So, we're going to do something really unique with this conversation: basically go through the enterprise sales life cycle step by step. Let's set this up.

Let's start with how do I even get the first meeting? We're in this flood-the-zone moment of everyone trying to break into the enterprise, but what exactly are you solving for them as a problem? That's level one, but most importantly, the alpha—and it needs to be different.

Step two is basically running the intro call.

This is the most important call out of all of them. This is what I like to do: super informal. Don't show them a demo. Don't show them slides. Focus on them. Have a one-on-one dialogue for 30 minutes. The whole game is to slow down to go fast. And by the way, do not bring a recorder to this call.

What are the benchmarks for how often you get through each of these stages?

The win rate for enterprise is usually around 30 to 35%. If your win rate is higher than that, your price is too low.

What are some signs that your salesperson is not doing a great job?

The most successful salespeople are not trained salespeople. The 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.

It's literally so fun. People read these sales books, go to these sales trainings, and 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 at 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 third time on the podcast. For those that don't know Jen, she's co-founder of JJELLYFISH, 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 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 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 lennyspromos.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 three. 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 going to basically go through the enterprise sales life cycle step by step. You'll talk about this, but many people think it's like five steps. You talk about how it's actually something like 15 steps, and a lot of people ignore a lot of these steps.

The idea is I want to create a very concrete and tactical playbook for how to do enterprise sales. Just suck all the secrets out, make everybody amazing at sales. It'll be great.

Awesome.

This touches on just why I think the podcast is really helpful to people, and just the Valley vibe even though you don't live in the Valley. There's so much win-win-win in helping people learn these things. It may feel like, why is she giving away all these things? But maybe actually let me ask you that: why do you share these things?

Well, it's so interesting because there's so much art to this that even if you gave someone a 15-step playbook, there's so much of a feeling that you have to go off of. Sales is one-on-one, right? You're dealing with a variable, which is another individual. And if you ran the same flow every single time, it's going to probably not hit one out of every four times because everyone's different.

Some people like to joke, some people like the small talk opener, others want to jump right into it, some are technical, some are not technical. So everybody's so different that even as we go through all these 15 steps, while it's 80% of it, the other 20% is obviously the art of 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. There's too much to cover today, so we'll stick to the roadmap of how to close these deals.

I think the interesting thing about enterprise sales is even if you sell a $100,000 solution, it is the same exact process to sell a million-dollar solution. That's why it's an interesting process, because enterprise organizations are more sensitive to the process you take them through from a sales motion than they almost are with demoing the product.

Amazing. And I'll just give a plug for—if people want to continue learning, your Twitter feed is just the best. You share all this stuff constantly.

Yeah. It's like a diary, and it also helps me 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 was just like, "I just want to remember this stuff myself. I'm just going to 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 going to be using here?

Let's use a company like SpaceX, right? Recently has seen massive news pressings. Everyone's probably targeting them, right? So it's going to be a hard logo to go in and win. They are a technical organization, but I think what we do is target a non-technical team.

So we're going to really get into the nuance of this. Let's do SpaceX, and 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 budget, right? Sometimes three to four times other budgets, and it's forever. There's always more money for legal.

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

100%.

Amazing. And I'll just add, the reason I love to have you on this podcast is I've left both of our previous conversations just so fired up about selling. 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.

Sales is marketing, marketing is sales to some extent, right?

All right, 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 one of the enterprise sales cycle?

No, I think SpaceX and targeting the legal function is good.

And then like a $100K deal, let's say. And to your point, it's the same process whether it's $100K or a million. And I will add a plug for a previous episode: you talk about why you want to be at least $100K as a deal to be a real enterprise company that will survive because of the ROI and 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 one: 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: how do I even get the first meeting? How do I even engage with these people?

There is so much nuance as you target, as we're using the case study of SpaceX today. You have the top of the rung, right, which is the General Counsel, the Head of Legal, the Chief Legal Officer. They all kind of have slightly different titles, but they all carry the same weight, which is: 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 two entry points: starting at the very, very tippy-top—meaning going direct to the decision-maker, the Chief Legal Officer—or finding the individual that would be maybe one step removed. 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-one.

In order for an enterprise deal to move forward, you need to have this extremely compressed storyline that lands immediately to the objective that they want to solve for at the organization. It has to go beyond just an AI mandate. I think every company today has an AI mandate, and I know everyone has an AI tool, but what exactly are you solving for them as a problem? That's level one.

Most importantly, the alpha: what does this executive uncover and unlock by bringing in a net new tool? Because bringing in a net new tool is risky. No one wants it. So if we're targeting the Chief Legal Officer and the N-minus-one, you get two to three sentences max. That might be through an email or 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 going to respond to a marketing campaign. They will respond one-on-one. And the best individual to go one-on-one to a corporate executive is the founder. Even if you're a Series B or Series C, the founder should be ecstatic to want to get in front of the Chief Legal Officer at SpaceX. I think any founder that is building something really meaningful knows the important role of that.

Second is you can get your AE or enterprise sales lead to target the N-minus-one, and you do what I call the pincer model because you're going after two different people and trying to get them together. The pincer model is: start at the very, very top, find that kind of floor, and work in between them.

These are the two layers you want to be targeting in landing that meeting because if you go any further than that, you risk they're not going to be able to communicate your storyline. It's a game of telephone, right? And now you're learning from someone that is not near the budget or the executive discussions, which is super risky because now you're learning about user value, not executive value. A $100,000 deal needs an executive sponsor to sign off on it to allocate the budget. This is why you need to start at these two layers only.

Wow. There's going to be fractals of questions and things to dig into with each of these steps. This is amazing. I love just how specific and tactical you are with all of these things. I'm going to try to summarize a couple of these tips, and then I have a follow-up question.

