. So if you haven't figured this out yet, you're trying to figure out why are a couple of my reps much better than the rest? Listen to their calls, watch their Zooms religiously, and you will see they're very, very good at this. They're— they listen to the customer's issues and they figure out how to use your product and tool to solve your problems. The rest are just order takers. And frankly, I'm not sure we need order takers for 90% of us in the world today. Okay, next one. This is related and we've touched on this in some other Workshop Wednesdays, but I think this is so important today, which is the best reps help you get going. The best reps help you demo, pilot, or try the product. I was just talking with the CEO at $20 million ARR the other day that has a PLG motion, and the PLG side of the business is going pretty well. The sales-led part is struggling. And I asked him how many folks on the sales team at $20 million can actually demo the product. And it turns out none. None of the sales reps are able or can demo the product. They bring in engineers, solution architects, other people. They grab the two founders, but none of the sales reps can help, can demo the product or run it for you. The best ones don't just talk about feature comparisons or why you're better than the competition, or again, Talk about a discount. They help you get going on it. There is almost 99% of products in business software have friction in deploying it. We, uh, 99% of sales teams forget about this. 99%. It's natural that sales is focused on sales, but sales is just a moment in time. You need discovery, you need to pilot, you need to roll out, you need to deploy, you need to iterate and stay for 7 years. And it's too much to expect, and we'll talk about this, it's too much to expect sales to stick around for the next 7 to 10 years after you buy a product. But the best ones find a way to dramatically increase the odds the demo, the pilot, or the trial go well. And watch for this. This is what the best ones do. Whatever gets the customer comfortable using the product. Um, 3, this is one to really listen for that the best reps are good at. And if they aren't, train your team. The best ones are utterly fluent and honest about the competition. Utterly fluent and honest about the competition. Again, when I'm talking to a great sales rep, it's not all about pricing. In fact, we can talk about this for a minute. Pricing, arguably, especially if you have somewhat transparent pricing, it doesn't even matter. I roughly know what the product should cost, but a rep that's very good in the competition, even though of course they'll be biased, they will save you time and research. Tell me about you versus Notion, you versus Webflow, you versus Datadog. A mediocre rep doesn't know or is struggling to find a tear sheet. The great reps will say, listen, Datadog is one of the greatest products out there for DevOps in the world, but they've gotten pretty big. And here are two things we actually do better than Datadog today. Two things. They do better than us at 98 things, don't get me wrong, but here are two things that we do great. And let me show you how it would work in your business. And even better, let me show you how one of your, a very similar company to you or one of your competitors uses the product. That's magical. That's magical. And they know where your 10x features are and when you're weak. The worst reps know nothing, and the mediocre reps just immediately go into bashing. They immediately, oh, Datadog's terrible. Not sure Datadog's terrible. They're at a couple billion in revenue, growing 30-something percent with one of the highest NPSs I've ever seen. I don't think bashing Datadog's the right one. So this is really something that the best reps nail. Related to this one, they're honest about weaknesses. Weaknesses. I just wrote this up on LinkedIn the other day, but recently Amelia and I got on a Zoom with a product we use with the sales team, and they had a huge bug, a huge bug, a fundamental bug in their product that had not been fixed in years. Not only did the CRO argue with us whether it was a bug, he said we had to pay $50,000 to fix it because it was a custom feature. The team just groaned. So listen, maybe that's a good sales tactic today. I really don't think so. We can talk about it. But the best folks in sales are honest about the products, the strengths and weaknesses, and they know how to backfill. And the best sales reps for startups will let some deals go to the competition when they're not ready. They'll know that line, and you have to be very careful and work with the team. But the best folks will know about this piece. The rest will just struggle. The rest will just struggle in the competitive landscape. Five, this one, I wish it was as crisply clear in 2024 as it's been in the past, but the best reps don't create friction with pricing. Now, when you're huge and you're at scale and you're Salesforce or whomever and you have a dominant brand— and Salesforce has a lot more competition than it used to. Even HubSpot's coming up on a billion in revenue for CRM. But at some point when you have a dominant brand and 9 figures or more in revenue, you can play some games. You can, you can have everything on a Contact Me, you can hide pricing, you can do this. But anyone on the scaling journey, your job is to remove friction from the sales process. The more friction you remove, the more deals that play. And so the best reps just don't play game with pricing. Because if I don't know upfront if the pricing is fair, how much of the discovery journey am I gonna do with a new vendor? How much can I do? So when you hear, like, the anecdote I just shared with a salesperson coming in telling us we have to pay $50,000 to fix a bug, Okay, or there's another leading cloud vendor who the other day sent us an email saying we were 2 seats over our addition and we had to pay 5 times as much and pay a 5-year prepaid contract. The best folks don't do this with price. Because as soon as I know the pricing is fair from the start, I'm taking an objection away. And again, if I— it's funny, if I even had to talk about one point where you can find a mediocre rep, it's when they spend all their time thinking about pricing and discounting. It doesn't matter. Does it really matter if your app is $5,000 a year or $5,100 or $5,800 or $4,200? No, let me know if your product's $5,000 a year and there's a competitor that's $500 a year and I'm gonna lose, use your low-end competitor, so be it. Like, at least, you know, discover me out of the deal. But, and if your product is reasonably fairly priced, take it out of the drama. Don't let sales spend all the time trying to play games about getting the extra nickel out of the deal. Or games on discount. You want to actually take it out of the game. Okay. 6. This is one of the top ways, and we talked about this, where you can really differentiate the best reps from the rest is that they're there for you after the deal. Because listen, let me be clear, 99% of sales reps do not care about you the minute the deal is signed. They don't even care as long as— especially if they get paid on contract being signed and not when cash is received, they're out of here. We're all outta here, folks. Everyone's outta here these days. And sales is perhaps the most of all, but the best reps somehow make you feel like they're still there for you. Sometimes it's for the upsell, sometimes it's for the renewal. I mean, incentives do matter, but the very best reps really make you feel like you're there. And, you know, I just saw an anecdote on LinkedIn yesterday about someone with the top vendor saying they'd canceled and gone to a competitor. The sales rep told them they had to pay for the renewal because it wasn't 60 days before the renewal was up. They complained and they sent them to legal. That's not being there for you after the deal closes. The best ones have this magical thing and care and carry these relationships in many cases for years. Seven. And boy, we don't see this enough these days. The best reps have done research on you before the first call. If you want to stand out in sales, with a prospect, with a renewal, for even for finding a job, let alone do 15 or 20 minutes of research, even 10 minutes of research before the call. There are so many great tools out there, including