I've always wanted to create a very  tactical episode on how to do sales, especially with a focus on founder led sales. A lot of early stage founders get tripped up  as they're taking late stage sales advice. The founder is the product. You have  studied. You have experienced something that most of the market hasn't even had  a chance to maybe see or visualize yet. A billion SaaS tools emailing me constantly  about their product. How do you get someone

to even want to talk to you and be open  to learning about what you're doing? So if you can focus the messaging in a way  that speaks to something that is a bit of shock value or is counterintuitive, you'll  get them to continue reading. When a problem is truly being felt by the market, people  will get on a call, people will respond. The next step I imagine is you're on the  phone with them trying to convince them to actually care. What do you do there?  How do you get them to engage further?

You need to be vulnerable. I would be very open  and honest with where you are. Hey, I'm an early stage startup. We have a lot to learn. Can we  kind of gain your insight into how this problem is manifesting on your side? Founder led sales is  not about revenue on day one. It is about learning as fast as humanly possible to get to that  pulse, so that you can earn the right to sell.

Today my guest is Jen Abel. Jen is the co-founder  of Jellyfish, where her and her team help early stage founders learn how to sell, do early  customer discovery, and set up a repeatable sales motion. Prior to Jellyfish, Jen was an enterprise  sales director at the Muse and a general assembly, and she's obsessed with helping founders in  the zero to one stage of their journey. In our

conversation, we get extremely tactical and in the  weeds on how to actually do sales as a founder. We talk through each step of the sales process, and  Jen shares what you should be doing and saying at every step. We go through how to find your  first set of leads, how to reach out to them, what to say in your message, how to structure your  first sales call, how to get through procurement,

and how to get that final signature. She shares actual words you should be using, and phrases and structures, and pitfalls that most  people run into at each of these steps. I've never heard a podcast episode with this much advice  that you can put into practice tomorrow, and I am very excited to hear how it goes for you. If  you enjoy this podcast, don't forget to subscribe and follow it in your favorite podcasting  app or YouTube. It's the best way to avoid

missing future episodes and it helps the podcast  tremendously. With that, I bring you Jen Abel. Jen, thank you so much for being  here. Welcome to the podcast. Thanks, Lenny. What I've always wanted to do is to create  a very tactical episode on how to do sales,

like how to actually have sales  conversations, how to find leads, how to close deals. Especially with a focus on  founder led sales, where founders are doing the early sales versus hiring salesperson. Which one,  I know you're a huge advocate of and we'll talk about this. And two, you basically spent all your  time working with founders and founding teams, helping them learn how to do sales, how to set up  their go-to-market motions, how to scale teams,

sales teams, how to hire sales people. So I'm  very excited to have you here to create a very in the weeds, hands-on episode on how to  do sales. How does that sound broadly? That sounds awesome, and thank you  so much for having me, Lenny. I mean, it's a true pleasure to be here with you. It's my pleasure. Many people have recommended  you come on this podcast. I'm excited we're doing this. Let me start with just this kind  of question, our founder led sales. Maybe just

briefly explain what that term means and  then talk about why this is so important, why this is the way you recommend  companies start doing sales? Founder led sales is really that first milestone  that a startup goes through on the commercial side, which is, how do I go out and get my first  few customers? Some people might say zero to one,

which is, how do I get my first million?  Others might say, how do I go out and get my first 10 customers? It's all kind of in the same  vein. And founder led sales is really, really, really important because in the very, very,  very early days, when there is no brand equity, when there is no marketing engine running, when  there is limited to no reference ability, the

founder is the product, right? Because the product  is still, could be abstract, could be an MVP or in it's really early formation. So the founder is  the product. When people say, well, what does that even mean? It means that you are a subject  matter expert on something highly specific. You have studied, you have experienced something  that most of the market hasn't even had a chance

to maybe see or visualize yet. So you have this  novel insight that you are building a business around. And it's that novel insight and the way  you see the world that gets the market excited, in absence of a product. And that's actually  happens even before you even show the product. So founder led sales is how do you bring the  founders vision into the world and have the

market, and understand what part of the market  accepts it, and then what part of that vision are they accepting? So it's aligning the  founders vision with the market reality. This episode is brought to you by Brave Search.  Brave Search is the private independent search engine that doesn't bias or censor results.  Brave Search and its answers with AI

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that's V-A-M-T-A dot com slash Lenny. And this is counter to what many founders hope is, I'm just going to hire a salesperson, they'll  handle sales. I'll build the thing, I'll wait for them to find deals. And this is like a lot  of people think this way. And founder led sales is the movement of just like, no, no, you should  be doing the sales for a long time as a founder.

Absolutely. I mean, it is the competitive  advantage. I don't think people realize how much of a competitive advantage the founder led sales  motion is, for three specific reasons. One is that the founder is the visionary. No one's going to be  able to speak to it like they can. No salesperson, really no non-founder. The second is that they  are the highest order in the hierarchy of the

startup. It's the founder. So the market is  excited to talk to a founder because they usually know something that the market doesn't  know. And they want to learn and maybe they want to experience something differently. So being able  to speak to the person that's running the vision, speak to the person that's crafted the vision. And then that third piece is that the founder

can see something budding in a conversation  that a salesperson won't be able to see. And it's those budding moments that's where  all the gold lives. And I don't think a lot of founders realize that. Their day one  market vision is never the same vision that takes them in a product market fit. And I say  that all the time. It's these little budding moments where it's like I was able to get to  that budding insight because I went deeper

and deeper and deeper and deeper through these  calls and these conversations, to fully refine how we want to go out and sell it. And only a  founder is going to be able to see those things. I love this because this connects  really well with an episode I just did with the CMO of Wiz. And the founders  went through this exactly. They had 10 to 15 conversations a day for weeks, and then  they're like realizing people keep telling

us they like it, but no one's buying, no  one's excited enough to want to actually move forward. And that was only happening  because the founders were on these calls. Yeah, I mean, the other thing too is that it  becomes a game of telephone. It's like, hey, this salesperson says that no cares about this. What do  you think the first thing the founder's going to say is? It's the salesperson. So much easier  to say that than, is it me? Is it my vision?

So it also kind of brings the accountability  closer to the pulse where decisions are made. It's interesting how similar  this is to product building, where there's this idea that a founder top down  can tell the team what to build, and it's this very waterfall cycle. When in reality the idea  of the product and feature is just like step one,

and then there's actually building it, testing  it, talking to customers about it, that actually turns that initial seed of an idea to  the real thing that people will want. Totally. Okay. So the catch 22, I don't know if that's  the term here. The challenge is, okay, so great, founders should be doing sales. Most founders  have never done sales. They just want to build

product. They're mostly product people,  design people. Sometimes there's founders that are salespeople. Rarely is that the case  in my experience. So doing sales is very hard, not something that comes naturally to a lot  of people. A lot of people are very afraid of it. So with that, let's get into how to  actually get better at the sales process.

