Lenny's Podcast: Product | Career | Growth - How to close $100K+ enterprise deals, step by step | Jen Abel

Episode Date: August 23, 2026

Jen Abel is the co-founder of JJellyfish and GM of enterprise sales at State Affairs. She is widely regarded as one of the sharpest practitioners in enterprise sales, and for that reason, this is her third visit to the podcast. In our first conversation we went deep on founder-led sales; in our second we mapped the $1M–$10M playbook. This time we do something I’ve never seen on another podcast: walk step by step through the full enterprise sales cycle. Most people think it’s five steps. Jen shows it’s closer to 15.In our in-depth conversation, we discuss:1. Why the standard five-stage CRM pipeline is a forecasting tool, not a sales process, and what the real 15-step cycle looks like2. The “pincer model” for landing the first meeting at the executive and N-minus-one level simultaneously3. How to craft a two-to-three-sentence message around giving them “alpha”4. How to run an intro call that extracts maximum intelligence before you ever show a demo5. The two-to-three-day pilot structure, how to define success jointly, and when to charge for a longer pilot versus giving it away6. Navigating pricing, procurement, redline negotiations, and the final signature without losing momentum—Brought to you by:WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and moreMercury—Radically different banking, now with Command—Where to find Jen Abel:• X: https://x.com/jjen_abel• LinkedIn: https://www.linkedin.com/in/earlystagesales• Website: https://www.jjellyfish.com—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction(02:49) Why Jen is giving away her enterprise sales playbook(05:54) Example: selling AI legal tech to SpaceX(09:11) Step 1: Landing the meeting(18:44) Step 2: Running the intro call(30:00) Step 3: Running a follow-up call(36:30) Step 4: Prepping the pitch/frame for demo(38:36) Step 5: Running the demo(46:45) Step 6: Post-demo debrief(48:59) Step 7 through 9: Preparing for and running the pilot(01:03:44) Why the standard five-stage CRM pipeline doesn’t work(01:04:49) Step 10: Post-pilot session(01:07:48) What a healthy enterprise win rate looks like(01:11:45) Steps 11 through 14: Navigating procurement and getting the signature(01:18:01) How to think about expansion(01:19:18) How buyers can say no without wasting everyone’s time(01:21:53) Why enterprise sales is a lot like product management(01:22:27) Closing thoughts—Referenced:• State Affairs: https://stateaffairs.com• The ultimate guide to founder-led sales | Jen Abel (co-founder of JJELLYFISH): https://www.lennysnewsletter.com/p/master-founder-led-sales-jen-abel• “Sell the alpha, not the feature”: The enterprise sales playbook for $1M to $10M ARR | Jen Abel: https://www.lennysnewsletter.com/p/the-enterprise-sales-playbook-1m-to-10m-arr• SpaceX: https://www.spacex.com• Lemlist: https://www.lemlist.com• Palantir: https://www.palantir.com• Jason Lemkin on X: https://x.com/jasonlk• We replaced our sales team with 20 AI agents—here’s what happened | Jason Lemkin (SaaStr): https://www.lennysnewsletter.com/p/we-replaced-our-sales-team-with-20-ai-agents• Building a world-class sales org | Jason Lemkin (SaaStr): https://www.lennysnewsletter.com/p/building-a-world-class-sales-org• Careers at State Affairs: https://stateaffairs.com/careers—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [e-mail].—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

So we're going to do something really unique with this conversation. 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're in this flood the zone moment of everyone trying to break into the enterprise. But like what exactly are you solving for them as a problem that's level one, but most importantly, the alpha? And it needs to be different. Step two is basically running the intro call.

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

What are the benchmarks for how often you get through each of these stages? The win rate for enterprise is usually around 30 to 35%. If your win rate is higher than that, your price is too low. What are some signs that your salesperson is not doing great? 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 never works that way. Most people think the sales process is five steps, and we're already in step 10. We're not even done. The worst thing you can do in the sales process is... Today, my guest is Jen Abel. This is her third time on the podcast. For those that don't know, Jen, she's co-founder of Jellyfish, GM of Enterprise Sales at State Affairs,

and most importantly is the person that I've learned the most from about the art and science of enterprise sales. In our first conversation, we went deep on FounderLet Sales, In our second conversation, we focused on the $1 million, $10 million enterprise sales playbook. And in this conversation, we do something I've never seen anyone do on another podcast. We go step by step through the full enterprise sales cycle. Most people think this is a five-step process. It turns out it's closer to 15 steps.

Most people ignore a bunch of these steps that you'll hear about. We go through everything that you need to know at each step to significantly increase the odds that you close your deals. This episode is incredibly tactical and specific. You will learn a ton I did for sure. Like I say in the episode, I always get so energized and just excited to sell something after talking to Jen. You will feel the same way after this conversation. I'm so thankful to Jen for sharing so much alpha with us.

Before we get into it, don't forget to check out Lenny's product pass.com for a free year of the hottest and most beautifully crafted AI products in the world, available exclusively to Lenny's new letter subscribers. With that, 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 there's actually something like 15 steps, a lot of People ignore a lot of these steps. And the idea is I want to create a very concrete and tactical playbook for how to do enterprise sales. Okay.

