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

0:00 So we're gonna do something really unique. With this conversation and basically go through the enterprise sales lifecycle step by step. Let's set this up. Let's start with how do I even get the first meeting. We are 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 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

0:43 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 thirty to thirty five percent. 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? The 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? Ninety percent. Wow. Like it's literally so fun. People read these sales books, go to these sales trainings, they try and take someone else's game and run with it, and it never works that way. Most people think the sales process is five steps. And we're already in step ten. And we're not even done. The worst thing you can do in the sales process is Today, my guest is Jen Able.

1:36 This is her third time on the podcast. For those that don't know Jen, she's co-founder of Jellyfish. Gym 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 Fenderlight sales.

1:52 In our second conversation, we focused on the one million to ten million dollar 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.

2:05 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'sProductPass.com.

2:40 For a free year. of the hottest and most beautifully crafted AI products in the world, available exclusively to Lenny's newsletter subscribers. With that. I bring you Jen Abel. Jen, thank you so much.

2:55 for being here. Welcome back to the podcast of very rare Third visit to the podcast, how does it feel? Round three, super excited to be here, Lenny. I'm even more excited. So we're gonna do something really unique.

3:07 With this conversation. I've never done anything like this before. We're gonna basically go. through the enterprise sales Life cycle. Step by step.

3:17 You'll talk about this, but many people think it's like five steps. You talk about how there's actually something like fifteen steps. A lot of people ignore a lot of these steps. And the idea is I wanna create a very concrete And um Tactical playbook. For how to do enterprise sales.

3:33 Okay. All let's that's the goal. Just just suck'em all out. Make everybody amazing at sales. It'll be great. Oh, um. And you know, this touches on just like why Well I think the podcast is really helpful to people and just the valley vibe, even though you don't live in the valley.

3:51 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? Uh, but maybe actually let me ask you that. Just like why why do you share these things? Well it's so interesting because Дерсомач арт тис, да і гв самое фітін степ плейбук. There there's so much of a a feeling that you have to go off of, like

4:13 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 gonna 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.

4:32 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 fifteen steps, while it's eighty percent of it. The other twenty percent 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.

4:51 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 h the if you sell a hundred thousand dollar solution, it is the same exact process.

5:08 to sell a million dollar solution. So That's why uh It's it's an interesting process because the enterprise organizations

5:19 Are more sensitive to the process you take them through from a sales motion. then they almost are with demoing the product. Amazing.

5:29 And I'll just give a plug for If people want to Continue learning your Twitter feed is just the best. Yeah. If you share all this stuff constantly. Yeah. And I think you you talk about there's like rational reasons to show the 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.

5:47 I I know exactly what you mean. That's why I started writing. I started I was just like I just want to remember this stuff myself. I'm just gonna share it. And crystallize 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 of what we're gonna be using here?

6:03 Let's use a company like SpaceX. Right. recently you know has seen massive news pressing It uh you know, everyone's probably targeting them. Right. So it's gonna be a hard logo to go in and and win.

6:17 Um They are a technical organization. But I think what we do is target a non-technical team. So we're gonna like really get into like the nuance of this. So Let's do space X. Why don't we pick legal?

6:32 Let's have some fun with legal. Interesting thing about legal, it's the largest budget line item in the Enterprise Uh But

6:43 Kind of budget. Right. Sometimes three to four times other budgets. And it's for ever There's always more money for legal.

6:53 That's why there's so many legal AI startups. I get it now. Hundred percent. Amazing. And I I'll just add the reason like the reason I love to have you on this podcast is I've oh I've left both of our previous conversations So just like fired up about selling.

7:08 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 sales. You're a master. You're actually a master at us. Sales is marketing. Marketing is sales to some extent, right? And I feel like you're using some sales technique on me to make me feel good about myself.

7:28 Okay. Anything else before we get into step one of the sales enterprise? No, I think this is good. Sale cycle. So space X and targeting. The legal function. And then like a hundred K let's say deal. And to your point. It's the same process, whether it's a hundred K.

7:43 A million. And I will add Uh plug for a previous episode you talk about why you wanna be at least a hundred K Something as a deal.

7:52 Uh A real enterprise. Company. That will li that will survive. Yeah. The R Y in the

7:59 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 OpenAI, Anthropic, Cursor, Replit, 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've felt the pain of integrating single sign on.

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9:14 Where does Where does it start? How do you start selling someone on your product? It's a great question. So I think we'll 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.

9:33 You have the top of the rung, right, which is the the general counsel, the head of legal, uh, the chief legal officer. They ca all kind of had slightly different titles, but they all carry the same weight, which is like who's the who's the lead of the team? And then underneath that You had a Bunch of people

9:50 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 my entry point? And there's only two entry points. Starting at the very, very tippy top.

10:05 meaning going direct to the decision maker, the chief legal officer. Or Finding the individual That would be Maybe one step removed.

10:16 Okay. I personally other people would argue with this. I personally would not be targeting anybody else. Ізекутив themselves. Or an N minus one. Okay.

10:27 So let's talk about like why. In order for An enterprise dial. To move forward, you need to have this extremely compressed storyline. That lands immediately

10:42 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 like what exactly are you solving for them? As a problem that's one, that's level one, but most importantly the alpha. What does this executive

11:00 Uncover and unlock. By bringing in a net new tool. 'Cause bringing in a net new tool. Okay. Is risky.

11:09 No one wants it. So If we're targeting the chief legal officer in the N minus one. You get two sent two two to three sentences max. Okay.

11:19 That might be through an email LinkedIn, that might be through a phone call, that might th be through An event? Um Or that might be through some marketing Capability.

11:29 Most ch most C level executives don't respond to marketing. They might see your brand, they're not gonna respond to a marketing campaign. Okay. It will respond one on one. And the

11:39 Best individual. to one on one to a corporate executive is the founder. Even if you're a series B, series C. Right. Із the founder shobbi ecstatic.

11:51 To want to get in front of the chief legal officer at SpaceX. I think any founder that is Um you know, building something really meaningful knows the important important role of that. Second

12:04 is you can get your enter your um AE or enterprise sales lead. And you do what you call this I call the

12:13 the pincher model'cause 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 and work in between that.