I think a nice framework for how we can go  through this is basically first let's talk about the sales cycle, the steps, the key steps  of a sales cycle. And then we'll just go through each step and help people learn some tactics  to get through each of those conversations. Sounds great. Okay. Yeah. Cool. So what's the simplest way  to think about the steps of a sales cycle? The traditional sales stages that most CRMs are  even set up as is you have your intro call. You

have your second call, which sometimes could  be the demo depending on the stage of market you're selling to. Then you have your third call,  which is going to be more about walking through a proposal, a scope of work, maybe going deeper  into the demo to contextualize it to everything you've learned. The fourth call is going to be  getting their feedback and kind of co-authoring

that scope of work even further. The fifth call  is going to be around probably an introduction to procurement. And then selling into procurement  in itself, it's its own little sales cycle, but we could talk about that in a sec. And then  post-procurement, it's going to be obviously getting that signature and knowing who the actual  signatory is. Sometimes it's not even the business

unit, it's sometimes legal, CFO, procurement  themselves. So just understanding who that is. Okay, great. So let's walk through each  of these steps. So I love that each call has its traditional goal, demo, proposal,  then co-authoring, and then procurement, and then post-procurement. I  love how consistent everybody is.

Yeah, well, it's also, it's interesting because  it's also predicated on their buying process as well. So if they're really used to buying, if  they're very mature in their buying process, they actually might guide you to what  the steps are. But most startups are turning non-consumers into consumers.  So that's why this kind of fits well.

Got it. So there's this intra call step.  So kind starting about where it begins. I think where a lot of people struggle most  is getting anyone to even pay attention. You don't want to talk to them. A billion  SaaS tools emailing me constantly about their product. So maybe we start there  of just like how do you get someone to even want to talk to you and be open  to learning about what you're doing? Yeah. And this is why that founder  led sales piece is so important. One

is when it's coming from the founder, it's  an entirely different weight. You're like, oh, interesting. This founder is reaching out to  me. Okay, I'm going to seek to go a layer deeper, knowing who is sending me this note. The  second piece is this is why that novel insight, that technical insight, that business model  insight that you've uncovered needs to lead

here. People are inspired by a new way of  thinking, usually something counterintuitive, something that's really different. I really  try and stay away from better, because that's really hard to define, and better means something  different to everyone. So if you can focus the messaging in a way that speaks to something that  has a bit of shock value, or is counterintuitive,

you'll get them to continue reading. So first  and foremost, I usually like to open it with, which is why is this relevant for me in my role? Why are you reaching out to me? So first and foremost is relevancy. I think that matters  even more so than personalization right now. I think it's so easy to personalize anything,  and it can also come across as really stressed

when you're like, hey, I noticed you were on  such and such podcast, and that was when they were previously two roles behind. So I always  say relevancy. If you can get to relevancy, that's the most important piece. The second most  important piece is really getting to that level of differentiation or counterintuitive nature.  So say something that would literally make them

say what? Or that makes no sense. Maybe not that  makes no sense, but what or how could that be? Or I've never thought about it that way. Or I  actually don't fully understand what they're saying, but there's something there that's  interesting. Get them to pause for a minute. And the most important piece is getting this done  where, if they get it on their mobile phone, which

everyone is looking at their mobile phone and on  email, they don't have to scroll. So usually three to four sentences max. That also, that's how a  founder writes. That's how an executive writes if you're selling top down. But most importantly,  leave them wanting more. Don't say everything, don't even talk about the solution. Talk about  the problem that you want to solve, and why it

needs to be solved or why it's not good enough  today. So those are the four main components. Just to reiterate, relevancy, bring some level  of counterintuitive or really different approach to the conversation, focusing in on a problem  that's predicated to them, and really concise. I love this. Is there an example  you could share that helps make

this even more real? Maybe an email  you helped with. And by the way, this is email and LinkedIn, I imagine  is where you're communicating mostly? LinkedIn, email, you would  be shocked to hear this, but cold calling. I never used to  do this. It is one of the most... The interest rates on cold calling are  a lot higher than email in many cases.

So it's calling, email, cold email and LinkedIn  DMs, is that the three channels generally? Yep, those are the three, yeah, the main ones. Cool. Yeah. Is there an example?  It doesn't have to be word for word which you've done or people  done, but just how do you... Yeah. Actually our first three years were built on  cold email before we actually had clients, before we got word of mouth from the founders we  worked with, I cold emailed the first 20 customers

we had at Jellyfish. And the line I used in  there was zero to one sales talent doesn't exist. That's why I want to have a conversation  with you. So that was kind of that leading, wait, what? What does that even mean? And what  I would do is tie that to them in some respects. If they recently raised the seed or series A,  where they are in that journey. But I would

lead with that and then tie it into like,  hey, I noticed you're looking to target X, Y, and Z based off of what your website.  I'd love to have a conversation with you. And that first piece is the relevance.  Here's why this is relevant to you. Yeah. And then I say, our belief at  Jellyfish is zero to one sales talent doesn't exist. That's why we built this model. Awesome. And you kept it really short.  So it's relevance, counterintuitive,

keep it really short. And then  what was the fourth piece? The fourth piece is just make sure it's concise  so that you don't have to scroll on mobile phone. While we're on this topic. What's a good  conversion rate of these sorts of cold outreaches? Conversion rate is interesting. Because  everyone's so focused on conversion rate. I get that in the beginning until you  have some wins, you have to focus there.

But I just want to reverse engineer it  backwards a bit. Once you kind of have this, and I'll talk about it in a sec, which is win  rate. Win rate is if I got Lenny on a phone call, and he went through the sales process, and  I signed him up. And I spoke to 10 Lenny's and only Lenny R was the one that signed.  That's one out of 10, that's a 10% win rate.

So if you have a really high win rate, let's  say 30 or 40%, you actually don't need as high of a conversion rate on the outbound, because  you know if you get someone in the funnel, the throughput is very healthy. If your win  rate is really low, you need that conversion rate to be much, much higher, because you need  more and more and more at bats. So conversion

rate is a funny thing. In the beginning I get it  because you don't have a lot of customers going through the pipeline yet. But there's people  focus on it in a little bit of a false sense because interest rate truly is also dictated  by win rate. So I just want to specify that. That's a really good point.

I would say if you're doing a win rate around 15  to 30% and you need to carry, oh I don't know, a million dollar quota. I would say a healthy  conversion rate from outbound probably sits

around, when it's mature, around five to 7%.  Sometimes it could be two to 3%. Sometimes I've seen eight to 15% because it's coming from the  founder, and they're solving a really heartfelt problem. So interest rate is also predicated on  the problem that the founder has decided they want

to solve for, and their insight on that problem. And everyone wants to keep going back to, well, email rate is really low, email doesn't work  anymore. LinkedIn, I'm not getting the connects I want. Yes, you can argue that the game has  changed a little bit, but when a problem is truly being felt by the market, people will  get on a call. People will respond. And if I

can compare two engagements at a time that we're  running, I see one where it's a 2% interested rate and then I'm seeing another one that's actually  at 12% interested rate. And we're doing nothing different. The only thing that's different is  the insight that the founder has on the market, which is a hard pill to swallow.  And I know that's hard to hear too. And those are two different  companies selling different things?