Google, Perplexity, ChatGPT 4.0, B.C.X. There's so many ways to do research. ZoomInfo, Apollo, whatever you want, a tool you want to use, do a little bit of research. How many employees do they have? Who's a competitor? And even more magical, who's a similar company or competitor that's already a customer? That is so magical. You know, if you're reaching out to Vanta and you can say, hey, Drata has been one of a super happy customer for 2 years, here's how Drata uses us, Vanta, they're gonna take that call. They're gonna take that call. I can't tell you, somehow since we all started working from home a few years ago, I gotta tell you, 90% of sales folks, they're, They don't want to do it. They just want to get you on a call. They just want to talk. They just want to sell. They don't do any work. I am so burnt out of— I'll get it. I'll get an outbound email from someone in sales or for other things, and I'll just say, I do this almost every week just for fun. I'm like, okay, tell me how your product would help SaaS. You know how many responses I get? Almost none. And of the responses I get, almost all of them are wrong or terrible. They— the rep can't even spend 90 seconds figuring out what Saastr is or Saastr does. Okay, these days have gone beyond it. You can stand out. And so find the best sales reps. Now, it doesn't mean you need to know everything about a prospect. You know, you got to do— the average sales rep to really scale has got to do 3 to 4 demos a day. You can't spend 8 hours doing research. But boy, boy, the best ones do a little bit. They really make you feel— this really makes you feel like you're a trusted vendor for them. Okay. So actually, in some ways, by the things they did right, I hit the things they did worse. But let's have a little bit of— let's just recap a few things. They make things worse, and then we can, we can break for questions on any of this stuff. Number 1, and really you gotta either root this out or move on from folks. They play endless games with price. Okay. And again, as founders, it'll take you— it may take you a little while to figure out that price is important, but it's not that important. You just need to— if your product is priced fairly in general, and it is priced fairly vis-à-vis the competition, price is not gonna be a huge issue. And taking a product that nobody wants to buy and discounting it 50% very, very, very, very, very rarely gets the deal done, right? It's the classic RFP trap, right? You know, one of the many frustrating things if you start doing RFPs as you go more enterprise is you're in an RFP, you know you're probably gonna lose it because you're the number one, you know who the number one is, and you go low on price and all they do is take that to your competitor, it doesn't make any difference. They don't— even if they've just already decided to buy Drata and, you know, someone, a new competitor comes in at a tenth the price, they're not going to take it. They're just going to use it to negotiate with Drata. Price sort of matters, but what matters is that it's fair and that it's roughly consistent with your competitor set, right? And this is why instead of playing games with pricing, this is why actually as you go more enterprise, As long as you do it the right way, it's totally appropriate in sales to ask if something's budgeted and even to ask what the budget is. It'll give a sense on both sides, but don't play games. Nobody wants these games. Okay. Number 2 that you see mediocre reps do, because this is so hard, is obnoxious urgency to buy now. It's— there was a thread yesterday I saw literally on Salesforce Now, and maybe this is only partially true, but there were enough folks on this thread that I'm sure it's at least directionally correct. We're telling everybody that they're going to have a 9% pricing increase again next year if folks don't renew for a multi-year contract today. A multi-year contract today. I don't like it. It may not be fake, I know, but it's this classic pressure field urgency. But getting this, getting this right is so hard. 90% of folks in sales cannot create urgency. It is so hard. And I would say 95% of founders cannot create urgency. The best way to create urgency, it turns out, is to add so much value during discovery, to add so much value during the pilot or the rollout or the testing phase, to add so much value when they ask questions about the competition and the feature set and the integrations, the gaps, to add so much value that you can just say, you know what, Bob, Linda, Caitlin, Jason M. Lemkin, I know the pilot's gone great, or I see you've got 10 users already on our product. Can we get you going this month? Can we bring you in this month? And when sales reps have added an inordinate amount of value to the sales process, the prospect usually is like, yeah, you know, I'll try to get it done in July for you. I'll try to do that for you in July because you've helped me so much and pricing wasn't really an issue because you didn't rip me off and you helped me so much in the pilot and you helped me so much. Sure, I'll sign in July. Might as well. And there's a classic SaaStr post on why the best sales teams bring in so much revenue on New Year's Eve. And the rest go home and bring in nothing. It's because they've added so much value that they can ask for a favor. Can you do it for me for Christmas? Can you do it for little Jackie and little Polly who need presents under the tree? Can you do it? And if you've added the value, you will. So many fake games, so much drama, so many— and so many threats today. We will delete your data. We will do this. It's a sign of a poor rep that does not know how to add value. That's what it is. Because if they knew how to add value, they wouldn't be doing the threats. And that's why these threats are all over the place. Like the vendor that told us the other day we had to prepay for 4 years. They've run out of ways to add value. This vendor has never reached out to us to see how they could add value. And so you're left with threats, but they're a sign of, in my opinion, a suboptimal sales rep and team. Next one that we kind of touched on. The best reps are very good at knowing the competitive landscape and how to spin it a bit. Don't get me wrong, how to spin it a bit. But To be good in the competitive landscape, you also have to admit somewhere where the competitor is strong or you can't build trust. Weak reps just lie. They just lie. They make crap up about the competition because they're lazy or because they don't know the answer. When you see this, you gotta pull them aside or maybe get rid of them. And the reason that this isn't just bad— it's bad because it don't work. It's bad because the prospects know. They can smell it when you're lying. And you know, again, the prospects, You're one of the, one of the mitzvahs, one of the great things a great sales rep does is make your discovery easier. And you won't— the smaller your, your deal size is, the closer you are to transactional sales, maybe the less this is true. But until you've really talked with a bunch of enterprise buyers, and maybe many of you have, but until you've been on the other side or talked to them, you don't realize that a great sales exec in the mid-market enterprise is the ally of the buyer. The buyer has decided, I'm going to do a big initiative this year. I'm going to upgrade my security. I'm going to upgrade my e-signatures. I'm going to upgrade my marketing platform. I'm going I'm gonna upgrade. They've made a tentative decision. I'm gonna do a couple initiatives this year. Okay? And look, there's a budget, whether that budget's $50 grand in their mind or $300 grand or a million, whatever. They've got a soft budget. And they're gonna reach out to the vendors. And immediately, the mediocre reps, it's all about price. But no, I want to do discovery. I want to figure out that I've read the Gartner report. I've gone online. I see you're number 2 in the space, but I'm giving you a shot. I want to hear why you're the best and why you're the right fit for me. Not everything about why is in competition. I'm doing discovery. And the best reps make that process easier for me. They outline the competition, they outline the market space, they outline the weakness and the strengths, and they make my job easier. And that's where sales becomes my ally. And