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

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 like 2. The “pincer model” for landing the first meeting at the executive and N-minus-one level simultaneously 3. 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 demo 5. The two-to-three-day pilot structure, how to define success jointly, and when to charge for a longer pilot versus giving it away 6. Navigating pricing, procurement, redline negotiations, and the final signature without losing momentum — Brought to you by: WorkOS https://workos.com/lenny—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more Mercury https://mercury.com/command?utm_source=lennys&utm_medium=sponsored_newsletter&utm_campaign=26q3_brand_campaign—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 [email protected] mailto:[email protected]. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com https://www.lennysnewsletter.com?utm_medium=podcast&utm_campaign=show-notes-no-free-preview-language

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Lenny Rachitsky?

  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.

• 0:08Speaker 01

  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.

• 0:22Lenny Rachitsky?

  Step two is basically running the intro call.

• 0:24Speaker 01

  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.

• 0:44Lenny Rachitsky?

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

• 0:48Speaker 01

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

• 0:55Lenny Rachitsky?

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

• 0:59Speaker 01

  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.

• 1:09Lenny Rachitsky?

  What percentage do you think are just doing it wrong?

• 1:13Speaker 01

  90%.

• 1:14Lenny Rachitsky?

  Wow.

• 1:14Speaker 01

  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. It never works that way.

• 1:23Lenny Rachitsky?

  Most people think the sales process is five steps. And we're already in step 10. We're not even done.

• 1:28Speaker 01

  The worst thing you can do in the sales process is...

• 1:34Lenny Rachitsky?

  Today, my guest is Jen Abel. This is her third time on the podcast. For those that don't know Jen, she is co-founder of Jellyfish, GM of Enterprise Sales at State Affairs, and most importantly, is the person that I've learned the most from about the art and science of enterprise sales. In our first conversation, we went deep on founder-led sales. In our second conversation, we focused on the 1 million to $10 million enterprise sales playbook. And in this conversation, we do something I've never seen anyone do on another podcast. We go step by step through the full enterprise sales cycle. Most people think this is a 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.

• 2:18Lenny Rachitsky?

  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 lennysproductpass.com for a free year of the hottest and most beautifully crafted AI products in the world, available exclusively to Lenny's newsletter subscribers. With that, I bring you Jen Abel.

• 2:53Lenny Rachitsky?

  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?

• 3:01Speaker 01

  Round three, super excited to be here, Lenny.

• 3:04Lenny Rachitsky?

  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 lifecycle 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. 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.

• 3:33Speaker 01

  Okay.

• 3:33Lenny Rachitsky?

  We've had conversations...

• 3:34Speaker 01

  We keep away our secrets.

• 3:35Lenny Rachitsky?

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

• 3:43Lenny Rachitsky?

  And, you know, this touches on just like, why, why I think the podcast is really helpful to people and just the valley vibe, even though you don't live in the valley. Just like, there's so much win, win, win in helping people learn these things. You know, it may feel like, why is she giving away all these things? But maybe actually, let me ask you that. Just like, why, why do you share these things?

• 4:02Speaker 01

  Well, it's so interesting because there's so much art to this that even if you gave someone a 15-step playbook, there, there's so much of a feeling that you have to go off of. Like, sales is, sales is one-on-one, right? You're, you're dealing with a variable, which is another individual. And if you ran the same flow every single time, it's going to probably not hit one out of every four times because everyone's different. Like, some people like to joke. Some people like the small talk opener. Others want to jump right into it. Some are technical, some are not technical. You know, so everybody's so different that even if I gave, even as we go through all these 15 steps, while it's 80% of it, the other 20% is obviously the art of like, how you make someone feel? Do they feel heard? Did you make it fun?

• 4:47Speaker 01

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

• 5:28Lenny Rachitsky?

  Amazing. And I'll just give a plug for if people want to continue learning, your Twitter feed is just the best.

• 5:34Speaker 01

  Yeah.

• 5:35Lenny Rachitsky?

  You share all this stuff constantly.

• 5:36Speaker 01

  Yeah.

• 5:36Lenny Rachitsky?

  And I think you, you talk about, there's like rational reasons to share this stuff. But I think there's, it feels like there's just like, I just need to get this stuff out. People need to...

• 5:42Speaker 01

  It's like a diary and it also helps me like, keep it in my mind, too.

• 5:46Lenny Rachitsky?

  Right.

• 5:46Speaker 01

  It's like my own education, yeah.

• 5:47Lenny Rachitsky?

  I know exactly what you mean. That's why I started writing. I started, I was just like, I just want to remember this stuff myself. I'm just 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, what we're going to be using here?

• 6:03Speaker 01

  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, and win. They are a technical organization. But I think what we do is target a non-technical team. So we're going to like, really get into like, the nuance of this. So let's do SpaceX. Why don't we pick legal? Let's have some fun with legal. The interesting thing about legal, it's the largest budget line item in the enterprise

• 6:43Speaker 01

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

• 6:54Lenny Rachitsky?

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

• 6:56Speaker 01

  100%.

• 6:58Lenny Rachitsky?

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

• 7:16Speaker 01

  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, you do that better than a lot of people.

• 7:25Lenny Rachitsky?

  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?

• 7:32Speaker 01

  No, I think this is good.

• 7:33Lenny Rachitsky?

  Sales cycle.

• 7:34Speaker 01

  SpaceX and targeting the legal function.

• 7:37Lenny Rachitsky?

  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 a plug for a previous episode. You talk about why you want to be at least 100K something as a deal to be a, a real enterprise company that will, that will survive.

• 7:57Speaker 01

  Yeah, that's right.

• 7:57Lenny Rachitsky?

  Because the ROI and the, and just the whole economics of that stuff. But we won't get into that. This episode is brought to you by our season's presenting sponsor, WorkOS. What do OpenAI, Anthropic, Cursor, Replit, Sierra, Klay, 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 up market ends up working with WorkOS. And that's because they are the best.

• 8:41Lenny Rachitsky?

  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 globe. 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?

• 9:18Speaker 01

  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?

• 9:25Speaker 01

  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, the chief legal officer. They all kind of had slightly different titles, but they all carry the same weight, which is like, who's the, who's the lead of the team? And then underneath that, you 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,

• 10:09Speaker 01

  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?

• 10:30Speaker 01

  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 and the N minus one,

• 11:15Speaker 01

  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 corporate 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

• 12:00Speaker 01

  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 you call this, I call it the pincher model, because you're going after two different people and trying to get them together. It's actually called the pincer model, which is start at the very, very top, find that kind of floor, and work in between them. Okay? So these are the two layers you want to be targeting in landing that meeting. Because if you go any further than that,

• 12:37Speaker 01

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

• 13:05Lenny Rachitsky?