Two different companies selling  to two different markets, but they're not fundamentally  drastically different markets. Got it. But one's basically got  more product market fit essentially? That's exactly right. So everyone always  comes back to we have the sales problem, we have the sales problem, we have an outbound  problem. And yes, there could be some technical

things going on that you need to look at. Maybe  you leveraged clay and you blasted a thousand people and now your domain health has been  impacted. But the vast majority of the time, maybe you're just not saying anything  interesting at all. Maybe the problem you're looking to solve just isn't widely  felt. Maybe the perspective you have needs

another level of refinement because  you're just not getting those bites. I feel like this question you just touched on is  something a lot of founders are always wondering, is this product not the thing people  want? Is it my sales skills? I guess I imagine this is a very difficult question  to answer, especially quickly. I guess is there anything there that's more likely  because of this, it means your product

isn't something anyone's want, versus  you're not doing a good job selling it? Remember that amazing chart you  drew where it talked about the length of time it took? I think  you picked the top 25 startups. For product market fit  timeline [inaudible 00:20:51]. Product market fit. Yeah, that amazing  image that I think has been reshared more times than anything I've ever seen.  It's interesting because if you look at,

I was looking at this closely the other day.  If you look at the top section where the time to product market fit is consolidated, and you go  all the way down to the air tables and the figmas, which a long time to get to product market fit.  If you think about the earlier ones, which were, it was like GitHub that had product market fit  pretty quickly. The SOC 2 compliant company.

Vanta. Vanta. There's this thing in my head and I haven't  fully validated it but I'm going to share it with you, which is did they start with the market  problem first and then build the product? Because they knew who their market was right  off the bat. Versus an air table and a figma that I think started with a technical insight  and then were trying to find their market.

I think that's absolutely right. Vanta, the way  they approached it, Christina, she was searching for a pain. She was obsessed with talking to  everybody about a pain that they needed solved, and then she just built it in spreadsheets.  So she started with the market very much so. And I think product market fit when you start  with the market first, it's accelerated. But I

will say this, I think that it's also capped  on the upside. Because you're starting with the market versus the air table and the figma,  which started with the technical insight and has uncapped upside. But one is certainly riskier  than the other. Starting with a product is a hell of a lot riskier. And this is where  I come back to so many people will say,

how did you get funding and not know  who your market is? And it's like, because if they do find it, that's a really,  really, really big win. Versus I think if you start with the market first, you could  potentially get a good win but is it more capped? Interesting. I don't know, it's just a thought. I  was staring at your grid for so long,

I was like, there's something here. And I  kept coming back to those were more like I kept breaking it down to market versus product. Yeah, I love this. I think there's  definitely something there. There's also horizontal versus a very  specific problem you're solving. Totally. Okay, so you mentioned clay and you kind  of nerd sniped me there of just what tools do you find useful? And it makes me think about  finding leads, which is kind of going backwards

through the sales process, but it might be  okay, so maybe let's spend time there. Just like what do you recommend to founders to find  the good leads? Glengarry Glen Ross good leads. So I say before you buy any tool, don't even  think about tools. I feel like people turn everything into this complicated mess with all of  the tools that they start integrating. And then

they're engineers, I get it. So now they start to  engineer these sales tools together and then they blast their market, and now they have 5,000 notes  out in one day and their domain takes a hit. So I think before you even overthink about the tools  right now, can you manually find 30 people that

you want to spend 15 to 20 minutes writing a  rock solid note to? Are there 30 people that you are deeply excited to learn from, that you  are willing to invest 15 to 20 minutes to write a really thoughtful note? Let's just start  there. So some questions. One, are they even discoverable? How hard is it to find 30 people? What have you noticed across those 30 people?

Are there any interesting insights? Maybe it's  the size of the team they work on, maybe it's the industry they're in, maybe it's the length  of time they've been in their role, maybe it's their previous roles in their career. Are there  some commonalities? There's always some level of a commonality usually in most cases. Okay, so  now you're starting to collect some parameters.

Just by doing this exercise, you're starting  to collect some parameters around who you want to learn from and sell to. Now if you send out  those 30 notes and you wrote them specifically, and you spend good quality of time on it. And  you've hit them on email, you've hit them on LinkedIn, maybe even tried to call them, maybe  you've sent them a Twitter DM, pulled out all

the stops. How many people respond? 1, 5, 0? If it's zero, it begs the question, do you now want to do another 30 in a very similar fashion?  Do you want to change the messaging a little bit?

Now it forces these natural experiments. Or do  you want to maybe go after a different role? So it forces you to answer these questions in  a very manual way before you even think about integrating and spending time on tools. And  then you get to a point where it's like, okay, now I'm starting to get some learnings and now  I've realized, okay, it's this group of people, I've spoken to maybe two or three, now I want  to go out and actually build a campaign to now

talk to the next 10 to 15 people in that group.  Truncate this as much as you can because I think people focus so much on volume in the beginning. Even if you're selling down market, mid market, enterprise, volume comes once you've identified  it and know the parameters. Parameters then allow you to do really strong enrichment with a clay.  You now know the types of questions to give it.

If you're not asking it the right questions,  these enrichment tools, these sales tools will yield nothing. So it all comes back to even  before you start your sales call, you need to make sure you're asking the right questions with  am I even engaging, or do the people that I want to learn from or sell to, am I even messaging  them in the right way? Are they even the right

person? And the only way you can do that is by  actually truncating these little experiments. I love how tactical that is. And what I love is  even one of your nuances you mentioned is can you even find them? This gives you a signal of how  are... You're going to have to have hundreds of these, thousands of these eventually. If 30 is  hard or impossible, you're in trouble already.

Totally. And it was funny, I was talking to  someone today that said they had a target segment of high net worth individuals that  they wanted to go out and serve. I'm like, how do you find those people? I guess when you  get to a certain level, your net worth may be public. I don't know. That stuff's very hard to  have certain parameters that are undiscoverable.

And then if they're undiscoverable and  it requires you getting on a call to understand if they are a fit, that does impact  conversion rates. Not necessarily in a bad way, but now you need to kind of bring that back  into the math equation, which is like, okay, if I speak to 10 people, I know two out  of these 10 will be qualified. But I don't know which of those two out of 10. Well, that  means you probably need more of those numbers.

So to quickly recap a few of the key  things that I've written down as we're talking. So if you're just trying  to figure out who to reach out to, make a list of 30 potential prospects  that you think are good fits, that would be excited about what you're  building. Spend 15 to 30 minutes writing them each an email. Do these emails have to be  really short the way you described previously? I would say the shorter the better,

but would you respond to that? If you  got this email, would you respond it? Got it. One of a great little tactical test is on Gmail, you can highlight the message and then have it  replay it back to you from an audio perspective. Oh wow. You'd be shocked how many notes I've changed  when it replays it back and I'm like, oh, that sounds really passive-aggressive.