as long as the price is fair and my procurement team gets an additional discount at the end of the process, I'm probably cool with it because you're my ally. You're my ally. Not so many folks in sales today are the prospect's nemesis. Quick one here. The worst raps don't quickly go into this, understand your budget and situation. Too many folks are still trying to force deals today under stress. Do I just want to do a pilot? Do I just want to start with 10 seats? Again, it is— if you haven't gotten over this, it is completely okay to ask if something's budgeting and do they have a sense of the budget. You don't need to ask a 1-seat deal these questions. You really don't. And that pricing should be transparent on your website. But any bigger deal, it's— this sounds like a used car salesman question. No, being a used car salesman is threats, not understanding the product. Asking if it's budgeted or not, and getting a sense is fair. And if it's not budgeted, realize you're probably coming out of an experimentation budget or a small budget. And I've written a little bit of this about SaaS, but if you're not familiar with how this works, and frankly, I didn't even know until I was a VP at a big tech company. I didn't even know as a SaaS CEO. When I was a VP at a big tech company, we had two budgets. We had the fixed budget for the year, and we started to get that done right about now. Right about now in the year, and we would work on our budgets for next year and submit them, and they would be fixed, and we'd work on the vendors, and renewals would take up like 80 to 90% of the budget. And then everyone would get a discretionary budget. Mine was the smallest in my business unit, but I still had like $400,000 or $500,000 a year for my team that I could use on extra stuff my team needed that we didn't get in done in the budget for this year. So if you asked me, if you had come into me when I was a VP at Adobe and I wanted to use your product, and you came in hot and you said, "Yo, you work at Adobe. It's going to be $3 million a year. You're going to lose me. You don't got to ask the question. Is this budgeted?" "No, it's not budgeted. I don't have budget. We've already locked up all the budget, but I do want to use it." "Okay. What are your goals?" "Well, I want to start with 10 seats this year, 15. I want to have a small team. And then I want to see how it goes for next year." And you got to listen. And too many folks don't even know how to do this, especially if your team does not have enterprise experience, or they're not all in, they don't do this. You got to understand and you got to go long. And sometimes you can close those big deals up front, but MongoDB today even takes 3 years to build up to a big deal. It might happen with you. So the best reps don't even know how to do this or don't even know, understand it. And they lose deals because they try to oversell these deals when they don't even understand that it's not even possible. They don't understand what the budget is and what the timing and whether it's discretionary or not. Okay, boy, this has been an issue for over 70 years in enterprise software. But it— but I know Amelia is going to nod when I bring this one up. This one has gotten even worse. Nobody checks in to help anymore. Nobody. Nobody. They only check in to threaten you, to tell you the prices are going up, to tell you need to pay $50,000 to fix the bug. I don't know what happened. And, and It's even worse today because we have weaponized customer success and turned it into part of the sales team. And so customer success doesn't even check in anymore because they all have commits. I would say 2 years ago, none of the investor updates I got had CS commits, opportunity commits. Now it's half, half. I literally got an investor update yesterday from a company at $15 million. 20% of the update was on the opportunity commits from CS and how that was coming up short. So CS has become part of the sales team. I think it's terrible. The ship has sailed. Everyone's doing it. But that means one less person who's going to check in and just say, do I need help? And sales— first of all, sales doesn't care. As we talked about, once the deal is signed, they got commission. But even worse, 99% of salespeople don't want to do it because they might be asked to do some work. You know, Amelia emails, hey, the app's not quite working how I'd like. And they just, you know, even if they ask, they're going to ghost you. But the very best reps, The ones that the customers love, they don't ghost you. They may not do as much as you like. They're like, okay, okay, I'm sorry you did not hear back from the CS team. I'm sorry something happened. You know who you need to talk to? Taylor on our team. Taylor knows how to solve these problems. She's done it. I know she's busy. I'm going to check in with Taylor. I'm going to get back to you. They find that extra 15 minutes, 20 minutes a week to check in with their top accounts. It is so magical. You love that sales rep and then you love that vendor. And I just, I just, I just almost never see it today. But the best reps are still checking in. They're still checking in when it's not all about the upsell. Um, okay, the other thing happened today is that in this upsell world where we've weaponized CS, a few do too many check-ins, especially some of the kids constantly checking in but not really to help. You don't need to check in every week for the upsell, okay? The— we, we need to— it's too many. Even in today's world, I can't— so many folks are doing the, the 10-step endless breakup email cadence. Like, we laugh about it on LinkedIn, But it's so common. We do not need to check in 11 times on whether someone wants to buy. 3 is enough, my friends. 3 is enough. Use Mixmax, use Salesloft, use Outreach, use Gong. You can see if they open— who doesn't know if you opened your email? You can even do this in Zoom now. If they opened your email 28 times, if they opened 3 emails 28 times and didn't respond, you know what? The 11,000th email where you don't understand the customer, didn't do any research, don't understand their business process, don't know their competitors, it's not going to help. It's not going to help. Can you send them an email in a couple of months telling them about a great new feature? Sure. Should you drop them into some drip marketing about a product release that's coming? Probably. But enough. When you see these over-check-ins, you got to check it on your team. It doesn't work. You know, you get on the team call. I emailed them 98, 18 times in the last 2 weeks and I can see the opens, but they won't get on the phone. I'm going to email the 19th and the 20th time. This is, this is what weak sales reps do. They know the right balance here and they move on. And it's really 3 times, 3 is enough. 3 is enough, especially if it's opened. Um, hey, we kind of hit this one before and I'll kind of wrap this up so I have a little bit of time, but ban the breakup email, folks. This is a sign of weakness. This, this, I get this worked in 2015 or '18. This doesn't work. And why does the breakup email work? Because the breakup email, uh, ties to the cardinal sin of the mediocre sales. Rep and the mediocre sales executive and the mediocre VP of sales. It's not all about you and it's not about pricing. Okay. And bear in mind, and I know most founders know this, but so few sales folks know this, which is, you know, if you're lucky, if 10% of your prospects are in market at any given time, they got another vendor, they don't have time. I don't want to switch today. I can't tell you how many emails I get. I'll do someone a favor and they'll be like, well, can we, can we get SaaS or using it tomorrow? I don't even have any time. We have 10,000 people coming to SaaS or annual in September. Even if I want your product, I don't have time until October. Okay? And people don't get it. Like, I tell people I don't have time until October. Certainly Amelia doesn't have time until October and Caitlin. 