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

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 1, but most importantly, the alpha, and it needs to be different.

Step 2 is basically writing 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?

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?

90%.

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 5 steps and we're already in step 10 and 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 3rd 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 founder-led sales. In our second conversation, we focused on the $1 million to $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 5-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'll 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 lennysproductpass.com 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 for being here. Welcome back to the podcast, a very rare third visit to the podcast. How does it feel?

Round 3, super excited to be here, Lenny.

I'm even more excited. So we're going to do something really unique. with this conversation. I've never done anything like this before. We're gonna basically go through the enterprise sales lifecycle step by step. You'll talk about this, but many people think it's like 5 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 wanna create a very concrete and, um, tactical playbook for how to do enterprise sales.

Okay.

We've had conversations.

Explain my secrets.

All, let's, that's the goal. Just suck them all out and make everybody amazing at sales. It'll be great.

Awesome.

And, you know, this touches on just like why I think the podcast is really helpful to people and just the Valley vibe, even though 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, 'cause there's so much art to this that even if you gave someone a 15-step playbook, there, there's so much of a, 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 gonna probably not hit one out of every 4 times, 'cause everyone's different. Like, Some people like to joke. Some people like the small talk opener. Others wanna 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, the, if you sell a $100,000 solution, it is the same exact process to sell a million-dollar solution. So, that's, that's why I, it, it's, it, 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.

Yeah.

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 wanna 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?

Yeah. Let's use a company like SpaceX, right? Recently, you know, has seen massive news pressings. It, you know, everyone's probably targeting them. Right? So, it's gonna be a hard logo to go in and, and win. 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 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, uh, uh, kind of budget, right? Sometimes 3 to 4 times other budgets. And it's forever, there's always more money for legal.

That's why there's so many legal AI startups. I get it now.

100%.

Amazing. And I, I'll just add the reason, like the reason I love to have you on this podcast is I, 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 wanna 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 people.

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 1 of the sales enterprise No, I think this is good. Sales cycle.

So, base stacks and targeting the legal function.

And then like a $100K, let's say, deal.

Yep.

And to your point, it's the same process whether it's $100K, a million.

Totally.

And I will add a plug for a previous episode. You talk about why you wanna be at least $100K something as a deal.

Yep.

To be a, uh, a real enterprise company that will, that will survive.

Yeah, sorry.

Because the 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, WorkOS. What do OpenAI, Anthropic, Cursor, Replit, Sierra, Clay, and hundreds of other winning companies all have in common? They are all powered by WorkOS. If you're building a product for the enterprise, you've felt the pain of integrating single sign-on, SCIM, RBAC, audit logs, and other features required by large companies. WorkOS 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 upmarket ends up working with WorkOS, 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, WorkOS is the fastest path to becoming enterprise-ready and unblocking growth. It's essentially Stripe for enterprise features. Visit workos.com to get started or just hit up their Slack where they have actual engineers waiting to answer your questions. WorkOS allows you to build faster with delightful APIs, comprehensive docs, and a smooth developer experience. Go to workos.com to make your app enterprise ready today. Okay. Step 1, 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 rung, right? Which is the, the general counsel, the head of legal, uh, the chief legal officer. They all kind of have 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 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 my entry point? And there's only 2 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 minus 1. Okay. So, let's talk about like why. In order for an enterprise deal to move forward, you need to have this extremely compressed storyline. Mm-hmm. That lands immediately to the objectives that they wanna 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 uncover and unlock by bringing in a net new tool? Okay. 'Cause bringing in a net new tool, okay, is risky. No one wants it. So, if we're targeting the chief legal officer and the N-1, you get 2 to 3 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 C-level executives don't respond to marketing. They might see your brand. They're not gonna respond to a marketing campaign. Okay? They 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 C, right? It is a, the founder should be ecstatic to wanna get in front of the chief legal officer at SpaceX. I think any founder that is, You know, building something really meaningful knows the importance, important role of that. Second is you can get your enter— your, um, AE or enterprise sales lead to target the N-1, and you do what you call this. I call it the, the pincher model, 'cause you're going after 2 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. Okay? So, these are the 2 types of— these are the 2 layers you wanna be targeting in landing that meeting. 'Cause 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, right? And now you're learning from someone that is not near the budget or the executive discussions, right? Which is super risky. 'Cause 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, this, these 2 layers only. Wow.