Interesting. And so you also shared  the structure for how to reach out to folks. So let me just share that again.  And that applies to this initial email too, but it sounds like as you automate, you want  to make it more precise and focused and not... Basically they're not as customized as  you start reaching out to more folks. Totally. So start with something, here's  why this is relevant to you. You're

looking for salespeople in this market. Here's  something that's unexpected or surprised, like zero to one salespeople don't exist. Keep  it short and then I always forget the last one. Focus on the problem. Focus on the problem. You don't even need to talk about the solution.  That's the big takeaway, which is if you get any

sales email, you get what's the primary focus of  that email? It's usually like here's what we do. But I bet if someone reached out to you with a  novel insight and said, I'm really passionate about solving this problem, if it's something  you're focused on, you'd probably reply. If it's a big problem. If it's like,  oh yeah, you're so right, I need this. The beauty with the American market,  and I say this because we do a little

bit of work with international startups  too, is if something doesn't feel right, people love to complain about it. And it's like  use that to your advantage. Get that intel. A note that I just looked at, that I wrote  down, that I think is very important is avoid using "this is better" as your pitch. Yeah, yep. Different. Here's something  shocking about what we're

doing. Here's something that'll surprise you. Yeah, or counterintuitive. Exactly. Counterintuitive. Yeah, it's interesting. I spoke to a good friend  that leads procurement at a massive organization. And he said to me, he goes, "One of the worst  things someone can say to me is we're better than X product. Then I ask them to define that. And  then I ask them, okay, how do we measure that?

And then I say, okay, should we give this  company another year to give them this feedback before we make this huge transition and disrupt  momentum?" Yeah, better is a dangerous place. I invest in a bunch of startups and I find  it's impossible to get anyone to care if things are good enough with what they  got today. I'm happy not using the best

possible product if my life is okay. And  I have so many other things I got to do, I'll just deal with this  good enough solution for now. Absolutely. Okay, amazing. So we talked about how to figure  out who to go after, how to pitch them to get them to want to talk. The next step I imagine  is you're on the phone with them trying to convince them to actually care. What do you do  there? How do you get them to engage further?

One is you need to be vulnerable. You're an  early stage startup, okay. The market, we're at a point now where the market is smart. I always  assume that the buyer I'm speaking to is highly educated and knows way more than I do. So just  have that perception because what I've learned is

a lot of the market will play dumb, and you can  get yourself caught pretty quickly. So when you speak to them, I would be very open and honest  with where you are. Hey, I'm an early stage startup. We are deeply passionate about solving  this specific problem. We have a lot to learn. Here's how we are thinking about it from a problem  priority perspective. Can we gain your insight

into how this problem is manifesting on your side?  And then let them open up. Now you have them one, talking about the problem. Now you're getting  the intel about their perception of the problem, and is it even a problem? When you say  you're early stage and there's still a lot to be done, it is easier to be honest. If you tell them you have a fully baked,

ready to go product, they're not going to  give you honest feedback. It's very hard to say to a founder and look them in the eyes  and say, hey, we built this product, can I show you what it is? You're just going to get  someone that's going to say, oh, this is great, this is wonderful. But when you're vulnerable  and when you tell them it's not fully built yet, even if it is, you will get more raw and honest  feedback. Because it is easier to tell someone,

hey, before you make this mistake, I actually  don't care about that. If you've already built it, they're not going to give you that feedback.  So the further you suggest you are, you're actually going to hamstring a lot of the  intel, hamstring yourself on gaining a lot of the intel. So that's one counterintuitive thing  that I think a lot of founders don't realize. This episode is brought to you by Paragon,  the developer platform for building native

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Visit UseParagon.com/Lenny to see  how Paragon can help you accelerate your products integration roadmap  today, and get $1,000 in credit on their pro and enterprise plans.  That's use P-A-R-A-G-O-N dot com. So I had April Dunford on the  podcast a while ago. I don't know if- She's awesome. Amazing. And her last book, it actually has  the opposite advice, but I think I know why,

which is she focuses on later stage companies  and her advice is the buyer. She has this really interesting insight that it's harder to buy  software now than to sell it, because there's so much to consider and your job is on the line if  you make a mistake. It's easier just to be like, forget it, I'm just going to go with what we have  today. I don't want to put my ass on the line for buying this new thing that someone's trying. And  so her advice is you actually have to educate the

buyer on the market and here's what's happening.  Here's where things are going, and here's why I think this is the future. But I think again,  I think that's focusing on later stage stuff. A hundred percent. And you raised such a good  point, Lenny, which is late stage sales and early stage sales are very, very different.  And I think that's where a lot of early stage founders get tripped up as they're taking  late stage sales advice, usually coming from

an investor. Or they've maybe hired a salesperson  that's focused on more mature sales. But I think she's spot on. Buying is just as hard, if  not harder, than selling right now. Because who wants to make a mistake and also who wants to  go through switching costs? Oh, it's so painful. Yeah. I think the other really important  point here that you're making is that

part of this initial sales experience of  founder led sales is not sell as much as you can. It's to learn what people want.  And so I love that you're sharing here's how to get the best possible feedback,  not necessarily close the most deals. Totally. And founder led sales is  not about revenue on day one. It is about learning as fast as humanly  possible to get to that pulse,

so that you can earn the right to sell.  There's this concept that I talk about, which is you're going out to run sales to collect  the research, which is what founder led sales is. And then you have sales for revenue,  which is that post founder led sales stage. And your milestone that you suggested  of how far to take founder led sales,

you said around a million ARR, right? Yeah. I think it's about, some people say 500, some people say a million. I think if  you get to 500K really, really fast, then I think absolutely you can move out of it.  If you get to 500K really, really, really slow,

you might not want to get out of it right away.  You haven't reached that velocity point yet. Awesome. I have a post that we'll link to  that has actually numbers and when all these big startups move from founder led sales. It's  in that same series about product market fit. There's two stories this makes me think of I'll  share real quick. One is Sprig. They shared a story of first round capital at their first  round and their partner there is just like,

we will not let you hire a salesperson until you  hit a million ARR. We're going to help you. We're going to have salespeople helping you through  it, but we're not going to let you hire someone. And he was really happy about that. The other is  Zip, which just raised a $2.3 billion valuation, a procurement company that I was lucky to be an  investor in. And their first founder led sales

motion was they just reached out on LinkedIn to  heads of procurement, and just leaned into what you're saving more, which is we just want your  advice on this product that we're building. Just tell us what problems you have. It was very advice  oriented versus we want to sell you this thing. Yeah, no, absolutely. I have this theory  that maybe you shouldn't hire any salespeople

until series A, right? Because seed is all about  experimentation and proving out that experiment, and then obviously series A is about exploiting  that learning. But I see so many people, I mean hiring for early stage sales is the odds  are actually more against you than trying to

get your next round of funding. Because it's  truly, truly such a counterintuitive stage. Interesting. Okay, so I kind of took  us on a whole tangent. You were sharing advice on how to get someone excited.  So the first is when you're engaging, you're talking to the prospect and company ABC.  Your advice is be very honest and vulnerable

about your stage. Tell them you're early  stage. You're building this thing. You're deeply passionate about this problem.  Here's what we're trying to do, here's our priority problem perspective, and  where we're focusing, and kind of get their feedback on your approach. Cool. You were going  to go to the next tip and I took us off course.