12:25 Okay. So you're so These are the two types of r 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 gonna be able to communicate your storyline. It's a game of telephone.

12:41 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 hundred thousand dollar deal.

12:56 Needs. A Executive sponsor to sign off on it. To allocate the budget. And this is why you need to start at these this these two layers only.

13:05 Wow. This is there's gonna be a fractals of questions and things to dig into with each of these steps. Uh, this is amazing. I love how just how specific and tactical you are with all of these things. I'm gonna try to summarize a couple of these tips. And then I have a follow up question. Okay, so tip one is go after either the exec, so in this case it'd be general counsel, head of legal sort of person, or N minus one.

13:26 Yeah. Uh, you wanna pitch them two or three sentences in like a text or email or in a At a conference. Uh And the key is to focus on the alpha, like the way

13:39 What your product will unlock. For them. Love that. Um and it sounds like there's still like a here's the problem we solve for you, but here's like really the alpha we unlock. Correct. Cause it for an executive. to bring something in and be the sponsor and like share this and disseminate this.

13:54 Down there down the They They need to stand behind something beyond hey, we're gonna make we're gonna r alleviate Yeah.

14:04 the num the time it takes to do X activity. That's not big enough. They want like They're like a founder too of their own business unit. Like you gotta sell the vision. And what are these people gonna how are they gonna get to the next stage? Um whether with their influence. Get more budget, get more people.

14:20 Um However they wanted to find that. Yeah. So it's it sounds like you don't wanna Like they wanna win and to win you need something unfair. Unfair advantage. That's exactly what you're pitching. That's exactly right. Yep.

14:33 Okay. And then this pincer move, I love it. So the idea here is for the exec state chief legal officer, grant general counsel. Founder needs to reach up. Yeah. And then this A E reaches out to the N minus one contact and you do this. You go from both directions.

14:47 Yeah. And I imagine the goals one of them at least responds. That's correct. And then 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 gonna loop in my so and so colleague who on your team should we also include? Or the Uh an enterprise executive could say.

15:05 Hey, I'm gonna bring in my founder. Could we see if your boss might want to be a part of this too? It's that parody of um Uh I kind of role.

15:16 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. Okay, two questions. Um How do you find this N minus one person and he just tricks as it just sitting on LinkedIn kinda figuring it out?

15:30 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 OpenAI 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.

15:58 Everyone is probably also targeting those people. Okay. And this is why you need to be s 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 had executive value. Meaning you cannot get

16:13 an executive ex 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 f reach out to them.

16:24 Any tips? No tools there to do to figure out their number or whatever. They're also unique. Cold calling works. It again, it depends on the role. You're not gonna cold call a highly technical person, but a non technical person, like It works.

16:38 Email. LinkedIn, Twitter. Are there tools to find these emails and things? Like is there something you recommend? Yeah, you can get like in there's a a ton of tools that do a uh to do enrichment. Um I also like I'll try like LinkedIn first and say, Hey, I shot you a note on

16:53 On LinkedIn, I just want to make sure you got it. Like most people don't check that on a daily basis. But yeah, I mean you you have like Um LEM list and all sorts of these enrichment tools that can give you the email. But I think the number one thing is

17:07 assume they're getting hit with Hundreds of emails. How are you gonna message your storyline to stand out. And that's that's not easy to do, and that's really why I think having

17:19 going back to our 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 that you think are good examples of this two to three cents pitch. Yeah, I think it comes down to like What is the differentiator to what you're offering?

17:39 Not even like what do you do ten x 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 What Flood the zone moment of like everyone trying to break into the enterprise.

17:56 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, jak we'll help you reduce the number of resources here, like No like

18:11 How are they going to show needle moving impact. to their C O, C E o You know, if they were to bring it to the board meeting, like what would they say about the product?

18:23 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're probably getting some percentage of people responding. Okay. So the advice is like keep try to reframe this. That's exactly right. Awesome. Okay. Anything else on

18:38 The first reach out before we get to the next step. No, I think I spoke to it. Okay. Okay, let's do it. I saw you shade your hand before you said it. In case people are confused. Okay. Uh Step two. Step two is basically running the intro call. Yes. Okay. This is the most important call.

18:53 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 in your крафт.

19:03 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.

19:20 So Keep it. And this is this is what I like to Super informal. Don't show them anything. Don't show them a demo.

19:27 Don't show them slides. Don't Like, focus on them, have a one on one dialogue for thirty minutes. Okay. Now again, if they're bringing in a C suite executive, you better have your founder join that call as well. I don't know any founder that wouldn't want to be in the room with a Fortune one hundred C suite executive.

19:44 So make sure you bring in your founder, uh if if you have that person on, but let's say you had the N minus one, you had like the VPI. Yeah. Like Super brief. Hey, and this is how we're typically open. Hey.

19:56 I'm gonna keep this super informal. I don't even know if we need a full thirty minutes. Put them on the back for like oh this person's not trying to take up my time. All I would like to do is swap intro and if it makes sense we can always get on another call and 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.

20:15 So I say, 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 s and tighten it to what they specifically care about. So and they also aren't like sitting there now listening to a pitcher like everybody. Exactly. Now they're talking, now they're conversing. Now it's like okay, now it's fun. Now this person's not pitching me. I'm in a conversation and a dialogue. Okay.

20:38 So now you're talking to them and they usually they usually do a very brief opening, like, Hey, um We didn't get a chance to look up that Chief legal officers. Uh SpaceX, obviously this is just a case, but like whoever that person's name is.

20:51 You know, I oversee the legal team and blah blah blah. Okay. Okay, great. They usually don't give you much. So they say, Okay, interesting. Like How are you thinking about um 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?

21:07 Mike. What are you looking for going into 2027? Like is anything need to change? Like As does anything need to change? Because again What they're going to usually default to is what

21:20 conversations have 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 twenty twenty seven that you did in twenty twenty six, or maybe not at all. And that's when they start to open up and

21:36 Again, you don't want to be too pointed of like anchoring them toward 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

21:50 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. Okay. Like

22:04 Is there a measurement to that right now? Like how are you guys like what is that look like internally in terms of Um If you've done that successfully in twenty twenty seven. And then they'll say, you know you're trying to understand like how mature is this thought, right?