  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. Okay, so tip one is go after either the exec. So in this case, it'd be general counsel, head of legal sort of person, or N minus one. Love the way describing it, maybe a VP. You want to pitch them two or three sentences in like a text or email or at a conference. And the key is to focus on the alpha, like the way, what your product will unlock for them. Love that. And it sounds like they're still like, here's the problem we solve for you, but here's like really the alpha we unlock.

• 13:48Speaker 01

  Correct. Because for an executive to bring something in and be the sponsor and like share this and disseminate this down their command, they need to stand behind something beyond, hey, 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 too 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? With their influence, get more budget, get more people. However, they wanted to find that.

• 14:23Lenny Rachitsky?

  Yeah, so it sounds like you don't want to, like, they want to win. And to win, you need something unfair, unfair advantage.

• 14:30Speaker 01

  That's exactly right. That's exactly right. Yep.

• 14:33Lenny Rachitsky?

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

• 14:41Speaker 01

  Yep.

• 14:41Lenny Rachitsky?

  And then this AE reaches out to the N minus one contact, and you do this, you go from both directions.

• 14:47Speaker 01

  Yep.

• 14:47Lenny Rachitsky?

  And I imagine the goal is one of them at least responds.

• 14:50Speaker 01

  That's correct. And then because you're only one step removed, they'll usually loop in that next person. And or you can say, the founder could say, hey, I'm going to loop in my so-and-so colleague, who on your team should we also include? Or the 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, of kind of role.

• 15:16Lenny Rachitsky?

  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.

• 15:22Speaker 01

  Exactly.

• 15:22Lenny Rachitsky?

  I didn't 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 it out? And then two is, any channel recommendations these days? Like, what's the best way to try to contact these people?

• 15:35Speaker 01

  So I'll use, you can ask, you can spar with OpenAI and Anthropic to like let them do the quick scan of like, hey, I'm looking to target the chief legal officer of SpaceX and their deputy, who are possibly 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 talked 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.

• 16:20Lenny Rachitsky?

  Got it. Okay. And then in terms of trying to reach out to them, any tips? Is it like, are there tools there to figure out their number or whatever?

• 16:28Speaker 01

  They're also unique. Cold calling works.

• 16:32Speaker 01

  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.

• 16:40Lenny Rachitsky?

  Are there tools to find these emails and things? Like, is there something you recommend?

• 16:43Speaker 01

  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, lend lists and all sorts of these enrichment tools that can give you the email. But I think the number one thing is, assume they're getting hit with hundreds of emails. How are you going to message your storyline to stand out? And that's not easy to do. And that's really why I think having, going back to our first episode, why Founder-led Sales is so important, to figure that piece out.

• 17:23Lenny Rachitsky?

  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?

• 17:33Speaker 01

  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, no.

• 18:10Speaker 01

  Like, how are they going to show needle-moving impact to their COO, CEO? You know, if they were to bring it to the board meeting, like, what would they say about the product? This product will allow me to do what? That's like the litmus test.

• 18:26Lenny Rachitsky?

  Is this a pitch that you iterate on over time?

• 18:28Speaker 01

  Yes.

• 18:28Lenny Rachitsky?

  Because you're probably getting some percentage of people responding.

• 18:31Speaker 01

  Yep.

• 18:32Lenny Rachitsky?

  Okay, so the advice is like, keep trying to refine this.

• 18:34Speaker 01

  That's exactly right.

• 18:35Lenny Rachitsky?

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

• 18:40Speaker 01

  No, I think that's good.

• 18:40Lenny Rachitsky?

  Okay. Okay, let's do it. I started shaking your head before you said it. I'm just super confused. Okay, step two. Step two is basically running the intro call.

• 18:48Speaker 01

  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.

• 19:34Speaker 01

  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 typically opens. 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 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 like, who you are, and I'd love to share what we are doing and why I specifically reached out to you. So I say, would you like to go first? Always let them go first.

• 20:18Speaker 01

  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. So.

• 20:29Lenny Rachitsky?

  And they also aren't like, sitting there now, listening to a picture like.

• 20:31Speaker 01

  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 opener. 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, blah, blah. Okay, okay, great. They usually don't give you much. So they say, okay, interesting. Like, how are you thinking about, like, do you guys have an AI mandate going on at the organization? Like, how are you thinking about the existing way you guys are doing work? Like, what are you looking for going into 2027? Like, is anything need to change? Like, ask, does anything need to change? Because again,

• 21:17Speaker 01

  What they're going to usually default to is what conversations have happened above them and have been transcended down. So the change is usually dictated from the top, which is great. So like, what needs to change going into 2027 that you did in 2026? Or maybe not at all. And that's when they start to open up. And again, you don't want to be too pointed of like anchoring them towards your product. Because again, the more they speak, you can start to like pull on the strings that matter. So they could say something along the lines of, you know, I'm making this up at this point, but we are really looking to figure out how to bring more of this work in-house and rely less, rely far less on external law firms.

• 22:01Speaker 01

  Right? Because now we have more tools and capabilities. Be like, okay, like, is there a measurement to that right now? Like, how are you guys, like, what does that look like internally in terms of, 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. Okay, like, why is that important now? Like, why didn't you, why not wait another year? I mean, you guys have so much going on. You just had this massive IPO. Like, what's, what's causing the team to want to reshape this or rework the way that they're managed internally? And that's usually the moment of like, where they start to really guide you

• 22:45Speaker 01

  in terms of like, how they want to structure their team. So now you're getting all of this information about where they want to go. Right? Now, when you talk about what you do, now you're the vehicle to get them there. Right? And so the, I try and spend maybe 10 minutes, the back 10 minutes explaining what we do and just keep asking them questions. Be like, oh, that's so interesting. Like, what an exciting role to be in. Be like, okay, full disclosure, right? And by the way, I take a step back for that. Do not bring a recorder to this call. Do not record the call. They will not be open, they will not be vulnerable. They might assume it's being recorded because I think everyone kind of operates under that assumption right now.

• 23:25Speaker 01

  But for the benefit of yourself, do not have a recorder present. Okay, just be like, off the record, between the two of us talking right now, of what you just shared, like, what really matters? Like, what, like, or like, what do you want to own?

• 23:45Speaker 01

  Or like, what's the chronological goal? Like, keep digging, digging, deep, because the more you dig, the deeper you go, the more information they give. Okay? Now, you can't sit there and just pepper them with questions. This is that, that art piece of like, how open is this person? Some people are poker faces, some people are not. You will be able to go much deeper with some and not deeper than other. You just have to improv. Okay? But after you now have that intel and you can now understand, okay, here's the frame I'm going to take, now you can give them the pitch. Okay? I will confirm every single conversation I have, 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.