95% of the sales execs I check don't even know what I'm saying. I'm like, hello, go to my website. I have 10,000 people coming to a party in less than 60 days. I don't have time to look at your app until October. I'm interacting because I'm interested. Like, you have— there's something interesting there. They don't get it. You want to send me a breakup email? Hey Jason, I know I've sent you 18 emails. I won't send it to you again unless you want to use our product, but I don't know anything about you. I don't know what you do. I don't know if it's a good fit. Enough. You don't want to break up. Don't break up. Ghost them if you have to, but don't break up. All you're doing is looking immature and breaking a relationship. This was, this was part of a hyper-transactional relationship. And don't get me wrong, here's the thing. Here's where there's disalignment between founders and sales. Sales needs to know which deals are real, which deals are commits, where they're on the pipeline. And look, a good breakup email, if nothing else, it helps the sales rep because then they can mark that deal to lost. But I also think it moves deals to lost that aren't lost. I think it's a weak play. Okay, I'll do one, two more really quickly and then we'll open up because I want to have time. This, this one has become the worst thing of all in SaaS, playing games on renewals. So many renewals are rip-offs. We talked about, we talked about the Salesforce, another 8%, 9% next year play if you don't give us a multi-year renewal. I talked about a web app we all use that told us because we were two seats over, we had to prepay for three years upfront for an addition that costs twice. This crap doesn't work unless it works. It doesn't work unless it works. And what's happening is that there's, for many folks, there's so much stress. It's so hard to find new logos. It's so hard to find new new deals, that someone's energy in sales is going into monetizing the existing base. And look, done right, it's a gift. Done right, it's a gift. Now, CrowdStrike had a rough week recently. You may have seen they had a rough week. They shut down our nation's air transport and others. But until then, they're about the number one player in SaaS and cloud. Almost $4 billion in revenue, growing over 30%, 120% NRR, very great cash flow economics. And how did they get there? They have 30 products. CrowdStrike has 30 products. Datadog is over 10. And so yeah, it's going to be a little bit rough for CrowdStrike for a couple quarters in the sales team. But until last week, people love CrowdStrike so much that they would want to buy more from them. When you rip folks off on the renewal, that's not how you earn more revenue. You know how you earn more revenue? You give folks 30 products and they buy more from you. That's what HubSpot's done for the most part, Maybe a few games lately from HubSpot, but that's how they did it. You build a CRM, you build support, you build the thing, you earn it, you earn it. Datadog mostly earned it. CrowdStrike earned it until the other day. This is how you build up a big NRR base, is by providing more value and charging for them, but not ripping off your base again and again so they're terrified of the renewal. And look, there's so many issues here, and at least as founders, you better make sure you know what's happening. So that story the other day where the CRO joined us late and wanted to charge us $50,000 to fix a bug. I don't know whether the CEO of this company knew about that or not. It's not a huge vendor. If they did, more power to them. Run your company into the ground. It's your company. But I find the majority of the time, the CEOs don't exactly know that these games are being played. And you just realize, it breaks our heart as leaders, but it's natural. It's natural. There are so many startups now that they're net new logo growth has slowed to zero. The net new logo growth is close to zero. Like, all the energy to get new logos is being offset by logo churn. So where do you go? You go to the base. Better make sure you're going long here and you know what you're doing, because a weak rep, a weak rep that can't close any new deals, doesn't know the product, can't help you with the pilot, can't help you onboard. You know what that weak rep's going to do the next day? They're going to pressure the base. They're going to, they're going to, they're going to put as much pressure on their base as they possibly can to hit their quota. It's just the reality. Okay, I think that's it unless I missed one. So thanks everybody, and let's— we can open it up for questions on this or related points and take it wherever it goes.
Awesome. Yep, get your questions ready. So we have some great questions already lined up in the queue. Thank you, Jason M. Lemkin, for that. Always love hearing your personal examples and how this is really happening. So Matt, I'm going to invite you up to the stage first to ask your question. He touched on some good check-ins, but would love him to dig in deeper about some more examples here. Welcome, Matt.
Hi. Yeah, I was just curious. You talked a little bit about check-ins and bad ways to do check-ins. Yes. Doing it too much, doing it not enough, doing it for the wrong reasons. And I was just wondering if you could talk through a couple of examples of good check-ins that you've seen and what some best practices are there. Yeah, well, first of all, let me step back. I think the worst practice is the one— it's fading, but it's become institutionalized— is the QBR, quarterly business review, quarterly check-in. In the old days, I think a QBR, uh, was great, um, a Q— but I think overall our industry has somewhat deteriorated since 2020. And the QBRs I see— first of all, I asked so many CS— when I interview CS folks, I ask them, do you do QBRs? And QBRs, if folks haven't seen them, it's a classic structured quarterly meeting. There's, there's almost— there's always a deck. The deck generally talks about— it used to talk about what's worked, what isn't. Now it typically only talks about what works in the upsell. Typically the QBRs no longer talk about what's not working, which is an issue. But I asked most of, most of the CS execs I talked to, how many folks show up to the QBRs, they're like 10 to 20%, 10 to 20%. And there's a lot of things happening there. Folks don't, don't view the QBR as useful to them anymore. If I'm just helping the CS team figure out how to monetize me, I'm not going to show up to that meeting, am I? So anyhow, so I wish I had the perfect answer to your question. What I'm going to tell you is I think the QBR should be close to dead unless you measure it and you see that the majority of folks show up to it. Right. So I don't have the general answer. What I can tell you is that QBR is not a band-aid and that set a goal, set a goal that for the team, like every customer above $20K a year or above needs, you need to have 4 meetings with them a year and let the team judge and log them in your HubSpot CRM or Salesforce. Log those 4 meetings, let them judge when they should happen. But I think this— a lot of things like the breakup email just get stale when we do them a long time. We don't have our heart in it and they become dated. And the QBR, I, I almost nobody honestly believes it works anymore. So those are my, those are my best answers. But the most important thing today in today's world, when folks are all remote, it's not clear how much people are working. It's not clear what they're doing anymore. It is what it is. You got to measure everything and make sure the activities happen. And, you know, we did— Sam Blonde did a deep dive in our Miami meetup the other day, and he did one in Europe the other day at SaaS Europa. And I just love his theme, which is that more and more in this world today— and he was a CRX— you have to measure all the actions of your sales team. We as founders, we want to trust the sales team to be autonomous to get it done. And look, the very best app— get out of there. The very best in anything, get out of their way. Backfill and get out of the way. But most of your sales reps, even at Brax, even at these leaders, they're not doing as many calls as you think. The CS team is not doing as many meetings as you think. If you don't measure it, everyone thinks they're working really hard, but they're not doing 4 meetings a day. They're not. No one is working nearly— 90% of folks in SaaS are not working nearly as well as they think they are in their mind. And if you don't measure it, It's, it's, it's worse than ever in the distributed world. So those are my, my, not my perfect ideas, but my best learnings. But don't rely on the QBR. So thanks for the question. Thank you.