22:19 Okay, so now they're they're going in and they say they can't really answer that fully. Okay. Make. 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 IP like what's what's causing

22:33 The team to want to reshape this or or rework the way that they're Um, manage it internally. And that's usually the moment of like Where they start to really

22:44 um 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. H now when you Talk about what you do.

22:55 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.

23:10 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.

23:19 They will not be open, they will not be vulnerable. They might assume it's being recorded'cause I think everyone kind of operates under that assumption right now, but Four The benefit of yourself do not have a recorder present. Off the record.

23:34 Between the two of us talking right now. of what you just shared like what really matters. Like what what like act and or like what do you want to own? Or like what's the chronicological like keep digging, digging deep'cause 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

23:57 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 um Improv. Okay. But after you now have that intel and you can now understand Окей хір'я.

24:12 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.

24:24 Or frame. For any call because it feels artificial. They feel it. It feels like you're putting them into a square box. Um

24:32 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. That last part seems really hard to adjust and make up like here's what you're focusing on and here's our product is gonna solve that problem for you.

24:50 So that's kind of where that art and skill comes in. That's right. And 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 counterintuitive, and we spoke about this on one other another call. The most successful salespeople are not trained salespeople. That's why founders are so good at this.

25:15 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. What percentage of the time are you just like, Okay, this isn't actually gonna help you that much?

25:31 So just we'll share we're up to nodding that happens. I would say Two to three out of every four calls. There's something real. One real. Yeah, there's something real. One out of 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

25:54 solve for X, Y or Z. The That's such a great question about the qualification. most people are not gonna be qualified, not because necessarily you're talking to the wrong person, because if you're in en if you're an enterprise executive or enterprise account executive.

26:09 Your job is to know who to talk to. Okay. Um And your job is also to quickly Um

26:16 quickly disqualify someone and it's probably one in every four calls. Well, simply because of maturity. Well, so you don't have to have this like intense pressure to nail it on every call. Here's the here's the pitch. Okay, awesome.

26:29 What I also want to comment on is I th this idea of like getting the share bunch. It may feel Tricky, like you're tricking them into sharing all this, but really They have problems they want to solve.

26:39 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 to bu their job is to buy solutions to these problems, right? That's why they have budgets. Right. Um So that's why the m the m and the f the

26:56 fastest way to commoditize yourself is to go into some sales scrap, 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.

27:12 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 this important. Because you want them to ask you those questions. Cause that's when you know you're building a relationship. Like I like I had a client Last week say to me.

27:29 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 it.

27:46 They just want to know you're vulnerable. Because then it doesn't feel like it it 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 wanna focus on lowering costs as a sales pitch. This is the cheaper option. Yeah.

28:03 Thoughts on if that just comes up a bunch. We just like legal, we just need to save costs. Yeah. So In pricing Their job is to There's gonna you're usually gonna be two motions.

28:15 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 sixty percent 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, two hundred and fifty, five hundred K.

28:31 Land Because the pro because it is A Um Uh high risk if you're dealing with legal, there's high risk to it.

28:40 Right. Missing information being delayed on something. Um Uh Not having people understand the importance of some new

28:50 regulation or or law Um Uh not being buttoned up. Um So I think for if you every organization looks differently, right? Like

29:01 marketing needs to ha needs to produ you know marketing and sales, it's very clear that number Numbers drive them. For legal. probably they they need to stomp out risk. Awesome. So yeah.

29:14 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. Exactly. Easier everything gets. Okay. Uh anything else before we get to step three?

29:24 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, your point 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 are

29:45 Versus you're in the funnel like oh shit I gotta actually make a decision, I'm gonna have to let them down if I don't want this. It's like Yeah, yeah, it's like dating. Yeah, they they like their openness to share more. It can start to clam up a little bit more, but we'll talk about how to make sure that doesn't happen too. Amazing. Okay, great. Great for shadowing.

30:01 Okay, so step three is writing a follow up intro call. Yes. Okay. Okay. So Usually right now the stages that most people have is Intro Demo

30:12 Proposal. contracting You know, close one or close loss. I there's five stages. They're very basic. People usually go from an intro call straight to a down.

30:24 Okay. The demo is your carrot in the process. Everyone wants to see this amazing thing you just spoke about. Okay. So there's 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

30:39 One it's You l you lost your leverage to like organize that group and rally them. But more importantly, it n 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 they're part 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 they want they want their the actual users to feel like that they were bought in on this too.

31:04 Okay, so you want to make this to be And this is the tricky part. You want it to be 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.

31:16 Okay. So the person that you had the intro call with, that's who you built the rapport with. That that's your That's your champion at this point, whether it's the C suite executive or um one step removed. I say champion m most champions are one step removed, but Let's just say the C suite executive has delegated this now to the champion to to to navigate. Okay. For that demo call. Наforю до демо.

31:39 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 fifteen minutes, by the way. 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?

32:03 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 they're the now it starts to feel like oh great, I get now they get to put their fingerprints on this. So it's like okay, if we when we demo to this group

32:18 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 value of this. And they'll be like, I'm actually gonna ask this question because it's gonna resonate more. So now you're building this demo alongside this. internal executive And

32:35 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.

32:52 So it's like okay, so now you're spending fifteen minutes trying to figure out okay, or thirty, right? Sometimes they won't give you it that much more time, but Us for thirty is probably Do fifteen. And say here are the five different things we can we can go into. From our first conversation, it sounds like these two things matter. Well let me show you all five.

33:09 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 it feel holistic. Okay. So now you just mapped out the storyline with an internal partner on their end. And now you're now you have the names of the right people. Now you're gonna To close that call.

33:28 Great. Is there a time we can look at everyone's calendar and put this on the on the calendar? Make the meeting an hour. The demo should be an hour. Okay. Now you can ask. Before this meeting.

33:40 Do we want to do a pre demo to um Maybe someone else on your team that would be excited by this. Before you race to the group demo. Um 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

33:57 Knowing if they want something like this, they probably want to bring in someone else before the big group. If they're like, No, no, no, this is something we wanna 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.

34:11 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.

34:24 Yeah. 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 I'm gonna for five minutes I was gonna catch you up on the the things that I just learned from so and so.

