"Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel

You need to vision cast. You need to sell to a gap. Don't sell to a problem. When you're selling to a leader, you need to be selling an opportunity. The market doesn't want to be sold to. They want to buy. Most founders would rather get 10, 10 K deals, then lose nine and get one 100 K deal. In the very early days, people will discount till the cows come home 'cause they think that's the way to get a deal done. The best clients are not going to do that to you. If they're sitting there nickel and diamond, they're not fully bought in on what you're selling them. It might be giving you a false sense of success and product market fit. As soon as you become a comparison, as soon as you become one of three that they're testing out, you've already sort of lost. It's all about differentiation. Here's what you will be able to do tomorrow because of how we're going to serve you today. Something else that you talk about is that enterprise sales is very creative. It's more of an art. It's all about deal crafting. It is a relationship you're building with someone. If they know they can call on you, people will turn over rocks for you. I have a client at a Fortune 10 company where I was like, "It's so important we get the deal done this year. "Is that possible?" And she's like, "It's a tall order, "but if it's going to help you, let's do it." These are how enterprise deals get done. It's relationships. - What's kind of like the state of the art on go-to-market outbound tooling? - I don't use a tool. The thing about AI tools is they're all pulling from the same databases. I want to email someone not in the database that's getting hit by a million folks. I want to take a back door in, not the front door where everyone else is, trick or treating. - Today, my guest is Jen Able, co-founder of Jellyfish where she and her team help early-state founders learn how to sell and how GMF enterprise at state affairs. If you want to become better at selling your product, this episode is going to blow your mind and make you so much better in every way. This is the second time Jen's been on the podcast. Our first conversation was focused around getting from zero to one million ARR, essentially founder-led sales. This conversation is part two, going from around one million in ARR to around 10 million. This is the most tactical and in the weeds discussion, you will find anywhere for free on how to actually become more effective at selling to enterprises. I'm so excited for you to listen to this conversation. If you enjoy this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube. It helps tremendously. And if you become an annual subscriber of my newsletter, you get 17 incredible products for free for an entire year, including Devon, Lovable, Replay, Bolt, and Aidan linear superhuman de-script with the ProploGamma Proplexity Warp Grenola Magic Patterns Raycast, Chapter D, and Mobbing. Head on over to Lenny's newsletter.com and click product pass with that at Ryu Jen Abel after a short word from our sponsors. Here's a puzzle for you. What do open AI, cursor, perplexity, versel, plat, and hundreds of other winning companies have in common? The answer is they're all powered by today's sponsor, WorkOS. If you're building software for enterprises, you've probably felt the pain of integrating single sign-on, skim, R-back, audit logs, and other features required by big customers. WorkOS turns those deal blockers into drop-in APIs with a modern developer platform built specifically for B2B SaaS. Whether you're a seed stage start-up trying to land your first enterprise customer or a unicorn expanding globally, WorkOS is the fastest path to becoming enterprise ready in unlocking growth. They're essentially striped for enterprise features. Visit WorkOS.com to get started or just hit up their Slack support where they have real engineers in there who answer your questions super fast. WorkOS allows you to build like the best with delightful APIs, comprehensive docs, and a smooth developer experience. Go to WorkOS.com to make your app enterprise ready today. This episode is brought to you by Lovable. Not only are they the fastest-growing company in history, I use it regularly and I could not recommend it more highly. If you've ever had an idea for an app, but didn't know where to start, Lovable is for you. Lovable lets you build working apps and websites by simply chatting with AI. Then you can customize it at automations and deploy it to a live domain. It's perfect for marketers spinning up tools, product managers prototyping new ideas, and founders launching their next business. Unlike no-code tools, Lovable isn't about static pages. It builds full apps with real functionality, and it's fast. We'll use to take weeks, months, or years. You can now do over a weekend. So if you've been sitting on an idea, now is the time to bring it to life. Get started for free at lovable.dev. That's lovable.dev. (gentle music) Jen, thank you so much for being here. Welcome to the podcast. Lenny, it's starting to feel familiar and I like it. I should have said welcome back to the podcast. So I actually shared on Twitter that you're coming back and I had so many people ask so many questions. Clearly there is a lot of confusion and a lot of need for learning how to get better. The stuff we're gonna talk about sales, enterprise sales. To frame the discussion, our first chat, which we're gonna point people to, if they wanna start there, we focused on Fenderlet sales, which is essentially the beginning phases of a startup kind of going from zero to about a hundred million AR. This discussion is on the next phase, which is going from about a million AR to about 10 million AR in enterprise sales, not like PLG or anything like that. You have a bunch of really strong and counter intuitive opinions and piece of advice on how to be successful at this. So I'm just gonna go through a bunch of these things. We'll see where it goes. Before I get into the first one, is there anything broadly? I don't know, is there anything broadly? You wanna share anything you wanna say before we dive in? No, let's dive right in. Okay, so the first thing that I haven't heard anyone talk about before is this point that you often make that the mid market does not exist. People often hear about enterprise companies. There's obviously SMBs and startups. There's also people just like, oh, I'm gonna go after the mid market somewhere between. You don't think that's real. Talk about your experience there, what people should know. - It's fascinating, 'cause you have, if you ask someone to describe the mid market, actually, if you ask someone to describe the enterprise, every single person has a different answer, right? It's either based off of revenue, it's either based off of market cap, it's based off of employee size. And I think a lot of people can get lost because selling to a hundred person organization is a radically different game than selling to a thousand person organization. And there's no like hybrid approach. So the best way to think about it is you have small business, which is typically can be really powered by marketing. And then you have enterprise, which is typically going to be sales led. If you bucket them into these two very specific silos, it makes it much, much easier to understand what game you're playing. Now, when we talk about mid market, I usually will say, are we talking about the upper end of small business, are we talking about the lower end of enterprise? And most people are usually seeing the lower end of enterprise. And I say, great, no, you're playing the enterprise game. Know the type of people you need to hire. Know the type of ACV day need, 'cause it makes it a lot easier than trying to have this middle ground that catches everything that doesn't distinctly define SMB in enterprise. So I say the mid market doesn't exist because what is a mid market hire? It's either low end enterprise or upper end SMB. And if you bleed those two games, you're gonna lose. They're so distinctly different. So that's kind of my theory on it. - You have this chart that you shared with me that we'll link people to where you kind of show the number of companies within each of these segments. And there's basically nobody in this kind of middle segment talking about that a bit. - That's right. And just like the power laws, I mean, if you look at the fortune 1000 and then the kind of the lower end enterprise from there, the like it trails off so fast. Like power laws totally exist in these like large corporations. And we can't be treating everyone the same. - This begs the question, where do you suggest companies start? There's obviously startups classically or just like innovators move fast can make quick decisions, enterprises have all the money. Usually the advice I hear is just don't go after the fancy companies to start because they take a long time. They're, you don't wanna screw it up. What's your advice on where to start for most companies? - The exact opposite. Early adopters are those logos because they have to continue to stay at the number one spot. So they'll take tons of swings to continue to stay in the number one spot the hardest part. Right? So those number one logos are like, if you can give me just a slight bit of alpha, just a tiny bit, that's where I get promoted, that's where I get the pat on the back because we are the world's leader in our industry and we cannot be disrupted there. So there's this running joke, we're not running joke, there's this running statement where a lot of VCs will say don't go after tier one logos, go learn down market or go learn from like logos that don't necessarily carry a lot of weight. The ones that carry all the weight of the ones that are willing to take a shot and wanna help, right? Because they also wanna be a part of it. They also wanna be able to dictate the roadmap. Now it's the founders job to decide what can be done and what shouldn't be done, but their voice takes you $100,000 deal