Testing the questions to ask. Where is that  aha unlock for you? But more importantly, where's that aha moment unlocked for them? Because  when they start getting their gears churning in their head about, and this is the beauty  about not having a product and not showing them anything, they're visualizing in their  head now. This is a really powerful thing,

which is like, so tell me how this looks in your  head? How are you seeing this? And they're like, I don't know if I can see it. And I'm like, great,  we'll show you that. Great insight to know by the way. Or so I think this is how, I guess this is  how it would work. Walk me through what's living in your head right now. You pick up on so much and  then all of a sudden they're like, wait a second, we've tried solving for this and it's still not  solved for. Or you know what? We hired someone

last year to manage this. Great understanding.  Is it being measured? Is it being managed and have they tried to solve for it? The leading  indicators that you're onto something here. I love this thread because this  is what everyone's always like, how do I know if I product market fit?  There's these signals that you're talking about of signs that there's something here. Like  a big enough pain point where they're excited to

basically they want to pay for it, they will  pay to solve a problem. So maybe just again, say the things you notice that are signs  like, okay, you have something here. So I think the first is it has to be a growing  and widening problem. No one's going to spend time fixing a pretty fixed problem, because it's  not necessarily really a priority anymore. It's

maybe a pain in the butt, but it's not a priority  if it's not growing or widening. So gate check one is like, what is the implication? Are you  measuring? Are you managing this problem today? Yes or no? If they don't know, great  to know. If they said no, okay, move on to the next. That's pretty powerful.  No, we're not measuring or managing this. Okay,

there's probably not much there.  If it is being measured or managed, then the next question you want to get into  is how have you tried to solve for it? Is it through that head count that you just hired?  Is it through another tool? Is it just still an open gap because nothing exists yet to solve  it? Just understand their maturity around how they've tried to plug it. These are all that make  the secret moments in intel to close that gap.

That's awesome. And essentially it's  showing you that there's a pain here that they're paying attention  to and are trying to solve. And what you're psychologically doing  is now you're flipping them into a buyer where they're like, wait a second, hold on. I  need to bring on so-and-so on the next call, they also think that this is not good enough.

That's funny because that's exactly what Wiz  noticed, is they moved from people being like, oh, this is cool. I like it, I like it. To,  okay, I'm going to pull in this person. I'm going to pull in this person to talk about it and  make sure we're... And they were pulling in other people exactly as you described it, because  they wanted to move forward on this thing. Absolutely. And that's when you know there's some  momentum behind it, which is when they're bringing

in other colleagues. Whether it be the potential  users, if you're reaching out to the executive, or the users like, hey, I actually want  to bring my boss on to the next call. Good sign. Cool. Anything else  along these lines of how to get someone excited slash understand  if there's going to be pull there? I guess the one thing is please, please, please do not ask questions like what keeps  you up at night? If you had a magic wand,

what are your pain points today? I can guarantee  you that answer changes every single day. That's super interesting. Is there any  tip for how to end one of these calls, as someone that's never done sales is like- Yes. Okay. Get the second call booked on the first call. Love it. Pull up calendars. Look at  calendars. Who else should be invited? It's just a natural  evolution to ending the call.

Great. So that's in 30 minutes though, right? And if they say, ah, I'll email you. I could say. That's also kind of a leading indicator. Yeah. So do you recommend not getting off the  call, trying to avoid that, or is it just- If they won't give you time on the calendar,  you could say, listen, great. Feel free to email me. Maybe they're just being honest  and they don't have their calendar available,

but nine times out of 10, it's usually I don't  have the heart to tell you I'm not interested. Yeah, it's hard. It's hard to tell people  you're not interested. Very cool. Okay. This is amazing. Okay, so the next step, if I remember  correctly, is kind of co-authoring and co... Yes. Okay, cool. Talk about that. In the early, early days, one of the biggest  ways you can get folks excited is it feels like

it's going to be built specifically  for them. The power of specificity, the power of being extremely focused. With that,  you can literally turn a customer into a guide by asking them to co-author the scope. The scope of  work. The co-authorship piece is important for two

reasons. It helps you understand where they're on  their biomaturity. Let me explain. If they do not have an existing process or strategy to solve  X problem, they can't buy a technology yet, which means you need to sell them. And this is  why I go back to you need to sell them some form of a service, right? Why? You want to be the one  in there educating. You also want to get the logo.

You also want to show the revenue. While it's  not recurring revenue, it still shows intent. And I think that that's really important.  Every founder I speak to is like, well, my investor really doesn't want service-based  revenue. That's fine. But then you can also tell your investor, great, should I wait 18  months to when they're ready to buy a solution, and be the one that's not the one selling  them because someone else educated them?

These are all of the implications of waiting.  So yes, is service-based revenue great? No, we all know why it's not great. But it's  great in the sense that it shows intent. It's great in the sense that you can call them  a customer. It's great in the sense that now you can use their logo. And it's great in the sense  because you are getting paid to educate them.

You are getting paid to help them design their  process. This is where all the power lives. And this is why so many AI startups a year and two  years ago were going in on services contracts, because they wanted to set the mindset with  the buyer around what this would look like. Is there anything you recommend  to time box contain the services

piece? Because I know a lot of companies- Yes, such a great point, Lenny. You absolutely  need to time box this. I would time box it as 90 days and then what you can say in the next 90  days, we'll scope where we are and what you need. Scoping out more than 90 days, listen, so much is  going to change. You might also not want to do it anymore, so you don't want to lock yourself up.  So I would look at 90 day increments. A specific

example. We had a founder that my colleague  was working with, and they were selling a very specific technology to a non-traditional...  Sorry, a very traditional industry. I don't want to be two bleeding with what it is, but a very  traditional industry that's not used to working with startups, or necessarily plugging in a  new technology right away. And they were very

honest. They said, listen, we haven't changed  vendors or partners in over five or six years. I actually don't even know how we would do that  today. Could you come in and explain to us, understanding where our workflow is and how we  would integrate this, before we even consider the technology? Which we did. We got paid a nominal  amount, but we're now a customer and now we get

to set the stage for how they think about this.  And then they won the technology contract. But everyone is so focused on selling the technology  really, really, really quickly. That works in markets that know how to buy that technology,  have a process in place, have a strategy in place, have an implementation team in place. If it's a new technology like AI right now,

they need a strategy and process like who's the  human in the loop? Is it them or is it you? How do we measure success? What does success look like?  What risks should we be aware of? Our legal team's not even aware of all these risks. You want  to be careful because legal can immediately, and procurement, can shut these things down if  it seems too novel, where it's foreign versus

they're so used to buying services, especially  at market. It's their largest budget line item. So it's interesting because most founders are very afraid of moving into services. I  hadn't heard this advice before. Probably going to get slapped for  saying all this stuff, by the way. Well, so along those lines, what percentage of companies that you've worked with or  see do that or have to do that step?

This is going to be a shocking step.  So I would 40 to 50% have to sell some form of service before they can sell a technology. Wow. Of B2B SaaS company? A B2B SaaS. And this, again, this is  specifically more top-down sales. But yeah, because the user and the buyer are different,  which means there's user value, there's buyer

value, there's all different players, there's  procurement you have to go through. But yeah. And just to make it even clearer, what's an example of a service that  you've seen company offer in a step? So I've seen, hey, can you come in and actually  help me pitch this, design a custom pitch to my boss as to why we should do this today? And  we literally got paid to build a sales pitch.