34:37 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.

34:50 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 go into one straight demo with no problem. Or worse.

35:05 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. Will you present this to four or five people? Don't Do it. It you're either a checkbox and you don't want you want to remove yourself from being a checkbox Or two, you're about to demo your product with no competitive intel.

35:28 Like You just lost the deal at that point. Enterprise deals are one on this feels so close to who we are. It feels like it was built specifically for me. That's the whole game. Amazing.

35:43 I love how just how much alpha not only you're sharing with us Like there's it's 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's the right word, but you're simply it's information edge. Yeah. It's the information edge that whoever I'm up against is not getting.

36:02 And you have to assume in in the enterprise you're always up against something. You're up against not doing anything at all. Or you're up against it. Competitor who who does some or an incumbent. Right, most likely the incumbent.

36:14 Бітсокрази томі хаманіплис а піч. With like no Yeah, you also have to make it informal and fun, like you need to You know. Um

36:26 People also buy from people they like. Right. I love how so far at least it feels very doable. Not that difficult. Feels like I could do this. Uh still could

36:37 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 time?

36:45 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 read in between the lines of what they were saying. And that's when I will follow up like Those those

37:01 Kind of pre 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

37:11 Did I interpret that correctly? Like is that is that the priority? Like And then again, they'll go deeper. Like the more 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 prompting humans at this point, right? Like go deeper and deeper and deeper and you're the answers you're gonna get are just gonna get so much more refined.

37:31 The whole game is to slow down To go fast. All of this should be should be within a ninety day sales cycle based off of their maturity.

37:41 To 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

37:54 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 fifteen thousand dollar solution. Which goes you can where do you how do you expand that? The whole game is expansion. If you're not going from a hundred

38:11 K or two hundred and fifty K to three fifty or five hundred the following year. Signed an enterprise motion. Okay, so just to kinda quickly summarize we're at step one, landing the meeting. Yep. Then running the intro call. Then there's this follow up intro call.

38:26 Which you pointed out is often ignored. Yeah and a big opportunity. to improve the demo. Yeah. I love the way you describe the demo. It's kind of this carrot that you're holding that you can use a little bit to kind of extract more. Yeah. And then there's Step four is prepping the pitch. And framing the demo. Yeah.

38:41 Um is there more to share there? No, I think I think we're at the point where it's like okay, now you're running a big demo. Okay, cool. So yes. So now you have You now you have all of the people involved in the demo. You might have somebody that's involved from their AI team that's gonna support Some some roll out. You might have somebody like you want all of the people involved in this decision at that table for the demo.

39:05 That's how important it is to not rush it. Okay, so you now you're running the demo. Now you're Before that demo on that on one of those calls Who are all these people? What do they care about? And what should I avoid?

39:18 I D 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 it's now they now this is like a great star for them of like I found this amazing tool.

39:32 It's gonna solve our problems. And now I get to put my name on it. Alongside One or two other people. Right. So for that demo

39:41 Just make sure you know exactly who's involved. What these people care about. And what does a successful demo look like for them? I just ask them, be like Hey. People do demos all the time, like

39:50 What looks good thirty minutes of a discussion, maybe ten minutes of showing. Ten minutes of discussion, forty minutes of in the product, like what you tell me like what the the organization likes. And on that demo there's gonna be people that We're not a part of any of these calls. Okay.

40:07 Your job is to take a step back and restart with Here's here we are. Here's why we are 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.

40:24 Now they'll now they're like leaning in being like okay, all right, somebody Did it. This is very aligned with what we need. Because they've no idea you've talked to all these people. No idea you talk to all these people. With their challenges and their priorities. They're like they're leaning in being like this feels different. Now this is also the whole part of like

40:40 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.

40:51 So now d y you could s you know, let them talk, let these net new people talk, be like, Hey, I 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 wanna 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.

41:08 Eighty percent of the value comes from twenty percent of the product. And you have learned on these previous calls. what that twenty percent is. Do not demo everything unless there is some reason to. Because now all of a sudden this tight frame, this tight narrative you've just crafted and spent all this time with.

41:29 Just gets thrown out the door'cause 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 just blow the whole thing out. And the amount of times enterprises are like, Hey

41:43 I'm not gonna I don't know if we wanna spend this much money for half the tool that we wouldn't use half the tool. Now all of a sudden you've 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.

42:00 owning that frame. owning that frame to exactly who these people are. And that's why this role is so hard. 'Cause 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

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43:35 How do you deal with someone that's just kind of taking things off track or Or just talking too long. I I imagine that's just like a you know 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 gonna that you're you're doing your outreach to. It's very hard to get to that.

43:52 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 at an executive level. Um, now of course there's some times where there's people that meander. You could say

44:10 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 it. Awesome. So there's kind of two people that might be leading this. Might be the founder, if you're still doing found relative sales, could be the AE.

44:27 Maybe a a VP of sales that VP of sales, yep. Okay. As say you're say you're not the founder and you're And you're d the VP of sales or any leading this? As a founder.

44:39 What are some signs that Your salesperson is not doing a great job. Up to this point, what are just like smells of like Hm, I should release everything this person. What is the timeline from intro called the demo? How many conversations have happened between those two?

44:57 Between those two buckets of like when people advance 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.

45:15 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 scaled approach with this When you're selling hundred thousand dollars minimum

45:29 Right. Again, it's the same effort as selling a million dollar. So it could be selling a million dollar deal. It is it's hard. Your 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.

45:46 It is not cram the pitch down their throat and hope that they Wanna buy something. Feels like a job AI will not replace any type of student for here. Yeah, I don't I do not um I'm not worried about AI replace because there's so much about it that's just human, right? Like

46:04 Do you vibe with this person? I mean, I've 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 It's such an in uh a point I've never heard before this idea of When you're demoing

46:19 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.

46:31 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 a sudden it feels like It's again built for them. They want to feel like it was built for them. And that Um It's different.

46:44 And they get alpha. Okay. Uh So step six, y uh you call the post demo discussion. Yes. Also something you say everyone ignores. Yes. Talk about that. Okay.

46:55 So as soon as the demo closes. You are texting the woman or the gentleman. Or whomever. That is h help guide you to this point. How do you think that went?