We've had conversations. All let's, that's the goal. Just suck them all out. 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 way all these things? But maybe actually, let me ask you that. Just like, 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. Like, 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. Like some people like to joke. Some people like the small talk opener. Others want to jump right into it. Some are technical. Some are not technical. You know, so everybody's so different that even if I gave,

even as we go through all these 15 steps, while it's 80% of it, the other 20% is obviously the art of like how you make someone feel. Do they feel heard? Did you make it fun? did you tell a good story? I mean, that's also a huge part of this. Too much to cover today. So we'll stick to the, we'll stick to the roadmap of like how to close these deals. But I think the interesting thing about enterprise sales is even if you're selling a, if you sell a hundred thousand dollar solution, it is the same exact process to sell a million dollar solution. So that's why it's, it's an interesting process because the enterprise. prize organizations are more sensitive to the process you take them through from a sales motion than they almost are with demoing the product.

Amazing. And I'll just give a plug for if people want to continue learning, your Twitter feed is just the best. You share all this stuff constantly. Yeah. And I think you talk about there's like rational reasons to show this stuff. But I think there's like 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. 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, you know, has seen massive news pressings. You know, everyone's probably targeting them, right? So it's going to be a hard logo to go in and win. They are a technical organization, but I think what we do is target a non-technical team.

So we're going to 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 kind of budget, right? Sometimes three to four times. other budgets. And it's forever. There's always more money for legal.

That's why there's so illegal a.S startups. I get it now. 100%. Amazing. And I'll just add, the reason, like, the reason I love to have you on this podcast is I've left both of our previous conversations so just, like, fired up about selling. I just, like, I have nothing to sell. But I'm always feeling like, I want to sell something now. I feel like I've learned all these things. It feels so fun. You are. You're a master. You're a master. You're actually a master at this. Sales is marketing. Marketing is sales to some extent, right? And 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 sales enterprise?

No, I think this is good. Sales cycle. SpaceX and targeting the legal function. And then like a 100K, let's say deal. And to your point, it's the same process, whether it's 100K, a million. And I will add plug for a previous episode. You talk about why you want to be at least 100K something as a deal to be a real enterprise company that will survive. That's right.

The ROI 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 Open AI Anthropic, Cursor, Replet, 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, skim, Rback, 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 seat 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 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 had slightly different titles but carry the same weight, which is like, 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. 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 one. 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 that lands immediately to the objective that they want to solve for at the organization. It has to go beyond just an AI mandate.

I think every company today has an AI mandate and I know everyone is an AI tool. But 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? Because bringing in a net new tool, okay, is risky. No one wants it. So if we're targeting, the chief legal officer in the N-minus-1, you get two to three sentences max. Okay? That might be through an email LinkedIn.

That might be through a phone call. That might be through an event or that might be through some marketing capability. Most C-level executives don't respond to marketing. They might see your brand. They're not going to respond to a marketing campaign. Okay. They will respond one-on-one. And the best individual to one-on-one to a corporation.

executive is the founder. Even if you're a series B, series C, right? The founder should be ecstatic to want to get in front of the chief legal officer at SpaceX. I think any founder that is, you know, building something really meaningful knows the important role of that.

Second is you can get your your AE or enterprise sales lead to target the N-1 and you do what you call this, I call it the Pinscher model because you're going after two different people and trying to get them together. It's actually called the Pinser model,

which is start at the very, very top, find that kind of floor and work in between them. Okay. So these are the two types of, these are the two layers you want to be targeting in landing that meeting because if you go any further than that, you risk,

they're not going to be able to communicate your storyline, It's a game of telephone, right? And now you're learning from someone that is not near the budget or the executive discussions, right, which is super risky. Because now you're learning about user value, not executive value. And a $100,000 deal needs a executive sponsor to sign off on it, to allocate the budget. And this is why you need to start at these two layers only.

Wow. There's going to be a fractals of questions and things to 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. Okay, so tip one is go after either of the execs.

So in this case, it would be general counsel, head of legal sort of person or N-minus 1. Yeah. Love the way describing it, maybe a VP. You want to pitch them two or three sentences in like a text or an email or at a conference. And the keys to focus on the alpha, like the way, what your product will unlock for them. Love that. And it sounds like,

there's still like, here's the problem we solve for you, but here's like really the alpha we unlock. Correct. Because for an executive to bring something in and be the sponsor and like share this and disseminate this down their, down their command, they need to stand behind something beyond,

hey, we're going to make, we're going to alleviate, you know, the time it takes to do X activity. That's not big enough. They want like, they're like a founder two of their own business unit like you got to sell the vision and what are

these people going to how are they going to get to the next stage um whether with their influence get more budget get more people um however they they wanted to find that yeah so it sounds like you don't want to win and to win you need something unfair unfair advantage that's exactly right that's exactly right okay and then this pincere move i love this so the idea here is for the exact state chief legal officer General Counsel, Founder needs to reach up. And then this AE reaches out to the N-minus-1 contact, and you go from both directions. And I imagine the goal is one of them at least responds.

That's correct. And then because you're only one step removed, they'll usually loop in that next person. Or you can say, the founder could say, hey, I'm going to loop in my so-and-so colleague. Who on your team should we also include? Or 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 parody of kind of rule. Yeah. And they might be like, wait, I've heard of that. I think I heard that name before because I got this other email. Exactly. I mean that remember. Okay, two questions.

How do you find this N-minus one person? Any just tricks? Is it just sitting on LinkedIn kind of figuring out of? And then two is any channel recommendations these days? Like, what's the best way to try to contact these people? So I'll use, you can ask, you can spar with Open AI and Anthropic to like let them do the quick scan of like, hey, I'm looking to target the chief legal officer of SpaceX and their deputy, who are possible people I should be targeting. And then go off that and do your own gut check and search from there. But usually they'll give you the 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 the tools there

to do the figure out their number or whatever? They're also 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, 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 want to make sure you got it. Like, most people don't check that on a daily basis. But, yeah, I mean, you have, like, LEM lists and all sorts of these enrichment tools. can give you the email. But I think the number one thing is assume they are getting hit with hundreds of emails. How are you going to message your storyline to stand out? And that's, that's not easy to do. And that's really why I think going back to our first episode, why founder

led sales is so important to figure that piece out. So that was my next question is what are some examples of two to three sentences if you have some in your head, maybe even from your current job that you think are good examples of this two to three sentence pitch. Yeah, I think it comes down to like, what is the differentiator to what you're offering? Not even like, what do you do 10x better? Because to them, it still sounds like a commodity. How are you rethinking the business model?