This is, there's gonna be 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 1 is go after either the exec, so in this case it'd be general counsel, head of legal sort of person, or N-1.

Yep.

Love that way of describing it. Maybe a VP. Uh, you wanna pitch them 2 or 3 sentences in like a text or an email or in a, at a conference. Uh, and the key is to focus on the alpha, like the way what your product will unlock.

Yep. 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 down their, down the, down their command, they, they need to stand behind something beyond, hey, we're gonna make, we're gonna alleviate, you know, the, 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, um, however they, they wanna define that.

Yeah. So it's, it sounds like you don't wanna, like, they wanna win. And to win, you need something unfair and unfair advantage.

That's exactly right.

That's what you're pitching.

That's exactly right. Yep.

Okay. And then this pincer move, I love this. So, the idea here is for the exec, say chief legal officer, general counsel, founder needs to reach out.

Yep.

And then this AE reaches out to the N-1 contact.

Yes, exactly.

And you do this, you go from both directions.

Yep.

And I imagine the goal is 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, hey, I'm gonna bring in my founder. Could we see if your boss might wanna be a part of this too?

Mm-hmm.

'Cause it's, it's that parity 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.

Exactly.

'Cause I got this other email.

Exactly.

Maybe they may not remember. Okay. 2 questions. Um, how do you find this N-1 person? Any just tricks? Is it just sitting on LinkedIn kind of figuring it out? And then 2 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. Everyone 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, are there tools there to do, to figure out their number or whatever?

They're all so unique. Cold calling works. Again, it depends on the role. You're not gonna 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, there's a ton of tools that do enrichment. I also like, I'll try like LinkedIn first and say, hey, I shot you a note on LinkedIn. I just wanna make sure you got it. Like most people don't check that on a daily basis. But yeah, I mean, you have like Lemlist and all sorts of these enrichment tools that can give you the email. But I think the number one thing is 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, 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 2 to 3 sentences, if you have some in your head, maybe even from your current job that, that you think are good examples of this 2 to 3 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 are 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, like we'll help you reduce the number of resources here. Like, No, 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 prob— you know, you're probably getting some percentage of people responding.

Yeah.

So, okay. So, the advice is like, keep trying to refine this.

That's exactly right.

Awesome. Okay. Anything else on the first reach out before we get to the next step?

No, I think that's good.

Okay. Okay, let's do it. I saw you shaking your head before you said it, in case people are confused. Okay. Uh, step 2. Step 2 is basically running the intro call. Yes.

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, this is what I like to do, super informal. Don't show them anything. Don't show them a demo. Don't show them slides. Don't, like, focus on them, 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 don't know any founder that wouldn't wanna be in the room with a Fortune 100 C-suite executive. So, make sure you bring in your founder, uh, if, if you have that person on. But, let's say you had the N-1, you had, like, the VP on.

Okay.

Like, super brief. Hey, and this is how it typically opens. Hey, I'm gonna keep this super informal. I don't even know if we need a full 30 minutes. Put them on the back foot like, oh, this person's not trying to take up my time. All I would like to do is swap intros, and if it makes sense, we can always get on another call and go much, much deeper. But I just wanna 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 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, and Tighten it to what they specifically care about.

So, and they also aren't like sitting there now listening to a pitch or like, I don't know.

