How to close $100K+ enterprise deals, step by step | Jen Abel

So we're going to do something really unique with this conversation. Basically go through the enterprise sales life cycle step by step. Let's set this up. Let's start with how do I even get the first meeting? We're in this flood the zone moment of everyone trying to break into the enterprise. But like, what exactly are you solving for them as a problem? That's level one, but most importantly, the alpha and it needs to be different. Step two is basically running the intro call. This is the most important call out of all of them. This is what I like to do. Super informal. Don't show them a demo. Don't show them slides. Focus on them. Have a one-on-one dialogue for 30 minutes. The whole game is to slow down to go fast. And by the way, do not bring a recorder to this call. What are the benchmarks for how often you get through each of these stages? The win rate for enterprise is usually around 30 to 35%. If your win rate is higher than that, your price is too low. What are some signs that your salesperson is not doing a great job? Most successful salespeople are not trained salespeople. Fastest way to commoditize yourself is to go into some sales script, budget, authority, need, timing. Like that should be in the back of your brain. You never actually ask those questions. What percentage do you think are just doing it wrong? 90%. Like it's literally so fun. People read these salesbooks, go to these sales trainings. They try and take someone else's game and run with it and never works that way. Most people think the sales process is five steps and we're already in step 10. We're not even done. The worst thing you can do in the sales process is today. My guest is Jen Abel. This is her third time on the podcast for those that don't know Jen. She's co-founder of Jellyfish, GM of enterprise sales at state affairs. And most importantly is the person that I've learned the most from about the art and science of enterprise sales in our first conversation. We went deep on Fenderlet sales in our second conversation. We focused on the $1 million 10 million enterprise sales playbook. And in this conversation, we do something I've never seen anyone do on another podcast. We go step by step through the full enterprise sales cycle. Most people think this is a five step process. It turns out it's closer to 15 steps. Most people ignore a bunch of these steps that you'll hear about. We go through everything that you need to know at each step to significantly increase the odds that you close your deals. This episode is incredibly tactical and specific. You will learn a ton I did for sure. Like I say in the episode, I always get so energized and just excited to sell something after talking to Jen. You will feel the same way after this conversation. I'm so thankful to Jen for sharing so much alpha with us before we get into it. Don't forget to check out Lenny's product pass.com for a free year of the hottest and most beautifully crafted AI products in the world available exclusively to Lenny's new letter subscribers with that and bring you Jen able. Jen, thank you so much for being here. Welcome back to the podcast. A very rare third visit to the podcast. How does it feel round three? Super excited to be here, Lenny. I'm even more excited. I've never done anything like this before. We're going to basically go through the enterprise sales life cycle step by step. You'll talk about this, but many people think it's like five steps. You talk about how there's actually something like 15 steps. A lot of people ignore a lot of these steps. And the idea is I want to create a very concrete and tactical playbook for how to do enterprise sales. Okay. If I had conversations, all let's, that's the goal. Just just suck them all out and make everybody amazing at sales. It'll be great. Um, and you know, this touches on just like why, why I think the podcast is really helpful to people and just the valley vibe, even that you don't live in the valley. Just like there's so much win, win, win in helping people learn these things. You know, it may feel like why is she giving away all these things? But maybe actually, let me ask you that. Just like why, why do you share these things? Well, it's so interesting because there's so much art to this that even if you gave someone a 15 step playbook, there, there's so much of a feeling that you have to go off of like sales is sales is one on one, right? You're, you're dealing with a variable, which is another individual. And if you ran the same flow every single time, it's going to probably not hit one out of every four times because everyone's different. Like some people like to joke, some people like the small talk opener, others want to jump right into it. Some are technical, some are not technical. You know, so everybody's so different that even if I gave even as we go through all these 15 steps, while it's 80% of it, the other 20% is obviously the art of like how you make someone feel, do they feel heard? Did you make it fun? Did you tell a good story? I mean, that's also a huge part of this too much to cover today. So we'll stick to the, we'll stick to the roadmap of like how to close these deals. But I think the interesting thing about enterprise sales is even if you're selling a, if you sell $100,000 solution, it is the same exact process to sell a million dollar solution. So that's why it's, it's, it's an interesting process because the enterprise organizations are more sensitive to the process you take them through from a sales motion than they almost are with demoing the product. Amazing. And I'll just give a plug for if people want to continue learning your Twitter feed is just the best, you share all this stuff constantly. Yeah. And I think you, you talk about there's like rational reasons to share this stuff. But I think there's, it feels like there's just like, I just need to get this stuff out. People need to, it's like a diary and it also helps me like keep it in my mind too. Right. It's like my own education. Yeah, I know exactly what you mean. That's why I started writing. I started, I was just like, I just want to remember the stuff myself. I'm just going to share it and customize it. Okay. So before we get into the steps, let's set this up. What are some things people should know? What's kind of like the case study? What we're going to be using here? Let's use a company like SpaceX, right? Recently, you know, has seen massive news pricings, it, you know, everyone's probably targeting them, right? So it's going to be a hard logo to go in and win. They are a technical organization. But I think what we do is target a non technical team. So we're going to like really get into like the nuance of this. So let's do SpaceX. Why don't we pick legal? Let's have some fun with legal. The interesting thing about legal, it's the largest budget line item in the enterprise at kind of budget, right? Sometimes three to four times other budgets. And it's forever. There's always more money for legal. That's why there's so way legally I started it. So I get it now 100%. Amazing. And I'll just add the reason, like the reason I love to have you on this podcast is I've left both of our previous conversations. So just like fired up about selling. I just like, I have nothing to sell. But I'm always feeling like I want to sell something now. I feel like I've learned all these things. It feels so fun. You are. You're a master. You're actually a master at this. Sales is marketing, marketing is sales to some extent, right? And all right, you do that. You do that better than a lot of you. I feel like you're using some sales technique on me to make me feel good about myself. Okay. Anything else before we get into step one of the sales enterprise? No. I think it's just good. Sales cycle. SpaceX and targeting the legal function. And then like a hundred K, let's say, deal into your point. It's the same process, whether it's a hundred K million. And I will add a plug for a previous episode. Do you talk about why you want to be at least a hundred K, something as a deal? Yeah. You be a real enterprise company that will, that will survive. Yes. That ROI and the, and just the whole economics of that stuff. But we won't get into that. This episode is brought to you by our season's presenting sponsor, work OS. What do open AI andthropic cursor, replet, Sierra clay and hundreds of other winning companies all have in common? They are all powered by work OS. If you're building a product for the enterprise, you felt the pain of integrating single sign on, skim, our back audit logs and other features required by large companies. Work OS turns those deal blockers into drop in APIs with a modern developer platform built specifically for B2B SaaS literally every startup that I'm an investor in that starts to expand up market ends up working with work OS. And that's because they are the best, whether you are a seed stage startup, trying to land your first enterprise customer or a unicorn expanding globally. Work OS is the fastest path to becoming enterprise ready and unblocking growth. It's essentially striped for enterprise features, visit work OS dot com to get started or just hit up their slack where they have actual engineers waiting to answer your questions. Work OS allows you to build faster with the life will APIs, comprehensive docs and a smooth developer experience. Go to work OS dot com to make your app enterprise ready today. Okay. Step one, where does, where does it start? How do you start selling someone on your product? It's a great question. So I think let's start with like, how do I even get the first meeting? How do I even engage with these people? There is so many, there's so much nuance as you target as, you know, as we're using the case study of SpaceX today. You have the top of the wrong, right? Which is the, the general council, the head of legal, uh, the chief legal officer, they all kind of have slightly different titles, but they don't carry the same weight, which is like, who's the, who's the lead of the team? And then underneath that, you have a bunch of people that carry a VP title, carry a director title, maybe just say lawyer on their LinkedIn. So you have to do the work to figure out what is This is my entry point, and there's only two entry points. Starting at the very, very tippy top, meaning going direct to the decision maker, the chief legal officer, or finding the individual that would be maybe one step removed, okay? I personally, other people would argue with this. I personally would not be targeting anybody else. It is the executive themselves or an N-1, okay? So let's talk about why in order for an enterprise deal to move forward, you need to have