into a million dollar deal in a very short period of time. It will literally guide you there. So when someone says hey, go after startups such as short sale cycle, yeah, that makes sense. I totally get that. It's a very easy to decide, define the decision maker. It's very easy, you don't have to go through procurement, but in the age of time, AI where it's all about sucking the oxygen out of the room and winning the deal and getting your foot in the door as quickly as humanly possible. Before someone else tries to take that, you want to get to the enterprises as fast as humanly possible. Just so folks understand what we're talking about here. When you say to your one, what's a good way to think about what's your one loveless? Your one is like your Walmart, your McDonald, your Nivitya, your Tesla, your Exxon mobile, your United Healthcare. The logos that are the leader in their space and their job is to stay in the number one spot. Wow. So your advice is because this is very counterintuitive. This is exactly what you're here not to do. Your advice is go after the Chevrons and the Moulby's and the Wal-Mart as a startup. Because if you can get them, that's all the proof you need. How do you approach finding someone? Let's just get tactical there. Just say you're going after Walmart. But I know this is like not like a five second answer, but just how it's going to approach finding someone at Walmart to sell to. First of all, make sure the founders involved. They love everyone loves talking to a founder. So we'll start with, let's get the founder involved as fast as human possible. The second is you need to vision cast. There's a very big difference between problem selling and gap selling. Problem selling is highly specific, more technical than not. It's the way that every salesperson is going to go about it. Find the problem and anchor to it. When you're selling to a leader, you need to be vision casting and you need to be selling an opportunity, right? Which is they are here. Here's where we can take you. You know that image where it's like Mario, or Mario, Mario, Mario. And then there's like the mushroom and then there's like Mario on blast. And everyone's like, don't sell the mushroom. Sell Mario on blast. Well, that's exactly what it's saying. It's about selling the opportunity. That's what gets the tier one logo is excited. And that is the best thing for a founder to sell, selling the vision versus the problem. And also it's what gets them to want to take a swing. Who wants to take a swing because you can do some small problem. They're not going to go to bat for that. What's an example of a vision cast in a company for just to make this real? That doesn't look like when you've done a great job. We have an ability to deliver alpha, meaning we have information, we have data, we have a way of working that no one else can do or is going to unlock a new way of thinking for you or an ability to deliver to a customer or an ability to solve a problem. Right now, this is you have an ability to access this level of information. I have an opportunity through our resources or through this like gated data we have access to to get you much further upstream so that you can get information faster sooner. It's kind of like the high frequency trading that one second, that one second, they didn't do much. They, you know, they didn't sell all we were doing fiber cable connects connectivity. We're giving you one second of alpha before everyone else. It's more of like that ability and that's not problem selling. That's opportunity selling. I like this phrasing of just giving them alpha. That's such a simple way to imagine what this should feel like. We'll link to that image you're talking about with the Mario and you know that image? Yeah. The person that made that image originally is Kathy Sierra, if you remember her. Do you remember? There's this person Kathy Sierra. She's from back in the day. This was a big, I don't know, lesson she taught is you want to not sell your people on like a feature or product. You want to sell them on them becoming a superhero. Yeah. They're now a superhero because of the thing you've built for them. And so, so the vision here is here's how you become a superhero. Here's how this alpha will help you become more successful. And that's why founders are so good at selling because they naturally go to vision selling and vision casting versus a typical train salesperson is find the problem. You know, ask these questions and it just kills the vibe. It just feels like you're talking to a salesperson. Right. It's like, what's your script? And it's like, that's not vision selling. That's like playbook selling and in the age of AI where it's all a lot of it is about alpha. It's about speed. It's about getting access to information is about training data like and look at them. Look at how the markets reacting to it. Right. It's all it's all opportunity and it's all. Yeah. It's all about the alpha. So just to make it more concrete for people, Sam like sales person at cursor. What would be an example of vision casting like the obvious idea there is. Your team will be more productive. You'll get more dynamic faster than everybody else. Is that the big enough vision to cast? I think it may be more of like you will be able to actually hire the 10 X engineers that you don't necessarily have access to because they want to be able to use this type of tool. It's about getting letting them get better, letting them get differentiated talent. Right. Or that's probably more of what I would anchor to of like this is the 10 X engineers use cursor. You don't do you want access to 10 X engineers? Like they won't even join your company if you're not using cursor. Yeah. Yeah. Like think about there's so many so many people are so specific about what they're able to especially I think especially technical folks like I'm not a technical person, but I would imagine that they're not going to go to you know, they don't like to go to these corporations because they're forced to use some like incumbent, incumbent tools. Going back to the going after these larger companies, I asked your colleague Justin what he sees you do that most impacts the success that teams have with their sales process. And there's a bunch of going to touch on, but one is most founders are insecure about asking for large ACVs for charging or they the way he put it as most founders would rather get 10 10 K deals than lose nine and get one 100 K deal. Talk about your advice there and what you see. There are in the very early days, people will discount till the cows come home because they think that's the way to get a deal done. The best, the best clients are not going to do that to you because they they they like of that's a qualification criteria right, which is like if they're sitting there nickel and diamond, you be like, no, I don't I don't I don't believe it's worth this. I don't believe it's worth that. They're not fully bought in on what you're selling them. So when when I say I'd rather get $100,000 or they'll then 10,000 dollar deals, I'd rather have one rock star client that's going to help me figure out the next stage of where this is going, then 10 or maybe five that are a good fit, five that are not and I still have to serve those five that are not a good fit and that's going to distract me. So this is why I love enterprise sales is they're not going to do the hard work of bringing you in if it's not critical or if it's not when I say critical, it's it's not going to it's going to impact them in a way that they're going to make it successful. That's what I love about enterprise sales. They have the resources to ensure that it gets implemented because most and today's day and age, if people are not using the tool, you just get rid of the tool, right? So they're going to want to make sure whatever they bring in what they go to bat for. Remember, they get a they go to bat once every two years, maybe once every three years, you've got to make it feel incredible. You've got to make it feel like they're going to be a superhero going back to it. Otherwise, what's the point because the way enterprises are structured is it is it is designed today to make it hard to buy because they want to make sure whatever you're bringing in you really, really want. It gets rid of the mediocre, you know, I think this would be good and it gets to this is going to change the way we work. It's going to it's going to impact our ability to capture some form of alpha. However, you want to define that for them and it's sticky because of that. So your advice here broadly is don't pay attention to the smaller 10kish kind of opportunities for for a bunch of reasons. One is it might be giving you a false sense of success and product market fit to those companies are maybe not as innovative and won't lead you in the right direction. Three is a probably discounts, just like your product and your pricing is just gets thrown off. And also like, you don't really get taken seriously for 10k. You get way more taken seriously for 100 cases much harder to get 100k deal done and like an executive use needs to be involved. I'd much rather have an executive sign off on something and spend two more months getting the deal done because you know that they are bought in. You know, you can now ensure what kind of value do they want in one mock and maybe you have an opportunity to turn them into a user which to me in today's day and age with our generation being the ones that are now the executives at these corporations. This is native to them. Who is this true for? Is this is the advice here basically if you're trying to build a successful B2B company, everybody should be aiming towards these 100k sort of deals. Is there a world where you can be successful with 10k's for a long time? If you have a super high win rate and a massive market because all you have to do is reverse engineer the math. If you need to generate $100 million in revenue, how many 10k deals do you need? And the expansion on a 10k deal is in parallel to that. Where can you go? 10 to 15? That's a 50% growth. Much easier to go to 100k to 500k because they want more bodies or they want more value out of you. Nanna Price they love to get more. of an existing customer, you're already trusted. So it's also about the type of company, or if you're a venture backed, you can't be selling $10,000 you'll see the enterprise, you'll get killed. Or you've already lost the game, 'cause you're playing a small business game in the wrong sector. - Have you seen startups C4 with succeed in that 10K, 20K bucket? Or is it really, really rare? - If they're going after the enterprise? - Yeah. - Yes, if it's the first three months, and then after three months, it turns into a 50K and then 100K and it ramps up quickly, sure. That makes sense, 'cause it got your foot in the door and you can expand it exponentially in a healthy manner. I think that that's fine. $10,000 a year, then going to 12, then going to 15, the math will break. - This is great. I feel like most founders listening to this are like, "No, no, we're kind of in that exception. We'll be all right. 