Right, 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, so now you're talking to them and they usually, they usually do a very brief opener. Like, hey, um, uh, we didn't get a chance to look up the chief legal officers, uh, at SpaceX. Obviously this is just a case, but like whoever that person's name is, 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? Like, what are you looking for going into 2027? Like, does anything need to change? Like, ask them, does anything need to change? Because again, what they're going to usually default to is what 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 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 wanna 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. Be like, 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, um, if you've done that successfully in 2027? And then they'll say, you know, you're trying to understand like how mature is this thought, right? Okay, so now they're going in, and they say they can't really answer that fully. 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 IPO. Like, what's causing the team to wanna reshape this or rework the way that they're managing internally? And, that's usually the moment of, like, where they start to really guide you in terms of, like, how they wanna structure their team. So, now, you're getting all of this information about where they wanna 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.

Yeah.

Be like, okay, full disclosure, right? And by the way, I take a step back for that. Do not bring a recorder to this call. Do not record the call. 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 for the benefit of yourself, do not have a recorder present. Okay? Just be like, off the record between the two of us talking right now. Of what you just shared, like what really matters? Like what, what, like, or like what do you wanna own? Or like what's the chronological, 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, how open is this person? Some people are poker faces, some people are not. You'll be able to go much deeper with some and not deeper than others. You just have to, um, 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. Um, the best thing you can do is listen actively and then feel confident enough to, to craft the pitch around what they just shared for you.

That last part seems really hard to— Yeah, it's very hard. Adjust and make up like, here's what you are focusing on and here's how our product is gonna solve that problem for you. 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 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.

What percentage of the time are you just like, Okay, this isn't actually gonna help you that much. So, let's just, we'll share where we're up to. Okay, you're nodding.

That happens. Yeah. One, I would say 2 to 3 out of every 4 calls, there's something real.

One out— Oh, wow. There's something real.

Yeah, there's something real. One out of every 4 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 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 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 1 in every 4 calls.

Well said.

Simply because of maturity.

Cool. So you don't have to have this like intense pressure to nail it on every call. And here's the, here's the pitch. Okay, awesome. What I also want to comment on is this idea of like getting them to share a bunch. It may feel tricky, like you're tricking them into 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 to, their job is to buy solutions to these problems. Right? That's why they have budgets, right? Um, so that's why the, the, 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 is 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?

'Cause 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, 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 wanna 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.

Mm-hmm.

I know classically you don't wanna focus on lowering costs as a sales pitch. This is the cheaper option.

Yeah.

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, there's usually gonna be 2 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, $250K, $500K land because the pro— because it is a high risk. If you're dealing with legal, there's high risk to it, right? Missing information, being delayed on something, not having people understand the importance of some new regulation or law, not being buttoned up. So, I think for— 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 upside.

Yeah.

The more you can be in that bucket, the more you can charge.

That's exactly right.

The easier everything gets. Okay. Uh, anything else before we get to step 3?

No, I think for step 1, 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, uh, 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— 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.

That's like dating.

Yeah. The, the, like their openness to share more.

Mm-hmm.

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 foreshadowing. Okay, so step 3 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, close won or close loss, right? There's 5 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 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, one, it's, you, you lost your leverage to like organize that group and rally them. But more importantly, it, 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. Okay? So, you wanna make this to be, and this is the tricky part, you want it to, you, 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, That's your champion at this point, whether it's the C-suite executive or, um, 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, to, to navigate. Okay. For that demo call. Now, 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 they're the, now it starts to feel like, oh great, I get, now they get to put their fingerprints on this. So it was like, okay, if we, when we demo 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 ask for 30 is probably— do 15 and say, here are the 5 different things we can, we can go into. From our first conversation, it sounds like these 2 things matter, but let me share you all 5. And then they might say, okay, I want you to do those 2 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, 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, do we wanna 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 knowing if they want something like this, they probably wanna 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. Okay, so now you have, do we wanna go into pre-demo? Do we wanna assume they checked off pre-demo or do we wanna 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, I'm gonna, for 5 minutes, I'm just gonna catch you up on the, 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 2 or 3 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 prep. Or worse, an 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 4 or 5 people? Don't do it. You're either a checkbox and you don't want, you wanna remove yourself from being a checkbox. Or 2, you're about to demo your product with no competitive intel. Like, you just lost the deal at that point.

