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

25:42And 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. Tronkate this as much as you can because I think people focus so much on volume in the beginning. Even if you're selling downmarking, midmarker 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.

26:19If you're not asking at the right questions, these enrichment tools, these sales tools will we'll we'll 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 tronkating these little experiments. 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 you going to have to have hundreds of these thousands of these eventually.

27:02Like if you 30 is hard and or impossible, you're in trouble already. Totally. And 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 that they wanted to go out and and serve. I'm like, how do you find those people? Like no one's you know is I guess when you get to a certain level, you're net worth maybe public. I don't know, but you know that stuff's hard. 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.

27:36Not necessarily a bad way, but you 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 two out of these 10 will 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. Okay. 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.

28:09Do these emails have to be really short the way you described previous. 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 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 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. You know, interesting. And, and so you also share the structure for how to reach out to folks. So let me just share that again and then apply it to this initial email too, but it sounds like as you automate, you want to make it more precise and focused and not like, basically they're not customized as you start reaching out to more folks.

28:53Totally. So it's start with something here's why this is relevant to you. Like you're looking for sales people in this market. Here's something that's unexpected or surprise like zero to one sales people don't exist. Keep it short. And then I always forget the last one. I 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. But I bet if someone reached out to us like a novel insight and said, I'm really passionate about solving this problem.

29:35If it's something you're focused on, you'd probably reply. If it's like a big problem, right? If it's, oh yeah. I mean, this the beauty with the American market. And I say this could we do a little bit of work with international startups too is 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. I know that I just looked at that I wrote down that I think is very important is avoid using this as better as your pitch. Yeah. Yep. Different. Here's something shocking about what we're doing. Here's something that'll surprise you.

30:07Yeah, or counterintuitive exactly. Yeah, that like 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 next product because then I asked them to define that. And then I asked them like, okay, how do we measure that? 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 disrupt momentum and yeah, better is a dangerous place. Yeah, like I invest in a bunch of startups and I find it's impossible to get anyone to care if they're already good, if things are good enough with what they got today.

30:48Like 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 is I'll just deal with this good enough solution for now. Absolutely. Okay, amazing. So we talked about how to find 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. Right?

31:24Like 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 we'll let them open up.

32:08Now you have them one talking about the problem. Now you're getting the intel about their perception of the problem and if it is even a problem. When you say your 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, 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.

32:51If 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 getting a lot of the intel. So that's like one counter -intuitive 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. Our 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.

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34:09That's useparg .com. So I had April Dunford on the podcast a while ago, and I have these amazing. And her last book, it actually has the opposite advice, but I think I know why, which is she focused 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, 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.

34:43And so her advice is you actually have to educate the buyer on the market. And here's what's happening. Here's what's 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 100 % and that's a good that 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 tricked up. Is there taking late -stage sales advice from an, usually coming from an investor or they've maybe hired a salesperson that's focused on more mature sales?

35:18But I think she is spot on. Bine 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. 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. A 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.

35:59There's this concept that I talk about, which is like 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 error, right? Yeah. I think it's about like some people say 500, some people say a million. I think it's where, like, 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.

36:39You haven't reached that velocity point yet. Awesome. I have a post that will link to that has actually numbers 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 share the story of the first year on capital led their first round and their partner there is just like, we will not let you hire salesperson until you hit a million error. 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.

37:07And you're really happy about that. The other is Zip, which just raised like a 2 .3 billion dollar valuation, it's a procurement company that I was lucky to be an investor and their first founder -led sales motion was they just reached out on LinkedIn to heads up a 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. We just tell us what problems you have. It was very advice oriented versus like 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.

37:43Because seed is all about experimentation improving out that experiment and then obviously Series A is about exploiting that learning, but I see so many people. I mean, early stage 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 counter -intuitive 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, I come to the ABC, your devices, be very honest and vulnerable, but your stage tell them, your early stage, you're building this thing, you deeply, you're deeply passionate about this problem.

38:29Here's what we're trying to do. Here's our priority problem perspective and what we're focusing and getting 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, right? 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, right? Which is like, so tell me like this looks in your head.

39:08Like, 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, 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, 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 onto something here.

39:44I love this thread because this is what everyone's always like. How do I know if I 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 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 like, it's not a priority if it's not growing or widening.