10K will do 20K. That's crazy to consider 100K." - Yeah, the math will break, and also the really good salesperson, your commission on a 10K deal. You're not going to get a great salesperson. They're going to want to be anchored to like, how can I sell $250,000? How can I sell a half a million dollar deal? That's the type of person you want. - And this is like a big part of this, is this is a good lens to force you to build the product that you can sell for 100K, 500K. - Yeah, absolutely. And again, this is about playing that enterprise game. If you're trying to sell, if you're a small business, if you're in the small business place and an enterprise company comes to you and is like, "I like this. Ensure that you structure it for an enterprise. Don't play the small business game with an enterprise company." - Talk more about that, what does that mean? - Let's say you're PLJ. And an big company like Walmart comes to and is like, "Hey, can we get access for three of our users?" And they're like, "This is so exciting." And then they sell them the small business pricing for three users to Walmart. Very, very hard now to go from those three users that you just priced them at a small business way, turn that into 100K, 'cause now it's documented what they're actually paying for this. So you're stuck. You've kind of like anchored yourself to this price. Not to mention, like, what's the, how are you gonna unlock the executives high level value so that you can get that? So you can get that senior executive to buy in and stamp this as well. Otherwise, it's just gonna be throwing it on the credit card. But like, again, you just ruined your enterprise game 'cause you're anchoring to a small business price. So this is why, like, when you bleed these two games, it's very, very, very dangerous because these are really smart companies. They're gonna say, "Well, wait a second. I just paid $9,000 last year. And now you wanna charge me $90,000. Well, what's the step change in value? What's the different, what's the 10x value I'm now getting?" That's super hard to prove. So the tip here is, your initial price will really screw you if you get it wrong. And so obviously we're not gonna give people the answer and their pricing strategy fully, but just, is the advice just charged more? Or like, what would you recommend? It is enterprise companies are very used to a land when I say like the first initial contract to assist somewhere between 75K and 150K. Very used to that. In fact, that's probably where you wanna start 'cause you also wanna understand where can you grow from this. Start contained, don't say 150K and sell the farm. Say it's 150K, here's who's gets access, here's the value we're gonna deliver, and here's where we're going over time. You also want them to know, here's what, here's what we plan to do roughly in year two, year three. I know it's hard to look that far out, but like plant the seed with them in terms of where this is going. If you come in at $10,000, it's so, even if they want to bring you in and wanna spend 100K with you, they have to be able to defend that. And now they see a $10,000, it can get really messy, especially 'cause a lot of them are using AI now to understand like contracts. So they're gonna quickly say, oh wait, you spend $1,000 with Lenny, and now Lenny's asking you for 100K, great, just help me understand why or defend it. - I could totally see Chad G.P.T. Big like, hmm, this is interesting. You should be able to-- - Yeah, exactly. - 1K, you know, it's 100K. What might be going on here? - Totally. But people don't realize, you know, how, again, know the game you're playing and don't be sloppy about it. - So your advice here is really interesting. It's, there's the land they expand. Expand is very important, but the landing may screw your expanding because it sets the wrong reference point. - 100,000% that's exactly right. You said it better than I did. - And so you may see like Matt, like in theory, if you land a 10K, go to 100K, that's like an amazing NRR. Everyone's gonna be really impressed. But you're saying people won't buy into that. It's gonna feel absurd and wrong and something. - Unless it's defendable. All in these, it's defendable, but who can really defend? That's very hard to defend a 10X jump. They're gonna wanna see 15X value. - Let's talk about design partners. - Oh yeah. - This is something most founders try to do. They find a few folks to work with to help them build the thing. What's your advice on when to start finding to design partners, how to find design partners, what a good relationship looks like? - Design partners are incredible. They are the hardest logos to upsell, meaning go from design partner to full rollout customer. So like, don't expect these people to be your million dollar pipeline. Expect these people to be the guide to help you understand. Maybe design partners could be a technology company in the Fortune 1000. So they're used to experimenting, they're used to technology, they're used to, they were once a startup so they get it. Those make really good design partners. Most of the design partners that I've closed are usually like technology based, right? They get it. And they also are excited about advancing the org and also giving the team an ability to have that startup feel. So like, if you're a large massive corporation, like Stripe, right? Stripe doesn't get that startup vibe as much, like that 50 person startup vibe, but like this can be a gift to give them that lens and give them that voice and give them that excitement that they don't get as a larger company. But those are great types of logos to be, early design partners because one, they wanna make sure they continue to stay on the cutting edge. But two is they are to try and build something without that guidance is really, really, really hard because they're not using it. So you need that user feedback and you also need to tie that to the executive value, right? So it's actually a lot, it's very hard to do. But if you can come out of it and upsell a design partner to a full rollout customer, such a huge win for the market, for you, for your team and also for your investors, because it's the hardest customer to actually truly convert. They've been it when it was messy. They got a really, they usually got a low price point, but if you again frame it, say, listen, I would love for you to be a design partner. I want a little skin in the game to get you to put in it. Here's where we want to go and you'll get a discount because you were in the beginning, but I'm setting the framing. Here's where we want to go with pricing. Here's where we are today. You'll always have 30% concession and perpetuity because you were there with us on day one. So again, it's not about asking for $10,000 and then not expecting that design partner to upsell and keep it flat because there's no growth there. It's a flat, it's about getting that early design partner set the framing, own the framing and let them know where you're going. Again, $100,000 to these large logos, if they want it, it's very easy for them to get it done. - There's this really interesting underlying piece of advice of finding a company that pulls you in the direction that leads to success. A company that's kind of a visionary. There's the obvious companies that everyone's always trying to get these days open AI and then throw up and strike, I think is one. Any advice for just picking the right early, what are signs that this is a company that will point you in the right direction? - I think they have to be part of the logo that is deemed start up friendly or in that world. And then I think it's the person. Is this person excited to give feedback? Does this person buy in to where we're going? Do they see this world differently with like us? Do they, are they in lock set with the founder vision? Are they excited to use a tool that's janky? 