No way.

Enterprise deals are won on, this feels 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 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 let's just say like—

No, no, no, it is. It's information edge. Yeah. It's the information edge that whoever I'm up against is not getting.

Mm-hmm.

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 a competitor who, who does some, or an incumbent. Right? Most likely the incumbent. But it's so crazy to me how many people just like spew out a pitch with like no, but you, you also have to make it informal and fun. Like you need to, you know, um, 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.

Yeah, absolutely.

And it, 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, those kind of pre, pre-run calls before a big demo. Like I'm ask— I'm clarifying all those questions like, Hey, I know you said this, like, 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, the answers you're gonna get are just gonna get so much more refined. The whole game is to slow down to go fast. All of this should be, should be within a 90-day sales cycle based off of their maturity.

So some people listening, 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, you can, where do you, how do you expand that? The whole game is expansion. If you're not going from $100K or $250K to $350K or $500K the following year, it's not an enterprise motion.

Okay. So just to kind of quickly summarize where we're at. Step 1, landing the meeting.

Yep.

Then running the intro call. Then there's this follow-up intro call.

Yep.

Which you pointed out is often ignored. Yep. And a big opportunity. to improve the demo. Yeah, I love the way you described the demo as 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 4 is prepping the pitch and framing the demo. Yeah. 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, right?

Okay, cool.

So yes, so now you have, you know, 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, like, 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? Like, 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, 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, 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, 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, you tell me, like, what the, the organization likes. And on that demo, there's gonna 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 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. Now they'll— now they're like leaning in being like, okay, all right, somebody— this is very aligned with what we need.

Because they have no idea you've talked to all these people.

No idea you talked to all these people.

Learn what their challenges are and priorities.

You're like, they're leaning in 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. These are, so now you could, 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 wanna get outta 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, 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 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 just gets thrown out the door cuz 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 could just blow the whole thing up. And the amount of times enterprises are like, hey, I'm not, 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 and 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? '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, it's, it, it's stuff that is, is doable. I mean, it's just psychology.

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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 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 sometimes where there's people that meander. You could say, I love this conversation, can we park it? Because I actually wanna 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 2 people that might be leading this, might be the founder, if you're still doing founder-led sales, could be the AE, could be a VP of sales.

VP of sales, yep.

Okay. As, say you're, say you're not the founder and you're, and you're the VP of sales or an AE leading this. As a founder, what are some signs that your salesperson is not doing a great job? Up to this point, what are just like smells of like, hmm, I should really think about this person?

I would say like, what is the timeline from intro call to demo? How many conversations have happened between those two, between those two buckets of like when people advance stages in the sales pipeline? Can the salesperson articulate exactly what they are gonna be demoing, why they're gonna be demoing it, and how they're gonna 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 scaled playbook? What's the scaled approach with this? When you're selling $100,000 minimum, right? Again, it's the same effort as selling $1 million. So it could be selling a million dollar deal. It, 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 gotta take a different approach. It is not cram the pitch down their throat and hope that they wanna buy something.

Feels like a job AI will not replace anytime soon from what I'm hearing here.

No, I, 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, do you vibe with this person? I mean, I've, I've definitely taken intro calls where the person probably did not appreciate with how I ran it, and that's okay. It was just, it happens.

It's such an in— uh, a point I've never heard before, this idea of when you're demoing, 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 you'd 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 wanna feel like it was built for them and that, um, it's different.

And they get alpha.

And get alpha.