Thanks, Matt. All right, Giovanna, I'm gonna invite you up to the stage to ask your question. Thanks for joining us.
Yeah, thank you, Jason. How can the CEO, CFO, Director of Operations can help the new Director of Sales to be successful in his first 3 months within joining the company.
How can the management team help the new director? Here's my new, my new life learning after all of this. When you, as much as possible in sales, but especially for the leadership, don't let them start until they're experts. This is the number one way you can help. My number one tip: do not let anyone in sales start until they're an expert. If let them, let them be in the background for 2 weeks, let them listen to calls, let them quietly join, let them observe, let them read documentation. Way too many folks up and down the stack in sales want to start and learn after. It does not work in today's world. It's okay in a trans— in a hyper— when in 2021, when folks would call in and it was a one-call close across SaaS, I guess you could learn on the fly. It doesn't work. And it took me a while to get this. I've written a lot about my journey in the past as a CEO, and my first VP of sales did not work out. And then I hired Brendan Caston, my second VP of sales, and he hit the ground running and there was no training or anything. But you know what? He actually had been at LinkedIn and used our product for a year and a half. So I wouldn't say he was a total expert, but he used the product for a year and a half. And I think that gave him training without realizing it. He'd been trained to an extent, right? Some other learnings. I just see so many directors and VPs, 90% of them fail when they think they can wing learning the product, the motion, the everything. And I was just talking with a sales leader this week that was going to take a new gig, right? And he's like, I want to make sure I can do it, do use my process. I want to use highly automated outbound. I want to use ChatGPT for this. And I'm like, okay, but I know this company. This is an ABM motion. Like, this automated endless thing is not going to work. None of this is going to work. I don't think you know that. You are super smart. You are great. I don't think you know the product well enough. I don't think you know the customer well enough. So we've got to slow. And if that means paying your director of sales for a month before she starts, quietly do it. It's your best dollar investment. And if after the month she says to you, well, you know what, Giovanna, this is not for me, that's good. That's good. In the old days, when Tony Hsieh, rest his— I never really knew him— came, he had this— when Amazon bought Zappos, he had a lot of ideas that seemed crazy at the time, but they were just ahead of it. And Zappos would famously pay people in their support team to quit after 30 days. He would pay people to quit. And it doesn't seem as crazy as it did at the time, but it's like, I don't want anyone here that doesn't want to be here and can't do the job, pay them to quit. I say let them work quietly for 2 weeks, learn the product cold, and then let them quit if it's not a fit. Do not let them flounder and flail after they start. And this, every founder makes this mistake. We want to be supportive. We want to be macro. Most of us want to be macro managers. We love, we love Jason M. Lemkin or Giovanni DePietro, whatever. No, make sure they can demo the product, know it cold before they start. And if that means 2 weeks in the background, great. Take those 2 weeks to learn the product cold. That's my number one bit of advice.
So then Jason, just another question there. Do you think it would be fair to say that a salesperson, a good salesperson could learn in a month? Like, like if you, we just hired that person already, can we let him learn and absorb everything for the first 30 days before he fully takes over the sales department?
Do you want someone running your sales department that can't sell your product?
No, but that's what I'm asking.
Let me put it differently. However you, however you approach the issue, this is my advice in 2024. Before. Don't hire anyone in this— ideally anyone in sales, in the founder-led sales, anyone in sales, but in the management role as you scale, that can't honestly sell the product before they start. Can they demo it? Like we stopped— the last point, and then I'll break on this one. Before March 2020, every single company had their sales team do multiple demos before they started as part of the interview process. It always happened. It never didn't happen. Today it almost never happens. It almost— it never happens. People just hire SDRs and AEs. They don't make them demo the product. And almost no founders ask their leadership to do this. Somehow we lost this. If— and if you want to give them a pass and you want to say Bobby or Linda isn't ready to— our product's kind of complicated, it's vertical, it's technical. Fine. Then give them a pass until the end of the recruiting process. Or if you really want, give them a pass after the offer letter until they start. But don't let someone start— you can't sell a product you don't know. You cannot sell a product. And way, way too many sales folks are winging it today and attempting to sell products they don't know. You find a time machine, go back to 2021. Good luck to you there. It doesn't work today.
Thank you.
All right. Thanks for the question.
Thank you.
All right, Shane, let's invite you up to ask your question. Thanks for joining us.
Great. Thank you. So Jason M. Lemkin, most of my experience up until the last couple of years have been large enterprise deals. So when I say large, a couple hundred thousand dollars ACV. Now, however, I am anywhere between 1,000 and 50,000, and we're shifting to an SMB on that 1,000.
Yep.
So my question, first of all, I totally agree with, I think, all of the observations. The only one that I added was I found that the best reps, especially enterprise, truly believe their solution solves the problem, meaning they took the time for discovery. They really believe in the product, they know it, etc. And then if you build enough pipeline, you're not going to feel that pressure to do stupid stuff to try to get someone to buy, you know, under some artificial timeline. Pipeline helps, you know, with that. My question is, at what ACV does those, those skills really come into play? And it's almost like going from a transactional click once to they need all of these, you know, traits that you described earlier.