47:05 Can we grab can I call you in like five minutes? I just want to d I want like a fresh debrief. They will give you an like raw reaction. I know you haven't spoken to 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's said like Where where did do you think we lost somebody?

47:25 Where do you think we did well? Um Is there someone we need to spend more time with? There's always someone in the organization that's gonna kill a deal. There's always somebody.

47:38 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, if for some reason Someone goes quiet for two weeks or three weeks.

47:54 You can now prompt with hey I know you guys are in the still in the process of like thinking through if this makes sense. Do you think it's worthy if I found fifteen or twenty minutes with Said individual

48:07 To just like hear their thoughts and and maybe we can And maybe we can um approach this a little bit more closely with how they would. Wanna see it. So you're just always looking for Ways this might explode and not work and

48:20 And this person that you're working with, would uh would you call'em what would um What was the term used for them? Yeah. Could the champion also be an executive? Right. Yeah.

48:32 And they're like excited at this point, in theory, very excited for this to work out. Like they're on your s on your side. They're not trying to Yeah. And I define champion as 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

48:47 Like the C suite executive could be the one shepherding this well, but they need to make sure that the people below them are bought in. Okay. Anything else around the demo? Or the post demo discussion before we move on to the next. No, I think we're good. Okay. So the next step, uh, 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

49:14 Allow them. Now you can control the the time line of butt Hey. I want you guys to go in for two to three days. the specific users. Don't put the do not put your C level executive into the product. They're not the user.

49:26 Yeah. Who are the users of this? I want them to experience the magic and the power of what this is. Okay. Run don't char you could charge them for a pilot if it's an extended period of time.

49:38 But I'd rather forego 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

49:51 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 onboarding that needs to happen, but Із зара сandбокс ви кон асесси валю. Um even if it's not on their own data. So this isn't yet the pilot, this is just like prepping for the actual. Correct. So there's two different pilots you can run.

50:13 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 Um 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.

50:30 Um Let's talk about something that they can get in two to three days. And it's a pretty Pretty much of a light left. Time box it's two or three days, don't make it two weeks. Okay.

50:41 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 Forty eight or seventy two hours. Now if you need something a bit more integrated and it and it's a

50:55 A far more technical solution. What I'd highly recommend is Do it for a month or two months. Charge them for it. And then use that.

51:04 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.

51:15 They have no problem paying for it. It's usually probably gonna come out as services anyway,'cause it's like a buying technology to buying the services to go through it. Um And also

51:25 Make it a credit on the back end. Don't Start the relationship up, shift. Start the relationship off on a good foot. I'm definitely feeling the feeling I feel when we chat is like I just wanna find something to sell. This really It's fun. It's so fine.

51:40 Like it's literally so fun. People I think people read these sales books, go to these sales trainings. And they they they may they try and take someone else's game. and run with it and never works that way. Like no one taught me this. I was just like, okay.

51:54 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 rock. It feels more real. Yeah. Yeah.

52:09 Okay, a couple of 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 that feels tough. So I would say here, this is what we typically do. Who are the three or four people we want to put in and assess the assess the value from a user perspective?

52:24 Okay. Make sure it's your person. Right assuming that it's no or Or the person closest to the C don't put your C suite executive in it. They're not gonna they're not gonna go into the product. And then two or three other people.

52:36 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

52:50 very thoughtful and explicit and descriptive with what you want them to do. Okay. Here's how we're gonna measure success. To find out with them.

53:01 Define that with co-author that. And that's no different than it's the thing that's a little bit longer where you require that integration and um and build out. coauther 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.

53:19 That puts the work back on them. Your job in sales. is to take all the work off their plate. Ninety nine percent of it. And help them discover the magic really.

53:32 You might have one of those users that's like oh I didn't like it. Great. of the in that three stage process, you just what did what didn't you like? What wasn't clear, what wasn't obvious, where did you get lost? The tighter it is.

53:44 Less people get lost, the mo the more. Um Ground it feels. And the more consistent the experiences. You don't want people having different experiences. Okay, so just um

53:54 Make it clear the steps involved here,'cause we've gone through I think three kind of a realm thing. 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. Lotta people ignore just like Yep. Who that person is and what the steps are.

54:10 Then there's prep for the pilot and then there's run the pilot. Run the pilot. Exactly. We've kinda talked through all these things. Now yeah. For prep 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. Ahead of time, before doing the part. Yes, ahead of it.

54:32 Um I should have clarified that this is all before before the you before the people's pilots start. This is in the prepilot stage. Okay. Assuming fingers crossed a successful pilot which I feel confident is gonna be. Um One is

54:45 When do we want to 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 till after the pipe totally.

55:03 But like Push them a little bit. Again, you're project managing it. Um, is there a security lead we should be working with to run due diligence on the product? Um, is there someone in legal Or is there a way for me to draft the paper?

55:16 To make this make sense. Now The one thing to take a step back on is You would have already gone through pricing discussions with them post demo. Okay.

55:26 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. Right,'cause 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.

55:43 Post pilot or post demo? Okay, cool. Yeah. So and the so you basically just kinda tell them what's We'll figure out pricing once we understand what you're looking for. And this is in the pre pilot stage, talk about pricing. Okay. Now if they're this far along, they you like If they're really concerned about pricing, they would have brought it up by now.

56:02 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. Uh two is Um if they ask and they push, give them a ballpark. Well, it depends, but like let's say it's somewhere between one hundred and fifty and two hundred fifty. And there's a lot of dependents on that.

56:18 I Um so you can give them a ballpark. But work with your champion and say, listen, here's what the price is. Um You I know you know why we price it this way.

56:30 Where Yeah. Before you put this in front of anybody. How are you gonna make the case? Right, like

56:39 Where are you gonna cut? How you can defend it. How can I build out a slide to defend this for you and show you the ROI? Let them t they will tell you. You don't have to go blind into it.

56:54 And then if they c 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.

57:10 And do you include the slide or the price in the demo, or is that like a post demo conversation? 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 cr they might say, Okay, I think this is I think I think we're all aligned. This is what's usually gonna happen there's three answers.

57:30 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.