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. Love that way of describing it; maybe a VP. You want to pitch them two or three sentences in a text, email, or at a conference. And the key is to focus on the alpha, what your product will unlock for them. It sounds like there's still, "Here's the problem we solve for you," but here's really the alpha we unlock.

Correct. Because for an executive to bring something in and be the sponsor and disseminate this down their command, they need to stand behind something beyond, "Hey, we're going to alleviate the time it takes to do X activity." That's not big enough. They're like a founder, too, of their own business unit. You've got to sell the vision. How are they going to get to the next stage, whether with their influence, get more budget, get more people, however they want to define that?

Yeah. It sounds like they want to win, and to win, you need an unfair advantage. That's exactly what you're pitching.

That's exactly right.

Okay, and then this pincer move: the idea here is, for the exec, say Chief Legal Officer or General Counsel, the founder reaches out. And then the AE reaches out to the N-minus-one contact, and you go from both directions. I imagine the goal is one of them at least responds.

That's correct. And then because you're only one step removed, they'll usually loop in that next person. Or the founder could say, "Hey, I'm going to loop in my so-and-so colleague. Who on your team should we also include?" Or an enterprise executive could say, "Hey, I'm going to bring in my founder. Could we see if your boss might want to be a part of this, too?" It's that parity rule.

Yeah. And they might be like, "Wait, I've heard that name before because I got this other email."

Exactly.

Okay, two questions. One, how do you find this N-minus-one person? Any tricks? Is it just sitting on LinkedIn kind of figuring it out? And then two is, any channel recommendations these days? What's the best way to try to contact these people?

You can spar with OpenAI and Anthropic to let them do the quick scan: "Hey, I'm looking to target the Chief Legal Officer of SpaceX and their deputy. Who are possibly people I should be targeting?" And then go off that and do your own gut check and search from there. Usually, they'll give you the proper names.

Now here's the interesting thing about this: everyone is probably also targeting those people, okay? And this is why it needs to feel so different, and it needs to be about alpha. 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? Are there tools to figure out their number, whatever?

They're all so unique. Cold calling works. Again, it depends on the role. You're not going to cold call a highly technical person, but a non-technical person, it works. Email, LinkedIn, Twitter.

Are there tools to find these emails and things that you recommend?

Yeah, there's a ton of tools that do enrichment. I'll also try LinkedIn first and say, "Hey, I shot you a note on LinkedIn. I just want to make sure you got it." Most people don't check that on a daily basis, but yeah, you have Lemlist and all sorts of these enrichment tools that can give you the email.

The number one thing is: assume they are getting hit with hundreds of emails. How are you going to message your storyline to stand out? That's not easy to do, and that's really why founder-led sales is so important to figure that piece out.

That was my next question: what are some examples of two to three sentences, if you have some in your head, maybe even from your current job, that you think are good examples of this two-to-three-sentence pitch?

Yeah, I think it comes down to what is the differentiator to what you are offering—not even what do you do 10x better, because to them, it still sounds like a commodity. How are you rethinking the business model? How can you help them rethink the way that they're structuring their team?

We're in this flood-the-zone moment of everyone trying to break into the enterprise. The number one thing that breaks into the enterprise is, "Here is how you should be thinking about the way you model your business unit in the age of AI." And it needs to be different. It can't just be, "We'll help you reduce the number of resources here." No, no, no. How are they going to show needle-moving impact to their COO or CEO? If they were to bring it to the board meeting, what would they say about the product? "This product will allow me to do what?" That's the litmus test.

Is this a pitch that you iterate on over time because you're probably getting some percentage of people responding? So the advice is: keep trying to reframe 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, step two: step two is basically running the intro call.

Yes. Okay, this is the most important call out of all of them, 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.

Keep it super informal. Don't show them anything. Don't show them a demo. Don't show them slides. Focus on them. Have a one-on-one dialogue for 30 minutes.

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 100 C-suite executive. So make sure you bring in your founder if you have that person on. But let's say you had the N-minus-one, you had the VP level.

Keep it super brief. This is how I typically open: "Hey, I'm going to keep this super informal. I don't even know if we need a full 30 minutes." Put them on the back 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 want to better understand who you are, and I'd love to share what we are doing and why I specifically reached out to you. Would you like to go first?"

Always let them go first. Give yourself the edge, right? Because the more information you are receiving before you speak, the more you can frame it and tighten it to what they specifically care about.

And they also aren't sitting there listening to a pitch like everybody else.

Exactly. Now they're talking, now they're conversing. It's like, "Okay, now it's fun. This person's not pitching me. I'm in a conversation and a dialogue."

So now you're talking to them, and they usually do a very brief overview: "Whoever that person's name is, I oversee the legal team and blah, blah, blah." Okay, great. They usually don't give you much. So you say, "Interesting. How are you thinking about—do you guys have an AI mandate going on at the organization? How are you thinking about the existing way you guys are doing work? What are you looking for going into 2027? Does anything need to change?"

Ask, "Does anything need to change?" Because what they're going to usually default to is what conversations have happened above them and have been transcended down. Change is usually dictated from the top, which is great. So, "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. You don't want to be too pointed, anchoring them towards your product, because the more they speak, you can start to pull on the strings that matter. So they could say something along the lines of—I'm making this up at this point—"We are really looking to figure out how to bring more of this work in-house and rely far less on external law firms because now we have more tools and capabilities."

"Is there a measurement to that right now? What does that look like internally in terms of if you've done that successfully in 2027?" You're trying to understand how mature is this thought, right?

And then they say they can't really answer that fully. "Why is that important now? Why not wait another year? I mean, you guys have so much going on. You just had this massive IPO. What's causing the team to want to reshape this or rework the way that they're managing internally?"

That's usually the moment where they start to really guide you in terms of how they want to structure their team. Now you're getting all of this information about where they want to go. When you talk about what you do, now you're the vehicle to get them there.