this extremely compressed storyline that lands immediately to the objective that they want to solve for at the organization. It has to go beyond just an AI mandate. I think every company today has an AI mandate, and I know everyone is an AI tool. But what exactly are you solving for them as a problem? It's one, that's level one, but most importantly, the alpha. What does this executive uncover and unlock by bringing in a net new tool, because bringing in a net new tool, okay, is risky. No one wants it. So if we're targeting the chief legal officer in the N-1, you get two to three sentences, Max. Okay? That might be through an email LinkedIn, that might be through a phone call, that might be through an event, or that might be through some marketing capability. Most sea level executives don't respond to marketing. They might see your brand, they're not going to respond to a marketing campaign, okay? It will respond one-on-one, and the best individual to one-on-one to a corporate executive is the founder. Even if you're a series B-series say, right, the founder should be ecstatic to want to get in front of the chief legal officer at SpaceX. I think any founder that is building something really meaningful knows the important role of that. Second is you can get your enter your AE or enterprise sales lead to target the N-1, and you do what you call this. I call it the pincher model, because you're going after two different people and trying to get them together. It's actually called the pincer model, which is start at the very, very top, find that kind of floor, and work in between that. These are the two layers you want to be targeting in landing that meeting, because if you go any further than that, you risk they're not going to be able to communicate your storyline. It's a game of telephone, right? And now you're learning from someone that is not near the budget or the executive discussions, right? Which is super risky, because now you're learning about user value, not executive value. And a $100,000 deal needs an executive sponsor to sign off on it, to allocate the budget. And this is why you need to start at these two layers only. Wow. There's going to be a fractals of questions and things to begin with each of these steps. This is amazing. Love had just how specific and tactical you are with all of these things. I'm going to try to summarize a couple of these tips, and then I have a follow question. Okay. So tip one is go after either the exec. So in this case, it should be general counsel, head of legal sort of person or N minus one. Love the way of describing it, maybe a VP. You want to pitch them two or three sentences in like a text or email or in a, at a conference, and the keys to focus on the alpha, like the way what your product will unlock for them. Love that. And it sounds like there's still like here's the problem we saw for you, but here's like really the alpha we unlock. Correct. Because for an executive to bring something in and be the sponsor and like share this and disseminate this down there down the down their command, they, they need to stand behind something beyond, hey, we're going to make, we're going to alleviate, you know, the time it takes to do X activity. That's not big enough. They want like, they're like a founder, two of their own business unit. Like you got to sell the vision. And what are these people going to, how are they going to get to the next stage, whether, with their influence, get more budget, get more people, how are they, they want to define that. Yeah. So it sounds like you don't want to, like they want to win and to win, you need something unfair, unfair advantage. That's exactly right. Yeah. Okay, and then this pincer move, I love this, so the idea here is for the exact, say, chief legal officer, general counsel, founder needs to reach out. Yeah. And then this AE reaches out to the N minus one contact and you do this, you go from both directions. Yeah. And I imagine the goal is one of them at least responds. That's correct. And then because you're only one step removed, they'll usually loop in that next person and or you can say, the founder could say, hey, I'm going to loop in my so and so colleague, who on your team should we also include or the, uh, and enterprise executive could say, hey, I'm going to bring in my founder. Could we see if your boss might want to be a part of this too? Does that parody of, um, of, uh, kind of role? Yeah. Uh, and they might be like, wait, I've heard of that. I think I heard that name before because I got this other email. Exactly. You can do that. Remember? Okay. Two questions. Um, how do you find this N minus one person? Is it just sitting on LinkedIn kind of figuring it up? And then two is any channel recommendations these days, like what's the best way to try to contact these people? So I'll use, you can ask, you can spar with open AI and anthropic to like let them do the quick scan of like, hey, I'm looking to target the chief legal officer of SpaceX and their deputy, who are possible people I should be targeting. And then go off that and do your own gut check and search from there. But usually they'll give you the, the, the proper names. Now, here's the interesting thing about this. Another one is probably also targeting those people, okay? And this is why you need to be, and we talk about this in other episodes. It needs to feel so different and it needs to be about alpha. And if you don't have executive value, meaning you cannot get an executive excited by your value proposition, then you probably shouldn't be moving up into the enterprise doing a top down strategy. Got it. Okay. And then in terms of trying to reach out to them, any tips? Is it like tools there to do the figure out their number or whatever? They're also unique, cold calling works. And again, it depends on the role you're not going to cold call a highly technical person, but a non technical person like it works email, LinkedIn, Twitter. Are there tools to find these emails and things like is there something you recommend? Yeah, you can get like, and there's a ton of tools that do, uh, did do enrichment. Um, I also like, I'll try like LinkedIn first and say, hey, I shot you a note on, on LinkedIn. I just want to make sure you got it. Those people don't check that on a daily basis. But yeah, I mean, you, you have like, um, when lists and all sorts of these enrichment tools that can give you the email, but I think the number one thing is assume they are getting hit with hundreds of emails. How are you going to message your storyline to stand out? And that's, that's not easy to do. And that's really why I think having going back to my first episode, why founder led sales is so important to figure that piece out. So that was my next question is, what are some examples of two to three sentences? If you have some in your head, maybe even from your current job that you think are good examples of this two to three sentence pitch. Yeah, I think it comes down to like, what is the differentiator to what you're offering? Not even like, what do you do 10x better? Because to them, it still sounds like a commodity. How are you rethinking the business model? How can you help them rethink the way that they're structuring their team? We're in this like flood the zone moment of like, everyone trying to break into the enterprise. And the number one thing that breaks into the enterprise is like, oh, the way I'm modeling my business unit, here's how I should be thinking about it in the age of AI. And it needs to be different. It can't just be like, oh, yeah, we'll help you reduce the number of resources here. Like, no, no, like, how are they going to show needle moving impact to their COO, CEO, you know, if they were to bring it to the board meeting, like, what would they say about the product? This product will allow me to do what? That's like the litmus test. Is this a pitch that you iterate on over time? Yes. Because it's probably, you know, you're probably getting some percentage of people responding so that, okay, so the advice is like, keep trying to refine this. Awesome. Okay. Anything else on the first reach out before we get to the next step? No, I think that's it. Okay. Okay. Let's do it. I started shaking it up before you said it. It's super confused. Okay. Step two. Okay. This is the most important call out of all of them, okay? Because you are setting the tone with how they think about you, how they respect you in your role and your craft, and the information they will tell you on the first call, they will clam up moving forward because it starts to feel like a sales process. So all of the information edge you can gain as a seller is on this first call, okay? So keep it, and this is what I like to do, super informal. Don't show them anything. Don't like focus on that have a one-on-one dialogue for 30 minutes, okay? Now, again, if they're bringing in a C-suite executive, you better have your founder join that call as well. I need a founder that wouldn't want to be in the room with a Fortune 100 C-suite executive. So make sure you bring in your founder if you have that person, but let's say you had the N-1, you had like the VP on that. Like super brief, hey, this is how it's typically open, hey, I'm going to keep this super informal. I don't even know if we need a full 30 minutes. Put them on the back for like oh this person's not trying to take out my time All I would like to do is swap intros and if it makes sense we can always get on another calling go much much deeper But I just want to better understand like who you are and I'd love to share what we are doing and why I specifically reached out to you So I said would you like to go first always let them go first? Give yourself the edge right because if the more information you are receiving before you speak the more you can frame it and Tighten it to what they specifically care about so and they also aren't like sitting there now listening to a picture like I Know they're talking another conversing now. It's like okay. Now. It's fun. Now this person's not pitching me I'm in a conversation in a dialogue. Okay, so now you're talking to them and they usually they usually do a very brief open and like hey, I'm We didn't get a chance to look up the chief legal officers Space X obviously this is just a case, but like whoever that person's name is You know, I oversee the legal team and blah blah. Okay. Okay. Great. They usually don't give you much So they say okay, interesting like How are you thinking about Like do you guys have an AI Mandate going on at the organization like how are you thinking about the existing way you guys are doing work like What are you looking for going into 2027 like is anything need to change like ask