3K.
ACB.
Yeah, because now listen, I just think the more enterprise you are, I, the more of these traits you have, right? You're not gonna be doing pilots and all these things if you're not enterprise, for sure. Yeah. This world is too competitive today and any deal that takes more than 1.5 calls to close requires this whole tool skillset. Any deal that requires more than 1.5, 1.5 calls to close, less than 1.5 means They can do discovery on your website. They can— you probably have a free trial. The customers are probably pretty techie or pretty webby. Okay. They're not asking much from sales. That's the thing. 20% of the world doesn't want contact me. 10% of the world doesn't even want to talk to a human. Maybe even depends on your category. It could be 90%. They don't. And, but that's not most of the world. Most of the world is looking for help, as we talked about. So if you're trying to figure out, okay, if every deal closes in one call, you don't— you know, you— they, they need to be able to answer 10 questions thoughtfully, and that's it. Um, what— but that's my simple answer. One and a half calls. You got to be a subject matter expert, and you got to be the, the ally of discovery, because more than one, one and a half calls means, again, to simplify all this stuff— sure— is the customer is doing discovery, or they just have a couple of questions? Yeah, they're very different. A couple of questions. Um, does your— how does your HubSpot integration work? I'm a little— it's a little murky to me. Um, how much if I buy 11.5 seats, what's the pricing? Um, you know, how do you really compare to Zendesk in a simple— like, sure, if it's 10 questions in one call, but more than that, it's discovery. And again, if you had the best sales reps, we had to distill all of this, are your ally during discovery. Everyone else is your nemesis. And that's why enterprise buyers— and if you go to hire any— and here's the related point, and then we can break— if you go to hire anyone in mid-market or enterprise sales, here's a tip. Nobody makes folks do demos anymore. And I'll tell you something else nobody ever does. This is magic. This is magic. When you go to hire anyone with more than 2 years of experience for mid-market enterprise sales, ask them for 1 or 2 customer references. Nobody does this anymore. We used— in the old days, most people didn't do it. If you're in enterprise sales and you did everything we're talking about, if you made the journey better, if you help with the pilot, if you help with the onboarding, if you help figure out the landscape, if you help make an enterprise buyer's year of discovery easier and were there for them afterwards and troubleshooted the issues afterwards, they will love you because most enterprise buyers don't buy themselves. Like the organization might have 400 SaaS apps, but that one BU, maybe brings in one app a year, maybe two. And if you made their job better, they will remember you for a decade and they will be your reference and they will get on the phone and they will say, yeah, listen, Amelia was great at Notion. She did this whole thing across our company. They will take that reference and then you'll see they can do this whole job. But as— so ask any mid-market or enterprise rep for a couple recommendations, see if they can even give you any and see if— and then you'll see what— can they run this playbook? Maybe they're not willing to do it today. But at least, at least a few years when the reference was they could do it. So thanks for the question. That's how I would do it. Get the questions and realize after one and a half calls, it's about discovery. Yeah, about discovery. And again, let's break— but that's the thing that takes folks a while to realize is, is it a transaction or discovery? And sales is either your, again, your nemesis or your ally during discovery. It's a lot of work to do discovery.
Thank you, Shane. All right, gonna bring Mark up. Getting a ton of questions about the recording. So yes, the recording will be on our YouTube, so check it out. Um, some folks are saying they want their sales teams to watch this, which is probably there already.
youtube.com/live tab. I think it's right now, it's at the live tab right now. It is. Um, and yeah, we'll clean it up and publish it on Saastr. But okay, next question. Yeah, have your sales team watch it, then we'll see if they like it or if they're angry at you. I'd like to get the feedback. See, okay. Goes.
Yeah, exactly. Mark, you're on mute, so I don't need to be.
I don't need to know the product. I'm a people person is what you're going to hear from a lot of people. My, my, my customers love me.
Hey, Jason, question is thoughts on differences when hiring and handling enterprise reps at, say, $2 to $15 million compared to like $50 to $100 million. And then specifically, if you have this experience, How to handle the transition after, say, that $15-20 million mark with your lone wolf, the big logo closer, always stacked rank number one, but also the biggest headache, right? Complain about comp, complains about lower performers, hates the CRM, goes over the CRO's head, goes straight to the CEO and founder. Or maybe you haven't had that experience.
No, no. Everyone's had a lone wolf.
Yeah.
In fact, I was just arguing the other day with one of the best VPs of sales I know. We were arguing over a particular sales executive, and he was saying, you can't work with this person because they're a lone wolf. And I'm like, well, in this particular environment, it's okay. They're producing twice of anybody else, right? So there's a lot of questions there. Let me simplify it to just one thing that you already know the answer is. When you truly have a great VP of sales, they gotta figure this out for you. Okay? And so my guess is implicit in your question is that you don't have the right— and if your VP of sales is watching or something, don't take it personally. I'm hypothesizing, abstracting away from you, but you probably don't have that person today because all these issues you're struggling with, how do I deal with a lone wolf? How do I get them scaled? How do I transition from that, you know, 2 to 15 to 15 to 40, you can't do it without a great VP of sales. And the more specialized the product is, the more domain expertise, the more vertical is, the more I've found founders often have to get to $10 to $15 million before they can find a VP of sales they trust and believe in. If you're hiring a salesperson to sell sales tools, they can probably figure it out pretty easily, right? But if they're trying to figure out complex environmental compliance financial regulations to weird entities, and they just want to answer 3 questions. It often takes you until $10 or $15 million. And so you're struggling with some of these questions. But a lot of this stuff, because as you scale up, here's the reason, as you scale beyond $10, $15 million, you need a much more heterogeneous sales team. You need the types of folks that you wouldn't hire as a founder, that wouldn't work with you, that would drive you nuts, or maybe don't know the product as well. But the VP of sales will backfill them. Maybe your VP of sales becomes this great expert and you're kind of frustrated that Charlie at $20 million never really learns the product. But Linda, your VP of sales, knows, and she knows when to get in the calls and get out of them, when to back them in. Charlie's still okay, but Charlie would've failed at $2 to $3 million. So you need your VP of sales is the simple answer. So let me flip that around, two things. And when you have the VP of sales, they will make the tough decisions on the lone wolf. They will make the tough— and you have to decide when you hire a VP of sales that you believe in and truly love, and they put points on the board and the curve tilts. That's the key. It's got to tilt. You can fall in love with your VP of sales, but if things don't get a little bit better, it's not a real VP of sales. A VP of sales job is not always to quadruple sales in a week. What it is, is to take 100 leads, 1,000 leads, 10 opportunities, and turn them into more revenue than before she started. That's the sign of a good VP of sales. Until then, they haven't proven themselves. But once you have them, you gotta backfill them. And you can go to bat for your lone wolf if you want to. You can coach them a little bit, especially if they're a first-timer, if they're a stretch. But if at some point they want to move them out, as painful as it is, try to find them another place in the company, business development, new initiatives, new something. Desperately try it. Don't