Okay. Uh, so step 6, uh, 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 has helped guide you to this point. How do you think that went? Can we grab, can I call you in like 5 minutes? I just wanna, I want like a fresh debrief. They will give you and be 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? 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. 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 2 weeks or 3 weeks, you can now prompt with, hey, I know you guys are in, still in the process of like thinking through if this makes sense. Do you think it's worthy if I found 15 or 20 minutes with said individual 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, and this person that you're working with, would, would you call 'em, what would, um, what was the term you used for them?

A champion.

It's a champion. Yeah. Yeah.

'Cause a champion can also be an executive, right?

Yeah.

Or C-suite.

And they may, and they're like excited at this point, in theory, very excited for this to work out. Like they're on your, on your side. They're not trying to, Yeah.

And, 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'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 bought in. Okay.

Anything else around the demo or the post-demo discussion before we move on to the next step?

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, they allow them. Now you can control the, the timeline of that. Hey, I want you guys to go in for 2 to 3 days, these specific users. Don't put the, do not put your C-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.

Okay.

Run, don't charge. You could charge them for a pilot if it's an extended period of time, but I'd rather forego the money and do a 2 to 3 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 2 to 3 days and, 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 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 2 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 2 very technical things. Um, let's talk about something that they can get in 2 to 3 days, and it's a pretty, pretty much of a light lift. Timebox it to 2 or 3 days. Don't make it 2 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 2 weeks by doing 2 to 48 or 72 hours. Now, if you need something a bit more integrated and it, and it's a, a far more technical solution, what I'd highly recommend is do it for a month or 2 months, charge them for it, and then use that, that fee that you charged 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, It, it, they're not buying technology, they're buying the services to go through it. Um, and also make it a credit on the back end. Don't start the relationship up, Shiv. 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 guy. It's really—

It's 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, they, they may, they try and take someone else's game and run with it and it never works that way. Like no one taught 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, you're chatting more often. You're not trying to just like, yeah, speedrun. It feels more real.

Yeah.

Yeah. Okay. A couple questions here. One is this idea of the 2 to 3 day pilot. How do you, Convince them you only get 2 to 3 days, 'cause that feels tough.

So I would say here, this is what we typically do. Who are the 3 or 4 people we wanna put in and assess the, assess the value from a user perspective?

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 2 or 3 other people. Okay? And I want you to say, we're gonna do 2 or 3 days. I'm gonna onboard you each differently. We're gonna do, 2 or 3 different like onboard sessions before those 2 or 3 days. And I want you to go in and I want you to do these 3 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, um, 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 really easily.

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 3-stage process, you just, 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, because we've gone through, I think, 3 kind of around the same.

We've gone through so much. Yeah.

We've gone through so much. So, we're kind of on Step 9. So, there's, uh, step 7, which is identifying the pilot move forward process. A lot of people ignore just like, yep, 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.

So, we've kind of talked through all these things. Now, is there anything else along? Yeah.

For prep for the pilot, the one thing I wanna 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 pilot?

Ahead of that. Yes. Ahead of it. Um, I should have clarified that this is all before, before the, before the people's pilots start. This is in the pre-pilot stage.

Okay.

Assuming, fingers crossed, a successful pilot, which I feel confident is gonna be, um, 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 till after the pilot. Totally. 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 to make this make sense? Now, the one thing I'm gonna take a step back on is, You would've 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 3 times what I'm spending and not know why it's 3 times, right? 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?

Right, post-demo. I apologize.

Okay, cool.

Yeah.

So, and so you basically just kind of tell 'em, let's, we'll figure out pricing once we understand what you're looking for.

Yeah. 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've 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. Uh, 2 is, um, if they ask and they push, give them a ballpark. Well, it depends, but like, let's say it's somewhere between $150,000 and $250,000, and there's a lot of dependence on that, right? So, you can give them a ballpark, but work with your champion to 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 2 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. Mm-hmm. Because they will help crack, 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 3 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 $20K? And you're like, oh, I would've gone much lower than that, right? You don't wanna negotiate with yourself, but work with them. You've gotten to this point, you've shown so many people, everyone's excited. 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 2 and sign a 2-year deal.

