The ultimate guide to founder-led sales | Jen Abel (co-founder of JJELLYFISH)

0:00 I've always wanted to create a very tactical episode. On how to do sales. Especially with a focus on founderlit 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 South Tools emailing me constantly about their product. How do you get someone to email gonna wanna talk to you and be open to learning about what you're gonna do. 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 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 like 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.

1:09 Today, my guest is Jen Able. 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.

1:24 Prior to Jellyfish, Jen was an enterprise sales director at the Muse and at 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 it 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.

1:58 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.

2:19 Able. Jen, thank you so much for being here. Welcome to the podcast. Thanks, Lenny. What I've always wanted to do

2:30 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 a salesperson.

2:45 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 team, sales teams, how to hire salespeople. So

2:59 I'm very excited to have you here. to kind of create a very like in the weeds hands on episode on how to do sales. Uh, how does that sound broadly? That 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.

3:21 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. Founderless sales is really that First.

3:31 milestone that a startup goes through on the commercial side, right? Which is How do I go out? and get my first few customers. M some people might say zero to one, which is how do I get my first million. Others might say, you know, how do I go out and get my first ten customers? It's all kind of in the same vein.

3:50 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.

4:05 Right?'Cause the product is still could be abstract, could be, you know, an MVP or really, really early. You know, um in its really early formation. So the founder is the product. And when people say, well, what does that even mean? It means that you are a subject matter expert on something highly specific.

4:23 You have studied, you have experienced something. That most of the market hasn't even um had a chance to um maybe see or visualize yet. So you have this like 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.

4:41 Right, 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 founder's 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 a lining.

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6:51 counter to what many founders hope is I'm just gonna hire a salesperson, they'll handle sales, I'll build a thing, I'll I'll wait for them to find deals. And this is like a lot of a lot of people think this way, right? And this is Fenerlite Sales is 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. Like I don't think people realize how much of a competitive advantage the founder led sales motion is.

7:14 For three kind of specific reasons. One is is that The founder is the visionary. No one's gonna be able to speak to it like they can. No salesperson. Really no non founder.

7:27 The second is that they are the highest kind of order on the in the hierarchy of the startup, right? It's the founder. So when the market 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.

7:42 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 is that The founder can you know, can see something budding in a conversation that a salesperson won't be able to see.

8:00 Right, 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 to product market fit. And I say that all the time. It's these like little budding moments where it's like, I was able to get to that buttonian insight because I went deeper and deeper and deeper and deeper through these calls and these conversations. To fulfine

8:22 how we want to go out and sell it and only a founder's gonna be able to see those things. I love this'cause this connects really well with a Episode I just did with the CMO of Wizard And the founders went through this exactly. They had all these convers they had ten to fifteen conversations a day.

8:38 For weeks. And then they're like realizing nobody people keep telling us this is they like it, but no one's buying, no one's excited enough to want to Actually move forward. And that was only happening'cause the founders were on these calls. Yeah. And the yeah, I mean the other thing too is that it becomes a game of telephone. It's like, hey, this fail salesperson says that no one cares about this. What do you think the first thing the founder's gonna say is?

8:57 It's the salesperson. So much easier to say that than you know, is it me, is it my vision? So it also kind of Brings the accountability uh closer to

9:08 Um the pulse where decisions are made. It's interesting how similar this is to product building, where there's this idea that a founder kind of 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

9:26 Building it, testing it, talking to customers about it, that actually turns that initial seed of an idea to the real thing that people want. Totally. Okay. So The catch twenty two, I don't know if that's the term here, the challenge is

9:40 Okay, so great. Founder should be doing sales. Most founders have never done sales. They just wanna build product. Uh You know, they're like mostly product people, design people, r like sometimes there's founder.

9:52 That are salespeople rarely. Is that the case in my experience? So Doing sale 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

10:05 the sales process. I think a nice uh framework for how we can go through this is basically First talk let's talk about the sales cycle like the steps, the key steps of a sales cycle.

10:16 Yeah. And then we'll just go through each step. And help people learn some tactics to get through each of those conversations. Okay. Yeah, cool. So What's the simplest way to think about like the steps of a sales cycle? The traditional sales stages that most CRMs are even set up as is like you have your intro call. Um you have your second call.

10:35 Um, which sometimes could be the demo depending on like the stage of market you're selling to. Then you have your third call, which is gonna be more about like walking through a proposal, a scope of work. Um Uh maybe going deeper into the demo to contextualize it to everything you've learned. the fourth call is going to be um getting their feedback and kind of co authoring

10:56 that scope of work even further. The fifth call is going to be around probably an introduction to procurement. And then you know selling into procurement in itself, it's its own little sales cycle, but that's we could talk about that in a sec. And then post procurement, it's gonna be obviously getting that signature. Um, and knowing who the actual signatory is,'cause sometimes it's not even the business unit. It's sometimes

11:19 Legal CFO procurement themselves, so just understanding who that is. Okay, great. So let's walk through each of these steps. So I love I love that like each call has its like traditional goal. Uh demo.

11:30 proposal. Then co authoring and then procurement and then post procurement. I love how Uh consistent everybody is. Yeah, it's um well it's also it's interesting'cause it's also predicated on their buying process as well.

11:46 Um, so if they're really used to buy like if they're very mature in their buying process. Um, they actually might guide you to what the steps are, but um You know, most startups are turning non consumers into consumers, so That's why this kind of fits well. Got it.

12:00 So I think So there's this intracall step, so kinda starting about where it begins. I think where pe a lot of people struggle most is like getting anyone to even pay attention. Like you wouldn't want to talk to them. Like why I A billion South 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?

12:19 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. Right. You're like oh interesting this founder is reaching out to me Okay. I'm I'm gonna I'm gonna

12:32 I'm gonna seek to go a layer deeper, um, knowing who who is sending me this note. The second piece is this is why It needs to that novel insight that That technical insight, that business model insight that you've uncovered needs to lead here.