'Cause it is janky in the beginning, but they know that where this can go can be incredible. So it's, I think it's really about the person and making sure that they're aligned for what they're getting into. And I think a lot of people, I think a lot of sales people oversell it. Think that's a common thing that happens, right? And that leads to churn, that leads to frustration, that leads to sometimes just canceling the contract. - They oversell the initial kind of design partners. - They oversell everything. - Yeah, design partner even full rollout. And it's so, so important to tell them, here's where we are today, here's what we cannot do, which is just as important, it builds trust. Here's what we will allow you to do in the next six months. Do you want to be on this journey with us? And it's really ugly right now, right? Barely anything exists, but like we would love your voice to be a part of it. - One of the biggest fears I think founders have is having a company pull, Basic. build just for their use case and then it ends up not being used by a lot of people. And so like how far do you go fixing their specific problems? Any advice on just how far to go with one company? That is the founders job. The founders job is to have a clear vision and do not let anything delineate from that. It's important to take feedback in terms of what is the market's reality, but like it is the found and this is why being a founder so hard. It is the founders job to interpret that because a lot of feedback you get is this is the old way, this is the responding this way because it's the old way of working. They want you to build this because it's the old, that's how they're traditionally expecting to do that. It is not, here's where we're going. This is why we're not doing that. I hear you, but here's why we're not going to do that because this, we're going to completely change the way you do this. I think we did a bunch of design partnerships late last year and there was a lot of feedback given. A lot of feedback given. The founder had such clarity with where he wanted to go that he was like 80% noise, 20% had I not asked this question. I wouldn't have gotten that cold in terms of where they are today. It's that 80, 20 roll or 80% of what they're going to tell you is probably going to be not related to where you want to go or based off of the old way, but that 20% of like, oh, I did not think about it that way. That drives everything. Have you seen a design partner pull a company in the wrong direction just going to screw their path? Have you seen that or is that pretty rare? No, I don't think it's that rare because we hear people complain about it all the time. I think it's more of an excuse. Moving back to this question of going after the enterprise versus SMBs and again, early advice we gave is there's no don't go in between either pick SMB small company, which I know you said there's a million ways to just kind of differentiate what this means, but what I guess I think of employee numbers like under some number over 1000 is maybe enterprise. Is that like a good way to think about just like? Yeah, I mean, it depends. Are you selling proceeds or are you selling based off of usage? Or are you selling off of like, I think it also depends on the pricey model a little bit. I look at headcount too because it's just like, it's just such an easy way to think about it because you can also gauge usage off that and a bunch of other things. But sometimes like the small companies like, I think we're going to see a lot more like a lot more larger companies become smaller because of AI, not like significantly smaller, but also like high margins allow them to experiment more to such an interesting point you're making there that like the way we designate enterprise versus SMB like base shift because number of employees may go down with AI. Yeah. Oh, yeah. So interesting. So going, so where I was going to go with this question is when people are deciding I'm going to go enterprise versus I'm going to sell to startups like YC companies are the typical example they sell to their own YC batches and you just brought advice of picking. Okay, we go enterprise versus no, let's actually go start it. I think it's about and I read this somewhere and I whole hardly agree with it because I've seen it live. I think it's about like what game does the founder best understand? Are they like an incredible marketer and have some like competitive edge for how they can like win a massive audience? I would say go SMB and marketing lead or are they a bit more, you know, really understand how large corporations work and really excited to deliver on $100,000 plus type of opportunities or the value that they are building for is way more relatable to an enterprise versus a small business. That is really interesting. I've never heard of it described that way. I think about linear which started very startup E and my take is they did that because changing the way work is really hard and that was like let's start with companies and grow with them and over time that becomes the default in reaction to that. I think that it sounds like that's a great way to work because that's a technical tool, right? So you also need to have the right infrastructure to sell, right? Like I think Slack, I mean look, Slack and Microsoft teams are still battling it out at the enterprise. I think it's also like how you plug in and how you integrate and do they even have the right systems to support you? The thing with OpenAI and is like they didn't have to connect to anything. Say more about that. So like the value people were bringing their own use cases to it, right? And they don't, it's not like they, they, and well, they can ingest and they built that. That's a brain of thing. And they started, they started, I think, this is someone told me this. So this is, this could be hearsay, but I believe that they had, they were already speaking to CTOs even well before they released to help them explain where this is all going and get their buy in. And it's, and it's much easier to get into the enterprise when you're like, we won't even touch your data. We won't even touch it. Just drop, like use it to solve problems. And then, and then we can build trust and then start to integrate and, and connect, and connect the pipes. Like part of the challenge is with selling the enterprise. They're like, all right, well, let's connect all your consumer data and like in the, whoa, that's extremely risky. So you have to start small and low risk, which is like, hey, here's what is the subset of consumers that churned? Let's figure out how we could have made them happier or whatever it may. So that data is lower risk. So again, it's also understanding your market and understanding, you know, what their ability to experiment is. It's interesting this distinction between open AI right now and anthropic. I don't know if you've been seeing kind of their growth feels like open AI is very consumer. First, and anthropic is more and more winning on B2B. I saw this chart recently where they're like overtaking open AI now on B2B. I don't know any reaction there of just like these two different approaches. I don't because most enterprises I'm talking to mentioned Gemini. Oh, interesting. Yeah, or Microsoft co-pilot. So I don't hear much about anthropic to be honest. So that might be more of like a small business startup B. I don't know or it's a different part of the organization that's using it. Yeah, that's all discussion of bundling right there of like Slack and Teams and then just yeah, Gemini just kind of coming in automatically. People don't have to adopt anything new. Yeah, totally. There's something else that you talk about that I love that I don't think people talk much about, which is that enterprise sales is very creative. Oh, yes. Talk about that. So I personally believe that small business sales is really a, I used to think it was more science than art, right? It was more like, you know, figuring out what didn't work, running experiments, you know, casting and validating, which I do believe that's that's that's that's to get to like foundations. Like where do we play? What do we want to do? Like that early, early, early zero to one from one to 10. I think it's more of an art, right? Which is how do I take my learning and how do I package it up where I own the framing? I can speak to very specific alpha. I can vision cast and where I better understand the problem over time better than the market does. And it's all about deal crafting. They just need to feel like the value they're getting out of it is way more than the cost. And it's sometimes about giving away things that don't really cost much to you, but are super expensive for them. We're selling X tool. We can build out Y specifically for you over the next year and integrate it because I know that you would have spent X number of dollars on engineering resources or you wouldn't have gotten an engineering head internally to do this. But we're just going to leave it to you. You got to give us a year to build it out again. You're not letting them sidetrack you too much. You're kind of containing it. We'll do that for you at no additional cost. That's huge value. Or hey, we're going to run an event and we want you at the forefront of it. We want you to be a speaker. Huge value. Right? So it's like all of these additional things that add value beyond just the product, but are all part of the product and the vision. Everyone keeps thinking the product is just what goes into their hand. The product is pricing. The opportunity, the framing and not letting them compare you to something else. And I know we talked about that on our first call, which is as soon as you become a comparison, as soon as you become one of three that they're testing out, you've already sort of lost. And it's all about here's what you will be able to do tomorrow because of how we're going to serve you today. So along those lines that reminds me in our first chat, you actually made this point that I've never heard anyone else make, which is that services are a really good way to start getting into the companies that were most founders here like, no, don't just like, don't do manual stuff for the company. Build a product that you can scale. Your advice to the opposite actually start with sell services. Talk about that. prize. is the number one thing they buy services. They know how to do it. It's super easy. It's they like they do it all of the time. It's like the most consistent thing they do. It's the largest budget item, right? External resources, consultants, whatever. If they have a very immature way of understanding the problem or they've never purchased technology to solve it, to some extent, right? Either one, you are doing something that's never been done before, which is rare in today's day and age. Or they might just be like laggards on the journey. So you have to decide, is this someone you really want to be working with? And if so, selling them at service, even though the technology is