I try and spend maybe the back 10 minutes explaining what we do and just keep asking them questions. Be like, "Oh, that's so interesting. What an exciting role to be in." Be like, "Okay, full disclosure..." And by the way, I take a step back on 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 because I think everyone kind of operates under that assumption right now, but for the benefit of yourself, do not have a recorder present.

Say, "Off the record between the two of us talking right now, of what you just shared, what really matters? What do you want to own?" Keep digging, digging, digging, because the more you dig, the deeper you go, the more information they give.

Now, you can't sit there and just pepper them with questions. This is that art piece of how open is this person. Some people have poker faces, some people do not. You will be able to go much deeper with some and not as deep with others; you just have to improv.

After you now have that intel and you understand the frame you're going to take, now you can give them the pitch. I will confirm: every single conversation I have, the storyline that I tell looks slightly different. I do not have a scripted pitch or frame for any call because it feels artificial. They feel it; it feels like you're putting them into a square box. The best thing you can do is listen actively and then feel confident enough to craft the pitch around what they just shared with you.

That last part seems really hard—to adjust and make up, "Here's what you're focusing on, and here's how our product is going to solve that problem for you." That's kind of where that art and skill comes in.

That's right. In enterprise sales, it's 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 another call: the most successful salespeople are not trained salespeople. That's why founders are so good at this. 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 going to help you that much," so we'll just share where we're at? You're nodding that that happens.

I would say two to three out of every four calls, 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. I'd love to revisit this in a year once you guys have a chance to solve for X, Y, or Z."

That's such a great question about qualification. Most people are not going to be qualified, not necessarily because you're talking to the wrong person—because if you're an enterprise account executive, your job is to know who to talk to—your job is also to quickly disqualify someone. It's probably one in every four calls simply because of maturity.

Cool. So you don't have to have this intense pressure to nail it on every call, like, "Here's the pitch."

What I also want to comment on is this idea of 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. Why would they not want to just say, "Here's what we need help with, here's the problem, here's our priority"?

Their job is to buy solutions to these problems, right? That's why they have budgets. The fastest way to commoditize yourself is to go into some sales script like BANT—budget, authority, need, timing. That should be in the back of your brain. You never actually ask those questions.

Cool. Okay, so the core lesson here is focus on learning and extracting their priorities. And what I felt as you described it is you push them to get more real and really pressure-test how big of a deal these are: why is this important?

Because you want them to ask you those questions, because that's when you know you're building a relationship. I had a client last week say to me, "What's the biggest learning your team has had this year?" Every product needs to get better, every product has a bug, every product isn't able to do X or Y as well as they said. And I was like, "That's so funny, we just had a conversation about that," and she was like, "Thank you for sharing that." They just want to know you're vulnerable, because then it feels less like sales.

I imagine priorities for a lot of companies these days is saving token costs. Classically, you don't want to focus on lowering costs as a sales pitch—like, "This is the cheaper option." Thoughts on if that just comes up a bunch, like, "In legal, we just need to save costs"?

Yeah. In pricing, there's usually going to be two motions: "I need the lowest-cost way to do X because it's low on the totem pole and I really don't care if it's 60% of the way there; no one's getting fired over it, I'd rather just save budget." Or you're solving a problem where you can charge a $250K to $500K land because it is high risk. If you're dealing with legal, there's high risk to it: missing information, being delayed on something, not having people understand the importance of some new regulation or law, not being buttoned up.

Every organization looks different. Marketing and sales, it's very clear that numbers drive them. For legal, they need to stomp out risk.

Awesome. Basically, this comes back to the idea of alpha and upside: the more you can be in that bucket, the more you can charge, and the easier everything gets. Anything else before we get to step three?

No. For step one and two, 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 low-pressure at that point: you're just exploring, so I could see why people come into it like, "Cool, let's learn, let's see what this is." Versus when you're in the funnel, you're like, "Oh, I've got to actually make a decision, I'm going to have to let them down if I don't want this."

Yeah, that's like dating. Their openness starts to clam up a little bit more. But we'll talk about how to make sure that doesn't happen, too.

Amazing. Great foreshadowing. Okay, so step three is the follow-up intro call.

Yes. Right now, the stages that most people have are intro, demo, proposal, contracting, closed-won or closed-lost. There's five stages, very basic. People usually go from an intro call straight to a demo. The demo is your carrot in the process. Everyone wants to see this amazing thing you just spoke about.

Your job is to make sure that when you do that formal demo, you have the right people on the call. If you don't, one, you lost your leverage to organize that group and rally them. But more importantly, you never want it to feel like one person's baby. If you're selling to that director or that VP, you need to make sure that executive feels like it's part of their baby and they have their fingerprints on it. And vice versa: the C-suite wants the actual users to feel like they were bought in on this, too.

You want to make this—and this is the tricky part—there's going to be someone that's going to champion it and get the deal done, but you've got to make it feel like a group effort.

The person that you had the intro call with, that's who you built the rapport with. That's your champion at this point, whether it's the C-suite executive or one step removed. Most champions are one step removed, but let's just say the C-suite executive has delegated this now to the champion to navigate.

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 support you guys." This call should be 15 minutes, by the way. "I'd love to do a demo, but before we do the demo, I want to 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 the product right now, what do you think would resonate with the team?"

Now you're collecting more intel. Now it starts to feel like, "Oh great, now I get to put my fingerprints on this." They'll say, "When we demo to this group, can you ask this question in the meeting? Because I want them to understand the value." Or, "I'm actually going to ask this question because it's going to resonate more."

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 are giving you from these conversations, and now they feel part of this journey. Now they trust you.