12:47 Right,'cause people are inspired by a new way of thinking. Something high 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 to some better means something different to everyone. Right. So if you can focus the messaging in a way that speaks to something that is a bit has a bit of shock value.

13:09 Um, or is counterintuitive. You'll You'll get them to continue reading. So First and foremost, I usually like to open it with is which is why is this relevant for me and my role? Like why are you reaching out to me?

13:22 So first and foremost is relevancy. I think that matters even more so than personalization right now, because I think it's so easy to personalize. anything and it can also come off cross as really stressed. When you're like, Hey, I noticed you were on You know. Such and such a

13:37 You know. podcast and that was when they were previously like two rolls behind, right? 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.

13:52 Um so say something that would like literally make them say, What? Or That makes no sen not maybe not that makes no sense, but like what or Um how could that be, or I've never thought about it that way, or I actually don't fulstand what they're saying, but there's something there that's interesting.

14:10 Right, like get them to like pause for a minute. And Can and the most important piece is getting this done where if they get it on their mobile phone, which everyone it is looking at their mobile phone and on email. They don't have to scroll. So usually three to four sentences max.

14:27 That also that's how a founder writes, that's how an executive writes if you're, you know, selling Top down. Um, but most importantly, leave them wanting more. Don't say everything. Don't even talk about the solution. Talk about The problem

14:39 That you want to solve and why? And why it needs to be solved or why it's not good enough today. So those are the kind of the four main components just to reiterate relevancy. bring some level of counterintuitive or really different approach to the Conversation.

14:55 Focusing it 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. Of e maybe an email you helped with. And by the way, this is like email and LinkedIn, I imagine, is where you're communicating mostly.

15:11 Uh, LinkedIn email you would be shocked to hear this, but cold calling. I n never used to do this. It is one of the most Uh The interest rates on cold calling are a lot higher. than email in many cases. So it's c calling

15:28 Email, called email, and LinkedIn DMs. Is that the three channels, generally? Those are the three, uh the main ones. Cool. Yeah, is there an example it doesn't have to be like word for word what you've s done or people done, but just how do you yeah. Actually our first three years were built on cold email. Like before we actually like had clients before we actually, you know, um

15:47 got word of mouth from the founders we worked with. I cold call I cold emailed the first twenty customers we had at jellyfish. And the 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 like that leading like wait, what? Um, what does that even mean? And what I would do is tie that to them in some respects, right? Like

16:10 you know, if they recently raised the Cedar series A where they are in that journey. But I would lead with that and then tie it into like hey, I notice you're looking to target you know, X, Y, and Z, um, based off of what your website like, I'd love to have a conversation with you. And that first piece is the relevance. Here's why this is the relevant to you. Yep. And then I say, like our belief at jellyfish is zero to one sales talent doesn't exist. That's why we built this model.

16:34 Awesome. Okay. Yeah. And he kept it really short. So it's Relevance. Counterintuitive. Keep it really short and then

16:40 Was the fourth piece? The fourth piece is just make sure it's concise so that you don't have to scroll on 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 you have to focus there.

16:59 But I just want to reverse engineer it backwards a bit. once you kinda have this and I'll talk to 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.

17:13 And I spoke to ten lennies and only You know. Lenny R was the one that um that sign, that's one out of ten. That's a ten percent one rate. Okay.

17:22 So if you have a really high win rate, let's say thirty or forty percent. 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.

17:39 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 cust you don't have a lot of customers going through the pipeline yet, but it is. There's people focus on it, um in a little bit of a false sense because Interest rate truly

17:58 is m also dictated by win rate. Um So I just want to kind of like Specify that. But that's a really good point. I would say if you are target if you're doing a win rate at of around

18:09 you know, fifteen to thirty percent And you need to carry Oh, I don't know. um a million dollar quota. Right. Um

18:21 I would say a healthy conversion rate. From Outbound probably sits around You know When it's mature around Five to seven percent.

18:31 Sometimes it could be two to three percent. Sometimes I've seen eight to fifteen percent 'Cause it's coming from the founder. And they're solving a really hard felt problem. So interest rate is also

18:44 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 You know, I'm not getting the connects I want. Yeah, sh yeah, you can argue that the game has changed a little bit.

19:05 But when a problem is truly being felt by the market. People get on a call. People will respond and There you know, if I can compare two engagements at a time that we're running, I see one where it's a two percent interest should rate and then I'm I'm seeing another one that's actually at twelve percent interest should rate.

19:23 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. So two different companies selling to

19:38 um two different markets but like they're not fundamentally drastically different markets. Got it. But one's like basically got more product market fit, essentially. That's exactly right. So everyone can keep coming always comes back to like we have the sales problem, we have the sales problem, we have, you know, an outbound problem. And Yes, there could be some technical things going on that you need to look at. Like maybe you've blast it you you leverage clay and you blast it a thousand people and now your domain health is, you know. been impacted.

20:05 But the vast majority of the time Maybe you're just not saying it. 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.

20:21 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 is there i I imagine this is a very difficult question to answer, especially quickly. I guess is there anything there that's like More likely because of this, it means your product

20:38 Isn't something anyone's want versus you're not doing a good job selling it. Remember that? um amazing chart you drew where it talked about the length of time it took. I think you picked the top twenty five Startups. Product market fit, timeline. Yeah. That amazing image that I think has been reshared more times than anything I've ever seen.

20:56 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 they um The time to product market fit is consolidated. And you go all the way down to like the air tables and the figmas, which long time to get to product market fet. If you think about the earlier ones which were um It was like GitHub that had product market for pretty quickly. Um

21:19 uh the SOC two compliant company. Um Vanta. I I there's like this This thing in my head and I haven't fully validated it, but I'm gonna share it with you, which is Did they start with the market problem first?