40:20So Gcheck 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 a 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.

40:59These are all the secret moments in Intel to close that gap. It's awesome. Essentially, it's showing you that there's a pain here that they're paying attention to and are trying to solve. 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 was noticed is they moved from people being like, this is cool. I like it. 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 in like they were pulling in other people exactly as you described it because they wanted to make move forward on this thing.

41:44Absolutely. 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 onto 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? Because I can guarantee you that answer changes every single day.

42:19That's super interesting. Is there any tip for how to end one of these calls? That's someone that's never done sales. 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 I said in 30 minutes, they're right. And if they say, I'll email you. I get to say it's also that's also kind of a leading indicator. So do you recommend not getting off the call like trying to avoid that? If they won't give you time on the calendar, you could say, listen, great, like, feel free to email me.

42:56Maybe 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. It's hard to tell people you're not interested. Very cool. Okay. This is amazing. 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.

43:43The co -author, the co -authorship piece is important for two reasons. It helps you understand where they are on their biometrality. 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 where you go back to. You need to sell them some form of a service. Why? You want to be the one in their 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. I think that that's really important. Every founder I speak to is like, well, my investor really doesn't want service -based revenue.

44:19That'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. 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.

44:51This is where all the power lives. 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 like time box contain the services piece? Yes, it's such a great point. You absolutely need a time box this. I would time box it as 90 days and then what you can say in the next 90 days will scope where we are and like what you need. Scoping out more than 90 days, listen, everything so much is going to change. You might also not want to do it anymore.

45:27So you don't want to lock yourself up. So I would look at like 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, like a very traditional industry. I don't want to be too bleeding with what 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 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.

46:07Could you come in and explain to us like understanding where our workflow is and how we would integrate this before we even consider the technology, 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 want they won the technology contract. But everyone is so focused on selling a technology really, really, really quickly. That works in markets that know how to buy that technology. You 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.

46:45Like 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 teams not even aware of all these risks. Like you want to be careful because legal can immediately impercure and can shut these things down if it seems too novel where it's like foreign versus they're so used to buying services, especially at market. So largest budget line item. So it's interesting because the most founders are very afraid of moving into services at and heard this advice before. How are you going to get slapped for saying all this stuff?

47:17Well, so on long as lines like what percentage of companies that you've worked with or see like do that or have to do that step. This would be it's going to be a shocking step. So I would say 40 to 50 % have to sell some form of service before they can sell a technology. Wow. A B2B SaaS company. A B2B SaaS. And this is again, this is specifically more top -down sales. Be up 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. And just to make it even clearer, what's an example of like a service that you've seen company offer like as in a step?

47:55So 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. Okay. So it's not necessarily providing a service. It could be just helping them sell this. Yeah, it could be it could be helping them sell in a way that like makes you, you know, you need to get some a lot more context on their business. It can also be, hey, we haven't actually thought about the a new process for how we can actually deploy something like this, right? We're currently using this technology, which we want to change from.

48:33Like 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 like map map this out? Got it. So it's like consultants almost like a, 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 it obviously are biased, but they also want the problem solved. They're like, great. You're gonna help us. You're gonna help me solve this problem because it's on my plate. And I need your help convincing leadership.

49:02Yeah. 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 like here's the format. It needs to be 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, you know, 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 us note down as you were talking. You recommended not doing a demo and just talking about it broadly.

49:34Yes. On the first call. 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, it's kind of like, you know, pitching an investor. Once they take a look under the hood that dream, dreamy -ness in their eyes, you know, they're like, oh, I saw it. So like, 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, let them invest a lot of time in you. Again, if it's qualified, I'd preface that if it's qualified.

50:13But 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. That is important. If you're selling a $3 ,000 total, you absolutely want to be demoing as fast as humanly possible because it's a high volume game. Up market, 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 is baby.

50:45So you wanted to make it feel like the group's baby versus this one individual's baby because it's very quick. You know, someone can easily say, 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 a figure out who to talk to, pitching them on talking to you, then having that first conversation, maybe there's like another conversation in there 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?

51:14Yeah. So if you are selling up market, right? And you now need to go to procurement, who is the group involved in the bot? Like, you know, they're the professional buyers. procurement is a very interesting function. They're very smart, very, very smart. Right? They do this for a living. Like, they are like professional buyers. So there's a couple 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, 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.