powering it on the back end, is the fastest way to get your foot in the door. It's what they know how to buy. Now, the idea is to once you sell that service, once you get that foot in the door, then it's to guide them towards the product. Hey, you're spending so much here, why don't we move it? Why don't we get you to come in and leverage the tool that's been powering this the whole time and move this more into technology serving you versus the human? Well, I think this will blow a lot of people's minds. How did you? How did you, this forward deployed engineer that's exactly what they're doing, right? Like, you know, there's a lot of companies out, like I'm sure, open AI. And this is what someone told me, they were in and talking to CTOs and helping them better understand how AI and their organization can better work together. And it was them coaching them and educating them, whether they did it for free or not, I don't know. But they got their foot in the door, they started to build trust, and then it gets adopted. This is the epitome of doing things I don't scale. That advice we always hear. This is like, okay, this is what that looks like. Like, we will solve this problem for you. We are using software to do it and then over time, oh, you could just do this yourself. It'll cost you less, you can scale this. Yeah, that's right. And they don't even need to know at first. That software is doing it. That could be the magic part, which is like, guys, we literally, we are literally doing this with our technology. - Today's episode is brought to you by Coda. I personally use Coda every single day to manage my podcast and also to manage my community. So I put the questions that I plan to ask every guest that's coming on the podcast. So I put my community resources, it's how I manage my workflows. Here's how Coda can help you. Imagine starting a project that work, and your vision is clear, you know exactly who's doing what and where to find the data that you need to do your part. In fact, you don't have to waste time searching for anything because everything your team needs from project trackers and OCRs, the documents and spreadsheets lives in one tab, all in Coda. With Coda's collaborative all in one workspace, you get the flexibility of docs, the structure of spreadsheets, the power of applications, and the intelligence of AI, all in one easy to organize tab. Like I mentioned earlier, I use Coda every single day and more than 50,000 teams trust Coda to keep them more aligned and focused. If you're a startup team looking to increase alignment and agility, Coda can help you move from planning to execution in record time. To try it for yourself, go to Coda.io/lini today and get six months free of the team plan for startups. That's C-O-D-A.io/lini to get started for free and get six months of the team plan. Coda.io/lini. There's a lot of talk these days about this idea forward-to-played engineer, something balanced. He was really famous for just essentially an engineer sitting in your office solving problems with you, like basically as an employee. And then through that, they learn what software to build. Is that something you're seeing too? - Oh yeah, I think that a lot of companies, a lot, sorry, a lot of folks that serve the enterprise, they have a button of seat in their office. Like you look at these large consultancies, like McKinsey, they're not in their headquarters or in their clients office all the time. And the other interesting thing and proof of this is how many people go to a deloitte-oriented center and expect them to be a channel partner. This is exactly what this is all about, which is they sell the service, they come in and then they introduce, hey, look at what this startup is doing over here, you might want to give them a shot. The problem with channel partnerships and why I don't believe them them is there are a hundred of you on this list. And you're expecting them to sell it on your behalf. Biggest no-no, they're not vision casters, they're not visionaries, they're consultants. But this is, that goes all towards like, go find, I remember startup saying, oh, I'm gonna go win over Accenture and then have them disseminate me into their clients and I'm like, as if that's a workable strategy. - Okay, you know what I'm gonna be helpful is, let me try to summarize some of the best pieces of advice you've shared so far. And this is specifically for folks trying to go from about a million AR to about 10 million AR. And then I want to ask you just what's most different about these two stages, but let me share this first. So advice one is go for tier one logos earlier than you think you should because they're early adopters, they can move fast, they can pull you in the right direction. - And they exciting esters too. - Yeah, for sure. And other leads are going up. And other, you know, talent, future employees, yeah, exactly. - So the counterintuitive insight here is, you think they will move slow and be too busy, but in they are actually the early adopters. - That's right. They have to maintain that number one spot. And also all of the people that are in the number two, number three, number four spot, all wanna do what number one is doing. So it's also like tier reference ability too. - And the point about them being the early adopters, like the people that join the stripes and open a eyes and then the tropics are like the, like they individually love technology and love the latest stuff. So like as a human they're like, oh, this is cool. - That's exactly right. I mean with myself, aren't I? That's kind of funny. - Yeah, that's a good sign. - So two is ideally try to price closer to about 100K, like 75 to 150ish K is what you said, most enterprises are used to buying. So instead of starting or even sticking with 10K, 20K for too long, you need to make yourself go towards 75 to 150K. - That's right. - Yep. And if you were to sell a service 'cause I know we're talking about selling services first, pro-weight that over time. So maybe it's 10K a month. So they start to get used to what that pricing looks like. - So this is a way to make it feel, this is like how you get to 75 to 150K is, there's a service attached to it. It's not just, here's my SaaS product. It's we will solve this problem for you. Our person will be sitting there doing this for you. - Yeah, or it's a technology too. I mean, you can add the services. I always, well, let me take that back. The services, whether the services is bundled into it or not, some people will unbundle it. Other people will say the services is a part of it. But yeah, it nets out to 75 to 150K. That's right. - And you're said that it's okay to start lower on ACVs and deals, but you need to push fast towards 100K. - It's good. - That's over a few months. - Yep, that's right. Like if you can get into, if you can get into an enterprise for 10K in a month, which is not doable. But if you could, and you could go from 10K to 50K in four months through an expansion strategy, all game. That makes sense. But it's really rare and very hard to do. - And so there's two different paths there. One is land cheap and grow quickly. The other is move your ACV average up quickly. That's right. - That seems like both. That's, the latter is probably the more common strategy is just keeping increasing. - Yeah, as the former, you can get tripped up because they could say, okay, now give me an economical price for doing this for 100 people. And then it all kind of evens out. 'Cause now you're at the 100K deal anyway. But it's much, there's more room for error, which is why I say go in and try to land 100K. - By the way, in our first chat, we talked a lot about the procurement process, which is what trips a lot of people up and is really painful. And I vividly remembered that conversation still. So if people are having issues getting through the sales process and procurement, a lot of good advice there. - And getting stuck in procurement is usually because you're not speaking to a senior enough person and they don't know how to navigate it, which is why I like that executive needs to be involved. 'Cause as soon as the executive picks up a phone and tries to get a hold of like their buying group, things move, right? Like when people say, oh, I'm stuck in procurement, I'm like, oh, that's a deck, just be a qualification error and you never get out of it 'cause you sold to someone to junior. So that's why the 100K is such a safe zone because even for 10K, you might have to go through procurement. So this is like the surest way to make sure that like, you don't, listen, I've seen 10K take nine months to close. - No way, no. - Yeah, so. - Okay, next piece of advice is this idea of vision casting instead of problem solving. So the advice here is instead of here's your problem, here's how our product solves it is. Here's how you will achieve alpha in the market by adopting the software. We talked about the example of cursor, where if you adopt cursor, you're gonna draw the 10X engineers that are joining other companies right now. This will give you a big advantage. - That's right. And yeah, it's pain versus opportunity, especially in the age of AI and I know that that's, we're moving into the next dimension. It's all about solving for a gap. It's seldom about solving for a very, very specific problem because people are trying to figure out what's our AI strategy, where are we gonna go with this? What is the world gonna look like? I wanna be a part of that new world. So it's a great time to be doing that. - And then there's a bunch of advice we shared that you talked you shared about design partners of just how to select them. Your advice is definitely have design partners because they will help you build the right thing. But as a founder, you need to have a clear vision and sense of where you wanna go and not just build everything there. Ask you to. That's right, because it's important to say no, right? Like, and that's all part of the framing, right? Which is like, here's, here's, we want a little skin