21:35 and then build the product. Cause they 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. Vansa, the way they approached it, Christina, she Uh was like searching for a pain. She was obsessed with

21:54 talking to everybody about a pain that they needed solved and then she just like built it in spreadsheet. 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

22:09 That it's also capped on the upside. Cause you're starting with the market versus the air table and the figma. which started with the technical insight. and has kind of uncapped upside. But one is certainly riskier than the other, right? Starting with a product is a hell of a lot riskier.

22:25 And this is where I come back to like so many people will say, How do you, you know? How 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. Right, versus I think if you start with the market first, you could potentially get

22:44 A good win. But is it more capped? Mm. Interesting. I don't know, it's just a thought. It was just

22:50 You know I I was staring at your grid for so long'cause I was like, there's something here and like I kept coming back to You know, those were more like I kept kinda breaking it down to like market versus product. Yeah, I love this. I think there's definitely something there. There's also like horizontal versus like a very specific problem you're solving.

23:07 Okay, so you mentioned Clay and you kinda nerd snipe me there of just like What tools are do you find useful? And it kinda makes me think about like finding leads, which is kinda going backwards through the sales process. But it might be okay, so maybe let's spend time there just like

23:22 What do you recommend to founders to find? Find the good leads. Yeah. Glenn Gary, Glenn Ross, good leads. So I say before you buy any tool, don't even think about tools. I feel like people get s turn everything into this complicated mess with all of the tools that they start integrating and then You know, they're engineers. I get it. So they now they start to engineer these Um

23:41 these sales tools together and you know, then they blast their market and now they have fifty five thousand 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 Thirty people.

23:58 That you want to spend fifteen to twenty minutes writing a rock solid note to. Are there Thirty people. that you are deeply excited to learn from that you are willing to invest fifteen to twenty minutes to write a really thoughtful note.

24:11 Let's just start there. So Leave some questions. One. Are they even discoverable?

24:18 How hard is it to find thirty people? What have you noticed across those thirty people? Are there anything Any um 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.

24:34 Maybe it's Um their pre their previous roles in their career. Like what is there are 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.

24:47 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 thirty notes and they're you know, you wrote them specifically and you know, you spend good quality of time on it. And you've you know, you've hit them on email, you've hip done them on LinkedIn, maybe you've even tried to call them, maybe you've tw sent them a Twitter DM. You know, pulled out all the stops.

25:09 How many people respond? One. Five. Zero. Right.

25:19 If it's zero B it begs the question. Do you now want to do another thirty in a very similar fashion? Do you want to change the messaging a little bit? It now forces these like natural experiments. Or do you want to maybe go after a different role?

25:35 So it forces you to answer these questions in a very manual way before you even think about you know, integrating and spending time on tolls. 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 ten to fifteen people in that group. truncate this as much as you can because

26:01 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 claim.

26:17 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 g we'll le yield nothing. Mm. 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

26:34 Am I we even engaging Or Do the people that um 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.

26:49 I love how tactical that is. And what I love is even like one of your nuances you mentioned is Can you even find them? Like this gives you a signal of How are they? Like you're gonna have to have hundreds of these and ha thousands of these eventually.

27:02 Like if you thirty is hard and when or impossible, you're in trouble already. Totally. And then it w it was funny. I was talking to someone today that said they wanted to They had a target segment of like high net worth individuals um that they wanted to go out and and start about being like, How do you find those people? No one's you know, is our I I guess uh when you get to a certain level your net worth may be public. I don't know, but

27:24 You know, that stuff's har it'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 a bad way, but you now you need to kind of

27:39 True. bring that back into the math equation, which is like Okay, if I speak to ten people, I know two o two out of these ten will will be qualified, but I don't know which of those two out of ten. Well, that means you probably need more of those numbers. Yeah. Okay. So to quickly recap a few of the key things that I've written down as we're talking.

27:56 So if you're just trying to figure out who to reach out to. Make a list of thirty potential prospects that you think are good fits that would be excited about what you're building. spend fifteen to thirty minutes writing them each an email. Uh Do these emails have to be really short the way you described previously?

28:11 I would say the shorter the better, but like would you respond to that? Like if you got this email, would you respond it? One of a a great little tactical test is on Gmail you can cop you can highlight the message and then have it replay it back to you from a An audio perspective. Oh wow. Um 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. You know. Interesting.

28:35 Yeah, and And so You also share 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

28:45 as you automate, you want to make it more precise and focused and not Like basically they're not us. Customized. As you start reaching out to more folks. Totally.

28:54 So it's uh start with something here's why this is relevant to you. Like your Looking for salespeople. In this market. uh here's something that's unexpected or surprise like zero to one salespeople don't exist.

29:06 Um Keep it short. And then I always forget the last one. Um

29:14 M focus on the problem. Focus on the problem. You don't even need to talk about the solution. Here's that's like the big takeaway, which is if you get any sales email you get, what's the what's the primary focus of that email? It's usually like here's what we do.

29:28 Um But I bet if someone reached out to you with like 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. Right. If it's like a big problem. Right. If it's like Oh yeah, you're so right. I need this. The the beauty with the American market, and I I say this'cause we do a little bit of work with international startups too is

29:47 If something doesn't feel right, people have to complain about it. And it's like use that to your advantage. Like get that intel. A note that I just looked at that I wrote down that I think is very important is Avoid

29:58 Using this is better as your pitch. Yeah. Yep. Different. Here's Something shocking about what we're doing here, something that'll surprise you. Yeah, or counterintuitive exactly.

30:09 Yeah, that like it's it's interesting. I I um 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, because then I ask them to define that. And then I asked them like Okay, how do we measure that?

30:28 And then I say, Okay, should we give this company another year to like give them this feedback and then before we make this huge transition and and disrupt momentum and Um Yeah, better's a dangerous place. Yeah, like I I invest in a bunch of startups and I find

30:42 it's impossible to get anyone to care if they're already good if things are good enough with what they got today. Like I'm happy not using the best possible product if my life is okay. And I have so many other things I gotta do. I'll just deal with That's good enough solution for now. Absolutely.