You're spending 15 minutes trying to figure out—ask for 30, but probably do 15—and say, "Here are the five different things we can go into. From our first conversation, it sounds like these two things matter, but let me show you all five." And then they might say, "Okay, I want you to do those two that we spoke about, but I also want you to show this because this is also part of our mandate, and this will make it feel holistic."

So now you just mapped out the storyline with an internal partner on their end, and now you have the names of the right people. Now you close that call: "Great. Is there a time we can look at everyone's calendar and put this on the calendar?" Make the meeting an hour. The demo should be an hour.

Now, you can ask before this meeting: "Do we want to do a pre-demo to maybe someone else on your team that would be excited by this before you race to the group demo, or should we just do the group demo?" They know their organization better than anyone else and how pressing this need is.

If they're less mature in 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 really want to 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.

How often does that pre-demo happen?

I try and push for it because, again, it's just more intel.

Yeah. So let's assume there's a pre-demo.

Okay. So now you have a new colleague on the phone and you could say, "Hey, for five minutes, I'm just going to catch you up on the things that I just learned from so-and-so. What can you add to that? What do you think?"

Do you see how you're just collecting more and more intel along the way? Now you're building the business case for them. Now they feel like they're buying, not being sold to. 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 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 four or five people?" Don't do it. You're either a checkbox—and you want to remove yourself from being a checkbox—or two, you're about to demo your product with no competitive intel. You just lost the deal at that point.

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 just how much alpha not only you're sharing with us—it feels like the theme of this is alpha, just like the alpha we're getting from this conversation—it also feels like a lot of this process is you getting alpha from the team. I don't know if alpha is the right word, but—

No, it is. It's information edge. It's the information edge that whoever I'm up against is not getting. And you have to assume in the enterprise, you're always up against something: you're up against not doing anything at all, or you're up against a competitor or an incumbent—most likely the incumbent.

It's so crazy to me how many people just spew out a pitch. You also have to make it informal and fun. 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. 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. Are there any time buckets that aren't obvious, where you spend a bunch of time on your own thinking about something?

Yeah. I spend so much time thinking about reading in between the lines of what they were saying. That's when I will follow up in those pre-calls before a big demo, clarifying all those questions: "Hey, I know you said this. Did I interpret that correctly? Is that the priority?" And then, again, they'll go deeper.

The more you infer, the questions you ask—it's almost like you just have to keep prompting. It's like prompting humans at this point, right? Go deeper and deeper and deeper, and the answers you're going to get are just going to get so much more refined. The whole game is to slow down to go fast. All of this should be within a 90-day sales cycle based off of their maturity.

To 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 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—where do you go? 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 quickly summarize: we're at step one, landing the meeting; then running the intro call; then there's this follow-up intro call, which you pointed out is often ignored and a big opportunity to improve the demo. I love the way you describe the demo: it's kind of this carrot that you're holding that you can use a little bit to extract more. And then step four is prepping the pitch and framing the demo. Is there more to share there?

No, I think we're at the point where it's like, okay, now you're running the big demo, right?

Cool. Yes.

So now you have all of the people involved in the demo. You might have somebody involved from their AI team that's going to support some rollout. 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.

Before that demo, on one of those calls, ask: "Who are all these people? What do they care about, and what should I avoid?" The person that you've now built this relationship with can give you all of the intel. At this point, they want this to go forward. Now this is like a great star for them of, "I found this amazing tool, it's going to solve our problems, and now I get to put my name on it alongside one or two other people," right?

So for that demo, just make sure you know exactly who's involved, what these people care about, and what does a successful demo look like for them. I just ask them: "Hey, people do demos all the time. What looks good? 30 minutes of a discussion, maybe 10 minutes of showing, 10 minutes of discussion, 40 minutes in the product? You tell me what the organization likes."

On that demo, there's going to be people that were not a part of any of these calls, okay? Your job is to take a step back and restart with: here's who we are, here's why we 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're leaning in, being like, "Okay, all right. This is very aligned with what we need."

Because they have no idea you've talked to all these people, learned what their challenges are.

They're leaning in being like, "This feels different." Now, this is also the whole part of it 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. They're like, "Wow, these guys are good."

So now you let these net new people talk. Be like, "Hey, I know we haven't had a chance to speak. What do you want to get out of the demo today? I want to make sure I focus for you." Now you're leaning a little bit more into these net new people so they feel the love, okay?

And then when you demo the product, 80% of the value comes from 20% of the product, and you have learned on these previous calls what that 20% is. Do not demo everything unless there 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 because it's like, "Oh, well, I wouldn't use that. I wouldn't use that. Everything she just shared is really only over here," and you could just blow the whole thing up.

The amount of times enterprises are like, "Hey, I don't know if we want to spend this much money for half the tool when 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 to exactly who these people are.

That's why this role is so hard, okay? Because it's a lot of improv, and it's a lot of leaning in, and it's a lot of reading in between the lines. But it's stuff that is doable. I mean, it's just psychology.

This episode is brought to you by Mercury: radically different banking loved by over 300,000 entrepreneurs, and now with Command.

I've been a customer of Mercury's for over six years. I have never once thought about leaving. Mercury is basically what happens when banking is built by product people, not by bankers. They make it so easy—dare I say fun—to send invoices, move money around, set up virtual cards for folks on my team. Does your bank have an API, a terminal-native CLI, or an AI-ready MCP server? I don't think so.

And just recently, they launched Command, a conversational interface built directly into Mercury which acts as your financial operator. I've been using Command to transfer money around, to figure out what categories I've been spending the most money in, analyze my cash flows, and just today I used it to find out how much I've made from a specific sponsor over the past year. I just asked, "How much have I made from X over the past year?" Ten seconds later, I have an answer. It is so freaking cool.

Visit mercury.com to learn more and apply online in minutes. Mercury is a fintech company, not an FDIC-insured bank. Banking services provided through Choice Financial Group and Evolve Bank & Trust, members FDIC.