in the game. Like you set the price. But here's where, here's what we're marching towards in the next six to 12 months. Like, are we aligned there? If we prove, if we deliver on what we say, we're going to deliver, are we aligned there? And do that kind of handshake. Is there anything else that I missed that you think is really important for this stage? So, one to 10 is no longer the founder. Maybe the founder comes in in very strategic points, but you need a really good enterprise salespeople, right? Taking someone from small business and expecting them to do enterprise sales big no no. It's a different game, right? Vavilika, different game. You need to understand how corporations buy. You need to understand how executives think. You need to better understand simply just like what the enterprise business models all about. And like their ability to take on risk. People will bring in like super junior enterprise sales reps. And I'm like, you're looking to sell to an executive and you have this tent like this person that's five years out of school with no corporate experience doing it. Again, where unless they have like some extremely, you know, deep experience in the industry, or are just like a unicorn in terms of like, wow, this person can sell ice to an Eskimo kind of thing. A junior person converting an executive, again, the founders involved. Maybe that's doable. But usually the founder can't be involved in every deal. And you need you need people that can I always say you need people that can cosplay a founder. Right? Which is like selling the vision, getting them excited. Like running through a wall to get the deal done and getting creative on how none of my deals look exactly the same. Every deal looks different. And that's okay because every organization has slightly different opportunities of where they want to go. And you have to kind of build towards that. And the framing may change. So it's this ability to like adapt from what you're hearing and like let that compound over time. But like I always say like, can this person cosplay the founder? I think that that's the best type of sales person because it doesn't feel like sales. It's more of the art. This is amazing advice. What is a common profile that you've seen be successful? Like what level of seniority, what kind of personality and he's traits to the core? Maybe a former founder. So you can get that. Because they're used to selling, right? They sold investors and they've sold employees. Two is someone with no sales experience, but has deep product experience or an engineer and can like think about things in a unique way where you can where the market's like, oh, this is so interesting. Taking a typical salesperson and putting them into a sales role almost always is where people get frustrated. The market, it feels salesy. Like the market doesn't want to be sold to. They want to buy. And I know that this is like, it's very hard to hire a really good enterprise sales person. I mean, the number of people that I've interviewed, I can count on my hand, the ones that I'm like, I get really, really excited by. It's almost like coming across a great founder. It's not as common as everyone expects. And I think that that's true for engineering. I think that that's true for sales. And I think a lot of people sales is like, oh, just throw a body into it. The product will do the work. Advice I often hear is don't hire kind of a senior VP of sales person from a bigger company. Yeah. You agree with that? How what's like to senior? So the bigger company thing, the brand was doing all of the work. The brand built the trust. You need this person to be able to build the trust. And like, they're usually the product is still so new. The product is the founder in the zero to one stage. The product is just starting to get like a case study. You probably have maybe a few references, but it's still very, very early days. You need the market to believe the sales person. And you need that market to know that they're trustworthy. A VP of sales at a large company, I would say, they're best suited for a large company because one to 10, you're running through walls. You have to figure out, you know, you're doing a lot of convincing. You're doing a lot of educating. You're doing a lot of creative deocrafting, a lot of owning the frame. It's not necessarily selling a product. It's selling that future value, which a VP of sales at a large companies. It's a very different. It's a different game. It's kind of like the SMB and enterprise. It's interesting. You said when you described the profile of a great hire here is you said they don't need to have done sales. If they have done sales, what's like a number of years or kind of like what's what you look for that tells you, okay, this is a good fit for the first hire. I actually think it's less about experience and more about the person. Does this person make you feel good? Do you want to buy from this person? I think Jason Lemkin said that best. Would you want to buy from this person? Can they sell you a pen? The client? Exactly. Do they mimic or mirror the market they're selling to? It's much easier to buy from someone that looks and feels like you than it does from somebody that's been a totally different realm. Also, an executive wants to talk to another senior person. They don't want to talk to someone that just graduated from college and is selling them the new way of working. What do they know? I think it's tricky. I would say someone with no sales experience makes it feel different and special. That's what I like about it. Someone with sales experience knows how to navigate and probably qualify better, but it's almost like the blend of those two things. That's why I go back to cosplaying the founder, which is like, could this person close a future employee? Do they get excited about the problems they're solving internally and the vision that they get to sell to? This actually was a reader question. Listen to your question from Twitter. Peter DeDenne asked, "How do you make this first sales person as enthusiastic about the product as you? Or something you can do is it more just they already are and you just leverage that." Incentives. Sales people love to make money. If they know it's possible, if they know it's possible, you'll be shocked what people can get done. If they see how much they could make. Amazing. I imagine there's still also has to be an innate excitement about the product and the opinion. I don't believe in the founder, but like incentives usually make the world go round. But yeah, is this person, are they asking the right questions to the founder? The best thing to do is have the founder join the first five calls. You know after five calls if this person has what it takes. Don't be afraid to fight. One in every two salespeople usually are fired. It's a very. Yeah, it's a very high failure rate. Because you can tell pretty quickly how it's going. You can tell or the vision of the founders is just very wrong. Speaking of incentives, do you have any quick advice on how to structure their comp? Just like how much they earn. It's usually 50/50. So it's 50% based salary, 50% OTE. And then how much of the sale do they typically get? Say the first sales hire. It depends on the price, the size of the deal. But in technology, it could be anywhere between like eight and 12%. So rounds out around 10%. Okay. Also. When do you hire the first salesperson around the one million A.R.? Mark usually. Yeah. It's around that one million A.R.R. mark and I. It's usually when you have your first seven to ten customers and there's some pattern recognition around it that you can share with somebody else. There's some consistencies. Otherwise it's just like, that would be very hard. Basically as a founder, you have to figure out how to sell enough times so that you can show someone here's what's working. And this is the common thing I hear. Well, I'm a ten million dollar business. I'm like in this small business space. You're zero dollars in enterprise. It's a zero to one right now in enterprise. It's a totally different game. It's a different value proposition. It's a different deal structuring. It's a different target market. It's a different risk tolerance. It's totally different. So don't be blindsided when. It doesn't work. There's a lot of unlearning that needs to happen when you move into a new market. So the advice here is make yourself sell up until around a million A.R.R. Especially if you're trying to go enterprise selling to enterprises yourself as a founder, which is really hard. You have so much to do and you have to be selling this thing for a long time. And then try and find someone that you get excited by. It's funny. If you ask the founder, are you excited by your salesperson? I'm curious what the real answer is. It's like, well, it's a button to see it in. It was hard to hire. Interesting. I remember, I think, as Jason's advice was to hire two people immediately. That's right. So you can compare them to your hard work. Yeah, because of the 50% failure rate, I think that's exactly right. So yeah, even a taller order go find two people that are good. But yeah, I think that that's right. Because. one in two will fail. - Okay, let me ask you another reader question from Hang Huang. This is kind of a different direction. So he says, "The biggest challenge is always cutting through the noise to get that initial meeting with the right decision maker. I'd even get their attention." - It's the vision. - What is the opportunity that you're selling? That if they are excited by that, they will take a call. I see it all the time. - And don't give away the farm. Keep to three sentences. And I know I said this on our first call, but say something counterintuitive. They could feel different. Make it feel like they can learn from you by taking a 15 minute call. You see the standards of like, "Oh, I came across your LinkedIn." And are you looking to grow your business by 15%. It's like, what kind of statement is that? - And this is