Awesome. Expand. Okay, so in the pilot step, Do you, how many people do you give, uh, access to the pilot? Any advice there?

3, 3 to 4.

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 and the same, but you do want your in that one individual that's been giving you all this intel to be part of the pilot because you want them to get So before we get to the next step, which is post-pilot discussion and session, I imagine many products, especially today, just take a lot of integration work and data ingestion and, you know, all that stuff.

This whole FDE emergence, thoughts there if your product is just like, wow, it's gonna take us a month to even get you onboarded.

And that's that when we talked about those 2 different pilots, there's like, hey, we can show you the value in 2 to 3 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's 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 like integrate enough to make it practical.

Yeah. Your, 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 9 months to get a deal done, you've got, you probably should be charging $250K, $300K.

What are your thoughts on, uh, forward-deployed engineers as a part of this process, just as a role?

My opinions sway back and forth. Like, is a forward-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 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.

Um, it's a bad sign.

Yeah.

Yeah. I feel like, like the original idea of forward-deployed engineer, and the Palantir guys talk about this, like the original idea was they work at a comp 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. Totally.

And I think that an FDE is great for an expansion for a land on— okay, if you're talking about like a Palantir where it's much more complex to like, like, I understand why they did that, right? But they're also charging multimillion-dollar deals.

That's right.

Right? So like, they're— the, the business model structure supports that. If you're selling a $100,000 deal and you're pulling a 4-deploy, like, your economics are— 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.

Totally. And, you know, I think 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, 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 FDEs 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-pilot session.

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 because you might wanna push out the pilot if they're like, hey, listen, this is probably gonna be another quarter. Don't put the people in the pilot now, 'cause now you've lost all the mo— 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?

I always see commitment. So there's like the commitment and also just, which is equivalent to rolling it out to the company.

That's exactly right.

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 that momentum and they're like, yeah, you, you've like, you've already exhausted all the stages.

Um, you don't wanna do that. You want the stages to align with how they're thinking, but you wanna project management as tightly as you can. And some it'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, so yeah, so 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 5 steps and we're already in step 10 and we're not even done. And you made this point actually before we started recording that you haven't touched on that I think is important for to share this idea of that these 5 steps kind of emerged out of like a CRM pipeline kind of check thing. Talk a bit about that.

Yeah, so everyone knows the traditional 5 steps: intro, demo, proposal, contracting, and then like closed won or, or closed loss, right? Those are like the, the typical, 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 proposal or something mid-funnel might be weighted at 50% of the deal value for the, for the, um, 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.

Mm-hmm.

Um, and I think a lot of people use those buckets to say, okay, I've, There's about 5 different meetings that need to happen. When it's like, no, there's like 3 meetings, maybe up to 5 meetings in each of those buckets that are critical, 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 wanna 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 $100K deal, you probably can accelerate it a little faster. Again, ensuring that they're qualified.

And then you'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 5-step process?

90%.

Wow.

Yeah, because, like, enterprise sales is, it's, it's, 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 going. 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? 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, I know we gave the— I know we gave everyone those 3 things, but most people only spent it on 2. 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 to control also, That you're capturing what they did in those pilots 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 15 minutes today. They didn't get past step 1. Don't tell them what they're doing. You shouldn't even be that, but like, they didn't get past step 1. Do you want to, 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 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, 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 it could all fall apart.

Yep.

Um, what I was gonna say is it feels like many people would naturally, like, they don't wanna, they wanna avoid confrontation. 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. Oh yeah, everything's great.

Just like VCs.

That's right. That's right. And so 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. Let's re-pick this back up. That's why having someone on the inside is so, so, so critical.

And yeah, the easier approach is just to stop responding and just hope that the salesperson understands they're a 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 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, 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 50%, meaning of all sales qualified leads or opportunities, a healthy win rate is usually around 30 to 35%.