How do you deal with someone that's just kind of taking things off track or talking too long? I imagine that's a skill and an art, but just any tips there?

The good news is that most senior people—the people that you're doing your outreach to—it's very hard to get to that title if you're verbose and long-winded and take things off track. So that's the good thing about going after executives: those people are really dialed in. No one takes a meeting off track at an executive level.

Now, of course, there's sometimes where people meander. You could say, "I love this conversation. Can we park it, because I actually want to spend another call just dedicated to that?" And if that needs to happen, then of course you can run with it.

Awesome. There's kind of two people that might be leading this: it might be the founder if you're still doing founder sales, or could be the AE or VP of Sales.

VP of Sales, yep.

Say you're the VP of Sales, or you're reviewing this as a founder. What are some signs that your salesperson is not doing a great job up to this point? What are some smells of like, "I should re-look at everything"?

I would say: what is the timeline from intro call to demo? How many conversations have happened between those two buckets of 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. Every single time. I don't think I've ever run a demo and it looks the same. This is when everyone comes back to, "Okay, what's the scaled playbook? What's the scaled approach with this?" When you're selling $100,000 minimum—again, it's the same effort as selling a million dollars, so it could be selling a million-dollar deal—it's hard. You're cracking some of the largest logos that every single startup goes after. You've got to be different. You've got to take a different approach. It is not cramming the pitch down their throat and hoping that they want to buy something.

Feels like a job AI will not replace anytime soon from here.

Yeah, I am not worried about AI replacing it because there's so much about it that's just human, right? Do you vibe with this person? I mean, I've definitely taken intro calls with a person who probably did not appreciate how I ran it, and that's okay. That happens.

It's such 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 solved," and that's shooting yourself in the foot.

Or let them guide you, like, "Can it also do this?" And be like, "Oh, it's so funny you say that, we just released this." And now, all of a sudden, it feels like it's, again, built for them. They want to feel like it was built for them, that it's different, and that they get alpha.

Okay, so step six you call the post-demo discussion. Also something you say everyone ignores. 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 I call you in five minutes? I just want a fresh debrief."

Get their 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 solidifies everything that was said? Where do you think we lost somebody? Where do you think we did well? Is there someone we need to spend more time with?"

There's always someone in the organization that's going to kill a deal. There's always somebody. You need to protect against 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 if for some reason someone goes quiet for two weeks or three weeks, you can now prompt with, "Hey, I know you guys are still in the process of thinking through if this makes sense. Do you think it's worthy if I found 15 or 20 minutes with said individual to just hear their thoughts, and maybe we can approach this a little bit more closely with how they would want to see it?"

So you're just always looking for ways this might explode and not work. And this person that you're working with—what was the term you used for them?

The champion.

Yeah, because the champion can also be an executive, right?

Yeah. And I define champion as: who is the individual that really wants this to come to life, that was there from day one? Not necessarily the C-suite executive—they could be the one shepherding this as 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 you call identifying pilot move-forward process.

The best thing you can do, assuming that you've built an incredible solution—if you're now this far in, you usually have something—allow them now to control the time on, "Hey, I want you guys to go in for two to three days, these specific users." 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."

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 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.

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 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 prepping for the actual pilot?

Correct. There's two different pilots you can run: a pilot that does not require their data to be in the product to get the value, or a pilot that you want to charge for because they need to see some level of integration on their end for the whole product to actually work, right? I understand that those are two very technical things.

Let's talk about something that they can get in two to three days and it's pretty much a light lift. Timebox it to two or three days. Don't make it two weeks, okay? I've done this enough times to say people will go in usually for half a day and get what they need out of it, okay? Shorten your sales cycle by two weeks by doing 48 or 72 hours.

Now, if you need something a bit more integrated and it's a far more technical solution, what I'd highly recommend is do it for a month or two months, charge them for it, and then use that fee that you charge them 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 going to come out as services anyway because they're buying the services to go through it. And make it a credit on the back end. Don't start the relationship off on a bad foot; start the relationship off on a good foot.

I'm definitely feeling the feeling I feel when we chat, which is like: I just want to find something to sell. This is really—

It's fun. It's literally so fun. People read these sales books, go to these sales trainings, and they try and take someone else's game and run with it, and it never works that way. 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 more fun that way. You're building a relationship more, you're chatting more often, you're not trying to just speed-run. It feels more real.

A couple of questions here. One is this idea of the two- to three-day pilot. How do you convince them they only get two to three days? Because that feels tough.

This is what we typically do: "Who are the three or four people we want to put in and assess the value from a user perspective?" Make sure it's your person—assuming that's the person closest to the C-suite; don't put your C-suite executive in it, they're not going to go into the product—and two or three other people, okay?

And say, "We're going to do two or three days. I'm going to onboard you each differently. We're going to do two or three different onboarding sessions before those two or three days. And I want you to go in, and I want you to do these three specific tasks." Be very, very thoughtful and explicit and descriptive with what you want them to do.

"Here's how we're going to measure success." Define that with them, co-author that. And that's no different than the thing that's a little bit longer where you require that integration and build-out: co-author it with them. What does success look like? What are the specific things they should be doing? They should not just be logging in and meandering. That puts the work back on them. Your job in sales is to take all the work off their plate—99% of it—and help them discover the magic.

And also, you might have one of those users that's like, "Oh, I didn't like it." Great. In that three-stage process, what didn't you like? What wasn't clear? What wasn't obvious? Where did you get lost? The tighter it is, fewer 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 it clear the steps involved here, because we've gone through three kind of around the scene: there's step seven, which is identifying the pilot move-forward process, which a lot of people ignore—just 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.

Is there anything else?

For prep for the pilot, the one thing I want to say is: before we put everyone in, let's work backwards from, if this is successful, how do we get this deal through?

Ahead of time, before doing the pilot?