• 24:29Speaker 01

  It feels like you're putting them into a square box. The best thing you can do is listen actively and then

• 24:38Speaker 01

  feel confident enough to craft the pitch around what they just shared for you.

• 24:42Lenny Rachitsky?

  That last part seems really hard to

• 24:44Speaker 01

  Yeah, it's very hard.

• 24:44Lenny Rachitsky?

  Adjust and make up, like, here's what you're focusing on and here's our product that's going to solve that problem for you. So that's kind of where that art and skill comes in.

• 24:53Speaker 01

  That's right. And enterprise sales,

• 24:56Speaker 01

  it's so, so hard to hire for because the more someone is trained in sales, the less natural it feels. I know this is counterintuitive and we spoke about this on 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.

• 25:27Lenny Rachitsky?

  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 what we're up to. Okay, you're nodding, that happens.

• 25:34Speaker 01

  One, I would say two to three out of every four calls, there's something real.

• 25:41Lenny Rachitsky?

  There's something real.

• 25:42Speaker 01

  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 in, 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, quickly disqualify someone and it's probably one in every four calls.

• 26:20Lenny Rachitsky?

  Awesome.

• 26:20Speaker 01

  Simply because of maturity.

• 26:22Lenny Rachitsky?

  Cool. So you don't have to have this like intense pressure to nail it on every call. And here's the, here's the pitch. Okay, awesome. What I also want to comment on is this idea of like getting 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.

• 26:46Speaker 01

  Their job is to, their job is to buy solutions to these problems. Right? That's why they have budgets. Right?

• 26:53Speaker 01

  So that's why the, and 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.

• 27:05Lenny Rachitsky?

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

• 27:21Speaker 01

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

• 27:51Lenny Rachitsky?

  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.

• 28:03Speaker 01

  Yeah.

• 28:03Lenny Rachitsky?

  Thoughts on if that just comes up a bunch? We just, like legal, we just need to save costs.

• 28:06Speaker 01

  Yeah. So in pricing, their job is to, there's going 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 the, because it is a, a high risk. If you're dealing with legal, there's high risk to it. Right? Missing information, being delayed on something,

• 28:46Speaker 01

  not having people understand the importance of some new regulation or, or law,

• 28:54Speaker 01

  not being buttoned up.

• 28:57Speaker 01

  So I think for, if, every organization looks differently, right? Like, marketing needs to have, needs to, you know, marketing and sales, it's very clear that number, numbers drive them. For legal, it's probably they, they need to stomp out risk.

• 29:12Lenny Rachitsky?

  Awesome. So, yeah. Basically, this comes back to the idea of alpha and

• 29:16Speaker 01

  Yep.

• 29:16Lenny Rachitsky?

  upside.

• 29:17Speaker 01

  Yeah.

• 29:17Lenny Rachitsky?

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

• 29:19Speaker 01

  That's exactly right.

• 29:20Lenny Rachitsky?

  Easier everything gets. Okay. Uh, anything else before we get to step three?

• 29:24Speaker 01

  No, I think for step one, like, that, that, that is the most important meeting. And I feel like people just spend so much time talking about themselves and miss all the competitive advantage to win the deal.

• 29:35Lenny Rachitsky?

  Yeah, your point about how, as a buyer, it's so like low pressure at that point. You're just exploring. And so I could see why people come into it like, cool, let's learn. Let's see if this, versus you're in the funnel like, oh shit, I gotta actually make a decision. I'm going to have to let them down if I don't want this.

• 29:50Speaker 01

  Yeah.

• 29:50Lenny Rachitsky?

  It's like dating.

• 29:51Speaker 01

  Yeah, like their openness to share more, start to clam up a little bit more. But we'll talk about how to make sure that doesn't happen too.

• 29:58Lenny Rachitsky?

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

• 30:04Speaker 01

  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. Okay? The demo is your carrot in the process. Everyone wants to see this amazing thing you just spoke about. Okay? So there's, your job is to make sure that when you do that demo, the formal demo, you have the right people on the call. Because if you don't, one, it's, you 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?

• 30:49Speaker 01

  If you're selling to that director or that VP, you need to make sure that that executive feels like they're, it's part of their baby and they're helping craft it and they have their fingerprints on it. And vice versa, like, you want the C-suite, if they, they want, they want their, the actual users to feel like that they were bought in on this too. Okay, so you want to make this to be, and this is the tricky part. You want it to, you, there's going to be someone that's going to champion it and get the deal done.

• 31:14Speaker 01

  But you gotta make it feel like a group effort. Okay, so the person that you had the intro call with, that's who you built the rapport with. That that's your that's your champion at this point, whether it's the C suite executive or 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 get to, you know, support you guys. This call should be 15 minutes, by the way.

• 31:51Speaker 01

  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.

• 31:59Speaker 01

  Can you help me understand from the conversation we had earlier? And as I'm walking you through, now I'm walking you through the product. What do you think would resonate with the team? Now you're collecting more intel. Okay, now they're the now it starts to feel like, oh, great. Now they get to put their fingerprints on this. So it's like, okay, when we demo 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.

• 32:42Speaker 01

  You now have the alpha of the intel they're giving you from these conversations.

• 32:48Speaker 01

  And now they feel a 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 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.

• 33:18Speaker 01

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

• 33:49Speaker 01

  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 go into pre demo? Do we want to assume they checked off pre demo or do we want to do group demo?

• 34:18Lenny Rachitsky?

  How often does that pre demo happen?

• 34:20Speaker 01

  If you're, I mean, I try and push for it because again, it's just more intel.

• 34:24Lenny Rachitsky?

  Yeah, so let's say, let's assume there's a pre demo.

• 34:26Speaker 01

  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 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 straight demo with no problem. Or worse, a enterprise organization might reach out to you

• 35:08Speaker 01

  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. If you're either a checkbox and you don't want you want to remove yourself from being a checkbox. Or two, you're about to demo your product with no competitive intel.

• 35:28Speaker 01

  Like, you just lost the deal at that point.

• 35:32Speaker 01

  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.

• 35:41Lenny Rachitsky?

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

• 35:57Speaker 01

  No, no, it is. It's information edge. Yeah, it's the information edge that whoever I'm up against is not getting. And you have to assume in the enterprise, you're always up against something. You're up against not doing anything at all. Or you're up against a competitor who who does some or an incumbent, right? Most likely the incumbent. But it's so crazy to me how many people just like spew out a pitch with like no. But you also have to make it informal and fun like you need to, you know. People also buy from people they like, right?