and does anything need to change? because again What they're going to usually default to is what Conversations have happened above them and have been transcended down. So the change is usually dictated from the top Which is great. So like what needs to change going into 2027 that you did in 2026 or maybe not at all and that's when they start to open up and Again, you don't want to be too pointed of like anchoring them towards your product because again the more they speak You can start to like pull on the strings that matter. So they could say something along the lines of You know, I'm making this up at this point, but we are really looking to figure out how to Bring more of this work in house and rely less rely far less on external law firms Right because now we have more tools and capabilities. Yeah. Okay. Like is there a measurement to that right now? Like how are you guys like what does that look like internally in terms of? If you've done that successfully in 2027 And then they'll say you you're trying to understand like how much sure is this thought right? Okay, so now they're they're going in and they say they can't really answer that fully because they okay Like why is that important now like why didn't you why not wait another year? I mean you guys have so much going on you just had this massive. I feel like what's what's causing the team to want to Re-shape this or or rework the way that they're Managed internally and That's usually the moment of like where they start to really guide you in terms of like how they want to structure their team So now you're getting all of this information about where they want to go Right now when you talk about what you do now you're the vehicle to get them there Right and so the I try and spend maybe 10 minutes the back 10 minutes explaining what we do and just keep asking them questions Be like oh, that's so interesting like what an exciting role to be in be like okay full disclosure right and by the way I take a step back to that do not bring a recorder to this call Do not record the call they will not be open. They will not be vulnerable It might assume it's being record exciting everyone kind of operates under that assumption right now But for the benefit of yourself do not have a recorder present Okay, you take off the record between the two of us talking right now of what you just share like what really matters Like what let like or like what do you want to own? Or like what's the chronological like keep digging digging because the more you dig the deeper you go the more information They give okay now you can't sit there and just pepper them with questions. This is that that art piece of like How open is this person some people are poker faces some people are not you will be able to go Much deeper with some and not deeper than other you just have to Improv okay, but after you now have that intel and you can now understand. Okay, here's the frame. I'm going to take Now you can give them the pitch Okay, I will confirm Every single conversation. I have this the storyline that I tell looks slightly different I do not have a scripted pitch or frame for any call because it feels artificial They feel it it feels like you're putting them into a square box The best thing you can do is listen actively and then Feel confident enough to to craft the picture on what they just shared for you Well, last part seems really hard to it's very hard to adjust and make up like here's what you're focusing on Here's our product is gonna solve that problem for you. So that's kind of where that art and skill comes in that's right in enterprise sales It's so so hard to hire for because the more someone is trained in sales The less natural it feels. I Know this is counter-tributed and we spoke about this on one another another call The most successful salespeople are not trained salespeople. That's why founders are so good at this Like they don't give themselves enough credit. What are they not good at probably following this process? What are they great at pulling out information pulling on strings getting people excited by vision? No one can do that better than they can we're percentage of the time where you just like Okay, this isn't actually gonna help you that much. So let's just we'll share we're up to okay, you're nodding that happens one I would say two to three added every four calls. There's something real one at the real yeah There's some real one added every four calls I'm like listen based off of the maturity of where you guys are and where we are It's too much of a gap like I'd love to revisit this in a year like once you guys have a chance to like solve for xyz the that's such a great question about the qualification Most people are not going to qualify not because necessarily you're talking in the wrong person because if you're in an if you're an enterprise Executive or enterprise account executive your job is to know who to talk to okay um, and your job is also to quickly um Quickly disqualify someone and it's probably one in every four calls Also because of the charty. Well, so you don't have to have this like intense pressure to Yeah, let on every call and out here's the here's the pitch. Okay, awesome What I also want to comment on is if this idea of like getting to share a bunch It may feel tricky like you're tricking them to sharing all this but really they have problems they want to solve And you're there to help them solve a problem and so Why would they not want to just like okay? Here's what we need help with here's the problem here's our priority Their job is the their job is to buy solutions to these problems, right? That's why they have budgets right um So that's why them and the the fastest way to commoditize yourself is to go into some sales script like Budget authority need timing like that should be in the back of your brain you never actually ask those questions Cool, okay, so the core kind of lesson here is focus on learning and extracting their priorities and what I Felt as you push them to get more real and and like really pressure test. How big of a deal are these why are this? Why is it important because you want them to ask you those questions because that's when you know you're building a relationship Like I like I had a client last week say to me. What's the biggest learning your team has had this year? Like every product needs to get better every product has a bug every product You know isn't able to do X or Y um as well as they said and they're and I'm like that's a really good. I'm like That's so funny. We just had a conversation about that and I she was like thank you for sharing That's what they just want to know you're vulnerable Because then it doesn't feel like it just feels less like sales I imagine um priorities for a lot of companies these days is saving token costs I know classically. You don't want to focus on lowering costs as a sales pitch. This is a cheaper option Yeah, thoughts on if that just comes up a bunch. We just like legal. We just need a safe cost. Yeah So In pricing Their job is to there's going to use usually going to be two motions I need the lowest cost way to do X because it's low on the totem pole and I really don't care if it's 60% of the way there No one's getting fired over it. I'd rather just save budget Or you're solving a problem that you can charge You know 255 500k land because the because it is a um Uh high risk if you're dealing with legal there's high risk to it right missing information being delayed on something um Uh Not having people understand the importance of some new regulation or or law um Not being buttoned up um So I think for if every organization looks differently right like Marketing needs to have needs to produce you know marketing and sales. It's very clear that number Numbers drive them For legal. It's probably they they need to stomp out risk. Awesome. So yeah Basically this comes back to the idea of alpha and yeah upside. Yeah, the more you can be in that bucket the more you can charge That's exactly right easier everything gets Okay, uh anything else before we get to step three No, I think for step one like that that that is the most important meeting and I feel like people just Spend so much time talking about themselves and miss all the competitive advantage to win the deal Yeah, you're pointing about how As a buyer it's so like low pressure at that point you're just exploring And so I could see why people come into it like cool. Let's learn. Let's see if this uh versus you're in the funnel like Oh, should I get actually make a decision? I'm gonna have to let them down if I don't want this yeah Yeah, it's like dating yeah, like your openness to share more Mm-hmm start to clam up a little bit more But we'll talk about how to make sure that doesn't happen to amazing and get pretty - Agreed for a shatter. Okay, so step three is writing a follow-up intro call. - Yes. Okay, so usually right now, the stages that most people have is intro, demo, proposal, contracting, you know, closed one or closed loss. There's five stages. They're very basic. People usually go from an intro call straight to a demo, okay? The demo is your carrot in the process. Everyone wants to see this amazing thing we just spoke about, okay? So your job is to make sure that when you do that demo, the formal demo, you have the right people on the call. Because if you don't, one, it's, you lost your leverage to like organize that group and rally them. But more importantly, you never want it to feel like one person's baby, right? If you're selling to that director or that VP, you need to make sure that that executive feels like it's part of their baby and they're helping craft it and they have their fingerprints on it. And vice versa, like you want the C-suite. If they want, they want their actual users to feel like that they were bought in on this tail. Okay, so you wanna make this to be, and this is the tricky part. You want it to, there's gonna be someone that's gonna champion it and get the deal done. But you gotta make it feel like a group effort, okay? So the person that you had the intro call with, that's who you built the rapport with. That, that's your champion at this point, whether it's the C-suite executive or one step removed. I say champion, most champions are one step removed, but let's just say the C-suite executive has delegated this now to the champion to navigate. Okay, for that demo call, now before you do the demo, get on another call with them. Hey, I had so much fun on our first call. I think that there is a great opportunity to get to, you know, support you guys. This call should be 15 minutes, by the way. Okay, I'd love to do a demo, but before we do the demo, I wanna make sure we have the right people in the room and I'm demoing the right things. Can you help me understand from the conversation we had earlier? And as I'm walking you through, now I'm walking you through the product, what do you think would resonate with the team? Now you're collecting more intel, okay? Now there are the, now it starts to feel like, oh great, now they get to put their fingerprints on this. So it's like, okay, when we demoed to this group, at this point I want this question to be asked, can you ask this question in the meeting? 