How can you help them rethink the way that they're structuring their team? We're in this like, flood the zone moment of like everyone trying to break into the enterprise. And the number one thing that breaks into the enterprise is like, oh, the way I'm modeling my, business unit, here's how I should be thinking about it in the age of AI. And it needs to be different. It can't just be like, oh, yeah, we'll help you reduce the number of resources here. Like, no, no, like, how are they going to show needle moving impact to their CEO? You know, if they were to bring it to the board meeting, like, what would they say about the product? This product will allow me to do what? That's like the litmus test.

Is this a pitch that you iterate on over time? Yes. Because it's probably, you know, you're probably getting some percentage of people responding. Yeah. 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 better. Okay. Okay, let's do it. I started shaking your head before you said it. Okay.

Okay. Step two. Step two 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 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 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 like the VP on. Okay. Like super brief, hey, and this is how it's typically open. Hey, I'm going to keep this super informal. I don't even know if we need a full 30 minutes.

Put them on the back for like, oh, this person's not trying to take out my time. All I would like to do is swap intros. And if it makes sense, we can always get on another calling, go much, much deeper. But I just want to better understand, like, who you are. And I'd love to share what we are doing and why I specifically reached out to you. So I'd 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 tighten it to what they specifically care about. And they also aren't like sitting there now listening to a picture. 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 do a very brief open. They're like, hey, we didn't get a chance to look up the chief legal officers 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, but, but, okay, okay, great. They usually don't give you much.

So they say, okay, interesting. Like, how are you thinking about, like, do you guys have an AI mandate going on at the organization? Like, how are you thinking about the existing way you guys are doing work? Like, what are you looking for going into 2027? Like, is anything need to change? Like, does anything need to change? Because, again, what they're going to usually default to is what conversations have happened above them and have been transcended down. So the change is usually dictated from the top, which is great.

So like what needs to change going into 2027 that you did in 2026 or maybe not at all? And that's when they start to open up. And again, you don't want to be too pointed of like anchoring them towards your product. Because again, the more they speak, you can start to like pull on the strings that matter. So they could say something along the lines of, you know, I'm making this up at this point. But we are really looking to figure out how to bring more. more of this work in-house and rely less, rely far less on external law firms, right? Because now we have more tools and capabilities.

Okay. Like, is there a measurement to that right now? Like, how are you guys? Like, what does that look like internally in terms of if you've done that successfully in 2027? And then they'll say, you'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. because they, okay, like, why is that important now? Like, why didn't you, why not wait another year? I mean, you guys have so much going on. You just had this massive appeal. Like, what's, what's causing the team to want to reshape this or rework the way that they're managed it internally? And that's usually the moment of like where they start to really guide you in terms of like how they want to structure their team. So now you're getting all of this information about where they want to go, right?

Now, when you talk about what you do, now you're the vehicle to get them there. Right. And so 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. And like, what an exciting role to be in? Be like, okay, full disclosure, right? And by the way, I take a step back to that. Do not bring a recorder to this call.

Do not record the call. They will not be open. They will not be vulnerable. It might assume it's being record, because I think everyone kind of operates under that assumption right now, but for the benefit of yourself, do not have a recorder present. Okay. You should take off the record between the two of us talking right now of what you just shared, like what really matters. Like what, like, or like what do you want to own? Or like, what's the chronological?

Like keep digging, digging, deep 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 like, how open is this person? Some people are poker faces. Some people are not. You will be able to go much deeper with some and not deeper than other. You just have to improv. 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 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 for you. That last part seems really hard to adjust and make up.

Like, here's what you're focusing on. Here's our product is going to 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 counterintrudent. 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. 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 going to help you that much? So it's just, we'll share we're up to. Okay, you're nodding that happens. One, I would say two to three out of every four calls. There's something real. There's something real.

Yeah, there's something real. One out of every four calls, I'm like, listen, based off of the maturity of where you guys are and where we are, it's too much of a gap. Like, I'd love to revisit this in a year, like once you guys have a chance to, like, solve for X, Y, or Z. The, that's such a great question about the qualification. Most people are not going to 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? And your job is also to quickly, um, quickly disqualify someone. and it's probably one in every four calls. Awesome. Simply because of maturity.

Cool. So you don't have to have this like intense pressure to nail it on every call. Yeah. Here's the pitch. Okay. Awesome. What I also want to comment on is this idea of like getting to share a bunch, it may feel tricky. Like you're tricking them to sharing all this.

But really, they have problems they want to solve. And you're there to help them solve a problem. And so why would they not want to just like, okay, here's what we need help with. Here's the problem. Here's our priority. Their job is the, job is to buy solutions to these problems, right? That's why they have budgets, right? So that's why 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 like really pressure. test, how big of a deal are these? Why are this? Why is this important? Because you want them to ask you those questions. Because that's when you know you're building a relationship. 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 as well as they said. And I'm like, that's a really good. I'm like, that's so funny. We just had a

conversation about it. She was like, thank you for sharing. That's what. They just want to know you're vulnerable because then it doesn't feel like it feels less like sales. I imagine priorities for a lot of companies these days is saving token costs. I know classically, you don't want to focus on lowering costs as a sales pitch. This is the cheaper option. Thoughts on if that just comes up a bunch. We just like legal. We just need a save cost.