30:59 Okay. Amazing. So We talked about how to find, figure out who to go after, how to pitch them to get them to wanna 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?

31:15 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.

31:24 Right, like I always assume that the buyer I'm speaking to is highly educated. And knows way more than I do. So just Just have that perception because

31:35 What I've learned is a lot of the market will play dumb. And uh 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.

31:59 Can we can we kind of gain your insight into like how this problem is manifesting on your side? And then op let that 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 if it is it even a problem. When you say you're early stage and there's still a lot to be done.

32:18 It is easier to be honest. If you tell them you have a fully baked ready to go product, they're not gonna give you honest feedback. It's very hard to give uh 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 gonna get someone that's gonna 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

32:41 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 you the the further you suggest you are, you're actually going to hamstring a lot of the intel.

33:01 hamstring yourself on gaining a lot of the intel. So that's like 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 customer-facing integrations with third-party apps. Or native integrations on your product roadmap, whether it's to ingest context from your user's external data and documents, or to sync data and automate tasks across your user's other apps, integrations are mission critical for B2B software products today. But building these integrations in-house cost an average of three months of engineering, according to the 2024 State of Integration Survey, which results in difficult roadmap trade-offs. This is why engineering teams at copy AI

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34:05 And get$1,000 in credit on their Pro and Enterprise plans. That's use P-A-R-A-G-O-N.com. So I had April Dunford on the podcast a while ago. I don't know if you've got to be. Amazing. And her last book Actually has the opposite advice, but I think I know why, which is she focuses on later stage companies. And her advice is.

34:26 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 your job is on the line if you make a mistake. It's easier just to be like, forget it. I'm just gonna go with what we have today. I don't wanna My ass on the line for buying this new thing that someone's trying.

34:43 And so her advice is you actually have to educate the buyer on the market and here's what's happening, here's what they can't see going, and here's why I think This is the future. But I think again, I think that's focusing on later stage stuff, like Yeah. A hundred percent. And that's a good that you raise such a good point, Lenny, which is late stage sales and early stage sales are very, very different.

35:02 And I think That's where a lot of early stage Um founders get tripped up as they're taking late stage sales advice. from an inv usually coming from an investor or they've maybe hired a salesperson that's

35:14 you know, focused on more mature sales. Um But but I think she is spot on. Buying is just as hard, if not harder, than selling right now. 'Cause who wants to make a mistake and also who wants to go through switching costs.

35:29 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. I found out that sales is not sell as much as you can. It's to learn

35:41 what people want, right? 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 more about is not 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.

35:59 there's this concept um that I talk about which is like You're going out to run sales to collect the research. Right, which is what founder led sales is. And then you um have sales for revenue, which is that post founder led sales stage. And like the your milestone that you suggested of like how far to take vendorless sales, you said like around a million ARR, right?

36:19 Yeah. I think it's about like It sh some people say five hundred, some people say a million. I think it's we like if you get to five hundred K really, really fast, then I think absolutely you can move out of it. If you get to

36:33 Um five hundred K really, really, really slow. You might not want to get out of it right away. You haven't reached that like velocity point yet. Awesome. I have a post that we'll link to that has actually numbers on when all these big startups move from Fenerlit Sales. It's in that same series about product market fit. Um there's two stories this makes me think of I'll share real quick. One is Sprig.

36:53 There they shared a story of They uh first round capital led their first round and their partner there's just like we will not let you hire a salesperson until you had a millionaire or We're gonna help you, like we're gonna have salespeople helping you through it, but we're not gonna let you hire someone. And he was really happy about that.

37:08 The other is uh zip. Which just raised uh like a two point half, two point three billion dollar valuation as 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.

37:20 to heads up procurement and just Leaned into what you're saying even more, which is just we just want Your advice on this product that we're building. Wait. Just tell us what problems you have. Like it was very advice oriented versus like we want to sell you this thing.

37:33 Yeah, no absolutely. I have this Like theory That like Maybe you shouldn't hire any salespeople until series A.

37:42 Yeah. 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 early sta hiring for early stage sales is Oof.

37:58 The odd like the odds are actually more against you than You know, trying to get your next round of funding. Because it it's just it's truly, truly such a counterintuitive stage. Interesting. Okay.

38:09 So I c 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 at company ABC. Be very honest and vulnerable, but your stage tell them

38:24 you're early stage, you're building this thing, you You deeply you're deeply passionate about this problem. Here's what we're trying to do. Here's our pro uh priority problem perspective and where we're focusing And kinda get their feedback on your approach. Cool

38:40 Uh you were gonna go to the next tip. And and I took us off course. Testing the questions to ask, right? Like Where where is that aha unlock for you? But more importantly, where's that aha moment unlock for them? Because when they start getting their gears churning in their head.

38:58 about and this is the beauty about not having a product and not showing them anything, they're visualizing in their head now. It's like a really powerful thing, right? Which is like So tell me how like this looks in your head. Like how are you seeing this? And they're like, I don't know if I can see it. I'm like, Great, we'll show you that. Great insight to know. By the way.

39:14 Or like 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 like

39:29 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 You're on to something here.

39:44 I love this thread because this is what everyone's always like, How do I know if my product market fit? There's like 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

39:58 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 gonna spend time. Fixing a

40:12 pretty fixed problem because it's not necessarily really a priority anymore. It's maybe a pain in the butt, but like it's not a priority if it's not growing or widening. So B check one is like What is the implication are you measuring, are you managing this problem today? Yes or no?

40:29 If they don't know, great to know. If they said no Okay, move on to the next. Like that's a It's pretty powerful. No, we're not measuring or managing this. Okay, there's probably not much there.

40:40 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 headcount that you just hired? Is it through another tool? Is it Just still an open gap because nothing exists yet to solve it.