From qualified lead to signed contract.

Meaning you speak to 100, you're closing anywhere between 30 to 35, maybe slightly less. Maybe 25 to 30. That seems high actually. Yeah, 25 to somewhere between 25 and 35%. Why? If, 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? There's, those are all the chasms.

And the implication here is it's better off keeping your price high than winning more often.

Uh, yes, because the market talks too. The worst thing you can do is charge somebody's friend $50K and somebody else $500K. They talk, people, the market talks. You have to assume that.

Yeah, I'm in a lot of, a lot of WhatsApp groups with founders and they do exactly that.

That's exactly—

What kind of deal do you get for this, this product?

Yeah, that's exactly right. So the, 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, uh, deal— deals to not advance, right? But to a healthy win rate in the enterprise is typically be— I would say between 25 and 35%.

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 in So, it's usually like from qualified lead to like, um, you're coming outta demo, it's probably you lose half. And then—

Out of demo?

Out of demo. Yeah.

And then—

Post-demo offers. Yeah. It gets you to 30%.

So, from demo to, what was that step that you lose?

From demo to like, the more you move down the funnel, the less those numbers Uh, the less, uh, I see. wider those numbers. So like, Okay. so like, let's say if you speak to, um, and you're doing a really good job targeting the right people, maybe, uh, 70, 50% of those people move to a qualified lead, or 50 to 75% move to qualified lead. Of that, then, um, 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 a good deal qualification.

So, say you're at the pilot stage, what percentage should you expect drop off and earn?

80%.

80% succeed post-pilot? 80%, correct. Yeah. Okay. Amazing.

We find that.

Yeah. Okay. So, if you're below that, something's wrong with your pilot.

Yeah. Or you're not qualifying clearly or quickly.

I see.

Yeah.

You're almost doing too good a job convincing them this is the thing for them.

Correct. And the product's not there. Correct. So yeah, that, that's where, and again, like smart buyers always wanna do a pilot, so just have it part of your process.

Okay. There's 4 more steps to go before you're done, before the money's wired. Um, okay, so step 11, papering prep, setting timeline for procurement. Yes.

So you have now, um, 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 agreed to. Here's the pricing that's predicated on us getting this signed by this date. Here's the— give them something. Here's the kicker they're gonna give us if we get to this date. 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 cuz they're gonna always redline. 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 is in 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. Google, like Microsoft Office. Microsoft Word.

Yeah. Yeah. Most of these people can't access Google Docs, but yes.

And so, this says post-pilot, 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.

And again, your internal champion is, is you're working from N minus 1 from the exec— from the executive sponsor, or it's the executive sponsor themselves. You, you wouldn't have made it— they're not gonna put their team into a pilot if it doesn't have legs.

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 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, right? Very easy to blame procurement. Usually procurement is like a 30-day process, doing 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. That's their job. Procurement is the only person that can get you paid. Do not start any work till you go through 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, like, 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 11, 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 little gift you'll get if you do it by the state. Free month or whatever. Okay. Uh, step 12, papering review.

Yes. The best thing you can do is they're gonna send you back redlines, no question. If the redlines are extensive, okay, go ahead and accept the things that are easy. If the redlines are extensive, see if you can get legal on a call live and just talk through them. That will accelerate your sales cycle.

Versus a bunch of back and forth emails.

Versus 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 redline. Can we jump on a, a live call and just go through them? Focus on the things that are gonna impact the business and push in 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 lawyer, commercial legal team. Have a lawyer look at their redlines.

I imagine most companies have legal counsel.

Yes, I would hope. I would hope so. Yes.

Okay, cool. So papering review. So that's reviewing basically. It's interesting you call it the paper. Yeah. Um, is there like a more technical term for that? Like the—

Contract? I say papering. That's like corpo language, paper.

So interesting.

Yeah. Okay.