Yeah. So in pricing, their job is to 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 that you can charge, you know, 250, 500K land 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 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. The more you can be in that bucket, the more you can charge.

That's exactly right. Easier everything gets. Okay. Anything else before we get to step three? No, I think for step one, like that is the most important meeting. And I feel like people just spend so much time talking about themselves and miss all the competitive advantage to win the deal. Yeah, your point about how as a buyer, it's so like low pressure at that point, you're just exploring. And so I could see why people come into it.

Like, cool, it's learning. Let's see if this. Versus you're in the funnel like, oh, should I get actually. make a decision. I'm going to have to let them down if I don't want this. It's like dating. Yeah, like their openness to share more or to clam up a little bit more, but we'll talk about how to make sure that doesn't happen to. Amazing. Okay. Great. Great foreshadowing. Okay. So step three is writing a follow up. Yes. Yes. Okay. So usually right now, the stages that most people have is intro, demo, proposal, contracting, you know, close one or close loss. There's five stages. They're very basic. People usually go from an intro call straight

to a demo. The demo is your carry in the process. Everyone wants to see this amazing thing you just spoke about. Okay. So your job is to make sure that when you do that demo, the formal demo, you have the right people on the call. Because if you don't, one, it's, you lost your leverage to like organize that group and rally them. But more importantly, you never want it to feel like, one person's baby, right? If you're selling to that director or that VP, you need to make sure that that executive feels like it's part of their baby and they're helping craft it and they have their fingerprints on it. And vice versa. Like you want the C suite if they want, they want, they want their actual users to feel like that they were bought in on this too. Okay. So you want to

make this to be, and this is the tricky part. You want it to, there's going to be someone that's going to champion it and get the deal done. But you got to 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 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, to, to, to navigate. Okay. For that. Now, now, before you do the demo, get on another call with them. Hey, 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 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, 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 it starts to feel like, oh, great. Now they get to put their fingerprints on this. So it's like, okay, when we demoed to this group, at this point, I want this question to be asked.

Can you ask this question in the meeting? Because I want them to understand the values. And they'll be like, I'm actually going to ask this question because it's going to 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 five different things we can go into. From our first conversation, it sounds like these two things matter. But let me share 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. Okay. So now you just mapped out the storyline with an internal partner on their end. And now you have the names of the right people. Now you're going to close that call, great, is there a time we can look at everyone's calendar and put this on the calendar?

Make the meeting an hour. The demo should be an hour. Okay. Now, you can ask before this meeting, do we want to do a pre-demo to maybe someone else on your team that would be excited by this before you race to the group demo? Or should we just do the group demo? Like, they know their organization better than anyone else and, like, how pressing this need is.

Now, if they're less mature in knowing if they want something like this, they probably want to bring in someone else before the big group, if they're like, no, no, no, this is something we want to, you know, really move into. They probably are ready to go into a group. So you just need to figure out where they are on that maturity arc of their decision. Okay. So now you have, do we want to do we want to? to go into pre-demo? Do we want to assume they checked off pre-demo or do we want to do group demo?

How often does that pre-demo happen? If you're, I mean, I try and push for it because 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 going to, for five minutes, I was going to catch you up on the things that I just learned from so-and-so. What can you add to that? What do you think? Do you see how you're just collecting more and more intel along the way? So now you're building the business case for them. Now they feel like they're buying not being sold to.

Okay, so now you have two or three people at this point, already excited for the big group demo. The worst thing you can do in the sales process when you move into demo is just go into one street demo with no problem. Or worse, a enterprise organization might reach out to you because they're going through a due diligence process to say, hey, we'd love to see what you guys have built where you present this to four or five people, don't do it. You're either a checkbox and you don't want, you want to remove yourself from being a checkbox or two, you're about to demo your product with no competitive intel. Like, you just lost the deal at that point. Enterprise deals are one on this feels so close to who we are. It feels like it was built specifically for me. That's the

whole game. Amazing. 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 what you say? It's information edge. Yeah, it's the information edge that whoever I'm up against is not getting. And you have to assume in the enterprise, you're always up against something. You're up against not doing anything at all or you're up against the competitor 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. You also have to make an informal and fun. Like you need to, you know, people also buy from people they like, right? I love how so far at least it feels very doable, not that difficult. It feels like I could do this. Absolutely kind. 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, read in between the lines of what they were saying. And that's when I will follow up. Like those, those kind of pre-run calls before a big demo. Like I'm asking, I'm clarifying all those questions. Like, hey, I know you said this. Like, did I interpret that correctly? Like, Is that the priority? Like, and then again, they'll go deeper.

Like, the more you infer the questions you ask, it's almost like you just have to keep prompting humans at this point, right? Like 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 sale 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, how do you expand that? The whole game is expansion. If you're not going from 100K or 250K to 350K to 350 or 500 the following year, it's an enterprise motion. Okay. So just to kind of quickly summarize, we're at step one, landing the meeting,

then running the intro call, then there's this follow-up intro call, which you pointed out as often ignored and a big opportunity to improve the demo. I love the way to describe the demo is kind of this carrot that you're holding that you can use a little bit to kind of extract more. Yeah. And then there's step four is prepping the pitch and framing the demo. Yeah. Is there more to share there? No, I think we're at the point where it's like, okay, now you're running a big demo.

Okay, cool. Yes. So now you have, 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 this is like a great star for them of like, I found this amazing tool.