• 36:29Lenny Rachitsky?

  I love how so far at least it feels very doable, not that difficult. Feels like I could do this.

• 36:36Speaker 01

  Absolutely.

• 36:37Lenny Rachitsky?

  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?

• 36:50Speaker 01

  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 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 is that the priority? Like, and then again, they'll go deeper. Like, the more, the more you infer the questions you ask, it's almost like you just have to keep prompting. It's the whole, it's like prompting humans at this point, right? Like, go deeper and deeper and deeper. And 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.

• 37:36Speaker 01

  All of this should be should be within a 90 day sales cycle based off of their maturity.

• 37:41Lenny Rachitsky?

  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.

• 38:00Speaker 01

  Or you're stuck at you just sold the enterprise on a $15,000 solution, which goes, what do you, how do you expand that? The whole game is expansion. If you're not going from 100K or 250K to 350 or 500 the following year, it's not an enterprise motion.

• 38:17Lenny Rachitsky?

  Okay, so just to kind of quickly summarize, we're at step one, landing the meeting.

• 38:21Speaker 01

  Yep.

• 38:22Lenny Rachitsky?

  Then running the intro call. Then there's this follow up intro call, which you pointed out is often ignored.

• 38:27Speaker 01

  Yep.

• 38:28Lenny Rachitsky?

  And a big opportunity to improve the demo. I love the way described the demos, kind of this carrot that you're holding that you can use a little bit to kind of extract more.

• 38:35Speaker 01

  Yep.

• 38:36Lenny Rachitsky?

  And then there's step four is prepping the pitch and framing the demo.

• 38:40Speaker 01

  Yep.

• 38:41Lenny Rachitsky?

  Is there more to share there?

• 38:43Speaker 01

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

• 38:46Lenny Rachitsky?

  Okay, cool. So, yes.

• 38:48Speaker 01

  So now you have, you now you have all of the people involved in the demo. You might have somebody that's involved from their AI team that's going to support some some rollout. You might have somebody like you want all of the people involved in this decision at that table for the demo.

• 39:05Speaker 01

  That's how important it is to not rush it. Okay, so you now you're running the demo. Now you're before that demo on that on one of those calls. Who are all these people? What do they care about? And what should I avoid? Like, the the person that you've now built this relationship with can give you all of the intel.

• 39:25Speaker 01

  At this point, they want this to go forward. Now it's now they now this is like a great star for them of like, I found this amazing tool. It's 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, be like, hey, people do demos all the time, like, what looks good 30 minutes of a discussion, maybe 10 minutes of showing, 10 minutes of discussion, 40 minutes of in the product? Like, what you tell me like what the the organization likes?

• 40:02Speaker 01

  And on that demo, there's going to be people that were not a part of any of these calls. Okay, your job is to take a step back and restart with, here's who we are, here's why we 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 now they're like leaning in being like, okay, all right, somebody this is very aligned with what we need.

• 40:30Lenny Rachitsky?

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

• 40:32Speaker 01

  No way you talked to all these people.

• 40:33Lenny Rachitsky?

  Learn what their challenges are and priorities.

• 40:35Speaker 01

  You're like, they're leaning in being like, this feels different. Now, this is also the whole part of like, it's being different. Not only is your product different, not only is your pitch different, the way you're going through the sales process is different. So it's like, wow, these guys are good. Okay, all right. These are so now you could, you know, let them talk, let these net new people talk. Be like, hey, I 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.

• 41:19Speaker 01

  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. Well, everything she just shared, that's really only over here. And you could just blow the whole thing up. And the amount of times enterprises are like, hey, I'm not, I don't know if we 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.

• 41:53Speaker 01

  Enterprise sales is super, super, super tight project management. It's super, super tight narrative and framing, owning that frame, owning that frame to exactly who these people are.

• 42:07Speaker 01

  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.

• 42:18Speaker 01

  It's stuff that is doable. I mean, it's just psychology.

• 42:23Lenny Rachitsky?

  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,

• 43:06Lenny Rachitsky?

  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 ask, how much have I made from X over the past year? 10 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 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?

• 43:43Speaker 01

  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 verbose and long-winded and take things off track. So that's the good thing about going after executives is those people are 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.

• 44:17Speaker 01

  And if that needs to happen, then of course you can run with it.

• 44:20Lenny Rachitsky?

  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, maybe a VP of Sales.

• 44:29Speaker 01

  VP of Sales, yep.

• 44:30Lenny Rachitsky?

  Okay. Say you're not the founder and you're the VP of Sales or an AE leading this. As a founder, what are some signs that your salesperson is not doing a great job up to this point? What are just smells of like, hmm, I should release everything this person?

• 44:47Speaker 01

  I would say like, what is the timeline from intro called the demo?

• 44:53Speaker 01

  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 looked the same. This is like when everyone comes back to like, okay, what's the scaled playbook? What's the scaled approach with this? When you're selling $100,000 minimum, right? Again, it's the same effort as selling a million dollars. So it could be selling a million dollar deal.

• 45:35Speaker 01

  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.

• 45:53Lenny Rachitsky?

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

• 45:56Speaker 01

  Yeah, I do not, I'm not worried about AI replaced. Because there's so much about it that's just human, right? Like, do you vibe with this person? I mean, I've definitely taken intro calls with a person probably did not appreciate with how I ran it. And that's okay. It was just, it happens.

• 46:14Lenny Rachitsky?

  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.

• 46:31Speaker 01

  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.

• 46:44Lenny Rachitsky?

  And then get alpha.

• 46:45Speaker 01

  And get alpha.

• 46:45Lenny Rachitsky?

  Okay. So step six, you call the post demo discussion.

• 46:50Speaker 01

  Yes.

• 46:51Lenny Rachitsky?

  Also something you say everyone ignores.

• 46:53Speaker 01

  Yes.

• 46:53Lenny Rachitsky?

  Talk about that.

• 46:54Speaker 01

  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 like a fresh debrief. They will give you, be like, raw reaction. I know you haven't spoken to anyone. What do you think? How do you think that went? Do you think we need to go deeper with anyone?

• 47:18Speaker 01

  Before anyone like solidifies kind of everything that's said, like, where do you think we lost somebody? Where do you think we did well?

• 47:28Speaker 01

  Is there someone we need to spend more time with?

• 47:32Speaker 01

  There's always someone in the organization that's going to kill a deal. There's always somebody.

• 47:38Speaker 01

  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, and maybe we can approach this a little bit more closely with how they would want to see it.