Papering review. Okay. Step 13, papering procurement process.

Yes. So this is where, um, we kind of talked about this. We kind of merged 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 gonna be a lot in there that you're gonna need to—

Redline.

Redline. 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, you know, they're gonna give you the kitchen sink. Know that it's all negotiable, but, but pick your battles. Pick your battles.

Yeah. Don't be afraid, like, the deal will fall apart if you—

Yeah, no, don't be afraid.

See something in there you shouldn't.

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.

Okay. And the final step, signature. Ta-da!

Yep.

Anything special other than signing?

No, that's, this is like the really exciting point, which is, um, just figuring out who the signatory is before it goes routed 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. Um, and you just wanna make sure you, everyone knows who that individual is because if there's a 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.

Yes.

Let's go. Steak dinner, champagne. I don't know what else people do when they close a deal. Ding a bell. There's bells often.

You know what we do? Okay, what's the next one? That's it.

Yeah.

'Cause you're all, you are in sales, you're only as good as your pipeline.

Hmm. Uh, so fun. It must be the best feeling after all this work.

It is. It is. But then you're like, oh, now Like literally the feels is like 5 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?

Yeah.

Once the deal's signed?

Yeah. Um, 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. Um, once these people are in to understand like what part of the product is, um, custom to what these people need and do we wanna build out, you know, do we wanna charge for services? Again, here's the other thing too, services, and I know every company is an ARR recurring revenue focus, but services is still the largest line item in budgets.

And so, you're saying, uh, it's okay to offer services.

It's okay to offer services. Yes.

Yeah.

Yeah.

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.

Yeah.

Being a part of software companies.

It's what they know how to buy. They're so used to it. Consultants, lawyers, you name it. Um, 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 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's not right. It usually comes down to timing, or why they're not mature enough to be able to, um, be in a position to— it, it's interesting. You have to be, your 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 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.

Mm-hmm.

But like, if you are in a, if your sales maturity in the enterprise is further, uh, further down the road, you wanna start with selling the technology versus the services.

And if you talk about how it's not the right timing, you're not mature, 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 tell them why you think it's not the right time.

Yeah. And you, 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 up said 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.

Yeah. But like, you think, listen, I know you need this. 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 and say, okay, here's what everyone else is doing in this space.

Well, exactly. Or like, hey, listen, on our first 2 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. 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, I don't want X to get in the way of that.

Mm-hmm.

And there, and then there's obviously, they're gonna 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 of this podcast are product managers, product people. It just feels very producty and product management-y in terms of the organization and the step-by-step and just like, or just staying 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 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. It's like, yeah, unexpected. We did it, Jen. We did it. We went through it all. Is there anything else? Anything else we haven't touched on? 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, uh, oh, I was going to say, I love that AI. I don't think it came up 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 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?

Exactly.

It always comes back to that.

Exactly.

And I know you talked about this last time, just like, Craft your own email and text. Don't, don't use the boilerplate. Yeah. Don't use your AI.

Emails are living and breathing. I swear to God that like people can read you saying the email out loud. Mm-hmm.

Mm-hmm. Yeah. Okay, Jen.

Uh, this is awesome.

This was amazing. Everything I wanted it to be. This is gonna be— I'm excited for like the— not to talk about AI, but just like the AI summary of this especially. That's just gonna be like step 1, 2, 3, 4.

Here it is. Yeah. Yeah.

Uh, final questions. Anything you wanna plug? Anywhere you wanna 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, we are actively hiring and I will teach you everything I know. Wow.

And this is at State Affairs?

It's at State Affairs.

Holy shit. What an opportunity. Yeah. So there's multiple roles, not just one.

Multiple roles. Yeah.

Wow. Uh, you'll be paid to learn from Jen directly.

Yes, 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 folks want to check that out.

Awesome.

Amazing. Um, Jen, thank you so much for being here.

I knew this was awesome.

It's 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 review, as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.