It's going to solve our. problems and now I get to put my name on it alongside one or two other people. 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 organization likes. And on that demo, there's going to be people that were not a part of any of these calls. 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 like leaning in being like, okay, all right, somebody, this is very aligned with what we need. Because they've no idea. You've talked to all these people. Learn what their challenges are in 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. So now you get, you know, let them talk.

Let these net new people talk be like, hey, I know you, I know we haven't had a chance to speak. like, what do you want to get out of the demo today? I want to make sure I focus for you. Now you're leaning a little bit more into these net new people so they feel the love. Okay? And then when you demo the product, 80% of the value comes from 20% of the product.

And you have learned on these previous calls what that 20% is. Do not demo everything unless there is some reason to. Because now all of a sudden, in 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.

Well, everything should just share, that's really only over here. And you could just blow the whole thing out. And the amount of times enterprises are like, hey, I'm not, I don't know if we want to spend this much money for half the tool that we wouldn't use half the tool. Now, all of a sudden, you've just unraveled all the work you've just done. enterprise sales is super super super tight project management and super super super tight narrative and framing owning that frame owning that frame to exactly who these people are and that's why this role is so hard okay because it's a lot of improv and it's a lot of

leaning in and it's a lot of reading in between the lines but like it's stuff that is 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,

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banking services provided through Choice Financial Group and column NA, members FDIC. How do you deal with someone that's just kind of taking things off track or just talking too long? I imagine that's just like a skill and an art, but just any tips there. The good news is, is that most. senior people, like the people that you're doing your outreach to, it's very hard to get to that title if you're like verbose and long-winded and like take things off track. So that's the good thing about being going after executives is those people are like really dialed in. Like no one takes a meeting off track at an executive level.

Now, of course, there's some times where there's people that meander. You could say, I love this conversation. Can we park it? because I actually want to spend another call just dedicated to that. And if that needs to happen, then, of course, you can run with that. Awesome. So there's kind of two people that might be leading this, might be the founder. If you're still doing founder-led sales, could be the AE.

Yep. Yeah. VAPSales, yep. Okay. As, say you're not the founder and you're the VP of sales or an AE leaving 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 everything this person. I would say like, what is the timeline from intro called the demo?

How many conversations have happened between those two buckets of like when people advance stages in the sales pipeline? Can the salesperson articulate exactly what they are going to be demoing, why they're going to be demoing it, and how they're going to open it? the demo looks different every single time, every single time. I don't think I've ever run a demo and it looks 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 a million dollars.

So it could be selling a million dollar deal. It is, 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 cram the pitch down their throat and hope that they want to buy something. Feels like a job AI will not replace any type soon. No, I'm not worried about AI replaced. Because there's so much about it that's just human, right? Like, do you vibe with this person. I mean, I've definitely taken intro calls where the person probably did not

appreciate with how I ran it. And that's okay. It was just, it 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. 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 and that it's different. And they get alpha.

And get alpha. Okay. So step six, you call the post-demo discussion. Yes. Also something you say, everyone ignores. Yes. Talk about that. Okay.

So as soon as the demo closes, you are texting the woman or the gentleman or whomever that has helped guide you to this point. How do you think that went? Can we grab, can I call you in like five minutes? I just want to, I want like a fresh debrief. they will give you, 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 said, like, where did, do you think we lost somebody? Where do you think we did well?

Is there someone we need to spend more time with? There's always someone in the organization that's going to kill 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 two weeks or three weeks, you can now prompt with, hey, I know you guys are 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 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, would you call them, what was the term you used for them? A champion. Yeah. Because the champion can also be an executive, right? Yeah.

And they may. And they're like excited at this point, in theory, very excited for this to work out. Like they're on your side. They're not trying to. And I define champion as who is the individual that really wants this to come to life that's like was there from day one. Not necessarily like the person that's like the C-suite executive could be the one shepherding this well, but they need to make sure that the people below them are brought in. Okay. Anything else around the demo or the post-demo discussion before we move on to the next 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, right? If you're now this far in, right, you usually have something that they allow them. Now you can control the time on above. 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. Who are the users of this?

I want them to experience the magic and the power of what this is. Okay. 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. But I usually would, I'd rather go in for two to three days and let them see if they

can get the value from it. If they can, sometimes I understand that there needs to be some level of configuration and, you know, extensive onboarding that needs to happen. but 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. So there's two different pilots you can run. A pilot that does not require their data to be in the product to get the value or a pilot that you want to charge for because they need to see some level of like integration on their end for the whole product to actually work. Right. Like I understand that those are two very technical things. let's talk about something that they can get in two to three days,

and it's pretty much of a light left. Time box it to two or three days. Don't make it two weeks. 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. Shorten your sale 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 for a month or two months, charge them for it, and then use that fee that you charge them for and credit it back to them if they move forward. 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 it's like a, they're not buying technology. They're buying the services to go through it. And also make it a credit on the back end.

don't start the relationship off, shift. Start the relationship off on a good foot. I'm definitely feeling the feeling I feel when we chat is like, I just want to fight something to sell. This sounds really. It's fun. It's so fun. Like it's literally so fun.

People, I think people read these sales books, go to these sales trainings. And they try and take someone else's game and run with it and never works that way. Like 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, speed running. It feels more real. Yeah. Yeah.

Okay, a couple questions here. One is this idea of the two to three day pilot. How do you convince them? You only get two to three days because that feels tough. So I would say here, this is what we typically do. Who are the three or four people we want to put in and assess the 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 going to, they're not going to go into the product. And then two or three other people. Okay. And I want you to 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 like onboard sessions before those two or three days. And I want you to go in and I want you to do these three specific tasks. Be very, very thoughtful and explicit and descriptive with what you want them to do. Okay. Here's how we're going to measure success.