'Cause I want them to understand the values, and they'll be like, I'm actually gonna ask this question 'cause it's gonna resonate more. So now you're building this demo alongside this internal executive and none of your competitors are doing this. No other startup you're competing with is taking these extra steps. You now have the alpha of the intel they're giving you from these conversations. And now they feel part of this journey, okay? Now they trust you. So it's like, okay, so now you're spending 15 minutes trying to figure out, okay, or 30, right? Sometimes they won't give you that much more time, but us for 30 is probably, do 15. And say here are the five different things we can go into. From our first conversation, it sounds like these two things matter, but let me show you all five. And then they might say, okay, I want you to do those two that we spoke about, but I also want you to show this because this is also part of our mandate, and this will make you feel holistic, okay? So now you just mapped out the storyline with an internal partner on their end. And now you have the names of the right people. Now you're going to close that call. Great, is there a time we can look at everyone's calendar and put this on the calendar? Make the meeting an hour. The demo should be an hour, okay. Now you can ask, before this meeting, do we want to do a pre-demo to maybe someone else on your team that would be excited by this, before you race to the group demo? Or should we just do the group demo? Like they know their organization better than anyone else and like how pressing this need is. Now if they're less mature in knowing if they want something like this, they probably want to bring in someone else before a big group. If they're like, no, no, no, this is something we want to, you know, really move into, they probably are ready to go into a group. So you just need to figure out where they are on that maturity arc of their decision. Okay, so now you have, do we want to go into pre-demo, do we want to assume they checked off pre-demo or do we want to do group demo? How often does that pre-demo happen? If you're, I mean, I try and push for it 'cause again, it's just more Intel. Yeah, so let's say, let's assume there's a pre-demo. Okay, so now you have a new colleague on the phone and you could say, hey, for five minutes, I was going to catch you up on the things that I just learned from so and so. What can you add to that? What do you think? Do you see how you're just collecting more and more Intel along the way? So now you're building the business case for them. Now they feel like they're buying not being sold to. Okay, so now you have two or three people at this point, already excited for the big group demo. The worst thing you can do in the sales process when you move into demo is just going to one straight demo with no problem. Or worse, a enterprise organization might reach out to you because they're going through a due diligence process to say, hey, we'd love to see what you guys have built when you present this to four or five people, don't do it. You're either a check box and you don't want you want to remove yourself from being a check box. Or two, you're about to demo your product with no competitive Intel. Like you just lost the deal at that point. Enterprise deals are one on this feel so close to who we are. It feels like it was built specifically for me. That's the whole game. Amazing. I love how just how much alpha, not only you're sharing with us, like, it feels like the theme of this is alpha, just like the alpha we're getting from this conversation. It also feels like a lot of this process is you getting alpha from the team. I don't know if alpha is the right word, but. No, no, it is, it's information edge. Yeah, it's the information edge that whoever I'm up against is not getting. And you have to assume in the enterprise you're always up against something. You're up against not doing anything at all or you're up against a competitor who does some, or an incumbent, right? And most likely the incumbent. But it's so crazy to me how many people just like spew out a pitch with like no. You also have to make it informal and fun. Like you need to, you know, people also buy from people they like, right? I love how so far at least it feels very doable. Not that difficult. It feels like I could do this. Absolutely kind of. And it doesn't feel like it takes that much time to do any of these steps so far. It's like a call, learn some stuff, think about it. Is there any like times, time buckets that we, that aren't obvious of like where you spend like a bunch of time on your own thinking about something? Yeah, so I will, I spend so much time thinking about what, reading between the lines of what they were saying. And that's when I will follow up. Like those kind of pre-run calls before a big demo. Like I'm asked, I'm clarifying all those questions. Like, hey, I know you said this. Like, did I interpret that correctly? Like, is that the priority? Like, and then again, they'll go deeper. Like the more you infer the questions you ask, it's almost like you just have to keep prompting. It's the whole, it's like, it's you prompting humans at this point, right? Like go deeper and deeper and deeper and the answers you're gonna get are just gonna get so much more refined. All of this should be within a 90 day sales cycle based off of their maturity. So some people listening to this may sound like a lot of work. I imagine that this is what separates companies and products that win deals versus not. You know, you could have a better product, you could have a better price, a lot of things, but just not executing in this way through the sales process is probably shooting yourself in the foot. Or you're stuck at, you just sold the enterprise on a $15,000 solution, which goes, would you, how do you expand that? The whole game is expansion. If you're not going from 100 K or 250 K to 350 or 500 the following year, it's not an enterprise motion. - Okay, so just to kind of quickly summarize, we're at step one, landing the meeting, then running the intro call, then there's this follow up intro call, which you pointed out is often ignored, and a big opportunity to improve the demo. I love the way it describes the demo, it's kind of this carrot that you're holding and you can use a little bit to kind of extract more. And then there's step four is prepping the pitch and framing the demo. Is there more to share there? - No, I think we're at the point where it's like, okay, now you're running a big demo, right? - Okay, cool. - So now you have all of the people involved in the demo. You might have somebody that's involved from their AI team that's going to support some rollout. You might have somebody that you want all of the people involved in this decision at that table for the demo. That's how important it is to not rush it. Okay, so now you're running the demo. Now you're before that demo on one of those calls, who are all these people? What do they care about? And what should I avoid? The person that you've now built this relationship with can give you all of the intel. At this point, they want this to go forward. Now this is like a great star for them of like, I found this amazing tool. It's going to solve our problems and now I get to put my name on it alongside one or two other people, right? So for that demo, just make sure you know, exactly who's involved, what these people care about and what does this successor demo look like for them? I just ask them, be like, hey, people do demos all the time. Like, what looks good? 30 minutes of a discussion, maybe 10 minutes of showing, 10 minutes of discussion, 40 minutes of in the product. Like what do you tell me like what the organizing is? And on that demo, there's going to be people that were not a part of any of these calls. Okay? Your job is to take a step back and restart with here's who we are, here's why we're doing what we are doing and it's fully in their frame. You now have all the context to put this in their frame. So now for these net new people, they're like, holy shit, this was built for us. Sorry for my French. Now they're like leaning in and being like, okay, all right, somebody, this is very aligned with what we need. Because they've no idea you've talked to all these people. No idea you talked to all these people. Learn what their challenges are. They're like, they're leaning in and being like, this feels different. Now, this is also the whole part of like, it's being different. Not only is your product different, not only is your pitch different, the way you're going through the sales process is different. So it's like, wow, these guys are good. Okay, all right, so now you could, you know, let them talk. Let these net new people talk. I know you, I know we haven't had a chance to speak like, what do you want to get out of the demo today? I want to make sure I focus for you. Now you're leaning a little bit more into these net new people so they feel the love. Okay. And then when you demo the product, 80% of the value comes from 20% of the product. And you have learned on these previous calls, what that 20% is. Do not demo everything unless there are some reason to. Because now all of a sudden this tight frame, this tight narrative, you've just crafted and it's been all this time with. Just get thrown out the door because it's like, oh, well, I wouldn't use that. I wouldn't use that. Well, everything she just shared, that's really only over here. And you can blow the whole thing up. And the amount of times enterprises are like, hey, I'm not, I don't know if we want to spend this much money for half the tool that we wouldn't use half the tool. Now all of a sudden you just unraveled all the work you've just done. Enterprise sales is super, super, super tight project management. It's super, super tight narrative and framing owning that frame. Owning that frame to exactly who these people are. And that's why this role is so hard. Okay, because it's a lot of improv and it's a lot of leaning in and it's a lot of reading in between the lines. But like, it's stuff that is doable. I mean, it's just psychology. This episode is brought to you by Mercury. Radically different