57:47 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 want to put it on them. Because they might come back and say, Is there any way we can cut twenty K? And you're like, Oh, I would've gone much lower than that, right? You don't want to negotiate with yourself. But work with them. You've gotten to this point, you've shown so many people. Everyone's excited.

58:09 This is when you know you can win them over through the um The co authorship. And remember, you can always do the full value in year two. And sign a two year deal. Awesome. The expand.

58:23 Okay, so in the pilot step. Do you how many people do you give uh uh access to the pilot? Any advice there? Three three to four. Okay, so very small. Very small, very tight. Who are the power users? Who are the people that are gonna be in on a 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 in the same but you do want your In that one individual that's been giving you all this intellect to be part of the pilot.

58:48 Because You want them to get you prepped for everything. So before we get to the next step, which is postpilot discussion and session. Uh I imagine many products, especially today, just take a lot of integration work.

59:01 And data ingestion and in you know, all that stuff. This whole F E Yeah. Um thoughts there if your product is just like, wow, it's gonna take us a month even to get you onboarded. And that's that when the we when we talked about those two different pilots, there's like, hey, we can show you the value in two to three days, or it's the hey, we have to show you the value in thirty days. For the thirty day value charge.

59:24 And credit it back. to them, but know that your sales cycles gonna probably be s 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 like integrate enough to make it your price should be predicated on your sales cycle. Right. Like if you can get a deal done in ninety days for a hundred K, do that all the time.

59:43 Right? If it takes nine months to get a deal done, you've got you probably should be charging two fifty, three hundred K. What are your thoughts on uh for deployed engineers as a part of this process, just as a role? My opinions 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?

1:00:05 I think people use them I 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 is it are you using um a forward deployed engineer because your product's so gnarly and hard to hard to do. Like they can't do it on their own.

1:00:22 Um It's a bad sign. Yeah. Yeah. I feel like Like the original idea of Ford to Plate Engineer.

1:00:28 And the palantier guys talk about this, like The original idea was they work at a Inside of your company building custom software. for you to solve your problems and then they figure out how to make that A broad product they can sell to other people. And I think that an FDE is great.

1:00:45 For an expansion for a land. On if okay, if you're talking about like a palantir where it's much more complex to Like Tw like I understand why they did that. Right, but they're also charging multi million dollar deals. That's right. Right. So like the their the the business model structure supports that. If you're selling a hundred thousand dollar deal and you're pulling a four deploy like

1:01:05 Your economics are Yeah. It's gonna get messy. Just like you will not make money if you have a full time an engineer salesperson sitting there working on this. And uh you know, I I think w I also know like there's a lot of folks in like account management whose job is to service and and up you know expand and upsell.

1:01:21 And they just take on the title left FDE. So they're just another salesperson. Yeah, it's just a nice yeah, it's a cool title. I think the pound through people called the F to use at most companies sparkling sales engineers. That's awesome. Yeah.

1:01:34 Okay. Uh anything else on the pilot? Up to the pilot step. 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 wanna run this before you put everyone in it.

1:01:49 Because you might want to push out the pilot if they're like, Hey, listen, this is probably gonna be another quarter. Well put the people in the pilot now,'cause now you've lost all the mo you need the momentum to continue and 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

1:02:08 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 on doing that. Correct. Yeah. Awesome. Because you're saying you may lose that momentum and then like it's like you've already exhausted all the Stages. Um, 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.

1:02:31 And sometimes it's out of your control, but yeah. And yeah, it's not like you can Push them to Deploy it. Broadly.

1:02:37 That's like a thing that is probably very hard to Yeah. So So yeah. Working with that seems really important. Okay, so step ten.

1:02:46 And again, uh as you point out at the beginning, most people think The sales process is five steps. And we're already in step ten. And we're not even done. And you made this point actually before we start recording that I you haven't touched on that I think is important for 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

1:03:06 Everyone knows the traditional five steps intro. Demo. proposal contracting and then like close wonder or close loss, right? Those are like the The typical

1:03:18 Or 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

1:03:30 proposal or something mid funnel might be weighted at fifty percent. The deal value for the For the um For the pipeline. Something in contracting might be weighted at eighty percent and something in intro might be weighted at ten percent.

1:03:43 That's what those stages are for. That's not the stages you take a client through. Like those are just the Broad buckets. Um and I think a lot of people use those buckets to say okay I 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.

1:04:03 Um to get the deal done. Now we're We're still speaking at it at a very macro level, like You know, obviously selling a million dollar deal, you want to have more of those upfront meetings. Um 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 a hundred K deal, you probably can accelerate it a little faster.

1:04:21 Again, ensuring that they're qualified. And he've worked with a lot of Founders and salespeople over the years. What percentage do you think are just doing it wrong? In that way and treating it like this five step process.

1:04:33 Ninety percent. Wow. Yeah. Because Enterprise sales is it's it's it's mirroring their buying process.

1:04:43 It's trying to control their buying process, it's not plopping these people into your sales process. Amazing. Yeah. Okay. Let's keep going. Step ten. Post pilot session. Yes. Um, you can send a survey, they might want to send a survey.

1:04:58 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?

1:05:11 Okay. You need to make sure that you are mirroring their experience, right? From a technical perspective, like 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 like going into that call to say, Hey

1:05:29 I know we gave the I know we gave everyone those three things, but most people only spent it on two. Why? And that may be okay. But you but like you don't want them to be like, oh well You know, we wish it did this. Well, yeah, but no one spent time on that. We do do that, but no one spent time on that. So you just need a control also. That You're capturing what they did in those pilots.

1:05:51 And making sure that you're syncing up or you could go to your champion and be like Hey I know so and so logged in for like fifteen 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.

1:06:06 Думаю, чек із. 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

1:06:20 Getting a deal done at the enterprise. It is set up. to have as much friction as possible. Right. Is the people that will kill the deal. Then you gotta deal with procurement, then you gotta deal with legal, then you gotta deal with finding the executive sponsor.

1:06:34 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.

1:06:45 So many ways it could all fall apart. Um What I was gonna say is it feels like Many people would naturally Like they don't want they want to avoid confrontation.

1:06:56 They won't want to say this is not gonna be we don't want this. They're gonna probably be like, It's fine, it's good it's good. Yeah, everything's like PCs. That's right. And so

1:07:07 It feels like a lot of this process is to 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 and I need to really When you're in 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's gonna 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.