Yes, ahead of it. This is all in the pre-pilot stage. "Assuming, fingers crossed, a successful pilot—which I feel confident is going to be—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? Do you have a procurement lead that should be educated in this process?" And they might say, "Let's wait till after the pilot." Totally, but push them a little bit. Again, you're project-managing it. "Is there a security lead we should be working with to run due diligence on the product? Is there someone in legal, or is there a way for me to draft the paper to make this make sense?"

Now, the one thing I'm going to take a step back on is: you would have already gone through pricing discussions with them post-demo. Try to hold out on talking about pricing until post-demo because they might assume, "Oh, this is three times what I'm spending," and not know why it's three times, right? Because all these other people might not have been involved in those initial discussions. Talk through pricing post-demo once everyone's excited.

Post-pilot or post-demo?

Post-demo, I apologize.

Okay, cool, yeah.

Basically, you just tell them, "We'll figure out pricing once we understand what you're looking for." In the pre-pilot stage, talk about pricing.

Now, if they're this far along, if they're really concerned about pricing, they would have brought it up by now, right? So these are the little cues: "Okay, I think I could probably push them a little bit here, or go a little bit further."

Two is: if they ask and they push, give them a ballpark. "Well, it depends, but let's say it's somewhere between $150K and $250K, and there's a lot of dependence on that." So you can give them a ballpark, but work with your champion to say, "Listen, here's what the price is. I know you know why we price it this way. Before you put this in front of anybody, how are you going to make the case, right? Where are you going to cut? How are you going to defend it? How can I build out a slide to defend this for you and show you the ROI?"

Let them tell you. You don't have to go blind into it.

And then if they come back and say, "Listen, I don't know if I can go to bat for this," be like, "I hear you. Let's work on this together. 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?"

Do you include the slide or the price in the demo, or is that a post-demo conversation?

If they push you to do it, give a ballpark, but do pricing one-on-one with the individual you've been working with, because they will help.

This is what's usually going to happen. There's three answers: "We're all aligned, I'm not too concerned about this," or, "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 going to discount, don't throw out numbers. Be like, "I need your help to tell me how to make this work." 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 20K?" And you're like, "Oh, I would have gone much lower than that," right? You don't want to negotiate with yourself.

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 co-authorship. And remember, you can always do the full value in year two and sign a two-year deal.

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

Three to four.

Very small.

Very small, very tight. Who are the power users? Who are the people that are going to 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, but you do want that one individual that's been giving you all this intel to be part of the pilot because you want them to get you prepped for everything.

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, data ingestion, and all that stuff—this whole forward-deployed engineer emergence. Thoughts there if your product is just like, "Wow, it's going to take us a month to even get you onboarded"?

When we talked about those two different pilots, there's, "Hey, we can show you the value in two to three days," or there's, "Hey, we have to show you the value in 30 days." For a 30-day pilot, charge and credit it back to them, but know that your sales cycle is going to probably be a month longer because of that. But that's okay because you're probably charging more anyway.

Got it. And just do the work to integrate enough to make it work.

Your price should be predicated on your sales cycle, right? If you can get a deal done in 90 days for $100K, do that all the time, right? If it takes nine months to get a deal done, you probably should be charging $250K to $300K.

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

My opinions sway back and forth. 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 are you using a forward-deployed engineer because your product's so gnarly and hard to use that they can't do it on their own? That's a bad sign.

Yeah. The original idea of forward-deployed engineer—and the Palantir guys talk about this—the original idea was they work inside of your company building custom software for you to solve your problems, and then they 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. If you're talking about Palantir where it's much more complex, I understand why they did that, right? But they're also charging multi-million dollar deals.

That's right.

Right. So the business model structure supports that. If you're selling a $100,000 deal and you're pulling in a forward deployed engineer, your economics are going to get messy. You will not make money if you have a full-time engineer/salesperson sitting there working on this. And you know, I think there's a lot of folks in account management whose job is to service, expand, and upsell, and they just take on the title of FDE, so they're just another salesperson.

Yeah, it's a cool title. I think the Palantir people called FDEs at most companies "sparkling sales engineers."

That's awesome.

Okay. Anything else on up to the pilot step before we get to the post session?

Yeah, I think because now you've talked about the timeline: if this is successful, what does that look like? Again, you want to run this before you put everyone in it because you might want to push out the pilot. If they're like, "Hey, listen, this is probably going to be another quarter," don't put the people in the pilot now, because now you've lost momentum. You need the momentum to continue; you need the steps to happen. So use that: "Hey, if this is a successful pilot, how far out are we from a commitment from you guys?"

Oh, I see. Commitment, which is equivalent to rolling it out to the company. So if they're not ready in a month to roll this out if this is a huge success, then wait on doing it.

Correct. Yeah.

Awesome, because you're saying you may lose that momentum.

Yeah, you've already exhausted all the stages. You don't want to do that. You want the stages to align with how they're thinking, but you want to project manage it as tightly as you can. Some of it is out of your control, but yeah.

And yeah, it's not like you can push them to deploy it broadly. That's a thing that is probably very hard to shift. 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 five steps, and we're already at step 10, and we're not even done. You made this point actually before we started recording that you haven't touched on that I think is important to share—this idea that these five steps kind of emerged out of a CRM pipeline check thing. Talk a bit about that.

Yeah, so everyone knows the traditional five steps: intro, demo, proposal, contracting, and then closed won or closed lost, right? Those are the typical stages, or maybe there's some variation of that. That's not how you run sales. Those are buckets to understand a weighted forecast. A proposal or something mid-funnel might be weighted at 50% of the deal value for the pipeline. Something in contracting might be weighted at 80%, and something in intro might be weighted at 10%. That's what those stages are for. That's not the stages you take a client through; those are just the broad buckets. I think a lot of people use those buckets to say, "Okay, there are about five different meetings that need to happen," when it's like, no, there are like three to five meetings in each of those buckets that are critical to get the deal done. Now, we're still speaking at a very macro level. Obviously selling a million-dollar deal, you want to have more of those upfront meetings, and you want to make sure you know who the executive sponsor is and all that. You always want to know who the executive sponsor is, but for a 100k deal, you probably can accelerate it a little faster, again ensuring that they're qualified.