52:00Why 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. They didn't, it didn't feel different. 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.

52:32So you can get easily sideline 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 MSI, which is going to ask you for $5 million in an insurance policy and all sorts of other things.

53:15The ability to look at your book at any point in time. 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 make it easy for them. Make it simplified. You can also truncate your contracts. Meaning, let's say IT is made 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.

53:53Service 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's getting to procurement is also creative. 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 spod on, which is buying is just as hard as selling. As I'm here, you describe this. I feel like we might be discouraging people from selling because this feels very not fun.

54:30All these steps, all these procurement work. Anything you can say to get people to feel like, okay, this is a little weird thing. 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. What do you think procurement is going to say? This is why it's so important to get into the enterprises as fast as humanly possible while it's a headache to get through. If you project manage it, you'll be good.

55:07If you make an accountability, just like if you were to go through fundraising, if you are a part of a team that had a 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 $100 ,000 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 growth, your growth journey really gets accelerated. The beauty with enterprises, once you're in, you beat out your competitor for a short period of time.

55:48There is a little bit of a moat there, but it's not forever. You will have intel that no one else will have, meaning you're a part of 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 you here.

56:29What's the size of the device you've been sharing so far, roughly? I've been talking a lot about enterprise sales, which is, I would say anywhere north of 500 to 2 ,000 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. As you go down market, let's talk about small business first second. The user and the buyer are the same person. There's no procurement.

57:06If they like what you've 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, 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, turn. Small business, challenge with small business is the turn. If they get pissed off, if they don't feel like it's good enough, they are gone.

57:42Faster than you don't even realize. They might even tell you, they'll just cancel. 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 rational. Because sometimes it's, maybe it's their money through a small business. Small business in mid market, while sales is a bit faster, you really got to be on the product market that side. We're worried about churn. They also got a business at a high rate. Exactly. You have that kind of churn. A churn piece too. Yeah. Exactly. Amazing. Okay. What comes next?

58:17We're kind of in procurement at this point. Okay. 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 had 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?

59:00I was, this was a 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?

59:39What does this person care about? And again, it just created so much anxiety. And now I'm back in the bottom of the queue because she's probably here. 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 like, this is just to say, like 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 cue spot. So many ways to fail. And this was you selling jellyfish or this was you working with it. This is me helping helping you.

1:00:16Anything else in that step that might be helpful to folks? Yes. One thing that 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. 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. Yeah. Unless that's finally unless the signature is on the paper. Yeah. 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.

1:01:05Like certain segments like small business, you should leave a little bit of room for a buffer because sometimes that's their own money. It's like their own small business. Mid -marking an 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? Like you can kind of like play it a little bit like that. I don't recommend it, but like that's kind of what they're saying. But discounting is great if they're doing something for you far and beyond. Like 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 is a good reason to give back to somebody that's giving to you, but not as like a strategy to get a deal done.

1:01:57Okay, is there anything beyond this step of getting a say to enter or we done? Yeah, I hope you celebrate because 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 this. Yeah, no, this is exactly this is exactly what people need. This is amazing. And your your prep talk was really helpful to 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 you as the like how well are you project managing it?

1:02:33Like for example, it's you know, I'll say, 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 because that's 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 like a highly regulated and industry nine to 12 months on like conservative on the conservative side. Again, if there is their budget, it's tricky because is there a budget light item dictated towards it yet?

1:03:11Or are you creating budget? How how painful is the problem? And how senior have you gone? Like if you're talking to like the SVP or see, you know, chief, just you know, chief of whatever, they're pretty good at about being able to like navigate the traps. If you're dealing with a director or a mid level person, they made me have not purchased something before and like just make some internal mistakes. So it's it's 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, but seen six and 12 months.

1:03:48Really 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 their system. That's why they're willing to spend so 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 but don't be crazy. Like I've seen people try and go in with a million dollar deal as a seed stage startup. Like, 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.

1:04:39So there are these things just to be aware of. Like in most cases, like 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 because you take a hundred thousand dollar deal and bring it down to 20 ,000. It's just like you know, just be careful that like you're stripping some of the value out. But like 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 like again, I want to encourage yes, this is a lot of work, but the payoff is exponential.