banking loved by over 300,000 entrepreneurs and now with command. I've been a customer of Mercury's for over six years. I have never once thought about leaving. Mercury is basically what happens when banking is built by product people, not by bankers. They make it so easy, dare I say fun to send invoices, move money around, set up virtual cards for folks in my team. Does your bank have an API, a terminal native CLI or an AI ready MCP server? I don't think so. And just recently they launched Command, a conversational interface built directly into Mercury, which acts as your financial operator. I've been using Command to transfer money around to figure out what categories I've been spending the most money in, analyze my cash flows. And just today I used it to find out how much I've made from a specific sponsor over the past year. I just asked how much have I made from X over the past year, 10 seconds later I've an answer. It is so freaking cool. Visit mercury.com to learn more and apply online in minutes. Mercury is a Fintech company, not an FDIC insured bank. Banking services provided through choice financial group and column NA members FDIC. How do you deal with someone that's just kind of taking things off track or just talking too long? I imagine that's just like a skill in an art, but just any tips there. The good news is, is that most senior people, like the people that you're doing your outreach to, it's very hard to get to that title if you're like verbose and long winded and like take things off track. So that's the good thing about being going after executives is those people are like really dialed in. Like no one takes a meeting off track at an executive level. Now, of course, there's sometimes where there's people that meander. You could say, I love this conversation. Can we park it because I actually want to spend another call just dedicated to that. And if that if that if that needs to happen, then of course you can run with that. Awesome. So there's kind of two people that might be leading this might be the founder. If you're still doing founder of sales could be the AE be a VPS sales that. Yep. Okay. As say you're say you're not the founder and you're. And you're the VP of sales or any leading this as a founder. What are some signs that your salesperson is not doing great job up to this point. What are just like smells of like I should really say like what is the timeline from intro called the demo. How many conversations have happened between those two between those two buckets of like when people advanced stages in the sales pipeline. Can the salesperson articulate exactly what they are going to be demoing why they're going to be demoing it and how they're going to open it. The demo looks different every single time every single time. I don't think I've ever run a demo and it looked the same. This is like when everyone comes back to like okay what's the scale playbook what's the scale approach with this when you're selling hundred thousand dollars minimum right again it's the same effort is selling a million dollar so it could be selling a million dollar deal. It is it's hard you're you're cracking some of the largest logos that every single startup goes after you've got to be different you've got to take a different approach. It is not cram the pitch down their throat and hope that they want to buy something feels like a job AI will not replace any time soon. Yeah I don't I do not I'm not worried about AI replaced because there's so much about it that's just human right like. Do you vibe with this person I mean I've definitely taken intro calls with a person probably did not appreciate with how I ran it and that's okay it was just. What happens it's such an in a point of never heard before this idea of when you're demoing it demo kind of as narrow a slice. Of the product as you can that addresses their priorities and needs because to your point they may feel like why do we need all this stuff we just want this one problem. And that's shooting yourself in the foot or let them guide you like can it also do this and be like oh it's so funny you say that we just released this and now all of us feels like. It's again built for them they want to feel like it was built for them and that it's different and they get alpha and get off. Okay so step six you call the post demo discussion yes also something you say everyone ignores yes talk about that okay so as soon as the demo closes you are texting the woman or the gentleman or whomever that is help guide you to this point. How do you think that went can we grab can I call you in like five minutes I just wanted to I want like a fresh debris. They will give you a big raw reaction I know you haven't spoken anyone what do you think how do you think that went do you think we need to go deeper with anyone. Before anyone like solidifies kind of everything that said like where where did do you think we lost somebody where do you think we did well. Is there someone we need to spend more time with. There's always someone in the organization that's going to kill it y'all there's always somebody. You need to protect that as much as possible and make sure everyone is aligned and excited by what this is and again the more intel you collect on these people. Because again it for some reason someone goes quiet for two weeks or three weeks you can now prompt with hey I know you guys are in the still in the process of like thinking through this makes sense. Do you think it's worthy if I found fifteen or twenty minutes with said individual to just like hear their thoughts and maybe we can and maybe we can approach this a little bit more closely with how they would want to see it. It's always looking for ways this might explode a network and and this person that you're working with what would you call them what would what was the term use for them. It's champion champion yeah the champion also be an executive right. Yeah and they may and they're like excited at this point in theory very excited for this to work out like earners on your side they're not trying to. Yeah and I define champion is who's the individual that really wants this to come to life that's like was there from day one not necessarily like the person that's. Like the C suite executive could be the one shepherding this well but they need to make sure that the people below them are brought in. Okay anything else around the demo or the post demo discussion before we move on to the next no thing we're good. Okay so the next step you call identifying pilot move forward process. The best thing you can do assuming that you've built an incredible solution right if you're if you're if you're now this far in right you usually have something that they allow them. Now you can control the time on about hey I want you guys to go in for two to three days the specific users and don't put the do not put your sea level executive into the product they're not the user. Okay who are the users of this I want them to experience the magic and the power of what this is. Don't charge you could charge them for a pilot if it's an extended period of time but I'd rather for go the money and do a two to three day pilot so that at least I can control the sales cycle a bit more. Okay but again if they ask for a month and there's a good reason for it do charge for that but I usually would I'd rather. I'd rather go in for two to three days and let them see if they can get the value from it if they can sometimes I understand that there needs to be some level of configuration and. You know, extensive on. boarding that needs to happen, but is there a sandbox where they can assess the value? Even if it's not on their own data. - So this isn't yet the pilot, this is just like prepping for the actual pilot. - Correct. - So there's two different pilots you can run. A pilot that does not require their data to be in the product to get the value, or a pilot that you want to charge for because they need to see some level of like integration on their end for the whole product to actually work, right? Like I understand that those are two very technical things. Let's talk about something that they can get in two to three days, and it's pretty much of a light left. Time box it to two or three days, don't make it two weeks. Okay, I've done this enough times to say, people will go in usually for half a day and get what they need out of it. Okay, shorten your sales cycle by two weeks, by doing two to 48 or 72 hours. Now, if you need something a bit more integrated, and it's a far more technical solution, what I'd highly recommend is do a for a month or two months, charge them for it, and then use that fee that you charge them for, and credit it back to them if they move forward. Okay, if they're willing to pay, that is a huge, huge signal, especially if you're about to put in all this work. They have no problem paying for it. It's usually probably gonna come out as services anyway, 'cause it's like a, they're not buying technology, buying the services, go through it. And also, make it a credit on the back and don't start the relationship shift, start the relationship off on a good foot. - I'm definitely feeling the feeling and I feel when we chat is like, I just wanna fight some to sell. - Yeah. - This is really fun. It's so fun. - Fun, yeah. - Like it's literally so fun. People, I think people read these sales books, go to these sales trainings, and they try and take someone else's game and run with it and never works that way. Like, don't talk me this. I was just like, okay, if I collect more intel than the competitive set, that will be my special sauce. - And it's like, more fun that way. You're building a relationship more, chatting more often. You're not trying to just like- - Yeah, speed rocking. - It feels more real. - Yeah. - Yeah. - Okay, a couple questions here. One is this idea of the two to three day pilot. How do you convince them? You only get two to three days 'cause I feel tough. - So I would say here, this is what we typically do. Who are the three or four people we wanna put in and assess the value from user perspective, okay? Make sure it's your person, right? Assuming that it's no, or the person closest to the seat. Don't put your C suite executive in it. They're not gonna go into the product. And then two or three other people, okay? And I want you to say we're gonna do two or three days. I'm gonna onboard you each differently. We're gonna do two or three different like onboard sessions before those two or three days. And I want you to go in and I want you to do these three specific tasks. Be very, very thoughtful and explicit and descriptive with what you want them to do, okay? Here's how we're gonna measure success. Define that with them. Define that with co-author that. And that's no different than the thing that's a little bit longer where you require that integration and build out, co-author it with them. What does success look like? What are the specific things they should be doing? They should not just be logging in and meandering. That puts the work back on them. Your job in sales is to take all the work off their plate. 