So it's not necessarily providing a service.  It could be just helping them sell this. Yeah. It could be helping them sell in a  way that makes you... You need to get a lot more context on their business. It can also  be, hey, we haven't actually thought about a process for how we can actually deploy something  like this. We're currently using this technology,

which we want to change from. You've kind of hit  this at the right time. How would we implement or how is it best to integrate with this tool? Can  we get both of you guys in a room to map this out? Got it. So it's like consultants almost, like  coming in to help you solve this problem. It's a great point. It's consulting them towards the acquisition of the product. It's  not consulting as one-off consulting.

Got it. And they know that obviously  you're biased, but they also want the problem solved. And they're like, great,  you're going to help us solve this problem, because it's on my plate and I need your  help convincing leadership that this is- And I need to craft the storyline  as to why we need to do it anyway, so I will pay you to do it, but  here's the format it needs to be in. Fascinating. Wow. Okay.  Anything else along those lines?

And then of course, if you're in a  position to actually sell the technology, because the market is able to acquire and adopt it  and not have to create a new strategy or process, then obviously sell the technology.  You don't need to be selling services. I want to come back real quick. The  previous call, I wrote this note down as you were talking. You recommended not doing  a demo and just talking about it broadly. Yes. Is that your advice there?

On the first call. Yeah. On the first call,  my fundamental belief is that the demo is a bit of the only carry you control in the  sales process, right? Once they see it, it's kind of like pitching an investor. Once  they take a look under the hood, that dreaminess in their eyes, they're like, oh, I saw it. So  leave them wanting more. And the demo is that,

leave them wanting more. Even when you do a  demo, don't demo everything. Leave it for a second call. Let them invest a lot of time in  you. Again, if it's qualified. Preface that, if it's qualified. But everyone races  through the sales process like let's do a demo call as quickly as humanly possible. Yes, that is important down market. That is

important if you're selling a $3,000 tool, you  absolutely want to be demoing as fast as humanly possible because it's a high-volume game.  Upmarket, when you're talking about hundreds of thousands of dollars, you want to slow that  down as fast as possible. Because you want to, one, make sure all of the right people are in the  room. As soon as there's one lead on this, and if it requires other people involved, it doesn't  feel like anyone else's baby. So you want it to

make it feel like the group's baby versus this one  individual's baby because it's very quick. Someone can easily say, I'd rather use this tool. And  then there's this stalemate of nothing happens. Just to maybe reiterate, so far we've  talked about figure out who to talk to, pitching them on talking to you, then having  that first conversation. Maybe there's another conversation in there to get them excited. And  then there's just getting them past the finish

line, keeping everyone aligned. Is that roughly  the next step or how should we think about this? Yeah, so if you are selling upmarket  and you now need to go to procurement, who is the group involved in the bot. They're  the professional buyers. Procurement is a very interesting function. They are very smart,  very, very smart. They do this for a living.

They are professional buyers. So there's a couple  things that you need to be aware of. You need to sell them as well. You need to really make this  sound... Don't over complicate it. Don't add in jargon. Make it feel like, okay, I can wrap my  head around this. The second piece is it's got to feel different from anything else out there.  Because the professional buyer, it's much easier

to say, wait a second, we have these 17 other  preferred vendors that do similar ish work. Why don't you just go use one of them? Because,  oh, by the time this gets through procurement, it could be another three to four months. I've seen deals die on the vine because procurement actually suggested they go use another  vendor in the system, that this buyer wasn't even aware of, because they didn't differentiate.  It didn't feel different. It just felt slightly

better. That's how it was positioned. The  third piece is when you get to procurement, you're going to have to do all the work. Make  their job easy. You are probably a very small piece into the very large deals that a lot  of these people buy. So you can get easily sidelined just because you're just a small buy.  So do the work for them. Literally say, I want to

make this as easy as possible for you. Give me  the forms that you need to fill out. I'll fill them out for you, and you can do it yourself. You  can edit them. Do the lift for them. If you don't, it's so easy for it to just go there and die. Another piece that's important with procurement is explaining exactly what you  do and don't do. Because if you say you do a

bunch of things and they can't really place you,  they're going to send you to the kitchen sink of contracting an MSA, which is going to ask you for  $5 million in an insurance policy and all sorts of other things. And the ability to look at your  book at any point in time. And the reason they did that is because they can't classify you. So the  easiest thing to do is classify you as high risk.

So make it easy for them, make it simplified. You  can also truncate your contracts, meaning let's say IT is maybe, and you want to ask this, how  long does it take to get through IT due diligence? They might say, oh, it's a 90-day backup,  it's a 60-day backup, it's a 30-day backup. There's no backup. If there's a backup, you  also don't want it to die and you want it

to give an incentive. So this is when you  want to truncate contracts to a technology contract and a service contract. Service contract  allows you to onboard them, get them prepped, come in and educate all of the users about what  they're about to go through. So that then there's an incentive to get that technology piece through.  There's all these little things to think about, and I think everyone... Getting to procurement  is also creative. And knowing who you're dealing

with and how to make their job as easy as  humanly possible. Because what you said and what April said is spot on, which  is buying is just as hard as selling. As I'm hearing you describe this, I feel  like we might be discouraging people from selling because this feels very not fun.  All these steps, all these procurement work, anything you can say to get people  to feel like, okay, this is worth it?

Yes, I can get people very excited by this.  Once you are in, you are in. Once you are in, you are now a preferred vendor. You now  have the ability to cross over into other business units. You are now the reason  that, hey, if your competitor comes in, well, you got there first. So what do  you think procurement's going to say?

This is why it's so important to get into the  enterprise as fast as humanly possible. While it's a headache to get through, if you project manage  it, you'll be good. If you make an accountability, just like if you were to go through fundraising.  If you are a part of a team that had to raise money, it's no different. There's always  some level of due diligence. There's always

you doing more of the work than them. That's  just enterprise sales. But if you prove value, your hundred thousand dollars deal could be  $500,000 next year. Your $500,000 deal could be a million dollars the following year. This is where stuff begins to compound, and this is where your growth journey really gets  accelerated. So the beauty with enterprise is once

you're in, you're in. You beat out your competitor  for a short period of time. There is a little bit of a moat there, but it's not forever. You all  have intel that no one else will have. Meaning you're a part of the conversations, you  have the badge, you can join the meetings, you can ask for introductions. They'll do it.  It doesn't feel like sales anymore. You're now

a partner. This is why it's so powerful to get  into the enterprise because there's so many compounding effects. If you put the effort  in on the sales side, the return is insane. That was awesome. Nailed it. I'm excited.  Just for folks that are listening, just to calibrate what size of company  you're talking about selling to here,

what's the size of the advice  you've been sharing so far? Roughly? So I've been talking a lot about enterprise  sales, which is I would say anywhere north of 500 to a thousand employees. Just mental model.  I'm talking about enterprise sales specifically because there's so much nuance involved in it,  because the user and the buyer are very different,

right? As you go down market, let's talk  about small business for a second. The user and the buyer are the same person. There's no  procurement. If they like what you've built, it's pretty straightforward process. In the mid-market,  mid-market is a funky place because you either are anchoring towards the lower end of mid-market,  which is more upper end of small business,

or you're anchoring towards lower end enterprise.  Those are two very different divides. So mid-market, just if you're talking about lower end  enterprise, again, this is all relative. If you're talking about lower end small business, again,  your user and the buyer probably are the same person, which makes sales a lot more streamlined. But churn. Small business, challenge with small

business is the churn. If they get pissed  off, if they don't feel like it's good enough, they are gone faster than you don't even realize.  And they might even tell you. They'll just cancel. And we always see this on Twitter. They'll call  American Express and say, cancel these charges. I don't want to talk to these people anymore.  They're just more irrational because sometimes

maybe it's their money if they're a small  business. So small business in mid-market, while sales is a bit faster, you really got to be on  the product market fit side, worried about churn. And they also go out of business at a higher rate. Exactly. And so you have that kind of churn. A churn piece too. Yeah, exactly. Amazing. Okay. What comes next? So we're  kind of in procurement at this point.