Define that with them. Define that with, co-author that. And that's no different than the thing that's a little bit longer where you require that integration and build out. Co-author it with them. What does success look like? What are the specific things they should be doing? They should not just be logging in and meandering.

That puts the work back on them. Your job in sales is to take all the work off their plate. 99% of it. And help them discover the magic release. Help them discover the magic. And also continue to, you might have one of those users that's like, oh, I didn't like it. Great. In that three stage process, 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 experiences. You don't want people having different experiences. Okay. So just to make it clear the.

steps involved here because we've gone through, I think, three kind of around the same. So we've gone through so much. So we're kind of on step nine. So there's step seven, which is identifying the pilot, move forward process. A lot of people ignore just like who that person is and what the steps are. Then there's prep for the pilot and then there's run the pilot. Exactly. We've kind of talked through all these things. Now, is there anything else long? For prep for the pilot, the one thing I want to say is, okay, before we put everyone in, let's work backwards of if this is successful, how do we get this deal through? Okay?

Ahead of time before doing the pilot. Yes. Ahead of it. I should have clarified that. This is all 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 going to be.

One is when do we want to get signatures on these papers? Let's work backwards from there. Do we think we can get this closed by the end of next month? Yes, I do. Great. Who needs to be involved in that? Like, do you have a procurement lead that we should be educated in this process? And they might say, let's wait till after the pipe.

Totally. But like, push them a little bit. Again, your project managing it. Is there a security lead we should be working with to run due diligence on the product? Is there someone in legal or is there a way for me to draft the paper to make this make sense? Now, the one thing I'm going to take a step back on is you would have already gone through pricing discussions with them post-demo. Okay? Try to hold out on talking about pricing until post-demo because you might, they might assume,

oh, this is three times what I'm spending and not know why it's three times. Because there's all these other people that might not have been involved in those initial discussions. Talk through pricing post-pilot once everyone's excited. Post-pilot or post-demo? Right, post-demo. I apologize. Okay, cool. Yeah. So you basically just kind of tell them, we'll figure out pricing once we understand what you're looking for.

This isn't a pre-pilot stage. Talk about pricing. Okay. Now, if they're this far along, they, like, if they're really concerned about pricing, they would have brought it up by now. Right. So these are like the little cues, like, okay, I think I could probably push them a little bit here, right? Or like go a little bit further. Two is, um, if they ask and they push, give them a ballpark. Well, it depends. But like, let's say it's somewhere between 150 and 250 and 250. And there's a lot of dependence on that, right? Um, so you can give them a ballpark. But work with your champion and say, listen, here's what the price is.

I know you know why we price it this way. Where before you put this in front of anybody, how are you going to make the case? Right? Like, 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, 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 work on this together. How can, what do you feel comfortable going to bat with? And can we do a step up for year two to get to the actual full value of what we know we charge? And do you include the slide or the price in the demo or is that like a post demo conversation? If they push you to do it, give a ballpark, but do pricing one on one with the individual you've been working with because they will help, they might say, okay, I think this is, I think,

I think we're all aligned. This is what's usually. going to have there's three answers. We're all aligned. I'm not too concerned about this. I don't know if I feel comfortable going to bat with this number. That's when you say, okay, I hear you. Let's take a step back. Let's figure out how to make this work. Don't say you're going to 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 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. 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 co-authorship. And remember, you can always do the full value in year two and sign a two-year deal. Awesome. They expand. Okay. So in the pilot step, do you, how many people do you give access to the pilot? Any advice there? Three to four. Okay, so very small. Very small, very tight. Who are the power users?

Who are the people that are going to be 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 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. 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 going to take us a month to even get you onboarded. And that's when we talked about those two different pilots, there's like, hey, we can show you the value in two to three days or it's the, hey, we have to show you the value in 30 days. For the 30 day value, 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 like integrate enough to make it magical. Your price should be predicated on your sale cycle. Right. Like if you can get a deal done in 90 days for 100K, do that all the time. Right. If it takes nine months to get a deal done, you've got it.

You probably should be charging 250, 300k. What are your thoughts on forward deployed engineers as a part of this process just as a role? My opinion sway back and forth. Like, is a forward deployed engineer there because the product's super hard and 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 taken the work off their plate and accelerating and controlling

the situation all day every day. But is it, are you using 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. It's a bad sign. Yeah. Yeah. I feel like, like the original idea of Ford Deployed engineer and the Pallenture guy's

about this. Like, the original idea was they work at a company, 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 FDE is great for an expansion, for a land. Okay. If you're talking about like a Palantir where it's much more complex to, like, I understand why they did that. Right. But they're also charging multi-million dollar deals. That's right. Right. So like, they're the, the, the business model structure supports that. If you're selling a $100,000 deal and you're pulling a four-deploy, like, your economics are, it's going to get messy.

Just like you will not make money if you have a full-time engineer salesperson sitting there working on this. 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, 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 Pellantir people called FDs at most companies. company's 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 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. We'll put the people in the pilot now because now you've lost all the, you need the momentum to continue.

You need the steps to happen. So use that, hey, if this is successful pilot, how far out are we from like a commitment from you guys? Oh, I see commitment. So there's like the commitment and also just, which is equivalent to rolling it out to the company. And it'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. 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 a project management as tightly as you can. And something gets 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 five steps. And we're already in step 10. We're not even done. And you made this point actually before we start recording that you haven't touched on that I think is important to share this idea of that these five steps kind of emerged out of like a CRM pipeline kind of check thing. Talk a bit about that. Yeah. So everyone knows the traditional five steps. Intro, demo, proposal, contracting, and then like closed one or close loss, right?