99% of it. - And help them discover the magic releases. - Help them discover the magic and also continue to, you might have one of those users that's like, oh, I didn't like it. Great. In that three stage process, what didn't you like? What wasn't clear? What wasn't obvious? Where did you get lost? The tighter it is, less people get lost. The more grounded it feels and the more consistent the experience is, you don't want people having different experiences. - Okay, so just to make clear the steps involved here, 'cause we've gone through, I think, three kind of around so much. - Yeah. - We've gone through so much. So we're kind of on step nine. So there's a step seven, which is identifying the pilot, move forward process. A lot of people ignore just like who that person is and what the steps are. Then there's prep for the pilot and then there's run the pilot. - Run the pilot, exactly. - We can't talk through all these things. - Now. - Is there anything else long? - For the pilot, the one thing I want to say is, okay, before we put everyone in, let's work backwards of, if this is successful, how do we get this deal through? Okay. - I had a time before doing the pilot. - I had a time. - Yes, I had a bit. I should have clarified it. This is all before, before the people's pilots start, this isn't the prepound stage. Okay. Assuming fingers crossed a successful pilot, which I feel confident is gonna be, one is, when do we wanna get signatures on these papers? Let's work backwards from there. Do we think we can get this closed by the end of next month? Yes, I do. Great. Who needs to be involved in that? Like, do you have a procurement lead that we should be educated in this process? And they might say, let's wait 'til after the pilot totally. But like, push them a little bit. Again, your project managing it. Is there a security lead we should be working with to run due diligence on the product? Is there someone in legal or is there a way for me to draft the paper to make this make sense? Now, the one thing I'm gonna take a step back on is you would have already gone through pricing discussions with them post-demo, okay? Try to hold out on talking about pricing until post-demo because you might, they might assume, oh, this is three times what I'm spending and not know why it's three times. Because there's all these other people that might not have been involved in those initial discussions. Talk through pricing post-pilot once everyone's excited. - Post-pilot or post-demo? - Post-demo, I apologize. - Okay, cool. - Yeah. - So you basically just kind of tell them, what's, we'll figure out pricing once we understand what you're looking for. - Okay, this isn't a pre-pilot stage. Talk about pricing, okay? - Now, if they're this far along, they, like, if they're really concerned about pricing, they would have brought it up by now, right? So these are like the little cues, like, okay, I think I could probably push them a little bit here, right? Or like, go a little bit further. Two is, if they ask and they push, they give them a ballpark. Well, it depends, but, like, let's say it's somewhere between 150 and 250, and there's a lot of dependence on that, right? Um, so you can give them a ballpark. But work with your champion and say, listen, here's what the price is. You, I know you know why we price it this way. Where, before you put this in front of anybody, how are you gonna make the case? Right, like, where are you gonna cut? How are you gonna defend it? How can I build out a slide to defend this for you and show you the ROI? Let them, they will tell you. You don't have to go blind into it. And then if they come, and then say, okay, and if they push back and they're like, listen, I don't know if I can go to bat for this. Be like, I hear you. Let's, let's work on this together. How can, what do you feel comfortable going to bat with? And can we do a step up for year two to get to the actual full value of what we know we charge? And do you include this slide or the price in the demo or is that like a post demo conversation? If they push you to do it, give a ballpark. But do pricing one-on-one with the individual you've been working with? Because they will help, they might say, okay, I think this is, I think we're all aligned. This is what's usually gonna happen, there's three answers. We're all aligned, I'm not too concerned about this. I don't know if I feel comfortable going to bat with this number. That's when you say, okay, I hear you. Let's take a step back. Let's figure out how to make this work. Don't say you're gonna discount. Don't throw out numbers. Be like, I want you to, I need your help to tell me how to make this work. Now, this is the one part where you wanna put it on them, because they might come back and say, is there any way we can cut 20 K? And you're like, oh, I would have gotten much lower than that, right? You don't want to negotiate with yourself. But work with them. You got into this point, you've shown so many people. Everyone's excited. This is when you know you can win them over through the co-authorship. And remember, you can always do the full value in year two and sign a two year deal. - Awesome, they expand. - Okay, so in the pilot step, do you, how many people do you give access to the pilot and advice there? - Three, three to four. - Okay, it's very small. - Very small, very tight. Who are the power users? Who are the people that are gonna be on an daily level? You don't want everyone in there. You want it to feel like they're buying into it too, not like the same people and the same. But you do want your, that one individual that's been giving you all this in total to be part of the pilot because you want them to get you prepared for everything. - So before we get to the next step which is post-pilot discussion and session, I mentioned many products, especially today, just take a lot of integration work and data ingestion and all that stuff. This whole FDE emergence, thoughts there if your product is just like, wow, it's gonna take us some months even to get you onboarded. - And that's when we talked about those two different pilots, there's like, hey, we can share you the value into two to three days or it's the, hey, we have to show you the value in 30 days. For the 30 day value, charge and credit it back to them. But know that your sales cycle is gonna probably be a month longer because of that. But that's okay because you're probably charging more anyway. Got it and just do the work to integrate enough to make it magical. - Your price should be predicated on your sales cycle, right? Like if you can get a deal done in 90 days for 100K, do that all the time, right? If it takes nine months to get a deal done, you probably should be charging 250, 300K. - What are your thoughts on four-deployed engineers as a part of this process, just as a role? - My opinion sway back and forth, like is a four-deployed engineer there because the product's super hard to navigate? Or is it there because you're taking the work off their plate? I think people use them. I'm all about it if it's taking the work off their plate and accelerating and controlling the situation all day every day. But are you using a Florida-deployed engineer because your product's so gnarly and hard to do? Like, they can't do it on their own. - It's a bad sign. - Yeah. - Yeah. I feel like the original idea of a Florida-deployed engineer, and the Palantir guy's talk about this. The original idea was they work inside of your company building custom software for you to solve your problems. And then they figured out how to make that a broad product they can sell to other people. - Oh, and I think that FDE is great for an expansion for a land. - Okay. If you're talking about a Palantir where it's much more complex to, like, I understand why they did that, right? But they're also charging multi-million dollar deals. - That's right. - Right. So, like, the business model structure supports that. If you're selling a hundred thousand dollar deal and you're pulling a four-deployed, like, your economics are, it's gonna get messy. - Just, like, you will not make money if you have a full-time engineer salesperson sitting working on this. - Totally. - And, you know, I think, I also know, like, there's a lot of folks in, like, account management who's job is to service and, you know, expand and upsell. And they just take on the title of FDE. So, they're just another salesperson. - Yeah, it's just a nice, yeah, it's a cool title. I think the Palantir people call the hefty use at most companies sparkling sales engineers. - That's awesome. - Yeah. Okay. Anything else on the pilot up to the pilot step before we get to the post? - I think, I think, yeah, I think, because now you've talked about, like, the timeline to if this is successful, what does that look like? Again, you want to run this before you put everyone in it because you might want to push out the pilot. If they're like, hey, listen, this is probably going to be another quarter. Well, put the people in the pilot now 'cause now you've lost all the, you need the momentum to continue. You need the steps to happen. So, use that, hey, if this is successful pilot, how far out are we from, like, a commitment from you guys? - Oh, I see, commitment. So, there's, like, the commitment and also just, which is equivalent to rolling it out to the company, if they're not ready in a month to roll this out. If this is a huge success, then wait, undoing the pilot. - Wait, correct. - Yeah. - Awesome. Because you're saying you may lose them and you're like, you've already exhausted all the stages, you don't want to do that. You want the stages to align with how they're thinking, but you want a project management as tightly as you can. And something that's out of your control, but yeah. - And yeah, it's not like you can push them to deploy it broadly. That's like a thing that is probably very hard to shift. So, yeah, it was understanding that and working with that seems really important. Okay, so step 10. And again, as you pointed out at the beginning, most people think the sales process is five steps and we're already in step 10. And we're not even done. And you made this point actually before we start recording that you haven't touched on, that I think is important to share this idea of that. These five steps kind of emerged out of