• 48:16Lenny Rachitsky?

  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?

• 48:24Speaker 01

  A champion.

• 48:25Lenny Rachitsky?

  Your champion.

• 48:26Speaker 01

  Yeah. Because a champion can also be an executive, right?

• 48:29Lenny Rachitsky?

  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.

• 48:38Speaker 01

  And I define champion as who's the individual that really wants this to come to life? That's like, was there from day one, not necessarily like the person that's, like, the C-suite executive could be the one shepherding this well, but they need to make sure that the people below them are brought in.

• 48:52Lenny Rachitsky?

  Okay. Anything else around the demo or the post demo discussion before we move on to the next?

• 48:57Speaker 01

  No, I think we're good.

• 48:59Lenny Rachitsky?

  Okay. So the next step, you call identifying pilot move forward process.

• 49:04Speaker 01

  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 allow them, now you can control the timeline of, hey, I want you guys to go in for two to three days. These specific users, don't put the, do not put your C-level executive into the product. They're not the user. Okay. Who are the users of this? I want them to experience the magic and the power of what this is. Okay. Don't chart, 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.

• 49:49Speaker 01

  But I usually would, I'd rather, I'd rather go in for two to three days and let them see if they can get the value from it. If they can, sometimes I understand that there needs to be some level of configuration and, you know, extensive 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?

• 50:07Lenny Rachitsky?

  So this isn't yet the pilot. This is just like prepping for the actual pilot.

• 50:10Speaker 01

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

• 50:31Speaker 01

  Let's talk about something that they can get in two to three days and it's pretty much of a light left. Time box it to two or three days. Don't make it two weeks. Okay? I've done this enough times to say, people will go in usually for half a day and get what they need out of it. Okay? Shorten your sales cycle by two weeks by doing 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 charged them for and credit it back to them if they move forward. Okay? If they're willing to pay, that is a huge, huge signal, especially if you're about to put in all this work.

• 51:15Speaker 01

  They have no problem paying for it. It's usually probably going to come out as services anyway, because it's like,

• 51:21Speaker 01

  they're not buying technology, they're buying the services to go through it. And also make it a credit on the backend. Don't, start the relationship up, shift. Start the relationship off on a good foot.

• 51:32Lenny Rachitsky?

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

• 51:38Speaker 01

  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 it never works that way. Like, no one taught me this. I was just like, okay, if I collect more intel than the competitive set, that will be my special sauce.

• 51:59Lenny Rachitsky?

  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.

• 52:06Speaker 01

  Yeah, speed run.

• 52:06Lenny Rachitsky?

  It feels more real.

• 52:07Speaker 01

  Yeah.

• 52:08Lenny Rachitsky?

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

• 52:15Speaker 01

  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 the person closest to the, don't put your C-suite executive in it. 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.

• 52:59Speaker 01

  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.

• 53:11Speaker 01

  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.

• 53:19Speaker 01

  That puts the work back on them. Your job in sales is to take all the work off their plate. Ninety-nine percent of it.

• 53:27Lenny Rachitsky?

  And help them discover the magic really easily.

• 53:29Speaker 01

  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. Of in that three-stage process, you just, what did, what didn't you like? What wasn't clear? What wasn't obvious? Where did you get lost? The tighter it is, less people get lost, the more, the more grounded it feels. And the more consistent the experience is. You don't want people having different experiences.

• 53:53Lenny Rachitsky?

  Okay, so just to make clear the steps involved here, because we've gone through, I think, three kind of around the same.

• 53:58Speaker 01

  So much, yeah.

• 53:59Lenny Rachitsky?

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

• 54:08Speaker 01

  Yep.

• 54:08Lenny Rachitsky?

  Who that person is and what the steps are. Then there's prep for the pilot, and then there's run the pilot.

• 54:12Speaker 01

  Run the pilot, exactly.

• 54:13Lenny Rachitsky?

  We've kind of talked through all these things.

• 54:14Speaker 01

  Now.

• 54:15Lenny Rachitsky?

  Is there anything else along? Yeah.

• 54:16Speaker 01

  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.

• 54:25Speaker 01

  How do we get this deal through? Okay.

• 54:29Lenny Rachitsky?

  Ahead of time, before doing the pilot.

• 54:30Speaker 01

  Yes, ahead of it. Um, I should have clarified that. This is all before, before the, before the people's pilots start. This isn't the pre-pilot stage. Okay. Assuming, fingers crossed, a successful pilot, which I feel confident is going to be.

• 54:44Speaker 01

  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 pilot. Totally. But like, 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.

• 55:25Speaker 01

  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. Right? Because there's all these other people that might not have been involved in those initial discussions. Talk through pricing post pilot once everyone's excited.

• 55:43Lenny Rachitsky?

  Post pilot or post demo?

• 55:45Speaker 01

  Right, post demo, I apologize.

• 55:46Lenny Rachitsky?

  Okay, cool.

• 55:46Speaker 01

  Yeah.

• 55:47Lenny Rachitsky?

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

• 55:52Speaker 01

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

• 56:26Speaker 01

  You, I know you know why we price it this way. Where?

• 56:32Speaker 01

  Before you put this in front of anybody, how are you going to make the case?

• 56:38Speaker 01

  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?

• 56:49Speaker 01

  Let them, they will tell you. You don't have to go blind into it. And then if they, and then say, okay, and if they push back and they're like, listen, I don't know if I can go to bat for this, be like, I hear you. Let's, let's work on this together. How can, what do you feel comfortable going to bat with? And can we do a step up for year two to get to the actual full value of what we know we charge?

• 57:10Lenny Rachitsky?

  And do you include the slide or the price in the demo? Or is that like a post demo conversation?

• 57:15Speaker 01

  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 happen. There's three answers. We're all aligned. I'm not too concerned about this. I don't know if I feel comfortable going to bat with this number. That's when you say, okay, I hear you. Let's take a step back. Let's figure out how to make this work.

• 57:44Speaker 01

  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 twenty K? 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, the co-authorship. And remember, you can always do the full value in year two.

• 58:20Speaker 01

  And sign a two-year deal.

• 58:21Lenny Rachitsky?

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

• 58:30Speaker 01

  Three, three to four.

• 58:32Lenny Rachitsky?

  Okay, so very small.

• 58:33Speaker 01

  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, not like the same people and the same. But you do want your, 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.

• 58:52Lenny Rachitsky?

  So before we get to the next step, which is post-pilot discussion and session.

• 58:57Lenny Rachitsky?

  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?