let them go, right? But at the end of the day, if there's no other place for them and your VP of sales can't keep them, they will have— but let it be their job. My advice, until you have the VP of Sales, don't let your lone wolf go because you probably need them. You probably need them until you have this great VP of Sales. And if you hire a VP of Sales and in the back of your mind you're not sure that she or he's the one, keep the lone wolf to keep the lone wolf. And they are disruptive. And but this is part of scaling a company. We also need them. And these lone wolves are also attracted to environments where they can excel as a lone wolf. Right? And then when they find them, sometimes they're your best closer almost forever, especially in these complicated products, especially in vertical SaaS and niche products. Sometimes only the lone wolf really gets it. Only the lone wolf and the founders really get it. And when you lose that, I mean, I've watched several companies that are very specific, very vertical, very focalized SaaS companies that lost their lone wolf and never, never got it back until 8 figures in revenue, they never got that mojo back. They never got that. So be— I know it's tough, but, you know, it's a great one. But you gotta keep them until you have a great VP of sales that makes the tough call. And if it's a tough call, try to find another place for that domain knowledge, right? And the last point I'll make, and then we'll break, but there's so many great questions in there. One of the jobs as founders that generally an outside CEO won't get, new executives won't get, is you can't let any of the great ones go. Sometimes they have to go, they have to start their own company, they have to live van life for a year. That's a different type of go. Okay? Still try to get them to go. But the tragedy is when you have these quirky early people that know your market and your product so well, and they don't fit in with the new management team and they don't fit in with it, but you don't somehow try to find them a place in your org, I find 61.3% of the time you regret it. Okay? In the short term, the simple thing is to move Lemkin out of the organization, but you never get back those super domain experts. Right? So only the founders will truly get this because you're in this for decades and try not to let them go, unless they're toxic. Unless they're toxic, try not to let them go. And I— you'll just, you'll just regret it. You'll just regret it. So anyhow, a lot of great questions in there. Hopefully it's helpful.
Thank you very much. Thank you.
All right. So many great questions. Rizabal, going to add you up to ask your question now.
Hey, Jason, thank you so much for doing this. I follow the large majority of your content. So really appreciate it. I was curious how you think about telling whether a ramping rep is going to be great. So before they're sort of quota at full quota, what are the leading indicators that you look for in a ramping rep that sort of start to tell you, hey, this is going to be someone who's going to be great or exceptional, or are they just going to be sort of middle of the pack?
Yeah. So let's, Like the last question, let's break it up into two phases. When you have a VP of sales that you trust, that has inflected the curve, okay, that has made things better, at least a little bit better, they will hire a lot of folks you would never hire as a founder. And, and in many cases, they will give folks more time and more rope than you would. Okay, they may be right, they may be wrong. But if that sales leader is willing to backfill them, be in the deals, trust them, let them hire folks that take a while if they're willing to still hit their number. If they're willing to say, look, okay, I know you're not sure about Linda. I know you're not sure about Jason, but I'm going to— if the plan is to— I'm going to grow 100% this year. I'm going to take you from 2 to 4 or 6 to 12. But you got to trust me. I know Jacob seems quirky. I know he talks a little weird. I know he's a little bro. I know he wears his hat backwards and he's got the watch and he's got the Miami vibe, but he is great. He is. I know you don't see it. I know you couldn't work with you. Trust, you got to back your— you got to give them a little bit of feedback, but then back someone because you are going to need a very heterogeneous sales team later. Okay? You're going to need quirky people. You're going to need charismatic people. You're going to need all different types. And so let them do it. You can't scale without it. And sometimes— and I was thinking a sales exec I worked with a while back that for 3 years was the number 1 rep at a certain organization, number off the charts. Didn't get on the board for 4 months. And I personally would never have hired this person, but the leader that brought him in said this was one of the best he'd ever worked with. Okay. So that was a good reminder, carried the person for a while. And the founder-led stage, no friggin' way. In the founder-led stage, you are going to make so many mistakes and you are going to stick with nice people. You are going to stick with people that seem very aggressive and are waving their hands a lot and doing a lot of things. You're— you in founder-led sales, you need folks that are on your wavelength, that are aligned with you. And if you're not there in one sales cycle, move. You already know it's not going to work. So just like you need a solution-oriented approach after 1.5 calls, if in the founder-led sales, they have to put points on the board in a sales cycle and a half, and that's it. Otherwise it's never, ever, ever going to happen. And I say this to founders all the time. They want to give these folks more time. I'm like, okay, what's your sales cycle? It's 60 days. Okay, so what's half of, you know, a sales cycle? How has it been in 90 days? Nothing. But our sales is hard. Sorry. It's just maybe when you have a VP of Sales, it may work. Founder, it's hopeless. I don't care how nice they are. I don't care that— and founders also are like, well, okay, he hasn't really closed anything, but he's taken a lot of work off my plate. He's not taking any work off your plate because he didn't close anything. It feels like it. In the founder-led stage, we're so overwhelmed because we got a new product and this and sales and everything that sometimes we use the crutch of the person that doesn't complain much, right? But if they don't close anything, I'd rather have the complaint. So you'll know in a sales cycle in the founder-led stage, and you got to move on in a sales cycle. And also always recognize it was your fault for making a mis-hire. It's not their fault. Don't get angry. A lot of founders, not in the beginning, but as the years go on in this in the hard part of founder-led sales until we have that VP of sales, we kind of almost get angry at reps for closing nothing, for not working 40 hours a week, for not doing it. And it's true, like a lot of folks phone it in these days and never learn the product before they start. But you should have figured it out before you hired them. You're like sales folks especially. Here's a last related— it's not exactly what you're asking, but it's close and then we'll break. Sales reps, especially in a distributed world, especially today, And this goes all the way up to the CRO level. They can't do enough diligence today. They don't, they never understand what they're getting themselves into. Then folks are moving quicker and quicker these days to find jobs, to leave jobs. And I almost find they almost never understood what they're getting themselves into. So always slow it down at the very end of hiring and even give them an offer letter and say, but now let's spend a week to make sure you wanna do this. Here's your offer letter, here's your comp, here's your salary. But I don't want you to bounce in 30 days. So let's slow it down and make sure it's a fit for you. I try to really do that with VPs, maybe in ICs you can't do it, but come close, make sure it's— because it's always your fault if they fail. You did not do enough diligence in a startup because, look, we can try to do enough diligence on CrowdStrike and Datadog and Salesforce and these public companies. Your little startup, almost always they get the narrative wrong, they get the data wrong, they don't get the board decks, they don't get the financials, they don't know. It's your job to make sure So if they fail, it's on you. So take the extra, extra time, and then maybe it's a lower odds they're going to fail after a sales cycle. But thanks for the question.