40:55 Like just understand like their maturity around how they've tried to plug it. These are all like the in that make the secret moments and intel. to um To close that gap. That's awesome. And essentially it's like

41:08 Showing you that there's a pain here. Yeah. That they're 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 Mm. Hold on, I need to bring down so and so on the next call, like

41:23 They also think that this is this is like not good enough. That's funny'cause that's exactly what Wiz noticed. is they move from people being like, Oh, this is cool. I like it. I like it. to okay, I'm gonna pull in this person, I'm gonna pull in this person. to talk about it and make sure we're

41:38 And like they were like pulling in other people exactly as you described to Because they wanted to like make move forward on this thing. Absolutely. And that that's when you know there's some momentum behind it, right? Which is when they're bringing in other colleagues, whether it be The potential users Um, right, if you're reaching out to the executive or the user is like, Hey, I I actually want to bring my boss on to the next call.

41:57 Good sign. Cool. Anything else along these lines of how to get someone ex Excited slash understand if there's gonna be poll there. I guess the one thing is please, please, please

42:07 Do not ask questions like what keeps you up at night. Um if you had a magic wand Um You know, what are your pain points today? Uh,'cause I can guarantee you that answer changes every single day.

42:19 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 Okay. Get the second call booked on the first call. Pull up calendars, look at calendars, who else should be invited. It's just a natural evolution to ending the call.

42:35 Great. So I'd say in thirty minutes, though, right? And if they say, Ah l you know, I'll email you. I could say. It's also that's also kind of a leading indicator, yeah.

42:46 Mm. So do you recommend not getting off the call, like trying to to avoid that? If they c if they won't give you time on the calendar Um you could say, listen, great, like feel free to email me. Maybe they're just being honest and they don't have their calendar available, but nine times out of ten, 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.

43:09 Okay. Uh 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

43:23 feels like it's gonna 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

43:35 A guide. by asking them to co author the scope. Scope of work. Um The co author Sir Peep is in

43:44 Cool authorship piece is important for two reasons. It helps you understand where they are on their biomaturity. Let me explain. If they do not have an existing process or strategy to solve X problem. They can't buy technology yet. Which means you need to sell them.

43:59 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. Right. And I think that that's really important. Every

44:15 founder I speak to is like well my investor really doesn't want you know service based revenue that's fine But then you can also tell your investor, great, should I wait eighteen months till when they're ready to buy a solution? And be the one that's not the one selling them'cause someone else educated them? Like these are all of the implications of waiting.

44:31 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

44:47 To educate them. You are getting paid to help them design their process. This is where all the power lives. Right. And This is why so many AI startups A year and two years ago.

44:59 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 like time box contain the services piece? Yeah. Such a great point, Lani. You absolutely need to timebox this. I would time box it as ninety days and then you well you can say in the next ninety days we'll scope where we are and like what you need.

45:21 Scoping out more than ninety days, listen, everything so much is gonna change. Um, you might also not want to do it anymore. So you don't wanna lock yourself up. So I would look at like ninety day increments. A specific example, we had a uh founder that we um my colleague was working with. And um they were selling a very specific uh technology to a non traditional, like a v sorry, a very traditional industry.

45:43 Uh I don't want to Be too bleeding with But it is but a very non a very traditional industry that's not used to working with startups or like necessarily plugging in a new technology right away. And they were very honest. They said, Listen, like

45:58 We haven't changed um you know, vendors or partners in over, you know, five or six years, like I don't I actually don't even know how we would do that today. Like, could you come in and explain to us Like understand where our workflow is and how we would integrate this. before we even consider the technology.

46:15 Which we did. We got paid. Nominal amount. But we're now a customer. And now we get to set the stage for how they think about this. And then we won they they won the technology contract, but

46:28 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? We don't our legal team's not even aware of all these risks. Like You want to be careful because legal can immediately and procurement can shut these things down if it seems too novel.

47:01 Where it's like Foreign. Um versus they're so used to buying services. Especially up market.

47:07 So largest budget line item. So it's interesting'cause most founders are I'm very afraid of moving into services. I hadn't heard this advice before. Probably gonna get slapped for saying all this stuff, by the way, but Well so on along those lines, like what percentage of companies that you've worked with or see like

47:22 Do that or have to do that. Step you this would be this is gonna be a shocking step. So um I would say Forty to fifty percent have to sell some form of service before they can sell a technology. Well Oh, B to B Sass.

47:36 And this is again this is Specifically more top down sales. Yeah, because the user and the buyer are different. Which means you know, there's user value, there's buyer value, there's all different players, there's procurement you have to go through, but yeah.

47:50 And just to make it even clear, what's an example of like a service that you've seen company offer, like as 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? Um, as to why we should do this today. And we literally got paid to build a sales pitch. Okay. So it's not necessarily providing a service.

48:11 Uh it could be just helping them sell this. Yeah, it could be it could be helping them sell in a way that like g makes you you know, you need to get some a lot more context on their business. It can also be Hey We uh haven't actually thought about the a new a process for how we can actually deploy something like this, right? We're currently using this technology, which we all we want to change from. Like you've kinda hit this at the right time. How would we implement or how is it best to integrate with this tool?

48:39 Um, can we get both of you guys in a room to like map map this out? Got it. So it's like consultants almost, like um becoming 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 like one off consulting. Got it. And they know that obviously your bias, but they also want the problem solved. And they're like, Great, you're gonna help us. You're gonna help me solve this problem'cause it's on my plate. And I need your help convincing leadership that's going to be. Yeah. And I need and I need to craft the storyline as to why we need to do it anyway. So if I will pay you to do it.

49:08 But like here's the format it needs to be in. Fascinating. Well. 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 and not have to

49:21 you know, um create a new strategy or process and 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, uh, you recommended not doing a demo and just talking about it broadly. Yeah. Is that your advice there? Yeah, on the first call. My fundamental belief is that the demo is a bit of the only carrot you control in the sales process. Right. Once they see it.