And 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 five-step process?

90%.

Wow.

Yeah. Because enterprise sales is mirroring their buying process. It's trying to control their buying process. It's not plopping these people into your sales process.

Amazing. Okay, let's keep going. Step 10: post-pilot session.

Yes. You can send a survey, or they might want to send a survey to get the intel, or go one-on-one to each of these users and say, "Hey," or let your champion discuss internally and say, "Hey, how was that?" You need to make sure that you are mirroring their experience from a technical perspective. How much time did they spend in the product? Did they run into any bugs? What were they using the most of? Because you need to be prepared going into that call to say, "Hey, I know we gave everyone those three things, but most people only spent time on two. Why?" That might be okay, but 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 it. So you just need to control 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 one. Don't tell them you're tracking them, but they didn't get past step one. Can you check in on them and make sure they're having a good experience?" Use your champion. 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 level is set up to have as much friction as possible. There are people that will kill the deal, then you've got to deal with procurement, then you've got to deal with legal, then you've got to deal with finding the executive sponsor—which usually comes at the very top of the funnel. 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.

Yeah.

What I was going to say is it feels like many people would naturally want to avoid confrontation. They won't want to say, "We don't want this." They're going to probably be like, "It's fine. It's good. Everything's great."

Like VCs.

That's right, that's right. And so it feels like a lot of this process is to pull out, "Okay, here's the concern, here's the problem." Are there any other signs of like, okay, they're actually not interested, this is not going well, and I need to really look at this?

When they go quiet. This is why your internal champion is so important. When they go quiet on you, that's when you know. And listen, 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 pick this back up later." That's why having someone on the inside is so, so, so critical.

Yeah, the easier approach is just to stop responding and just hope that the salesperson understands they're not excited.

Oh man.

Okay. What are the benchmarks for how often you get through each of these stages? You mentioned a few, just from demo to the next stage.

Usually, once something is qualified—meaning you're speaking to the right person, they are excited by the alpha, and 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, but everyone speaks to the same problem and it commoditizes you, which is why I don't like to overly emphasize it. The win rate for enterprise—a good, healthy win rate is actually probably going to surprise you. It's not 50%. Meaning of all sales qualified leads or opportunities, a healthy win rate is usually around 30 to 35%.

From qualified lead to signed contract?

Meaning you speak to 100, you're closing anywhere between 30 to 35, maybe slightly less, maybe 25 to 30. Somewhere between 25 and 35%. Why? If your win rate is higher than that, your price is too low. There's a part of the market that's just not at a maturity level to take you on, and that's healthy, right? Those are all the chasms.

And the implication here is it's better to keep your price high than win more often.

Yes, because the market talks, too. The worst thing you can do is charge somebody's friend $50k and somebody else $500k. People talk; the market talks. You have to assume that.

Yeah, I'm in a lot of WhatsApp groups with founders and they do exactly that: "What kind of deal did you get for this product?"

That's exactly right. 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 boomerang a year later of the ones that have been lost, that's probably another 25%. So it is totally normal and natural for deals to not advance. But a healthy win rate in the enterprise is typically between 25 and 35%.

Okay, that is incredibly helpful. How about key stages along the way, just percentage drop-offs?

Usually from qualified lead coming out of demo, you'd probably lose half.

Out of demo, post-demo.

Yeah, that gets you to 30%. The more you move down, the narrower those numbers get. Let's say if you're doing a really good job targeting the right people, maybe 50 to 75% of those people move to a qualified lead. Of that, another half move to demo, and then from there another quarter advance beyond that. Once you're in the bottom of the funnel, you usually don't lose too much from there if you're doing good deal qualification.

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

80% succeed post-pilot.

Okay, amazing.

I find that, yeah.

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

Yeah, or you're not qualifying clearly.

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

Correct, and the product's not there. So that's where smart buyers always want to do a pilot, so just have it part of your process.

Okay, there are four more steps to go before you're done, before the money's wired. Step 11: papering prep, setting timeline for procurement.

Yes. So you have now spoken prepilot about the timeline of what we're reverse engineering. Now you're going to document it in an email so that the champion 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 kicker they're going to give us if we get to this date." There's always got to be a reason to create urgency. And then what you want to do is say, "Here's our paper." Send a Word document. Do not send a PDF, because they're always going to redline. Always send a Word document of your paper and ask the question: "Do you want to use our paper? Here's a Word doc version. Or do you want to lift from it and 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 there, because they might say, "Well, in order for us to hit that timeline, we've got to use our paper."

And it's not Google Docs; it's Microsoft Word.

Microsoft Word, yeah. Most of these people can't access Google Docs.

And so this says post-pilot feels like it's gone well. You're saying the next step is basically getting the contract to procurement that early.

Again, your internal champion is N minus one from the executive sponsor, or it's the executive sponsor themselves. They're not going to 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 procurement. Here's something interesting a lot of people don't realize: people will use procurement as the excuse to not want to give you the bad feedback. "Oh, it's lost in procurement," right? Very easy to blame procurement. Usually, procurement is like a 30-day process between the back and forth on the legal 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 until 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: don't start any work until the papers are signed.

Start work meaning implementing, rolling out, onboarding people. Got it. Okay, amazing. So that's step 11: papering prep, setting timeline for procurement, kind of getting on board with what is it going to take to sign by this date, here's a little gift you'll get if you do it by this date—free month or whatever. Step 12: papering review.