Okay, so now we're at signature, right? Okay. Okay. So as you enter procurement, okay, you  want to know before you get to the next stage, who is signing this deal? Here are some examples  of signers I've seen. Chief financial officer, chief legal officer, the business unit head  themselves, the head of procurement. You want to know who that person is so that you can  literally say to the head of procurement,

hey, listen, I want to make sure this person  has everything they need when they review this, to know what they're signing. Who is it and  how can I give you a few bullets to share that you can maybe respond to, that we get tight so  that they know exactly what they're looking at? This was two or three years ago, I was involved  in getting a deal over procurement that was just

truly, it was a pharmaceutical company and it was  very, very long process. And we got to the finish line and the CFO was the signature. And this is  when I made the mistake. CFO responds back to the procurement lead who sent it to the business  unit, who sent it to me and was like, what am I signing? I don't actually understand what these  people are doing and why are we doing this?

So then she quickly said to me, hey, listen,  we need to defend this. Can you put together some bullets? And I'm like, well, what kind of  bullets do I need? What does this person care about? And again, it created so much anxiety  and now I'm back in the bottom of the queue. Probably he or she's looking at the things  that come in in an order of priority. So now I've elongated this by another month simply  because I didn't plan. So this is just to say

I'm learning from my own mistake of know who  the signature is, because if they don't know what they're looking at, they're going to kick  it out and you're going to lose your queue spot. So many ways to fail. And this was you selling  Jellyfish or this was you working with a company? This was me helping [inaudible 01:00:15]. Oh man. Okay. Anything else in that  step that might be helpful to folks?

Yes. One thing to caveat is you do not get  paid until you are approved by finance, and procurement has a signature on the  contract. Meaning don't start any work. Or if you do start work, know that there  is no payment. The business unit can't

just pay you. It's paid through a purchase  order, which is paid through by finance. So don't rely on that money unless  it's finally, unless the signature's on the paper. Quick tangent, thoughts on  discounting at any parts of the journey? If there is a reason as to why. So discounting  just to get the deal over the line, you're negotiating with yourself. Unless they ask for it  and then ask them to defend it. Certain segments,

like small business, you should leave  a little bit of room for buffer because sometimes that's their own money. It's like their  own small business. Mid-market and enterprise, there's got to be a reason why and ask them.  Be like, hey, so if I give you a 30% discount, can I remove 30% of the value? You can kind  of play it a little bit like that. I don't recommend it, but that's kind of what they're  saying. But discounting is great if they're

doing something for you far and beyond.  For example, if they're a design partner, if they're going to be a reference for two  years, if they're going to give you something far beyond just using the technology, then  yeah, I think a discount is a good reason to give back to somebody that's giving to you,  but not as a strategy to get a deal done.

Okay. Is there anything beyond this step  of getting the signature? Are we done? Yeah. I hope you celebrate because- Okay, great. You got a signature  from this whole process. Yeah. Hopefully I'm not making this sound too daunting. I'm just really trying to  lay out all the mistakes I've made. Yeah, no, this is exactly what people  need. This is amazing. And your pep talk was really helpful too. Along the way.  What's the general timeline for sales

process like this in your experience,  with these 500 plus ice companies? So there's three things that dictate sales cycle.  One is how well are you project managing it? For example, I'll say, let's have our second or third  call in two weeks. Two weeks? Do a week. Why are you elongating this? Keep your calls as tight  as possible because that shortens your sales

cycle. The second is just how complex the  organization is. If you're dealing with a highly regulated industry, just know it's going  to take a bit longer, sometimes 20 to 30% longer. So a highly regulated industry, nine to 12 months  on conservative, on the conservative side. Again,

it's tricky because is there a budget line  item dictated towards it yet, or are you creating budget? How painful is the problem?  And how senior have you gone? If you're talking to the SVP or chief of whatever, they're pretty  good at about being able to navigate the traps. If you're dealing with a director or  mid-level person, they maybe have not

purchased something before and just make  some internal mistakes. I always say it can range anywhere. I've seen enterprise deals  close in 90 days, believe it or not. Rare, but I've seen it. I've also seen enterprise  deals typically take anywhere between six and 12 months. Really important but. Enterprises know  that the process and the length to get the deal

done is what costs more than the technology  itself. Meaning the effort it takes to get through their system. That's why they're willing  to spend so much. Sometimes that's actually more expensive than the technology itself. So don't  negotiate with yourself, understand the value

you're delivering, but don't be crazy. I've seen  people try and go in with a million dollar deal as a seed stage startup. Oh, interesting thing.  So interesting tactic. I've seen contracts in the enterprise that state that the deal cannot  exceed more than 20% of the existing revenue.

So there are these things just to be aware  of. In most cases, you can ask them be like, is that a hard line? Is that hard, hard line?  Or how negotiable is that? Sometimes it's negotiable. Sometimes it's like, no, this is a  hard rule. But then it seems silly because you take a hundred thousand dollar deal and bring  it down to 20,000. It's just be careful that

you're stripping some of the value out. But I kid  you not. I've seen an enterprise deal go from, it lands at 60 and it turns into  280,000 in four months. So again, I want to encourage, yes, this is a lot  of work, but the payoff is exponential. What's a good ACV to start with if  you're trying to sell to enterprise,

to make it all worth it for your startup? I would say anywhere between 50 to 200K  depending on the business unit you're selling to. That's kind of like sweet spot.  They're used to something in that realm. And this is a startup  selling [inaudible 01:05:38]. Early stage startup, like  founder led, early stage. Initial contract. Wow.

Yep. Initial contract. I would say, okay,  probably caters more towards like 50 to 100K. But I've seen people sell to...  Again, it's how big is the problem? Who are you selling it to? Is it the SVP that you  started with and they've got a large budget, and it's a pretty healthy business  unit? Or are you selling to a director?

If you're not able to sell your product at  that price? What's your advice to teams? If you are a startup, I always ask the founder, did you build this for the enterprise and is  that the model you want to play? Or did you build this for small business? Small business is  a marketing game. Marketing intensive activity,

right? It's high velocity, high volume, lots of  dials. It's a very different game than enterprise. So which game do you want to play? Let's just  start there. Which game is more attractive to the founder. Or who is more exciting to serve?  What's the storyline you want to tell investors? That plays a lot of it into it too. And do you  have an enterprise product? Are you solving an

enterprise problem or do you think you're solving  an enterprise problem but you're not sure yet? And your point is also mid-market  is it's rarely to be successful. It's hard to start there because you're  straddling two very different go-to-markets, right? One that's of high value, one that's  of high volume. And also mid-market companies,

this is where a lot of people don't... If it  requires heavy integration, they don't have those resources. That's usually outsourced to  an Accenture or some of these consulting firms, and now you're having to rely on third  parties to be involved. It gets messy. This is fascinating. I have a list of questions  from the audience that you pulled from Twitter.