in the cold email they get and that's this pitch. - Yes. - Awesome. So this is a good segue to another reader question from Hugo Alvez, co-founder of synthetic users. He asked, "What's the best advice for going from healthy inbound to targeted outbound?" - Healthy inbound usually is a marketing lead initiative. So that's a marketing game. It depends like what deal value you're selling. Are you selling a $5,000 deal? It's gotta be marketing lead to make the engine work. If you're selling a $100,000 deal, you're doing App Bound Day one. So again, it breaks it into those, this is like that blending of the, I see a blending up that question. This is where you're doing small business, marketing lead activities or US sales lead organization selling $100,000 deal. - And the reason this important just in case, it's not obvious is you're not gonna make money if you're selling people are spending time closing deals that are making 10, 20K. Just the ROI on that won't work for your business model. - That's right. - Awesome. By the way, let me just say, Jen, this is like an incredible conversation. Ready, we've got-- - Yeah, it's awesome. - Through so much, this is like exactly what I was hoping to get through. We've done, gone through so much advice that I think is gonna be so helpful to so many people. There's a few things that your partner Justin also suggested I ask you about that I wanna touch on. One is, you have this question, you ask founders a lot that opens up their mind. You ask them, if you give your product away for free, would people even use this? And every founder's like of course, and then you ask a customer this and they're like, nah, we wouldn't use this and that just blows their mind. Talk about just the power of that and how you recommend people approach this. - I always say, ask the question you're afraid to 'cause that truth is gonna get you closer and closer to the answer. So I'll ask a client straight up on a call. I'll say, honestly, do we think we're gonna get the deal done this year? Like is it possible? They'll give you the real answer. Like, and people are afraid to ask. But like the other side is sort of, you know, if they're in it with you, they don't care about that question. Right, can't ask that question on day one. But like if you are, and we didn't talk about this, but maybe this is important. Every single enterprise deal I have done, the deal is done, the deal is closed and pretty much done through text. So I don't email anymore. It is a relationship you're building with someone where if my enterprise client called me, I'm picking up that phone immediately or I'm responding them to immediately because that builds so much trust. If they know they can call on you, they're gonna get you to pick up and they know that you're gonna do everything humanly possible to make sure that this is successful. People will, people will, you know, turn over rocks for you. Like I have a client at a Fortune 10 company where I was like, it's so important we get the deal done this year like, is that possible? And she's like, it's a tall order, but like, if it's gonna help you, let's do it. Like these are how enterprise deals get done. It's relationships and it's this like, and this is why I'm saying like structuring the deal, make it feel like you went to bat for them and in often cases you are going to bat for them. And structuring in a way that makes sense for them. Everyone kind of just tries and page in whole, page in whole and deal structuring consistency is important for a $10,000 sub $10,000 deal. A $100,000 deal, it could, it very commonly will look different every time. April done, Ferdinand was on the podcast and she shared this really interesting insight that the reason people behave this way is the person at the company buying this thing their asses on the line also. Like their reputation is on the line for this thing to work out. So they wanted to go really well. That's right. Again, it's that what they do this one in every three years, one in every two years, maybe one in every five years, hell, I don't know. It is not it, they don't do this every year. It's very rare. It's no one likes a new tool. No one, not you, not me, unless it, unless it changes everything. - Yeah, Figma was a great example. That's slack. - Everything you've touched. (laughing) - Everything that worked out. You said that you asked these questions that people are afraid to ask. What are some other examples of questions you often ask that people are afraid to ask? - I will say, listen, this, this is a $150,000 engagement. I will co-author it with you where we can make this a little bit bigger if you need something else. We can make it a little bit smaller in year one, but in year two it steps up. Like how do we get this done? So when you go to bat, it's a win. They sell them, sell them, do they like, take it to the wrong side and like try and discount you? I've actually never seen that because at that point you have a relationship. So the co-authoring, the pricing is so important because they need to know that they go to bat, they can say, I got this out of them if we get this deal done. Right, so this is why like when I say every deal looks the same. You're asking great questions because it's explaining kind of why I meant by that, but like this is another example of like why every deal in the enterprise sort of looks somewhat different because a lot of it is co-authored. So again, if someone wants a slightly lower price, give it to them, but maybe them lock them in a little bit longer. - There's another point that Justin makes that, you've touched on a bit, but it's when you hear, you know, the way he phrased it is, Jen always talks about how know is the best answer to guess because know is data that you can use. Talk about that. - I am a qualification crazy person. I will not get another call with someone because on the first call it's either a yes or a no. There's no in between. Like it is people, humans are like we're so different and we're so unpredictable, we're also so predictable at the same time, right? Like it's very obvious if someone is excited and wants to do something. It is so obvious when someone is just trying to be nice. So I will say to them on that call like, I'm sort of getting the vibe that this might not be a good fit or might not be good timing. Like did I miss interpret that? And they will usually say, yeah, you're right. It's probably not a good, and then a great, I would love to stay in touch. You've just saved a relationship and you just saved yourself a time of time. - And the implication here is just to your point, you're limited on time. You don't wanna be spending time going down or rather low on getting anywhere. - Yeah, exactly. - I'm gonna take a quick tangent on tools. What's kinda like the state of the art on go-to-market outbound tooling? - Mm. - Because I believe in the manual, okay, and I'll explain why. Every single note I send is slightly different because I see a picture of them and I'm like, oh, I don't know if that's gonna land. I'm like, ooh, they actually might appreciate this. It's weird. Visual cues are so helpful. A picture is a visual cue. Looking at how long they've been in the role, looking how long they've been at the company. I use all of these little things, and I don't, I sell them customized a note in a way that people expect, which is that first customized sentence, 'cause AI does that, and everyone's doing that. So I go the opposite stream, which is like, remove it. And I customize it with how I frame it, or the subject line. Yeah, so it's like, I give I'm talking to someone like, like, here I might be, I might say like, quick question, like, cue cue. If I'm talking to someone that, you know, has a bit more experience, I might write a little bit of a tighter note, not all low-case. So like, it just depends on who you're speaking to. And again, this is why it's okay to spend a little bit of time on this, because it's a hundred thousand dollar, it's actually a million dollars at the end of the day, 'cause a hundred thousand dollar deal, if you play your cards, right, turns into a million dollar deal over three to five years. I love how much you enjoy this, it's so fun to. So essentially, what are you doing? You're sitting on LinkedIn, finding folks to ping, and then you call them individually manually. It's so weird, Lenny, like, I have no process, I kind of just go with like, the vibe, like I'll read an article about Tesla. And I'm like, "Huh, they could be interested in this." Not because that article had anything to do with the problem I'm solving, but because I'm like, this feels like a good Tesla day. Like, it's hard to describe, like it's a very emotional thing for me, and, you know, not to, not to my own horn, obviously, like, I've been successful in sales. And the most successful sales people can't explain why they're good at it. It just comes to them naturally. It's just like an emotional thing. It's like, the world's best founders, how do you be a good founder? It's very, very hard to define. How do you become a good engineer? Very, very hard to define. So like, I don't believe in like playbooks. I don't believe that like, there's like a feel to it. Like I emailed like the chief legal officer at a hedge fund once and he responded to me 'cause I wrote to him on Saturday. I knew it was gonna be busy. I made it one sentence and it was like tweaked for him. I feel like this is gonna be the way as AI, as DRs, just kind of take over and everyone's getting billions of emails that feel AI-ish. Yes. So I guess maybe speak more there. Just like the, is the alpha essentially just become human, don't automate. Yeah, and the other thing you should be. So I'm like, I wanna email someone not in the database that's getting hit by a million folks. I wanna take a back door in, not the front door where everyone else is trick-or-treating, you know? And this is effective for very large deal, which is what you need to be doing anyway 'cause it's taking, it takes a lot of time to do this, to do it this way. Yeah. Interesting. So you're not like sitting in clay, you're not like Apollo, I don't know, all those tools. You're just like finding people yourself. Yeah. Do you start with a target prospect list, at least, just like here's the companies that are the perfect fit for this and let's work through them? It's all in my brain. Because I've been doing this for so long, I have in my brain, I'm like, these are my early adopters. These are where I'm gonna go to after I close those logos 'cause they get excited by those logos. So it's just like experience of like, you know, you land, I don't know, you land a Walmart, you're gonna go to the rest of the industry and say, hey, we're working with Walmart, you know? Versus like you go to, you know, some, you know, Laura and Enterprise company and they're like, wait, what do you do? What, like, I can't even comprehend. Like, they're, also the most strategic people, some of the most strategic examples are at these tier one logos. That's why they're tier one. 