Yes. They're going to send you back redlines, no question. If the redlines are extensive, 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. Get them on a call. Be like, "Hey, we're 80% of the way there. I have a few questions based off of your redlines. Can we jump on a live call and just go through them?" Focus on the things that are going to impact the business and push in on those. Let the other stuff go if it's not super important. Obviously, have a commercial lawyer look at it from your side. Have a lawyer look at their redlines.

I imagine most companies have legal counsel.

I would hope so, yes.

Okay, cool. Papering review, so that's reviewing basically. It's interesting calling it the "paper." Is there a more technical term for that, like the contract?

I say paper. That's like corpo language: paper.

So interesting. Okay, papering review. Step 13: papering procurement process.

Yes. This is where you are getting the procurement lead and that legal lead on a live call to work through the questions or the things you cannot accept. Now remember, if they give you their paper, there's going to be a lot in there that you're going to need to redline. They're expecting that; they're just giving you the kitchen sink, right? If they ask for $10 million of liability insurance as a smaller company, you can push back and be like, "Listen, your exposure with what we're doing is not that high." Or maybe it might be and you need that, but they're going to give you the kitchen sink. Know that it's all negotiable, but pick your battles.

Don't be afraid that the deal will fall apart if you see something in there.

At this point, the deal will not fall apart. You just need to work closely with them to make sure they understand where you're coming from. That's more what it is.

Okay. And the final step: signature. Ta-da! Anything special there other than signing?

No, this is the really exciting part, which is just figuring out who the signatory is before it gets routed for signature so that your internal champion knows. Sometimes it's the CFO; it's not the executive sponsor. You just want to make sure everyone knows who that individual is, because if there's a delay, you just want to 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. Ring a bell? There are bells often.

You know what we do? "Okay, what's the next one?" Because in sales, you're only as good as your pipeline.

It must be the best feeling after all this work.

It is, but then you're like, literally the feeling is like five minutes and then you're 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, like how to start thinking about where this goes once the deal is signed?

Yeah. And this is where the expansion comes in. You either know the products that they can expand into—like you've been through this journey before and that's pretty straightforward. But if you are early in the journey and you're closing your first 10 enterprise customers, you need the founder involved once these people are in to understand what part of the product is custom to what these people need, and do we want to build that out? Do we want to charge for services? Again, here's the other thing too: services. I know every company has an ARR, recurring revenue focus, but services is still the largest line item in budgets.

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

Yes. Yes.

This has come up a number of times, I think with Jason Lemkin and you—just the rise in services 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. 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 towards the end here: say you're a buyer and you're talking to Jen and you're just not sure this is a fit. You don't want to disappoint; you don't want to drag her along. What are some things that people buying software products, when working with a salesperson, how should they communicate? What should they be saying to avoid disappointment?

Yeah, I would say as soon as humanly possible, explain why the timing is not right. It usually comes down to timing or why they're not mature enough to be in a position to take it on. It's interesting: your organization and the team has to be structured in a way to bring on the technology. There's a maturity you have to go through. 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 if your sales maturity in the enterprise is further down the road, you want to start with selling the technology versus the services.

And if you talk about how it's not the right timing or you're not mature, I imagine the salesperson will try to prod you and push you to see if maybe you are. So it's okay to just tell them what you think.

I've had clients say to me, "Hey, 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." Sometimes they just need to hear that. Again, you need to know if you're in a position to be able to say that. But 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 again, use the intel they've given you towards that.

And interestingly, you're talking to a lot of their competitors, so you would think you have insight into, "Okay, here's what everyone else is doing in this space."

Yeah, exactly. Or like, "Hey, listen. On our first two calls, you told me how important this is. Did that change?" "No, we're just in a weird spot." I'd be like, "Okay, listen. Here's what we're going to do. Let's start a little bit smaller. Let's get in. You admitted that this is something that you guys need. I know that we are going to crush it for you. I don't want X to get in the way of that." And then obviously there are going to be cases where it's just not the right time. They might be going through an acquisition, right? And bringing on net new vendors is just 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 manager-like in terms of the organization, the step-by-step, and just staying on top of all these little things. It's so interesting how you don't think sales and product management are at all alike, but...

...but they're so similar! And it's just like you being human, like the way a PM tries to understand what your pain points are. We're here to solve them.

Yeah, unexpected. We did it, Jen! We went through it all. Is there anything else? Anything else we haven't touched on? Anything else you want to leave listeners with before we wrap up?

We gave them a lot.

We did, which was the goal. Just the right amount.

Yeah.

I was going to say, I love that AI—I don't think it came up maybe one time in this conversation. Very rare these days in podcasts.

Which I love. Well, it's interesting, so many people will create AI reports that they can send to their clients, or AI imagery, or you name your flavor. And it's like, anyone can do that. It just feels salesy.

"What's your alpha?" It always comes back to that.

Exactly.

And I know you talked about this last time: just craft your own email and text. Don't use boilerplate; don't use AI.

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

Yeah. Okay, Jen, this was awesome. This was amazing, everything I wanted it to be. I'm excited for the AI summary of this especially, that's just going to be like step one here. Final questions: anything you want to plug? Anywhere you want to point people to, and how can listeners be useful to you?

Let me know if anyone has questions. I'm more than happy to go deeper into this. I would say, if anyone—here's a plug—if anyone is interested in enterprise sales, we are actively hiring and I will teach you everything I know.

Wow. And this is at State Affairs?

This is at State Affairs.

Holy—what an opportunity! There are multiple roles, not just one?

Multiple roles, yeah.

Wow. You'll be paid to learn from Jen directly.

Yes, I will teach you everything I know.

Whoa. Okay, cool. We'll link to the job descriptions in the description if you want to check that out.

Awesome.

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

Lenny, this was awesome.

It was 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!