like a CRM pipeline, kind of check thing. Talk a bit about that. - Yeah, so everyone knows that traditional five steps, intro, demo, proposal, contracting, and then like close one or close loss, right? Those are like the typical, maybe there's like some variation of that. Like that's not how you run the sales. Those are buckets to understand how to understand a weighted forecast, right? Like a proposal or something mid funnel might be weighted at 50% of the deal value for the pipeline. Something in contracting might be weighted at 80%, and something in intro might be weighted at 10%. That's what those stages are for. That's not the stages you take a client through. Like those are just the broad buckets. And I think a lot of people use those buckets to say, okay, there's about five different meetings that need to happen. When it's like, no, there's like three meetings, maybe up to five meetings in each of those buckets that are critical to get the deal done. Now we're still speaking at it at a very macro level. Like obviously selling a million dollar deal, you wanna have more of those upfront meetings. And you wanna make sure you know who the executive sponsor is and all that. You always wanna know who the executive sponsor is. But like for 100K deal, you probably can accelerate it a little faster. Again, ensuring that they're qualified. - And they've worked with a lot of founders and sales people over the years. What percentage do you think are just doing it wrong in that way in treating it like this five step process? - 90%. - Wow. - Yeah, because like enterprise sales, it's mirroring their buying process. It's trying to control their buying process. It's not plopping these people into your sales process. - Amazing. - Yeah. - Okay, let's keep you on. Step 10, post pilot session. - Yes. You can send a survey. They might wanna send a survey. Get the intel. Or one-on-one to each of these users and say, hey, or let your champion. I mean, there's a few ways you can do this. Or you can have your champion internally discuss and say, hey, how was that? You need to make sure that you are mirroring their experience. From a technical perspective, how much time did they spend in the product? Did they run into any bugs? What were they using the most of? Because you need to be prepared of going into that call to say, hey, I know we gave everyone those three things, but most people only spent it on two. Why? And that'd be okay. But you don't want them to be like, oh, well, we wish it did this. Well, yeah, but no one spent time on that. You do do that, but no one spent time on that. So you just need to control also that you're capturing what they did in those pilots. And making sure that you're sinking up or you could go to your champion and be like, hey, I know someone so logged in for like 15 minutes today, they didn't get past step one. Don't tell them what they're doing. You shouldn't even be that, but like, they didn't get past step one. Do you want it? Can you check in on them and making sure like they're having a good experience? Like use your champion to like, again, they've invested so much time into you, guide them with where they should be focused as well. Because at the end of the day, getting a deal done at the enterprise, it is set up to have as much friction as possible, right? There's a people that will kill the deal, then you got to deal with procurement, then you got to deal with legal, then you got to deal with finding the executive sponsor, right, which usually comes in the very top of the funnel, but there's so much friction to get a deal done. The project management and the individual on the inside, that's your key. - So funny. So many ways that could all fall apart. - Yep. - What I was going to say is it feels like many people would naturally, like they want to avoid confrontation. They won't want to say this is not going to be, we don't want this. They're going to probably be like, - Yes, fine, it's good. - Yeah, everything's good. - Just like PCs. - That's right, that's right. And so it feels like a lot of this process is still like pull out. Okay, here's the concern, here's the problem. Are there any other signs of like, okay, they're actually not interested in like, this is not going well in a year, really. - When you're, this is why your internal champion is so important, when they go quiet on you, that's when you know. That's why this individual, and listen, this individual is going to do you, if they've spent enough time with you, they will call you and be like, listen, if I'm reading the tea leaves, we should sit on this for a minute. Let's repick this back up. That's why having someone on the inside is so, so, so critical. - And yeah, these are your approaches just to stop responding and just hope that they, the salesperson understands very little, not excited. Oh man, okay. What are like the benchmarks for like, how often do you get through each of these stages? You mentioned like a few, just like, yeah, from demo to the stage. - Usually once something is qualified, meaning you're speaking to the right person, they are excited by the alpha, they admit that there's change that needs to happen. Notice I didn't say problem, but change. People get so fixated on problems, which are important, they are important, but like everyone speaks to the same problem and then it commoditizes you, which is why I don't like to like overly emphasize it. The win rate for enterprise, a good healthy win rate, is actually probably going to surprise you. It's not 50%, meaning of all sales qualified leads or opportunities, a healthy win rate is usually around 30 to 35%. - From qualified leads to signed contract. - Meaning you speak to a hundred, you're closing anywhere between 30 to 35. Maybe slightly less, maybe 25 to 30. That seems high actually. Yeah, 25 to, somewhat between 25 and 35%. Why? If you, if your win rate is higher than that, your price is too low. There's a lot of part of the market that's just not in a maturity perspective to take you on. And that's healthy. Right, those are all the chasms. - And the implication here is it's better off keeping your price high than winning more often. - Yes, because the market talks too. Well, the worst thing you can do is charge somebody's friend 50 and somebody else 500k. They talk, people, the market talks. You have to assume that. - Yeah, I'm in a lot of what's up groups of founders and they do exactly that. - It's what kind of deal do you have for this product? - That's exactly right. So then assume the market talks, especially at the corporate executive level. And someone might just not be ready yet. And that's okay. The amount of deals that come, that boomerang a year later of the ones that have lost, that's probably another 25%. So it is totally normal and natural for deals to not advance, right? But to a healthy win rate in the enterprise is typically, I would say between 25 and 35%. - Okay, that is incredibly helpful to people. A, I know, I've had like key stages along the way, just like percentage drop off up. - So it's usually like from qualified lead to like, you're coming out of demo. It's probably, you lose half. And then-- - Out of demo. - Out of demo, yeah. - Post demo, not first. - Yeah, I get you to 30%. - So from demo to, what was that step that you lose? - From demo to like, the more you move down - Too close. - A little bit less those numbers, the less wider those numbers. So like-- - Okay. - So like, let's say if you speak to, and you're doing a really good job targeting the right people. Maybe 70%, 50% of those people move to a qualified lead. Or 50% to 75% move to qualified lead. Of that, then another half move to demo. And then from there, another quarter advance beyond that. Once you're in the bottom of funnel, you usually don't lose too much from there. If you're doing-- - So like, - With deal qualification. - So say you're at the pilot stage, what percentage should you expect drop off? And are no-- - 80%. - 80%. - 80%, succeed. Post-pilot. - 80%, correct. - Yeah. - Okay, amazing. - I find that, yeah. - Okay, so if you're below that, something's wrong with your pilot. - Yeah, or you're not qualifying clearly. - I see, yeah. - You're almost doing too good a job convincing them. This isn't the thing for them. - Correct, and the product's not there, correct. So yeah, that's where, and again, like smart buyers always want to do a pilot, so just have a part of your process. - Okay, there's four more steps to go before you're done, before the money's wired. Okay, so step 11, papering prep, setting timeline for procurement. - Yes. - So you have now spoken pre-pilot about the timeline of what you were reverse engineering. Now you're gonna document it in an email, so that that champion that you're working with can forward that to procurement to say, hey, here's what we agree to. Here's the pricing that's predicated on us, getting this signed by the state. Here's the give them something. Here's the kicker they're gonna give us if we get to the state. There's always gotta be a reason to create urgency. And then what you wanna do is say, here's our paper, send a word document. Do not send a PDF 'cause they're gonna always read line. Always, send a word document of your paper and ask the question, do you wanna use our paper? Here's a word doc version, or do you wanna lift from it? And do you wanna use your paper? It might be a lot faster to use their paper. That's why you give them the option. And that's why the timing isn't there. Because they might say, well, in order for us to hit that time, we gotta use our paper. And it's not Google Docs, it's word like Microsoft Office. - Microsoft Word, yeah. Most of these people can't access Google Docs, but yes. - And so this has post-pilot, feels like it's gone well. You're saying the next step is here's like the contract, basically, get that to procurement that early. - And again, your internal champion is, you're working from N-1 from the executive sponsor, or is the executive sponsor themselves? - You wouldn't have made it. They're not gonna put their team into a pilot if it doesn't have likes. - And an implication here is procurement is a way that your deal might still die, even if people internally love your product. - Correct. If you get sent to procure, so here's something interesting that a lot of people don't realize. People will use procurement as the excuse to not wanna give you the bad feedback. - Oh, I gotta go to, oh, procurement, it's lost in procurement, or blah, blah, blah, blah, blah. It's very easy to blame procurement. Usually procurement is like a 30-day process between the back and forth on the legal, the paperene. Procurement's job is not to kill the deal. It's just to make sure that it is