1:07:33 Let's re pick this back up. That's why having someone on the inside is so, so, so critical. And yeah, the easier pro the easier approach is just to stop responding. And just hope that the the salesperson understands very little. I'm excited.

1:07:47 Oh man. Okay. What are like the benchmarks for like how How often do you get through each of these stages? You mentioned like a few. Just like

1:07:55 Yeah, from demo to the stage. Usually once it once something is qualified, meaning you're speaking to the right person. They are excited by the alpha. They they admit that there's change that needs to happen. Notice I didn't say problem, but change. People get so fixated on problems.

1:08:12 Which are important. They are important, but like everyone speaks to the same problem and then commoditizes you, which is why I don't like to like overly emphasize it. the win rate for enterprise, a good, healthy win rate. It's actually probably gonna surprise you. It's not fifty percent. Mien of all qua sales qualified

1:08:31 leads or opportunities. W a healthy win rate is usually around thirty to thirty five percent. From qualified lead to Sign contract.

1:08:41 Мінін ю спік то о Хрид. You're closing anywhere between thirty to thirty five. Maybe slightly less. Maybe twenty five to thirty. That seems high, actually. Yeah, twenty five to somewhere between twenty five and thirty five percent. Why? If

1:08:57 If it's 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 those are all the chasms. And the implication here is it's better off.

1:09:13 Keeping your price high than winning more often. Yes, because the market talks too. W the worst thing you can do is charge Somebody's friend fifty and somebody else five hundred K. They talk. Peep the market talks. You have to assume that. So I'm in a lot of a lot of WhatsApp groups with founders and they do exactly that. What kind of deal do you get for this product?

1:09:33 That's exactly. The m 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.

1:09:46 Of the ones that have lost, that's probably another twenty five percent. So It is totally normal and natural. For Uh

1:09:57 Deal deals to not Advance. Right. But to a healthy win rate in the enterprise. is typically bet I would say between twenty five and thirty five percent.

1:10:06 Okay. That is incredibly helpful to people A. I know uh How about like key stages along the way, just like percentage drop off up and So it's usually like from Qualified lead

1:10:19 Two Like Um you're coming at a demo, it's probably You'd lose half. And then

1:10:31 I guess you have thirty percent. So from demo to what was that step that you're going to do. From demo to like the more you move down, the less those numbers Uh the less uh wider those numbers. So like So like Леффю спік чи

1:10:46 Um And you're doing a really good job targeting the right people. Maybe Th uh seventy Fifty percent of those people move to a qualified lead.

1:10:56 Or so fifty to seventy five percent move to qualify late. Of that. Then Um Another half move to demo, and then from there another quarter advance beyond that.

1:11:07 Once you're in the bottom of funnel, you usually don't lose too much from there. If you're doing a deal qualification. So say you're at the pilot stage, what percentage should you expect drop off and or no twenty percent succeed. 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 qu clearly. Or.

1:11:28 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 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.

1:11:45 Um okay so step eleven papering Prep setting timeline for pro procurement. Yes. So you have now Um

1:11:53 Spoken pre pilot about the timeline of what's we're reverse engineering. Now you're gonna document it in in an email. So that that champion that you're working with can forward that to procurement to say, Hey

1:12:06 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 um kicker they're gonna give us if we'll if we Get to this state. Um, there's always gotta be a reason to create urgency.

1:12:21 And then what you want to do is say here's our paper, send a word document. Do not send a PDF'cause they're gonna always red line. Always. Send a word document of your paper and ask the question. Do you want to use our paper?

1:12:33 Here's a Word Doc version. Or do you want to lift from it? And Do you want to use your paper? It might be a lot faster to use their paper.

1:12:42 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 Doc. Google like Microsoft Office. Microsoft Word. Yeah. Most of these people can't access Google Docs, but yes. And so this has post pilot.

1:12:58 Feels like it's gone well. Um You're saying the next step is here's like the contract, basically. Get that to procurement that early. You're working from N minus one from the exec from the executive sponsor, or is the executive sponsor themselves?

1:13:15 You n you wouldn't have made it the They're not gonna point their team into a pilot if it doesn't have legs. And I an implication here is procurement is a way that your deal might still die. Even if people internally love your product.

1:13:29 It if you get sent to procure so here's here's something interesting that a lot of people don't realize. People will use procurement as the excuse to not want to get in. Um The the the bad feedback. Oh, uh I gotta go to oh it procurement it's it's it's lost in procurement or blah blah blah blah blah. Right. Very easy to blame procurement.

1:13:47 Usually procurement is like a thirty day Process. Between the back and forth on the legal, the papering. 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.

1:14:03 That's their job. The curman is the only person That can get you paid. Дуна старт аніворк. T you go to becoming.

1:14:12 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, like

1:14:22 Do don't start any work until obviously the papers are signed. Start work meaning implementing, rolling out people onboarding. Got it, got it, got it. Okay, amazing. Okay, so That's step eleven, papering prep, setting timeline for procurement. Kind of getting on board with like What is it gonna take to sign by the state? Here's a

1:14:38 Little gift you'll get if you do it by a state. Free month or whatever. Okay. Uh step twelve, papering review. Yes.

1:14:46 The best thing you can do is They're gonna send you back red lines. No question. If the red lines are extensive. Okay.

1:14:56 Go ahead and accept the things that are easy. The red lines are extensive. See if you can get legal on a call live and just talk through them. That will accelerate your sales cycle. A bunch of back and forth. Get them on a call be like hey

1:15:11 Everything we're eighty percent of the way there. I have a few questions based off of your life. Can we jump on a call a live call and just go through them? J Focus on the things that are gonna impact the business. And pushing on those, let the other stuff go.

1:15:25 If it's not super important. Obviously have a lawyer look at it from your side. You're dealing with a commercial lawyer uh com commercial legal team. Have a lawyer look at their red lines. I imagine most companies have legal counsel. Yes, I would I would hope so yes. Okay, cool. So paper review. So that's reviewing basically. It's interesting called the paper.