Those are like the typical, maybe there's like some variation of that. Like that's not how you run the sales. Those are buckets to understand how to. understand a weighted forecast, right? Like a proposal or something mid-funnel might be weighted at 50% of the deal value for the pipeline. Something in contracting might be waited at 80% and something in intro might be waited at 10%.

That's what those stages are for. That's not the stages you take a client through. Like those are just the broad buckets. And I think a lot of people use those buckets to say, okay, there's about five different meetings that need to have. happen when it's like, no, there's like three meetings, maybe up to five meetings in each of those buckets that are critical to get the deal done. Now, we're still speaking at it at a very macro level. Like, you know, 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 like for a hundred K deal, you probably can accelerate it a little faster, again, ensuring that they're qualified. And they've worked with a lot of founders and 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 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 want to 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 everyone those three things, but most people only spent it on two. Why? And that may be okay. 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 one. Don't tell them what they're doing. You shouldn't even be that. But like they didn't get past step one.

Can you check in on them and making sure like they're having a good experience? Like use your champion to like, again, they've invested so much time into you. Guide them with where they should be focused as well. Because at the end of the day, getting a deal done at the enterprise, it is set up to have as much friction as possible. Right? There's a people that will kill the deal. Then you'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, right, which usually comes in the very top of the funnel. But there's so much friction to get a deal done, the project management and the individual on the inside, that's your key. So funny. So many ways that could all fall apart. Yep.

What I was going to say is it feels like many people would naturally, like, they don't want to, they want to avoid confrontation. they won't want to say this is not going to be, we don't want this. They're going to probably be like, it's fine, it's good. Yeah, everything's great. 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 either really. When you're, this is why your internal champion is so important. When they go quiet on you, that's when you know. That's why this individual, And listen, this individual is going to do you.

If they've spent enough time with you, they will call you and be like, listen, if I'm reading the tea leaves, we should sit on this for a minute. Let's 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 very little. That's right. That's right. Oh, man.

Okay. What are like the benchmarks for like how often you get through each of these stages? You mentioned like a few. just like, yeah, from demo to the stage. Usually once something is qualified, meaning you're speaking to the right person, they are excited by the alpha. They admit that there's change that needs to happen.

Notice I didn't say problem, but change. People get so fixated on problems, which are important. They are important, but like everyone speaks to the same problem and then it commoditizes you, which is why I don't like to like overly emphasize it. The win rate for enterprise,

a good, healthy win rate, it's actually probably going to surprise you. It's not 50%. Meaning of all sales qualified leads or opportunities, a healthy ring rate is usually around 30 to 35%. From qualified lead to sign 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 it's, if you, if your win rate is higher than that, your price is too long, there's a lot of the market that's just not an immaturity perspective to take you on.

And that's healthy. Right? Those are all the chasms. And the implication here is it's better off keeping your price high than winning more often. Yes, because the market talks too. The worst thing you can do is charge somebody's friend 50 and somebody else 500K. They 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 do you get for this product? That's exactly right. So 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 lost, that's probably another 25%.

So it is totally normal and natural. for deals to not advance, right? But a healthy win rate in the enterprise is typically, I would say, between 25 and 35%. Okay, that is incredibly helpful to people, A. I know, 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 you're coming at a demo. it's probably you'd lose half. Out of demo. Out of demo, yeah. Post demo, not for us. Yeah.

They could shoot at 30%. So from demo to, what was that step that you lose? From demo to like, the more you move down, a little less those numbers, the less wider those numbers. So like,

okay. So like, let's say if you speak to, and you're doing a really good job targeting the right people. Maybe for, uh, 50% of those people move to a qualified lead.

50 to 75% move to qualified lead. Of that, then another half move to demo, and then from there, another quarter advance beyond that. Once you're in the bottom of funnel, you usually don't lose too much from there. If you're doing liquid deal qualification. So say you're at the pilot stage, what percentage should you expect drop off?

80% succeed post-pilot? Correct. Okay. Amazing. I find that, yeah. Okay. So if you're below that, something's wrong with your pilot. Yeah. Or you're not qualifying clearly. I see. Yeah. You're almost doing too good a job convincing them. This is the thing for that.

Correct. And the product's not there. Correct. So, yeah, that that's where. And again, like, smart buyers always want to do a pilot. So just have a part of your process. Okay. There's four more steps to go before you're done, before the money's wired. Okay, so step 11, papering prep, setting timeline for procurement. Yes. So you have now. spoken pre-pilot about the timeline of which we're reverse engineering, now you're going to document it in an email so that that champion that you're working with can forward that to procurement, to say, hey, here's what we agree to, here's the pricing that's predicated on us, getting this signed by the state, here's the give them something,

here's the kicker they're going to give us if we get to the state. There's always got to be a reason to create urgency. And then what you want to do, do is say, here's our paper. Send a word document. Do not send a PDF because they're going to always red line, 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 do you want to 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 got to use our paper. And it's not Google Docs. It's Word. Like Microsoft.

Office. Microsoft for it. Yeah. Most these people can't access Google Docs, but yes. And so this says post-pilot, feels like it's gone well. You're saying the next step is here's like the contract, basically. Get that to procurement that early. And again, your internal champion is you're working from N-minus 1 from the executive

sponsor or is the executive sponsor themselves. You wouldn't have made it. 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 procure. So here's something interesting that a lot of people don't realize. People will use procurement as the excuse to not want to give you the bad feedback. Oh, I got to go to. Oh, it procurement, it's it's lost in procurement or 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 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 obviously the papers are signed. Start work meaning implementing, rolling out.