aligned with how they need to buy. That's their job. Procurement is the only person that can get you paid. Do not start any work until you go to procurement. Business unit leaders can't just pay you. That needs to come from the finance team who pulls from the budget. So be very careful, don't start any work until, obviously, the papers are signed. - I start work meeting implementing, rolling out people on board and got it, got it, got it. Okay, amazing. Okay, so that's step 11, papering prep, setting timeline for procurement, kind of getting on board would like, what is it gonna take to sign by the state? Here's a little gift you'll get if you do it by the state, free, month or whatever. Okay, step 12, papering review. - Yes, the best thing you can do is, they're gonna send you back red lines, no question. If the red lines are extensive, okay, go ahead and accept the things that are easy. If the red lines are extensive, see if you can get legal on a call live and just talk to them. That will accelerate your sales cycle. - First is a bunch of back and forth, you know. - First is a bunch of back and forth. Get them on a call be like hey, everything, we're 80% of the way there. I have a few questions based off of your red line. Can we jump on a call live call and just go through them? Focus on the things that are gonna impact the business and pushing on those, let the other stuff go. If it's not super important. Obviously have a lawyer, look at it from your side. You're dealing with a commercial legal team, have a lawyer look at their red lines. - I mentioned most companies have legal counsel. - Yes, I would hope so, yes. - Okay, cool. So paper review, so that's reviewing basically. It's interesting called the paper. - Yeah. - Is there like a more technical term for that? Like the. - Contract? I say paper, that's like corporal language paper. - It's so interesting. - Okay, paper in your paper. Okay, step 13, papering procurement process. - Yes, so this is where we kind of talked about this. We kind of emerged that conversation. This is when you are getting the procurement lead and that legal lead on a live call to work through the questions or the things you cannot accept. Now remember, if they give you their paper, there's going to be a lot in there that you're going to need to. - Red line. - Red line. They're expecting that. They're just giving you the kitchen sink, right? Like if they ask for $10 million of liability insurance as a smaller company, you can push back and be like, listen, your exposure with what we're doing is not that high or maybe it might be and you need that. But they're going to give you the kitchen sink, know that it's all negotiable. But pay the battles, figure battles. - Yeah, don't be afraid like the deal will fall apart if you see something in there. - At this point, the deal will not fall apart. You just need to work closely with them to like, make sure they understand where you're coming from. That's more what it is. - Okay, and the final step, signature, ta-da. - Yep. - Anything special other than signing. - No, this is like the really exciting point, which is just figuring out who the signatory is. - Before it goes routed for signature so that you, that you make sure your internal client knows, you know, 'cause sometimes it's the CFO. It's not the executive sponsor. I just want to make sure you, everyone knows who that individual is because if there's a delay, you just want to make sure they get pinned. - Damn, we did it, Jen, we did it. We got through all the steps. We just signed a massive contract. Congratulations, Cisco. - Yes. - State dinner, champagne. I don't know what's else people do when they close the deal. Dingabell, there's bells often. - You know what we do? - Okay, what's the next one? - That's it. 'Cause you're all, you are in sales. You're only as good as your pipeline. - Hmm. So fun, it must be the best feeling, after all this stuff works. - It is, but then you're like, oh, now, like literally the fuels is like five minutes and you're like back to work. - Yeah, and I imagine part of this is also how do we expand this deal? - 100%. - Is there anything there just real quick, just like how to start thinking about how this where this goes once the deal's signed? - Yeah, and this is where I think the expansion comes in, you either know the products that they can expand into, like you've been through this journey before and that's pretty straightforward, but if you are early in the journey and you're closing your first 10 enterprise customers, you need the founder involved once these people are in to understand like what part of the product is custom to what these people need and do we want to build out, you know, do we want to charge for services? Again, here's the other thing too, services, and I know that every company is an ARR recurring revenue focus, that services is still the largest line item in budgets. - And so you're saying it's okay to offer services. - It's okay to offer as a part of this, yes. - Yeah. - Yeah, this has come up a number of times, I think with Jason also, Lemkin, and you just like the increasing, there's a rise in services being a part of software companies. - It's right, so they know how to buy. They're so used to it. - Consultants, lawyers, you name it. The budget, there's always budget for services. - Yeah, we talked about this last time, so we will get too deep into it. Something else I wanted to ask you kind of at the end here, say you're a buyer and you're, say you're talking to Jen and you're just like, not sure this is a fit, you don't want to disappoint, you don't want to drag you along. What are some things that people buying software products, working with a salesperson? How should they communicate? What should they be saying to kind of avoid disappointment? - Yeah, I would say as soon as humanly possible, explain why the timing is not right. It usually comes down to timing or why they're not mature enough to be able to be in a position to, it's interesting. You have to be your organization and the team has to be structured in a way to bring on the technology. technology. Like there's a maturity you have to go through. Now I know we talked about this before, where sometimes it's easier to sell the service first and then do the technology and counsel them towards the technology. But like if you are in a, if your sales maturity in the enterprises further further down the road, you want to start with selling the technology versus the services. And if you talk about how it's not the right timing or not mature, imagine the sales person will try to prod you and push you to see if maybe you're not so it's okay to just sell them way things. Yeah, and you know what you can get like I've had one, I've had clients say to me like, Hey, like I don't know if we're in a position to do this and I've straight upset to them. You are a liability not closing this gap. And they're like sometimes they just need to be like, again, you need to know if you're in a position to be able to say that. Yeah, listen, I know you need this. I know you need this. I'm not accepting you know as an answer, how do we figure this out together? Because because again, use the intel they've given you towards that. And like interestingly, you're talking to a lot of their competitors. And you would think you have insight into, okay, here's whatever else is doing in this space. Well, exactly. Or like, Hey, listen, on our first two calls, you told me how important this is. Did that change? No, we're just like in a weird spot. Okay, listen. Here's what we're going to do. Let's start a little bit smaller. Let's get in. I know you admitted that this is something that you guys need. I know that we are going to crush it for you. I do not, I don't want X to get in the way of that. And there, and then there's obviously they're going to be the cases where it's like, it's just not the right time. Like they might be going through an acquisition, right? And like bringing on net new vendors is just like not a priority right now. You just have to respect that too. I love how this whole process, a lot of listeners as podcasts are product managers, product people. It just feels very product, the product manager in terms of the organization and the step by step and just like, or just stay on top of all these little things. Like it's so interesting how you don't think sales and product management are at all alike. But they're, but they're so similar. And it's just like you being human like the way a PM tries to understand what your pain points are. We're here to solve them. Yeah, like it. Yeah, unexpected. We did it, Jen. We did it. We went through it all. Is there anything else? Anything else we haven't touched anything else you want to, I don't know, leave listeners with before we wrap up. We gave them a lot. We did. Which was the goal, just the right amount. Yeah. Yeah. I'm excited for like, oh, I was going to say I, I love that AI. I don't think it came up one, maybe one time in this conversation. Very rare these days and podcasts, which I love. Well, it's interesting. Like so many people will create like AI reports that they can send to their clients or like AI imagery or like, I don't know, you name your, your flavor. And it's like, anyone can do that. It just feels salesy. What's your alpha? They always come back to that. Exactly. And I know you're talking about this last time, just like craft your own email and text don't don't use the boiler plate. Yeah. Mills are living and breathing. I swear to God that like people can read you saying the email out loud. Yeah. Okay. Jen. This is awesome. This was amazing. Everything I wanted to be this is going to be I'm excited for like that. Not to talk about it, but just like AI summary of this, especially that's just going to be like step one through here. Yeah. Final questions. Anything you want to plug anywhere you want to point people to and how can listeners be useful to you? Let me know if anyone has questions. I'm more than happy to go deeper into this. I would say if anyone, here's a plug, if anyone is interested in enterprise sales, we are actively hiring. And I will teach you everything I know. Wow. And this is at state affairs. It's at state first. Holy shit. What an opportunity. Yeah. So there's multiple roles, not just one multiple roles. Yeah. Wow. You'll be paid to learn from Jen correctly. Yes. I will. I will teach you everything I know. Whoa. Okay. Cool. We'll link to the job descriptions in the description if possible. I'll check that out. Awesome. Amazing. Jen, thank you so much for being. I need this was awesome. So awesome. 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 view 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.