'Cause they've got like super smart, like really capable folks. They also extract the best talent, the best talent likes to experiment and continue to improve. So it's like it's this, it's like this compounding thing. For someone that isn't Jen and has all this experience, say like they're founder, they're hit a millionaire, they're just like, okay, where do we find our customers? You have any advice for coming up with a, just coming up with who we should go after? So they'd be using these tools, so they'd be hiring someone like Jen. Like I know this is what you do for companies. So, you know, one crowd is going to hire Jolly Thurst out them through this. But founder, the founder, I would say, the founder, this is sort of in tune with them in a way, they just have to like find it. They, like, it's all, it's so weird to say, it's all va, and I hate saying it because it's like, it's like a commonplace thing to say, but it's like, there's this thing about like flow. And it's like some of these brands are in flow with you right now, right? Like, you, you, you, you, you, you found this insight from somewhere. Who else, what's the next adjacent ring of people that like would buy into that? And so what I'm hearing is just like pay attention to what's happening, what companies are, and the news, what companies are doing interesting things. What are the kind of the early adopters in the market? - If it was just a database list and it was just about figuring out the right messaging and then, you know, emailing folks, we would have known by that by now. - That's so interesting. Okay, maybe one more question. This again is from Justin. He shares that when you hit resistance, you never argue, you reframe. If someone says, we already have X solution, you'll agree in pivot and totally X is great for this thing, but here's what we can do. - This is why it's sell to the alpha. Hey, I know, I, listen, that problem you just described your right, you have a tool for that. We're taking you much further upstream with value. This is the opportunity I want you guys to have access to. - I love it. Jen, I've gone through everything I was hoping to get through. On the other hand, I feel like we could do another hour on all these things. I feel like we need to do-- - I agree. - Yeah, we need around three on the next phase and all the things that people want to do further into. Before we get to our very exciting lightning round, is there anything else that you wanted to touch on or share? - This stuff is really hard. It's very hard. Sales is also all about learning very, very quickly from the rejection. The rejection is good because it's a forced learning and you never want to go through that again. But you have to be, I don't like to use the word cringe. You can't be afraid to. Cringy's like bringing your AI recorder into a call. That's Cringy. Well, sending 15 nodes to people that you can deliver serious value to, don't be afraid. And don't be afraid to ask the hard questions. Be different. The whole game is about, oh, this feels different. That's what people want access to. And everyone commoditizes themselves. Like they try mimic whatever, you know, they try mimic a forward deployed engineer. Just rename it. You don't have to use the same now, now I'm in creature. You know, like everyone gets excited by the new because the new could be the next thing. The thing that changes it all. So that's why I'm always like, don't be better, be different. - Hmm, an amazing way to end it. With that, Jen, we've reached our very exciting lightning round. I've got five questions for you. Are you ready? - Yeah. - First question, what are two or three books that you find yourself recommending most to other people? - I do Twitter accounts. - Oh, Twitter accounts to follow. - Yeah. - Okay. - Lenny, the day I have time to read a book. - Period. - Period. I would love to be reading books. - Cool. Twitter accounts to follow. - Yeah. - Obviously you, like you produce some of the best content truthfully. - I appreciate it. - Like you get into the minds of people that like, they're not even giving this insight on Twitter. - Who else do I absolutely love? Jason Lemkin. So for sales, Jason Lemkin is awesome. Awesome follow for sales. And also he had a great, great recording with you. So linked to that because that was a great piece. I actually learned a ton from it. I love Gavin Baker. Super nuance takes like, takes a lot of like obvious statements, but like shares a lot of the non-obvious insight. He's great. Jason Cohen. Have you ever had Jason Cohen on the cast? - Jason Cohen, a smart bearer, Jason Cohen. - Yeah, yeah. - Yeah. - He's coming on the podcast. - Yes. - At the end of the year. - Oh, that's awesome. What if you plug for him right there? Yeah, those three would be great. I know they're all met. - Great tips. - Yeah. Next question, is there a favorite recent movie or TV show that you've really enjoyed? And I said you have time to read. - This is gonna be embarrassing. Baywatch. - Baywatch. - Yeah. - I'm watching Baywatch channel. - It just is gonna nummy. And it's like 90s classic. Baywatch. - Wow. I've never heard that one before. So this is original Baywatch with. - This is original Hasselhoff, David Hasselhoff. - Yeah, Pamela Anderson. - Yes, me and Lee. Pamela Anderson, the original cast. - Amazing. - Okay, Deep Cut. Is there a product you recently discovered that you really love? - So the number one thing for me right now is an app called Playground, which is the pictures of my toddler that they upload into the preschool. So I can get like the daily updates on like what's going on in preschool when he's not home. - Amazing, any that. I would get like emails and Google photos. I would really love that. - Oh really? There was another one called like, like, Class Dojo, there's a few of them, but Playground's the one that this preschool's on. - Love Class Dojo, a small investor. - Are you really? - I am. How about that? Two more questions. Do you have a favorite life motto that you find yourself coming back to, find useful in work or in life? - Yeah, be direct. Like, cut the fluff, like, give me the one cent. Give me the bullet, not the paragraph. - Final question. I was told that by Justin, you've never read a sales book. You've just learned to do this. If you were to read a sales book, if there was someone else out there that you look up to learn from, is there anyone else out there in the world of sales that you most respect? - I think Jason Lemkin has the strongest understanding of sales. - His content is unbelievable. He speaks about it clearly and cleanly. I would say, like, and as I mentioned, like unbelievable Twitter follow. - I'm a big fan of his. I'm actually here to laugh from him too. Like the 50/50 thing or a higher two sales people, he's spot on. Failure rates actually probably higher than 50%. - I love that guy. And he's so like AI forward these days, he's just building. You almost took down Repplet with his complaints. It was a whole new cycle of Repplet to do. - At least you're correct. Like, sometimes he says things that are like, "Harsh, but you're like, he's not wrong." Love it. I gotta get him back on the podcast. Jen, this was incredible. This was everything I wanted to be. I feel like we just leveled up all the founders that have listened to this in their ability to close. We're gonna just create all the economic value. And a lot of happy VCs from all the sales that will be closed as a result of the advice you shared. Two final questions where can folks find you if they wanna either work with you or follow you online? And how can listeners be useful to you? Twitter. - Every new learning or I put red on Twitter so it's like my personal diary and super responsive on Twitter DM. What's your Twitter handle? Twitter handle. It's double J, so J, J, E, N underscore A, B, E, L. You did not make that easy for people to find you. No, I know. I know. I didn't. And the J's that from jellyfish is that we're the extra. Yeah, the double J's. And then also, well, someone else had the handle. So I was like, I need my name. You gotta, by the way, just tell people what jellyfish is in case that might be helpful to you. Yeah, so it's a consultancy that helps folks in the zero to one stage. And now I'm at general manager of enterprise at state affairs, which is basically giving giving citizens and corporations an insight peak into like what's actually going on inside state capital building. State policy is way more impact than on you than federal policy. Federal policy is written more about incredible. I only recently learned that that's what you're doing these days. And that is super impactful and important. So thank you for your work there. Steven democracy. Happy deal. Jen, thank you so much for being here. Thank you so much. This was a blast. 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 a leaving review as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at Lenny's podcast dot com. See you in the next episode.