1:05:19What'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. Like they're used to something like in that realm. And this is like a startup selling. It's your early stage startup. Yep. Like founder led early stage. Yeah. Initial contract. Yep. Initial contract. I would say, okay, probably cater 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?

1:06:05If 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 intends to 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. Like which game is more attractive to the founder? Sometimes, you know, or who is more exciting to serve? What's the storyline you want to tell investors?

1:06:43You know, that that plays a lot of it into it too. 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. It's a rare, rarely to be successful. It's hard to start there because you're straddling two very different go -to markets. 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 like an Accenture or like some of these consulting firms or like, in now you're having to rely on third parties to be involved, it gets messy.

1:07:25This is fascinating. Okay. 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 out 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 bit, we get initial validation from both small, 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 S companies do? I've seen companies successfully do in both of those motions, truthfully. We know all those, right?

1:07:56We know people that started small business and worked their way up into enterprise and we're successful. We've seen people be really successful by starting at the enterprise like a was. That's more like an internal question, which is like, what's, who did you build this for? Where's the problem most felt? Which good market game do you want to play? I think that latter part is so important. It sounds like, why should it be what I want? It's what's going to make a big business. But I think people forget, this is going to be your life for like 10 years, right? Do you want to be selling enterprises and building all the enterprise features?

1:08:29Would you prefer to build for small companies? It's pros and cons to both, but it's important to think about the life you're creating for yourself and your team. 100%. I built my career in enterprise sales, like upper and mid market enterprise sales. That's just the game I know the best. That's also an important part of it, just to double down on that as like, what do you, what do you have experience doing? Not like? Exactly. Where's the opportunity? Okay, another question that I love is and we touch on this initially, but I think it's good to come back to this. So, we're connected with what we're offering from the initial calls, but responsive momentum is too slow from there and would be great to know how to fix this.

1:09:10Yeah, that's it's tough because unless you're in the weeds to understand why, is it because you're, I'll give you some, if you 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 sidelineed 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 the implicate 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.

1:09:45The third is they've just been really nice and it's not going to go anywhere. I guess that's usually the latter and 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 that action speak louder than words. We've talked about all these steps. I'm curious when you come to a founder your team. Where do you find the most unlocked often? Which of the steps of the sales process do you find the biggest opportunity to improve conversion and say yes?

1:10:24It'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, wait, wait, wait, wait. 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, 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 your experience is they're just talking to the wrong people wasting their time.

1:11:15Yeah. Talking to the wrong people or using the wrong message or like pitching them something that can't happen forever. 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 con? I can't wait to just like all of a sudden their passion, they go like stone cold face. And it's like, bring the passion, bring the energy.

1:11:54That 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 like 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 built something you believe in and they have a problem, that's a beautiful thing. Truthfully, that's what makes the world go around.

1:12:27Is I have a solution to your problem. Now, you just need to make sure that the problem they're fake, that you just need to be honest, that the problem they have, your solution truly can sell 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.

1:13:03And then they can say, well, I also need that too. And all of a sudden, this beautiful, 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 your market will continually send you leads and word of mouth. So don't don't try and sell something just to prove to investors you sold something because it will be quickly seen on the other side when they churn. Amazing. Okay, Jen, so I'm going to cut the lighting around. I know you also have to run and do real work.

1:13:37So let me give you a chance to just to talk about what you do, how you help companies. Yeah. In case folks can find value. Yeah. Working with you deeply passionate about sales is I'm sure you can tell. We specifically help founders through this, this pain, navigating enterprise sales, mid market sales, and really trying to crack that first million of of ARR or sometimes even that first 500K of ARR if they move fast enough. And 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.

1:14:14And I think it's important to clarify this. Like you basically embed with the team and help them do this. 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 at 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.

1:14:48One of the interesting threads that I heard again and again is how many of them hired like a coach or consultant as a founder to help them learn to do sales. And that's essentially what you do. And I didn't even know service like this existed. So this is super cool. And we'll point people to what you do. I also have to ask you the question I ask everyone at the end is just how the listener is beautiful to you. Help each other out. Like if they like I think, you know, so many people have helped me in my career and in this world. And then this journey that the pay it forward model that exists in the technology space is so beautiful.

1:15:26So 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. This was so awesome. So excited for folks to hear it. I've learned a ton. Okay, let's 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 Lenny's podcast dot com. See you in the next episode.