Right. People onboarding. Got it, 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 going to take to sign by the state?

Here's a little gift you'll get if you do it by a state, free month or whatever. Okay. Step 12, papering review. Yes. The best thing you can do is they're going to send you back red lines. No question. If the red lines are extensive, okay? Go ahead and accept the things that are easy.

The red lines are extensive. See if you can get legal on a call live and just talk through them. That will accelerate your sale cycle. Versus a bunch of back and forth. Versus a bunch of back and forth. Get them on a call. Be like, hey, everything, we're 80% of the way they, I have a few questions based off of your red light.

Can we jump on a live call and just go through them? Focus on the things that are going to impact the business and pushing on those. Let the other stuff go if it's not super important. Obviously, have a lawyer look at it from your side. You're dealing with a commercial legal team. Have a lawyer look at their red lines. I imagine most companies have a legal counsel. Yes, I would hope.

I would hope. Yes. Okay, cool. So paper review. So that's reviewing basically. It's interesting called the paper. Yeah. Is there like a more technical term for that?

Like the contract. I say paper. That's like corpo language paper. So interesting. Yeah. Paper and review. Okay. Step 13.

Papering procurement process. Yes. So this is where we kind of talked about this. We kind of merged that conversation. This is when you are getting the procurement league and that legal league on a live call to work through the questions or the things you cannot accept. Now, remember. if they give you their paper,

there's going to be a lot in there that you're going to need to... Red line. Red line. They're expecting that. They're just giving you the kitchen sink. Right? Like, if they ask for $10 million of liability insurance,

as a smaller company, you can push back and be like, listen, your exposure with what we're doing is not that high, or maybe it might be and you need that. But, you know, they're going to give you the kitchen sink. Know that it's all negotiable. But pick your battles. Yeah. Don't be afraid like the deal will fall apart.

Yeah. No, no. At this point, the deal will not fall apart. You just need to work closely with them to like make sure they understand where you're coming from. That's more what it is. Okay. And the final step, signature. Tadda.

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 route to for signatures so that you, that your, make sure your internal client knows, you know, because sometimes it's the same thing. CFO. It's not the executive sponsor. I 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. Yes.

Steak dinner, champagne. I don't know what sales 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. Because you're all you are in sales. You're only as, good as your pipeline. So fun. It must be the best feeling after all this award. It is, but then you're like, oh, now, like, literally the feels is like five minutes and you're like back to work.

Yeah. And I imagine part of this is also how do we expand this deal? 100%. Is there anything there? Just real quick, just like how to start thinking about how this, where this goes once the deal signed. Yeah. And this is where I think the expansion comes in.

You either know the products that they can expand into. Like you've been through this journey before and that's pretty straightforward. But if you are early in the journey and you're closing your first 10 enterprise customers, you need the founder involved once these people are in to understand like what part of the product is custom to what these people need. And do we want to build out? You know, do we want to charge for services? Again, here's the other thing too. Services.

And I know every company is 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 as a part of it. Yeah. Yeah. Yeah. This has come up a number of times I think with Jason, also Lemkin, and you just like the

increasing, like there's a 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. 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 be in a position to.

It's interesting. You have to be, your organization and the team has to be structured in a way to bring on the technology. Like there's a maturity you have to go through. And I know we talked about this before where sometimes it's easier to sell the service first and then do the technology and counsel them towards the technology. but like if you are in a if your sales maturity in the enterprises further uh further down the road you want to start with selling the technology versus the services and if you talk about how it's not the right timing or not mature 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 what you think it's not right time 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 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, yeah. But like, 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 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 two calls, 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 going to do. Let's start it a little bit smaller. Let's get in. I know, you admitted that this is something that you guys need.

I know that we are going to crush it for you. I do not, I don't want X. to get in the way of that. And then there's obviously they're going to be the cases where it's just not the right time. Like they might be going through an acquisition. Right. And like bringing on net new vendors

is just like not a priority right now. You just have to respect that too. I love how this whole process, a lot of listeners as podcast or product managers, product people, it just feels very producty and product managery 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 at PM tries to understand what your pain points are. We're here to solve them. Yeah. Yeah. Unexpected. We did it, Jen.

We did it. We went through it at all. Is there anything else? Anything else we haven't touched anything else we want to, I don't know, leave listeners with before we wrap up. We gave them a lot. We did it. Which was the goal? just the right amount.

Yeah. Yeah. I'm excited for like, 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 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 flavor.

And it's like, anyone can do that. It just feels salesy. What's your alpha? Exactly. Exactly. And I know you talked about this last time, just like craft your own email and text. Yes. Don't use the boilerplate.

Yeah. Males 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.

This is awesome. This was amazing. Everything I wanted to be. This is going to be. I'm excited for like the, not to talk about it, but just like, Like AI summary of this, especially, that's just going to be like step one, two, three, four. Yeah, yeah, yeah.

Final questions, anything you want to plug, anywhere you want to appoint people to, and how can listeners be useful to you? Let me know if anyone has questions. I'm more than happy to go deeper into this. I would say, if anyone, here's a plug, if anyone is interested in enterprise sales, we are actively hiring, and I will teach you everything I know. Wow. And this is at State Affairs. It's at State Affairs.

Holy shit. What an opportunity. Yeah. So there's multiple roles, not just one. Multiple roles, yeah. Wow. You'll be paid to learn from Jen directly. Yes, I will teach you everything I know. Whoa. Okay, cool. We'll link to the job descriptions in the description. I want to check that out. Awesome. Amazing. Jen, thank you so much for me.

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 lenniespodcast.com.

See you in the next episode.