• 59:12Speaker 01

  And that's that, when we, when we talked about those two different pilots, there's like, hey, we can show you the value in two to three days. Or it's the, hey, we have to show you the value in thirty days. For the thirty-day value, charge. 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.

• 59:33Lenny Rachitsky?

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

• 59:36Speaker 01

  Your price should be predicated on your sales cycle. Right? Like, if you can get a deal done in ninety days for a hundred K, do that all the time. Right? If it takes nine months to get a deal done, you've got, you probably should be charging two fifty, three hundred K.

• 59:48Lenny Rachitsky?

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

• 59:52Speaker 01

  My opinions sway back and forth. Like, is a four deployed engineer there because the product's super hard to navigate?

• 1:00:00Speaker 01

  Or is it there because you're taking the work off their plate?

• 1:00:05Speaker 01

  I think people use them. I'm all about it if it's taking the work off their plate and accelerating and controlling the situation all day, every day. But is it, are you using, um, a four deployed engineer because your product's so gnarly and hard to, hard to do, like, they can't do it on their own?

• 1:00:23Lenny Rachitsky?

  It's a bad sign.

• 1:00:23Speaker 01

  Yeah.

• 1:00:24Lenny Rachitsky?

  Yeah. I feel like, like, the original idea of four deployed engineer, and the Palantir guys talk about this, like. The original idea was they work at a, inside of your company, building custom software for you to solve your problems. And then they figure out how to make that a broad product they can sell to other people.

• 1:00:41Speaker 01

  Total. 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, like, I understand why they did that. Right? But they're also charging multimillion dollar deals.

• 1:00:57Lenny Rachitsky?

  That's right.

• 1:00:57Speaker 01

  Right? So like, the, the, the business model structure supports that. If you're signing a hundred thousand dollar deal and you're pulling a four deploy, like, your economics are, it's going to get messy.

• 1:01:08Lenny Rachitsky?

  Just like you will not make money if you have a full-time engineer salesperson sitting there working on this.

• 1:01:13Speaker 01

  And, you know, I, I think, I also know, like, there's a lot of folks in like account management whose job is to service and, and up, you know, expand and upsell. And they just take on the title of FDE, so they're just another salesperson.

• 1:01:25Lenny Rachitsky?

  Yeah, just a nice, yeah, it's a cool title. I think the Palantir people call the FDEs at most companies sparkling sales engineers.

• 1:01:31Speaker 01

  That's awesome.

• 1:01:33Lenny Rachitsky?

  Yeah. Okay, uh, anything else on the pilot, up to the pilot step, before we get to the post pilot session?

• 1:01:39Speaker 01

  Yeah, I think, because now you've talked about like the timeline. To if this is successful, what does that look like? Again, you want to run this before you put everyone in it. Because you might want to push out the pilot. If they're like, hey, listen, this is probably going to be another quarter. Well, put the people in the pilot now, 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?

• 1:02:05Lenny Rachitsky?

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

• 1:02:10Speaker 01

  That's exactly right.

• 1:02:11Lenny Rachitsky?

  If they're not ready in a month to roll this out, if this is a huge success, then wait on doing the pilot.

• 1:02:16Speaker 01

  Correct, yeah.

• 1:02:17Lenny Rachitsky?

  Awesome. Because you're saying you may lose that momentum and.

• 1:02:20Speaker 01

  Yeah, you, you, like, you've already exhausted all the stages. You don't want to do that. You want the stages to align with how they're thinking, but you want a project management as tightly as you can. And some of it's out of your control, but yeah.

• 1:02:33Lenny Rachitsky?

  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.

• 1:02:39Speaker 01

  Yeah.

• 1:02:40Lenny Rachitsky?

  To shift. So, so yeah, so understanding that and working with that seems really important. Okay, so step ten. And again, uh, as you pointed out at the beginning, most people think the sales process is five steps. And we're already in step ten. We're not even done. And you made this point, actually, before we started recording, that you haven't touched on, that I think is important for, to share this idea of that. These five steps kind of emerged out of like a CRM pipeline kind of check thing. Talk a bit about that.

• 1:03:05Speaker 01

  Yeah, so everyone knows that traditional five steps, intro, demo, proposal, contracting. And then like closed won or closed loss, right? Those are like the, 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, for the, um, for the pipeline. Something in contracting might be weighted at 80% and something in intro might be weighted at 10%. That's what those stages are for. That's not the stages you take a client through. Like, those are just the broad buckets.

• 1:03:50Speaker 01

  Um, and I think a lot of people use those buckets to say, okay, I've, there's about five different meetings that need to happen. When it's like, no, there's like three meetings, maybe up to five meetings in each of those buckets that are critical, um, to get the deal done. Now, we're, we're still speaking at it at a very macro level, like, you know, obviously selling a million dollar deal, you want to have more of those upfront meetings. Um, and you'll 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.

• 1:04:22Lenny Rachitsky?

  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?

• 1:04:32Speaker 01

  90%.

• 1:04:34Lenny Rachitsky?

  Wow.

• 1:04:35Speaker 01

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

• 1:04:48Lenny Rachitsky?

  Amazing.

• 1:04:49Speaker 01

  Yeah.

• 1:04:50Lenny Rachitsky?

  Okay. Let's keep going. Step 10, post pilot session.

• 1:04:53Speaker 01

  Yes. Um, 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 the, I know we gave everyone those three things, but most people only spent it on two. Why?

• 1:05:34Speaker 01

  And that may be okay, but you, but like you don't want them to be like, oh, well, you know, we wish it did this. Well, yeah, but no one spent time on that. We do do that, but no one spent time on that. So you just need to control also that you're capturing what they did in those pilots. And making sure that you're syncing up, or you could go to your champion and be like, hey, I know so-and-so logged in for like 15 minutes today. They didn't get past step one. Don't tell them what they're doing. You shouldn't even be that, but like, they didn't get past step one. Do you want to, can you check in on them and making sure like they're having a good experience? Like, use your champion to like, again, they've invested so much time into you, guide them with where they should be focused as well.

• 1:06:18Speaker 01

  Because at the end of the day, getting a deal done at the enterprise, it is set up to have as much friction as possible. Right? There's a people that will kill the deal, then you got to deal with procurement, then you got to deal with legal, then you got to deal with finding the executive sponsor, right? Which usually comes in the very top of the funnel, but there's so much friction to get a deal done. The project management and the individual on the inside, that's your key.

• 1:06:44Lenny Rachitsky?

  So funny. So many ways it could all fall apart.

• 1:06:47Speaker 01

  Yep.

• 1:06:48Lenny Rachitsky?

  Um, what I was going to say is it feels like many people would naturally, like, they don't want, 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, it's good. Yeah, everything's great.