49:45 It's kind of like you know, pitching an investor. Once they take a look under the hood that Dream Dreaminess in their eyes. Yeah.

49:55 They're like, Oh, I saw it. So like J leave them wanting more. Like the and the demo is that. Like leave them wanting more. Even when you do a demo, don't demo everything. Leave it for a second call. Get them get Like

50:07 Let them invest a lot of time in you, again, if it's qualified. I preface that, if it's qualified. But like everyone races through the sales process like Let's do a demo call as quickly as humanly possible. Yes, that is important down market.

50:22 That is important if you're selling a three thousand dollar 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 in the room, as soon as there's one lead on this, and if it's like a requires other people involved, it doesn't feel like anyone else's baby.

50:45 So you want it to make it feel like the group's baby versus this one individual's baby because it's very quick e you know, someone can easily say, I I'd rather use this tool. And then there's like this stalemate of like nothing happens. Just to maybe reiterate, so far we've talked about getting Figure out who to talk to. Pitching them on talking to you. than having that first conversation. Maybe there's like another conversation in there.

51:04 To get them excited. And then there's just like Getting them past the finish line, keeping everyone aligned. Is that roughly the next step or how should we think about this?

51:14 Yeah, so if you are selling up market. Right. Um, and you now need to go to procurement, who is the group involved in the buy like you know, they're the professional buyers. Procurement is a very interesting function. They are very smart. Very, very smart. Right. They do this for a living. Like they are like professional buyers.

51:33 So there's a couple of things that you need to be aware of. You need to sell them. as well. Like, you need to really make this sound. Don't overcomplicate it. Don't add in jargon. Make it feel like

51:46 Okay, I can wrap my head around this. The second piece is it's gotta feel different from anything else out there because the professional buyer, it's much easier to say, wait a second, we have these seventeen 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

52:08 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 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

52:23 You're gonna have to do all the work. Right. 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're gonna you can get easily sideline just because you're just a small You know, a small

52:37 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, you know. You can do it yourself. You you can edit them. Um, do the lift for them. If you don't, it's so easy for it to just Go there and die.

52:55 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 gonna send you to the kitchen sink of contracting and MSA. Which are is gonna ask you for you know, five million dollars in an insurance policy and

53:14 all sorts of other things and like the ability to look at your Book. Um at any point in time. And the reason they did that is because they can't classify you. So they just the easiest thing to do is classify you as high risk. So like

53:27 Make it easy for them. Make it simplified. You can also truncate your contracts, meaning Let's say um IT is maybe and you want to ask this, like, how long does it take to get through IT IT due diligence? They might say, Oh, it's a ninety day backup, it's a sixty day backup, it's a thirty 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 it an incentive. So this is when you want to truncate contracts to a technology contract and a service contract.

53:54 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 like little things to think about and I think

54:08 Everyone's You know, getting through procurement is also creative. Right. Um and knowing who you're dealing with and how to make their job as easy as humanly possible,'cause what you said and what Apr April said is spot on, which is buying is just as hard as selling. As I'm hearing you describe this, um

54:25 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, I'm gonna say it's like people very excited by this. Once you are in. You are in.

54:40 Once you are in You are now a preferred vendor. You now have the ability to cross over into other business units. You're now the reason that hey if you're Your

54:52 competitor comes in, Well you got there first. So what do you think procurement's gonna 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 if you project manage it, it you'll be good. If you if you make an accountability, if you just like you just like if you were to go through fundraising, right? If you've if you've you know, are A part of a team that had a, you know, raise money. It's no different.

55:17 Right, 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 Right.

55:29 Your hundred thousand dollar deal could be five hundred thousand dollars next year. Your five hundred thousand dollar deal could be a million dollars the following year. This is where stuff begins to compound and this is where growth Your growth journey. really gets accelerated.

55:43 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'll have intel that no one else will also have. meaning. You're part of the conversations, you have the badge, you can join the meetings.

56:00 you can ask for introductions. They'll do it. Doesn't feel like sales anymore. You're now a Partner. This is this is why it's so powerful to get into the enterprise because there's so many compounding effects if you If you Put the effort in on the sales side.

56:17 The return is Is insane. That was awesome. Nailed it. I'm excited.

56:23 Just for folks that are listening, just to kind of calibrate what size of company you're talking about selling to here. Like what's the size of the device you've been sharing so far, roughly. So I've been talking a lot about enterprise sales, which is Um

56:38 Yeah. I would say anywhere north of five hundred 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.

56:53 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 Minmark's a funky place. Because

57:06 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

57:19 If you're talking about lower end enterprise Um, 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 Cher.

57:34 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. Right?

57:45 They're and they might even tell you. They'll just cancel or they'll and we always see this on Twitter, right? Like They'll call American Express and say, Cancel these charges. I don't want to talk to these people anymore. Like they're just more irrational. Because sometimes it's you know, maybe it's their money if they're a small business, right? So small business and mid market, while sales is a bit faster, you really gotta be on the product market fit side, worried about churn.

58:08 And they also got a business at a high rate. Exactly. And so you have that kind of churn. A churn piece, too, yeah. Exactly. Yeah. Amazing. Okay. What comes next? So we're kind of in procurement at this point. Okay, so now we're at signature, right?

58:21 Okay. Okay. So As you enter procurement. Okay, you wanna know before you get to the next stage who is signing this deal.

58:29 Here are some examples of signs I've seen. Chief financial officer. Chief legal officer. The business unit head themselves. The head of procurement.

58:38 You want to know who that person is so that You can literally say to the head of procurement Hey, listen, I wanna 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 can I give you a f a few bullets to share that you can maybe respond to

58:57 that we get tight so that they know exactly what they're looking at. I was uh This was a Two year th two or three years ago I was involved in uh getting a deal over procurement that was just um Truly

59:09 Is that pharmaceutical company and it was very, very long process and we got to the finish line. And uh the CFO was the signature. And this is when I made the mistake.