Thank you.
All right, probably our last question, um, for this week. Brian, come on up. Would love you to ask your question. Thanks for joining us.
Yeah, appreciate that. So real quick, what percentage of pipeline do you typically see sales being responsible for sourcing? This has been a point of contention, my current company and my last one. So I'm kind of curious as to what you're seeing out there. Well, look, I've never— every single— it's funny, someone I respect a lot, a sales leader I respect a lot, the other day wrote a tweet. Literally this last week, that honed a little bit of my thinking. I'm still a student. He said, I've never met a great sales executive that doesn't constantly complain. Okay. There's a lot of wisdom in that, which we could chat about. Related to that, I've never seen, I've never worked with a sales executive that, at least in a quiet moment, when I got her or him aside, when we were just talking, that didn't complain about marketing. Some complain very vocally and it's uncomfortable. You know, they'll go to the board meeting and they'll say, I missed the quarter because Brian didn't deliver the leads. Okay, that's the most extreme version. The other version is they love marketing, but this one month they came up a little bit short and I'm like, what happened, Amelia? Caitlin? Well, we did pretty good, but we just didn't get the pipe from marketing or the constant— the one that you hear from sales all the time is the leads are getting worse. Brian, the leads are getting worse. But you're like, you're like, okay, but, but, but, but, but, but Jim, our pipeline's up 50% or our raw leads are up 100%. But they're worse. You always hear they're getting worse. The leads are getting worse. So a lot of interesting caveats in that to say, but it's a tough question because a lot of environments, marketing gives them nothing. Nothing. And I'm going to bring up one adjacent point and then we can try to riff on the last question, then break. The number one mistake that founders make in marketing when they go to hire their first marketer, and unfortunately, sometimes their second, is they hire a brand marketer, a corporate marketer, a product marketer, anything other than a demand gen marketer that's gonna get you leads. And so, so many folks in sales have gotten very little support in their career in marketing. And actually the cheat code, the cheat code in all of this is to hire— if in a perfect world you would hire a VP of sales that is getting more marketing support in your environment than the last one. Then they fly, then they fly. Because if their last company, it was 90% outbound and they got some random leads for marketing, you've got kind of a decent marketing engine. They will come in and it's like, it's like walking on the moon or Mars or something. Like their job just got easier. On the converse, and almost no founders ask this question, if you take someone out of 100% inbound environment and put them into a hybrid environment or an outbound market, 99.362% of them fail. You gotta be really careful in an outbound or mixed outbound environment that you don't hire a sales leader that is come from a 100% inbound environment. I know a lot of folks on LinkedIn that I respect say these 100% inbound environments don't exist anymore, but it's not true. It's not true. Many of the best investments I've made have such strong brands and such good PLG motions that the majority of their leads come from inbound and come from organic. And, uh, I'm not saying that those, that sales there is necessarily easier. All sales is hard. But it sure is different than generating your own. Okay. So there is a spectrum of a self-serve model to a hyper enterprise no one's heard of, where you go from 100% of the pipe from marketing, you know, to sales has gotta do it all himself. And I don't know that there's any perfect answer. I don't know there's any perfect answer. All I can tell you is if you've gotten to even a million or two in revenue, you already have a pattern. Like even at 1 or 2 million, you can be like, okay, what, where's your pie chart? And if I was in the room with founders, I'd be like, okay, Where do your customers come from? Well, you know, 50% comes from outbound, 20% comes from marketing, and 30% comes from word of mouth, which is sort of marketing, right? And you're like, okay, that's your pattern. And then if you hire someone in marketing, their job is to increase the percent of the pie that comes from marketing. If we're getting 20% of our, of our revenue from marketing and you're gonna spend all the money on a marketer, she or he sure better grow that to 30% or 33%, maybe not 80%. And that should be the initial KPI. Is to grow, not grow the pie chart of what comes to marketing. If you can do that, your business is going to scale, right? Yeah. Best answer I can give you because it is. I wish it were one single metric, but founders, too many marketers, 80% of the first heads of marketing, I say startups don't generate any pipeline at all. 80%. Half of them want to hire a product, a Superstart product marketer that wants to talk about tear sheets and slick sheets and product additions. No, you want to hire someone who the first line of their LinkedIn is, I increased opportunities 118% at my last job. Hire that person first. And then their job is to do more of it on a budget, agree on a budget and do more of it. And then, and then that, and then you get sales some relief. That's the job is to get, if you're not in 100% inbound environment, your ultimate job is to get sales some relief and make their job incrementally easier. That's a tough job. So thanks for the question. Thanks for everybody for joining. And we'll, we'll keep the conversation going.
Love it. Thank you so much, Jason. Thanks for joining us again. Always love your great insights and just your tactical tips. So as you mentioned, we are getting ready for SaaStr Annual. So we hope to see everybody September 10th through 12th. We've got some great speakers lined up, some awesome content. We've got CEOs from Build.com, Klaviyo. We've got the president of Plaid. We've got CRO of GitHub, Atlassian, and so much more. We are gearing up for a huge AI summit as well with great AI companies and topics. So we hope to see you there. We are gonna be taking a break for a couple weeks on Workshop Wednesday. We will be back August 14th with the head of sales from Superhuman. So see everybody. Thanks so much again. Head to our YouTube to check out the recordings in the meantime.
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