1:15:45 Yeah. Is there like a more technical term for that? Like the contract. I say paper. That's like corporal language paper. So interesting. Paper in your review. Okay, step thirteen, papering procurement process. Yes. So this is where um

1:16:00 We kind of talked about this. We kind of merged that This is when you are getting the procurement leag and that legal league on a live call to work through the questions or the things you cannot. Now remember If they give you their paper.

1:16:16 There's gonna be a lot in there that you're gonna need to Red line. They're expecting that. They're just giving you the kitchen sink. Mm-hmm. If they ask for ten million dollars of liability insurance, as a smaller company, you can push back and be like, listen, your exposure

1:16:31 with what we're doing is not that high. Or maybe it might be and you need that. But you know, they're gonna give you the kitchen sink. Know that it's all negotiable. But but pick battles. Pick your battles. Yeah. Don't be afraid like the deal will fall. No see something in their own. At this point the deal will not fall apart. Um, 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.

1:16:52 Okay, and the final step Signature. Ta da. Yep. Anything special there other than signing? No, that's this is like the really exciting point, which is um Just figuring out who the signatory is.

1:17:05 before it goes about it for signature. So that you that your make sure your internal client knows You know 'Cause sometimes it's the CFO. It's not the Executive sponsor.

1:17:15 Um, and you just wanna make sure you everyone knows who that individual is because if there's no delay you just wanna make sure They get pinged. Damn. We did it, Jen. We did it. We got through all the steps. We just signed a massive contract. Congratulations. Let's go. Steak dinner, champagne. I don't know what salespeople do when they close a deal.

1:17:32 Ding a bell. There's bells often. You know what we do? Okay, what's the next one? That's it. Yeah. Because you're all you are in sales, you're only as good as your pipeline. Mm.

1:17:45 Uh So fun. It must be the best feeling after all this divorce. Like literally the feels 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. Hundred percent.

1:18:01 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. Um, and this is where I think the expansion comes in. You either know

1:18:14 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 ten Enterprise customers, you need the founder involved. Um Once these people are in to understand like What part of the product.

1:18:29 Is um 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 it every company is an AR. Recurring revenue focus.

1:18:44 But services is still the largest Line item. Budgets. And so you're saying uh it's okay to offer services. Okay to offer yes. Yeah. Yeah.

1:18:53 Yeah. This has come up a number of times, I think, with Jason also Lemkin and And you just like the Increasing Like there's a rise in services being a part of Software companies.

1:19:04 That's what they know how to buy. They're so used to it. Consultants. Lawyers You name it. Um

1:19:13 The the the the budget there's always budget for services. Yeah. We talked about this last time so we won't get too deep into it. Something else I wanted to ask you uh kind of at the end here. So you're the buyer and you're say you're talking to Jen and you're just like Not sure this is a fit, you don't wanna disappoint, you don't wanna drag you along.

1:19:31 What are some things that people buying software products w 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's not right. It's usually comes down to timing.

1:19:47 Or why they're not mature enough to be able to Um It's interesting.

1:19:55 You have to be Organization and the team has to be structured in a way to bring on the technology. Like there's a maturity you have to go through. And I 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 you're Sales maturity in the enterprises

1:20:14 Further. Uh 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, you're not mature.

1:20:23 I imagine the salesperson will try to prod you and push you to see if maybe You're not so it's okay to just sell them what you think it's not the right thing. And you know where 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 up said to them You are a liability not closing this gap.

1:20:45 And they're like sometimes they just need to be like But again, you need to know if you're in a position to be able to say that. Yeah. Listen. I know you need this.

1:20:55 I know you need this, I'm not accepting no 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 what everyone else is doing in this space. Well, exactly. Or like, Hey, listen.

1:21:13 On our first two calls you you told me how important this is. Did that change? No, we're just like In a weird spot, I'd be like, Okay, listen. Here's what we're gonna do. Let's start it a little bit smaller.

1:21:26 Let's get in. I know I You admitted that this is something that you guys need. I know that we are gonna crush it for you. I do not

1:21:37 I don't want X to get in the way of that. And there and then there's obviously the gonna be the cases where it's like it's just not the right time. Like they might be going through an acquisition. Right. bringing on net new vendors is just like not

1:21:50 a priority right now. You just have to respect that too. I love how this whole process A lot of listeners as podcaster product managers, product people. It just feels very product y

1:22:02 And 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 it all alike. But But they're so similar and it's just like you being human, like the way PM

1:22:18 Try to understand what your pain points are. We're here to solve them. Yeah. Unexpected. We did it, Jen. We did it.

1:22:25 We went through it all. Is there anything else? Anything else we haven't touched on, anything else you wanna I don't know, leave listeners with before we wrap up. We gave them a lot. We did it.

1:22:35 Yeah. Which was the goal. Just the right amount. Yeah. Yeah. I'm excited for like uh Oh, I was gonna say I I love that AI I don't think it came out one, maybe one time in this conversation. Very rare these days in podcasts. Which I love. Well it's it's interesting. Like so many people will create like

1:22:53 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

1:23:05 Anyone can do that. It just feels salesy. What's your alpha? Yeah, we've come back to that. Exactly. And I know you talked about this last time just like

1:23:15 Craft your own email and text don't. Don't use the Boilerplate. Yeah, email their living and breathing, I swear to God that like people can read you saying the email out loud. Yeah.

1:23:29 Okay. Chen. Uh this is awesome. This was amazing. Everything I want it to be. This is gonna be I'm excited for like the not to talk about AI, but just like AI summary of this especially, that's just gonna be like step one through the reverse. Yeah, yeah. Uh

1:23:44 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 um if anyone, here's a plug. If anyone is interested in enterprise sales.

1:24:02 We are actively hiring. And I will teach you everything I know. Wow. And this is at State Affairs. Is it at State Affairs? Holy shit. What an opportunity. Yeah. So there's multiple roles, not just one. Multiple roles, yeah. Wow.

1:24:16 Uh You'll be paid to learn from Jen directly. I will I will teach you everything I know. Whoa Okay, cool. We'll link to the job descriptions. Uh Uh in the description if you want to check that out. Awesome. Amazing. Um Jen, thank you so much for being. I knew this was awesome.

1:24:30 It's awesome. Hi, 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.

1:24:50 at Lenny's podcast.com See you in the next episode.

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