You asked on Twitter what questions to ask you  as you're coming on here. So there's one that's very related to this, which is someone said, if  you're still very early in pre-product market fit, but get initial validation from both  small to medium businesses and enterprise, how do you decide which one to focus  on? Is there a counter argument against starting or SMB going up market  over time like most companies do? I've seen companies successfully do in both of  those motions. Truthfully. We know all of those.

We know people that started small business  and worked their way up into enterprise and were successful. We've seen people be really  successful by starting at the enterprise, like a Wiz. That's more of an internal  question, which is like, who did you build this for? Where's the problem most felt and  which go-to-market game do you want to play? And I think that latter part is so important.  It sounds like why should it be what I want?

It's like what's going to make a big  business? But I think people forget, this is going to be your life for 10 years.  Do you want to be selling to enterprises and building all the enterprise features? Would you  prefer to build for small companies? Pros and cons to both but it's important to think about the  life you're creating for yourself and your team. A hundred percent. And I built  my career in enterprise sales,

upper-end mid-market enterprise sales, and  yeah, that's just the game I know the best. Yeah, that's also an important part of it. Just to double down on that is like what do  you have experience doing? Not like... Exactly. Yeah. Where's the opportunity? Okay.  Another question that I love is, and we touched on this initially, but I think  it's good to come back to this. Someone said,

customers are fascinated with what  we're offering from the initial calls, but responsive momentum is too slow from their  end. Would be great to know how to fix this. Yeah, it's tough because unless you're in the  weeds to understand why. I'll give you a few examples that it could be. Did you speak to  a buyer who now is trying to sell this up to

their boss, and it's just getting sidelined and  they don't know the executive value? They've just been selling the buyer value the whole time.  That's one reason things can slow down. Another reason things can slow down is you haven't  really framed the problem well and they don't understand the full implications of why they need  to solve it. So it's kind of just sitting there

a little bit. The third is they've just been  really nice and it's not going to go anywhere. I guess that that's usually the latter. Was  that true or it's kind of all over the place? It's so hard to give a founder  hard feedback. Because they've just dedicated their life to this thing.  Who wants to be the bearer of bad news?

And sometimes you just need to let  the actions speak louder than words. We've talked about all these steps. I'm curious,  when you come to a founder or your team, where do you find the most on lock often?  Which of the steps of the sales process do you find the biggest opportunity  to improve conversion in sales? It's qualification. Qualification because  if you spend your time on the wrong leads,

that equates to a zero. So if you don't get  that first level right, let me put it this way, everyone that I know says they have a bottom of  funnel problem. It's never a bottom of funnel problem. It's a top of funnel problem. I've  actually never seen a bottom of funnel sales problem. It's always qualification, which is a  symptom of not reaching out to the right person,

not having the right messaging, not solving the  right problem, or not being different enough. I love this. So basically the  biggest pitfall people fall into, in your experience, is they're just talking  to the wrong people, wasting their time? Yeah. Talking to the wrong people  or using the wrong message or...

Pitching them something  they can't actually deliver. Yeah. Here's the other thing too. Sales is  supposed to feel fun for the buyer. They should be like, this feels fun. This  person's invigorating. They're going to change my world. They're going to make  me see things differently. They're going to get me promoted. They're going to help me  increase my influence internally. And so many salespeople are so boring. How many times  have you got off a call and you're like,

I can't wait to get off this call? And founders  too, just like all of a sudden their passion, they go like stone cold face. And it's like  bring the passion. Bring the energy. That is felt by the market. Remember, some of these  people are in boring jobs. Give them an outlet. So along those lines, I think a lot of  people are just not... Like me included.

I feel weird doing sales. It's a weird  experience trying to convince someone to buy something. Is there any advice you  could share to get someone over that hump? If you have built something that you believe in.  Very hard to sell something you don't believe in. I think everyone agrees that. If you've built  something you believe in and they have a problem, that's a beautiful thing. Truthfully, that's what  makes the world go around, is I have a solution

to your problem. Now you just need make sure  that the problem, you just need to be honest, that the problem they have, your solution truly  can solve for. And you're not short selling just to get a logo and a deal over the line, and see  them churn in six months or nine months or three months. That what you are selling is truly  going to solve their problem. And be honest

about it. I can't tell you enough when I tell  someone, listen, I don't think I'm the right fit for you. They try and sell you on them. They're like, well, wait a second. Hold on. What if we did this, this, and this? And it's  like, no, no, no. Here's what we're great at. And then they can say, well, I also need that  too. And all of a sudden, this level of trust comes out. And trust is the number one currency  in sales. If you are a trusted salesperson,

people will recommend you all day and every day.  If you're a trusted founder, your market will continually send you leads and word of mouth.  So don't try and sell something just to prove to investors you sold something, because it'll be  quickly seen on the other side when they churn. Amazing. Okay, Jen, so I'm going to cut the  lightning round. I know you also have to run

and do real work. So let me give you a  chance just to talk about what you do, how you help companies in case folks  can find value in working with you. Deeply passionate about sales, as I'm  sure you can tell. We specifically help founders through this pain. Navigating  enterprise sales, mid-market sales, and really trying to crack that first million  of ARR. Or sometimes even that first 500K of ARR

if they move fast enough. And it is really hard.  It's counterintuitive to what most people think, but it can be really, really  fun when we show you the way. And you described to me how it works,  and I think it's important to clarify this. You basically embed with  the team and help them do this. Yes. So I fundamentally do not believe in  outsourcing the heartbeat of the organization,

which is sales. So what we do is we embed  alongside the founder and drive a lot of the execution, but make sure that they are the tip  of the spear engaging directly with their market, and learning directly from the market's  mouth, not playing this game of telephone. Amazing. And I mentioned this when we were  chatting, but I think of it again, is when I was interviewing all these companies about how they  started selling early on. One of the interesting

threads that I heard again and again, is how  many of them hired a coach or a consultant as a founder to help them learn to do sales. And that's  essentially what you do. And I didn't even know a service like this existed, so this is super cool.  It'll point people to what you do. I also have to ask you, the question I ask everyone at the end  is just, how can listeners be useful to you? Help each other out. I think so many  people have helped me in my career,

and in this journey, that the pay it forward model that exists in the technology space is  so beautiful. So just don't let that die. Beautiful. Well, Jen, thank  you so much for being here. Lenny, this was awesome. Thank  you so much for having me. So awesome. So excited for folks  to hear it. I've learned a ton.

Okay, I'll let you go. Bye everyone. Thank you so much for listening. If you found this valuable, you can subscribe  to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also,  please consider giving us a rating or leaving a review as that really helps other  listeners find the podcast. You can find all past episodes or learn more about the show at  Lennyspodcast.com. See you in the next episode.