• 1:07:03Speaker 01

  Just like DCs.

• 1:07:04Lenny Rachitsky?

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

• 1:07:18Speaker 01

  When you're, this is why your internal champion is so important. When they go quiet on you, that's when you know. That's why this individual, and listen, this individual is going to do you, if they've spent enough time with you, they will call you and be like, listen, if I'm reading the tea leaves, we should sit on this for a minute. Let's repick this back up. That's why having someone on the inside is so, so, so critical.

• 1:07:38Lenny Rachitsky?

  And yeah, the easier problem, here's your approach is just to stop responding and just hope that they, the salesperson understands where it's a little not excited. Oh, man. Okay. What are like the benchmarks for like how, how often you get through each of these stages? You mentioned like a few, just like, yeah, from demo to the stage.

• 1:07:57Speaker 01

  Usually once a, once something is qualified, meaning you're speaking to the right person, they are excited by the alpha, they, they admit that there's change that needs to happen. Notice I didn't say problem, but change. People get so fixated on problems, which are important, they are important, but like everyone speaks to the same problem and it commoditizes you, which is why I don't like to like overly emphasize it. The win rate for enterprise, a good, healthy win rate is actually probably going to surprise you. It's not 50%. Meaning of all sales qualified leads or opportunities, a healthy win rate is usually around 30 to 35%.

• 1:08:38Lenny Rachitsky?

  From qualified lead to signed contract.

• 1:08:41Speaker 01

  Meaning, if you speak to a hundred, you're closing anywhere between 30 to 35, maybe slightly less, maybe 25 to 30. That seems high, actually. Yeah, 25 to, somewhere between 25 and 35%. Why? If, if it's, if you, if your win rate is higher than that, your price is too low. There's a lot of part of the market that's just not in a maturity perspective to take you on, and that's healthy. Right? Those are, those are all the chasms.

• 1:09:11Lenny Rachitsky?

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

• 1:09:16Speaker 01

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

• 1:09:27Lenny Rachitsky?

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

• 1:09:33Speaker 01

  That's exactly right. So the, assume the market talks, especially at the corporate executive level, and someone might just not be ready yet, and that's okay. The amount of deals that come, that boomerang a year later of the ones that have lost, that's probably another 25%. So it is totally normal and natural for, uh, deals to not advance, right? But to a healthy win rate in the enterprise is typically, I would say between 25 and 35%.

• 1:10:06Lenny Rachitsky?

  Okay. That is incredibly helpful to people. A, I know, uh, how about like key stages along the way, just like percentage drop off up and?

• 1:10:14Speaker 01

  So it's usually like from qualified lead to like, um, you're coming at a demo, it's probably, you would lose half.

• 1:10:26Lenny Rachitsky?

  Out of demo.

• 1:10:28Speaker 01

  Out of demo, yeah.

• 1:10:29Lenny Rachitsky?

  Post demo, not for us.

• 1:10:30Speaker 01

  Yeah. They could shoot at 30%.

• 1:10:32Lenny Rachitsky?

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

• 1:10:35Speaker 01

  From demo to like, the more you move down, the less those numbers, uh, the less, uh, wider those numbers. So like, so like, let's say if you speak to, um, and you're doing a really good job targeting the right people, maybe 70, 50% of those people move to a qualified lead. Or 50 to 75% move to qualified lead. Of that, then, um, another half move to demo, and then from there, another quarter advance beyond that. Once you're in the bottom of funnel, you usually don't lose too much from there. If you're doing a deal qualification.

• 1:11:12Lenny Rachitsky?

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

• 1:11:16Speaker 01

  80.

• 1:11:17Lenny Rachitsky?

  80% succeed?

• 1:11:19Speaker 01

  80%.

• 1:11:20Lenny Rachitsky?

  Post pilot?

• 1:11:21Speaker 01

  Correct.

• 1:11:22Lenny Rachitsky?

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

• 1:11:26Speaker 01

  Yeah. Or you're not qualifying clearly.

• 1:11:28Lenny Rachitsky?

  I see.

• 1:11:29Speaker 01

  Yeah.

• 1:11:30Lenny Rachitsky?

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

• 1:11:31Speaker 01

  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 it part of your process.

• 1:11:40Lenny Rachitsky?

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

• 1:11:50Speaker 01

  Yes. So you have now, um, 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 agreed to, here's the pricing that's predicated on us getting this signed by this date. Here's the, give them something. Here's the kicker they're going to give us if we, if we get to this date. Um, 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 going to always 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.

• 1:12:35Speaker 01

  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 isn't there. Because they might say, well, in order for us to hit that time, we got to use our paper.

• 1:12:48Lenny Rachitsky?

  And it's not Google Docs, it's Word, Google, like Microsoft Office.

• 1:12:52Speaker 01

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

• 1:12:57Lenny Rachitsky?

  And so this has post pilot, feels like it's gone well. Um, you're saying the next step is here's like the contract, basically. Get that to procurement that early.

• 1:13:07Speaker 01

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

• 1:13:21Lenny Rachitsky?

  And an implication here is procurement is a way that your deal might still die, even if people internally love your product.

• 1:13:28Speaker 01

  Correct. If, if you get sent to procure, so here's, here's something interesting that a lot of people don't realize. People will use procurement as the excuse to not want to give you, um, the, the, the bad feedback. Oh, uh, I got to go to, oh, it procurement, it's, it's, it's lost in procurement or blah, blah, blah, blah, right? Very easy to blame procurement. Usually procurement is like a 30-day process, doing the back and forth on the legal, the papering. Procurement's job is not to kill the deal, it's just to make sure that it is aligned with how they need to buy. That's their job. Procurement is the only person that can get you paid. Do not start any work till you go through procurement.

• 1:14:12Speaker 01

  Business unit leaders can't just pay you.

• 1:14:16Speaker 01

  That needs to come from the finance team who pulls from the budget. So be very careful, like, don't start any work until obviously the papers are signed.

• 1:14:26Lenny Rachitsky?

  Start work meaning implementing, rolling out, people onboarding. Got it, got it, got it. Okay, amazing. Okay, so that's step 11, papering prep, setting timeline for procurement. Kind of getting on board with like, what is it going to take to sign by estate? Here's a little gift you'll get if you do it by estate, free month or whatever. Okay, step 12, papering review.

• 1:14:45Speaker 01

  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 sales cycle.

• 1:15:05Lenny Rachitsky?

  Versus a bunch of back and forth.