59:21 CFO response back to uh 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. You know, 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 it cr again, it just it created so much anxiety, and now I'm back in the bottom of the cube. 'Cause she's probably he or she's looking at the things that come in in in an in an order of priority.

59:51 So now we've elongated this by another month. Um, simply because I didn't plan. So like this is just to say like I'm learning from my own mistake. Uh

1:00:01 know who the signature is,'cause if they don't know what they're looking at. They're gonna kick it out and you're gonna lose your Q spot. So many ways to fail. And this was you selling jellyfish or this was you working with a with a This is me w this was me helping uh Helping something feel for that. No man.

1:00:16 Okay. Anything else in that step that might be helpful to folks? Yes. the one thing to caveat is You do not get paid until you are approved by finance and procurement has a signature on the contract.

1:00:31 Meaning don't start any work. Oh or if you do start work, know that There they There is no payment. Like 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.

1:00:46 Yeah. Unless it's finally unless the signature's on the paper. Yeah. Uh quick tangent, thoughts on discounting at any Parts of the journey. If there is a reason as to why. So um discounting just to get the deal over the line, you're negotiating with yourself.

1:01:02 Unless they ask for it and then ask them to defend it. Right, like certain segments like small business, you should leave a little bit of room for buffer because sometimes that's their own money. Right. It's like their own small business. Mid market and enterprise, there's gotta be a reason why.

1:01:17 And ask them, be like, Hey, so you know, if I give you a thirty percent discount, can I remove thirty percent of the value? Like you can kind of like play it a little bit like that. I d I don't recommend it, but like that's kind of what You know. What they're saying. Um

1:01:30 But I'm discounting is great if you're getting if they're if they're doing something for you far and beyond. Like, for example, if they're a design partner. Um, if they're allow if they're gonna be a a reference for two years If you're if they're gonna give you something far beyond, you know, just using the technology, then yeah, I think a discount um is is a good reason to um give back to somebody that's giving to you, but I not as I guess strategy to get a deal done. Okay. Is there anything beyond this step of getting the signature where we done?

1:02:01 Yeah, I hope you celebrate because Yeah. You got a signature from this whole process. Yeah. Uh hopefully I'm not making this sound too daunting. I'm just really trying to lay out all the exactly. This is exactly what people need. This is amazing. And your your pep talk was really helpful too. Oh I'm going.

1:02:19 Um What's the general timeline for sales process like this in your experience with these five hundred plus size companies? So there's three things that dictate Sale cycle. One is you as the foun like how well are you project managing it? Like, for example, it's you know, I'll say

1:02:35 You know, let's have our second or third call in two weeks. Two weeks. Do a week. Why are you elongating this? You know, like keep your calls as tight as possible'cause that shortens yourself like The second is just how complex the organization is.

1:02:49 If you're dealing with a highly regulated industry, Just know it's gonna take a bit longer. Sometimes twenty to thirty percent longer. So like a highly regulated industry nine to Twelve months?

1:03:03 Um on like conservative on the conservative side. Again, if there is there budget, it's it's tricky'cause is there a budget light item dictated towards it yet? Or are you creating budget? Um How how painful is the problem? And how senior have you gone? Like if you're talking to like

1:03:19 The S V P or C you know, chief uh just You know, chief of whatever. They're pretty good at doubt being able to like navigate the traps. If you're dealing with a director or mid level person, they maybe have not purchased something before and like just make some internal mistakes. So it's it's I I always say it can range any w I've seen enterprise deals close in ninety days.

1:03:40 Believe it or not. Rare, but I've seen it. Um, I've also seen enterprise deals typically take anywhere between six and twelve months. Really important, but Enterprises no.

1:03:53 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 their system. That's why they're willing to spend so

1:04:08 Much. Right. Like sometimes that's actually more expensive than the technology itself. So Don't negotiate with yourself. understand the value you're delivering and um

1:04:20 But don't be crazy. Like I've seen people try and go in with a million dollar deal as a seed stage startup. Right. Oh, interesting thing. So Interesting tactic. I've seen uh contracts in the enterprise.

1:04:31 That state. That The deal cannot exceed more than twenty percent. of the existing revenue. So there are these things just to be aware of. Like m in most cases, like

1:04:43 You can ask them be like, Is that a hard line? Like is that Hard hard line or like how negotiable is that? Sometimes it's negotiable. Sometimes it's like no, this is a hard rule like We can't But then it seems silly'cause you take a hundred thousand dollar deal and bring it down to twenty thousand, it's just like a You know, just be careful that like your

1:05:00 stripping some of the value out. But like I I I kid you not, I've seen an enterprise deal go from it lands at sixty and it turns into two hundred and eighty thousand in four months. So like again, I want to encourage Yes, this is a lot of work, but the payoff Is

1:05:17 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 fifty to two hundred K, depending on the s the business unit you're selling to. That's kind of like sweet spot. Like they're used to something like in that in that realm. And this is like a startup selling. Yep. Like founder led, uh early stage, um yeah. Initial contract.

1:05:43 Yep, initial contract. I would say Okay, probably caters more towards like fifty to a hundred K. But I've seen people sell two on again, it's how big is the problem? Um, who are you selling it to? Is it the C the S V P that you started with and

1:05:57 you know, they've got a large budget, um, and uh it's a pretty healthy business unit, or are you selling to You know, um You know, a director. If you're not able to sell your product at that price. What's your advice to teams?

1:06:10 If you are a startup, I always ask the founder for Did you build it are you Do you did you build this for the enterprise and is that the model you want to apply? Or did you build this for small business? Small business is a marketing game. marketing intensive activity. Right, it's high velocity, high volume.