• 1:15:06Speaker 01

  Versus a bunch of back and forth. Get them on a call, be like, hey, everything, we're 80% of the way there. I have a few questions based off of your red line. 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 lawyer, a commercial legal team. Have a lawyer look at their red lines.

• 1:15:36Lenny Rachitsky?

  I imagine most companies have a legal counsel.

• 1:15:38Speaker 01

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

• 1:15:40Lenny Rachitsky?

  Okay, cool. So paper review, so that's reviewing basically. It's interesting called the paper.

• 1:15:45Speaker 01

  Yeah.

• 1:15:46Lenny Rachitsky?

  Is there like a more technical term for that, like the?

• 1:15:48Speaker 01

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

• 1:15:52Lenny Rachitsky?

  So interesting. Okay, paper review. Okay, step 13, papering procurement process.

• 1:15:57Speaker 01

  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.

• 1:16:19Lenny Rachitsky?

  Red line.

• 1:16:19Speaker 01

  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 battles, pick your battles.

• 1:16:41Lenny Rachitsky?

  Yeah, don't be afraid like the deal will fall apart if you see something in there initially.

• 1:16:44Speaker 01

  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.

• 1:16:52Lenny Rachitsky?

  Okay, and the final step, signature. Ta-da.

• 1:16:55Speaker 01

  Yep.

• 1:16:56Lenny Rachitsky?

  Anything special other than signing?

• 1:16:58Speaker 01

  No, that's, this is like the really exciting point, which is just figuring out who the signatory is before it goes routed for signature so that you, that you're, make sure your internal client knows. You know, because sometimes it's the CFO. It's not the executive sponsor. I just want to make sure you, everyone knows who that individual is. Because if there's a delay, you just want to make sure they get pinged.

• 1:17:21Lenny Rachitsky?

  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. Ding a bell. There's bells often.

• 1:17:34Speaker 01

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

• 1:17:43Lenny Rachitsky?

  Hmm.

• 1:17:47Lenny Rachitsky?

  So fun. It must be the best feeling after all this.

• 1:17:49Speaker 01

  It is, but then you're like, oh, now, like literally the feels is like five minutes and you're like back to work.

• 1:17:56Lenny Rachitsky?

  Yeah. And I imagine part of this is also how do we expand this deal?

• 1:18:00Speaker 01

  Hundred percent.

• 1:18:01Lenny Rachitsky?

  Is there anything there? Just real quick, just like how to start thinking about how this, where this goes?

• 1:18:06Speaker 01

  Yeah.

• 1:18:06Lenny Rachitsky?

  Once the deal is signed.

• 1:18:07Speaker 01

  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.

• 1:18:47Lenny Rachitsky?

  And so you're saying it's okay to offer services as a part of?

• 1:18:51Speaker 01

  Yes, yeah, yeah.

• 1:18:53Lenny Rachitsky?

  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.

• 1:19:01Speaker 01

  Yeah.

• 1:19:02Lenny Rachitsky?

  Being a part of software companies.

• 1:19:04Speaker 01

  It's what they know how to buy. 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.

• 1:19:16Lenny Rachitsky?

  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?

• 1:19:40Speaker 01

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

• 1:20:20Lenny Rachitsky?

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

• 1:20:29Speaker 01

  You know what you can get, like, I've had one, I've had clients say to me like, hey, like, I don't know if we're in a position to do this. And I've straight up said to them, you are a liability not closing this gap. And they're like, sometimes they just need to be like, again, you need to know if you're in a position to be able to say that.

• 1:20:50Lenny Rachitsky?

  Yeah.

• 1:20:51Speaker 01

  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, because again, use the intel they've given you towards that.

• 1:21:03Lenny Rachitsky?

  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.

• 1:21:10Speaker 01

  Exactly. Or like, hey, listen, on our first two calls, you, you told me how important this is. Did that change? No, we're just like in a weird spot. I'd be like, okay, listen. Here's what we're 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 there, and then there's obviously there's going to be the cases where it's like, it's just not the right time. Like they might be going through an acquisition, right? And like, bringing on net new vendors is just like not a priority right now. You just have to respect that too.

• 1:21:54Lenny Rachitsky?

  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 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.

• 1:22:13Speaker 01

  But they're sure.

• 1:22:14Lenny Rachitsky?

  But they're so similar and it's just like you being human, like the way a PM tries to understand what your pain points are. We're here to solve them. It's like, yeah, unexpected. We did it, Jen. We did it. We went through it all. Is there anything else? Anything else we haven't touched on? Anything else you want to, I don't know, leave listeners with before we wrap up?

• 1:22:33Speaker 01

  We gave them a lot.

• 1:22:34Lenny Rachitsky?

  We did it. Which was the goal, just the right amount.

• 1:22:39Speaker 01

  Yeah, yeah.

• 1:22:40Lenny Rachitsky?

  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.

• 1:22:49Speaker 01

  Well, it's, it's interesting. Like so many people will create like AI reports that they can send to their clients or like AI imagery or like, I don't know. You name your, your flavor. And it's like, anyone can do that.

• 1:23:09Speaker 01

  It just feels salesy.

• 1:23:10Lenny Rachitsky?

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

• 1:23:12Speaker 01

  Exactly.

• 1:23:13Lenny Rachitsky?

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

• 1:23:19Speaker 01

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

• 1:23:28Lenny Rachitsky?

  Yeah. Okay, Jen.

• 1:23:31Speaker 01

  This is awesome.

• 1:23:33Lenny Rachitsky?

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

• 1:23:42Speaker 01

  Yeah, yeah, yeah.

• 1:23:44Lenny Rachitsky?

  Final questions? Anything you want to plug? Anywhere you want to point people to? And how can listeners be useful to you?

• 1:23:50Speaker 01

  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.

• 1:24:07Lenny Rachitsky?

  Wow. And this is at State Affairs?

• 1:24:08Speaker 01

  It's at State Affairs.

• 1:24:09Lenny Rachitsky?

  Holy shit. What an opportunity.

• 1:24:12Speaker 01

  Yeah.

• 1:24:12Lenny Rachitsky?

  So there's multiple roles, not just one.

• 1:24:13Speaker 01

  Multiple roles, yeah.

• 1:24:15Lenny Rachitsky?

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

• 1:24:18Speaker 01

  Yes, I will. I will teach you everything I know.

• 1:24:21Lenny Rachitsky?

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

• 1:24:26Speaker 01

  Awesome.

• 1:24:27Lenny Rachitsky?

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

• 1:24:29Speaker 01

  Lenny, this was awesome.

• 1:24:30Lenny Rachitsky?

  So awesome. Bye, everyone. Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify or your favorite podcast app. Also, please consider giving us a rating or leaving a 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.