1:06:28 Lots of dials. It's a very different game than Enterprise. So which game do you want to play? Let's just start there. Like which game is more attractive to the founder? Sometimes You know, or or who is more exciting to serve? Mm-hmm. Um

1:06:41 What's the storyline you want to tell investors? You know, that that plays a lot of it into it too. And it do you have an enterprise product? Like are you solving an enterprise problem or do you think you're solving an enterprise problem, but you're not sure yet? And you're Point is also mid market is it's a rare rarely to be successful. It's hard to start there because

1:07:00 you're 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, th this is where a lot of people don't um If it requires heavy integration, they don't have those resources. That's usually outsourced to like an Accenture or like a Some of these consulting firms are like

1:07:21 And now you having to rely on third parties to be involved, it gets messy. This is fascinating. Okay. I have a list of Questions from the audience that uh 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

1:07:41 small to medium businesses and enterprise. How do you decide which one to focus on? Is there a counter argument against starting or SMB? We got market over time, like most Saask companies do. I've seen companies successfully do in both of those motions, truthfully.

1:07:55 Like I we've we know all those, right? We know people that started small business and work their way up into enterprise and were successful. We've seen people be really successful by starting at the enterprise like a whiz. That's more like an internal question, which is like what's Who did you build this for? What how Where's the problem most felt? Um And

1:08:12 Which go to market game. Do you want to play? And I think that latter part is so important. Like it sounds like It's why should it be what I want? It's like what's gonna make a big business, but I think

1:08:21 People forget this is gonna be your life for like ten years, right? 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.

1:08:36 A hundred percent. And I like I built my career in enterprise sales, like upper end mid market enterprise sales and Yeah, that's just the game I know the best. Yeah. And that's that's also an important part of it. Just to double down on that is like what do you what do you have experience doing? Not like exactly. Yeah. Where's the opportunity?

1:08:55 Okay, another question that I love is And we touched on this initially, but I think it's good to come back to this. Uh, someone said customers are fascinating, we'll fascinated with what we're offering from the initial calls, but response and momentum is too slow from their end. Would be great to know how to fix this. Yeah. That's a t it's tough because unless you're in the weeds to understand why.

1:09:15 Is it because you're you s I'll give you some make 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 in the

1:09:37 the implic they ha they don't understand the full implications of why they need to solve it. So it's kind of just like Sitting there a little bit. Um, the third is they've just been really nice and it's not gonna go anywhere. I guess that that's usually the latter. And was that true or or it's kind of all over the place?

1:09:54 It's so hard. To give a founder Hard feedback. 'Cause they've just dedicated their life to this thing. Right? Like who wants to who wants to be the bearer of bad news?

1:10:07 And sometimes you just need to let the action 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 unlock often? Where which of the steps of the sales process do you find the biggest opportunity? Two

1:10:22 Improve conversion and 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, l let me put this right.

1:10:38 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, not qualification, which is a symptom of not reaching out to the right person, not having the right messaging. Not solving the right problem.

1:11:01 Or going or not um Not being different enough. I love this. So basically The biggest

1:11:09 Uh pitfall people fall into your experiences, they're just talking to the wrong people, wasting Their time Yeah. talking to the wrong people or using the wrong message or

1:11:19 Um Like pitching them something they can't actually deliver. Here's the other thing too. Sales is supposed to feel fun for the buyer. Like they should be like, This feels fun. This person's invigorating. They're gonna change my world. They're gonna make me see things differently. They're gonna get me promoted. They're gonna help me increase my influence internally. And so many salespeople are so boring.

1:11:41 Like how many times have you got off a call and you're like, I can't wait to get off this call. You know, um And founders too, they like, they like they just like all of a sudden their their passion, they go like stone cold face, and it's like, bring the passion. Bring the energy like That is felt by the market.

1:11:57 Remember, some of these people are in boring jobs. Like Give them an outlet. So along those lines, I think a lot of people are just like not Like me included, uh I feel weird doing sales. Like it's a weird experience trying to convince someone to buy something.

1:12:10 Is there any advice you could share to get someone over that? Some 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.

1:12:25 Truthfully. That's what makes the world go around. Is I have a solution to your problem. Now you just need to make sure that the problem they're f that you just need to be honest that the problem they have Your solution truly can solve for.

1:12:38 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 gonna solve their problem and be honest about it.

1:12:51 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, here's what we're great at. And then they can say, Well, I also need that too. And all of a sudden this beautiful this This level of trust comes out.

1:13:09 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 your market will continually send you leads and word of mouth. Um, so don't Don't try and sell something just to prove to investors you sold something because it will be quickly on the other side when they turn.

1:13:32 Amazing. Okay, Jen, so I'm gonna cut the lightning round. I know you also have to run and do real work, so let me give you a chance to just to talk about what you do, how you help companies and yeah in case folks can find value in working with you. Uh deeply passionate about sales, as I'm sure you you can tell.

1:13:47 Um, we specifically help founders through this this pain. um navigating enterprise sales, mid market sales. And really trying to crack that first million of of ARR or sometimes even that first five hundred K of ARR if they move fast enough. And

1:14:03 You know It is really hard. It's 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

1:14:16 Clarify this? Like you basically embed with the team and help them do this. So um I fundamentally do not believe in outsourcing. Um the Heartbeat of the organization, which is sales. Um, 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.

1:14:40 Amazing. And I mentioned this when we were chatting, but it I I think of it again as 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 hire like a coach or consultant. As a founder to help them.

1:14:55 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. And we'll point people to what you do. Uh 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. Like if they like I think

1:15:12 You know So many people have helped me in my career and and um in this world and in this journey. that um the the pay it forward mo the pay it forward model that exists in the technology space is so beautiful. So just don't let that die. Beautiful.

1:15:29 Well, Jen, thank you. So much for being here. Lenny, this was awesome. Thank you so much for having me. This was so awesome. I'm so excited for folks to hear it. I've learned a ton. Uh okay, I'll let you go. Uh 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.

1:15:49 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 Lenny's podcast dot com. See you in the next episode.

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