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

0:00 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 10k deals than lose nine and get one 100k deal. 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 clients are not going to do that to you. If they're sitting there nickel and diming you, 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 gonna 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.

0:59 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 like, if it's gonna help you, let's do it. These are how enterprise deals get done, it's relationships. What's kinda like the state of the art on go-to-market outbound tooling? I don't use a tooling tool. The thing about AI tools is they're all pull from the same databases. 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 treaty. Today, my guest is Jen Abel, co-founder of Jellyfish, where she and her team help early stage founders learn how to sell. And now GM of Enterprise at State Affairs. If you want to become better at selling your product.

1:45 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 light sales.

1:59 This conversation is part two. Going from around one million in Air. to around ten 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 am 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.

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4:34 At lovable dot dev That's lovable dot def. 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.

4:52 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 uh learning how to get better at the stuff we're gonna talk about, sales, enterprise sales. Two Frame the discussion.

5:06 the our first chat, which we're gonna point people to if they wanna start there. We focused on Fenderlet sales. Which is essentially the f beginning phases of a startup kind of going from zero to about a hundred million err. This discussion is on the next phase, which is going from about a millionaire to about Ten million error.

5:22 In enterprise sales, not like PLG or anything like that. You have a bunch of really strong and counterintuitive 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 we get into the first one, is there anything broadly, I don't know, is there anything broadly you want to share, anything you wanna say before we dive in?

5:41 No, let's dive right in. Okay. Okay, so the first thing that I haven't heard anyone talk about before is this uh point that you often make that the mid market Does not exist. People often hear about enterprise companies

5:54 There's obviously S and Bs and startups. There's also people just like, Oh, I'm gonna go after the mid market, somewhere in between. You don't think that's real. Talk about your experience there. What you what people should know. It's fascinating because you have if you ask someone to describe the mid market. F actually if you ask someone to describe the enterprise, every single person has a different answer. Right.

6:12 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.

6:31 And there's no 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

6:51 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 or are we talking about the lower end of enterprise? And most people are usually seeing the lower end of enterprise and I say great

7:08 Know you're playing the enterprise game. No, the type of people you need to hire. No, the type of A C V they need because it makes it a lot easier. Than trying to have this middle ground that catches everything that doesn't distinctly define SMB and Enterprise.

7:22 So I say the mid market doesn't exist because what is a mid market hire? It's either low it's either low end enterprise or upper end S B. And if you bleed those two games, you're gonna lose. They're so distinctly different. That's

7:35 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 talk about that a bit. That's right. And just like the power laws. I mean, if you look at The Fortune One Thousand.

7:53 Um and then and then the kind of the lower end enterprise from there. The the gay like it trails off so fast. Like power laws totally exist in these like large corporations. And I I I and we can't be treating everyone the same.

8:08 This begs the question, where do you Uh suggest Companies start. There's obviously startups classically are just like innovators move fast can make quick decisions. Enterprises have all the money. Uh cl usually the advice I hear is just don't go after the fancy companies.

8:24 to start because they take a long time. They're n you don't want to screw it up. What's your advice on where to start for most companies? The exact opposite. Early adopters. Are those logos.

8:36 Because they have to continue to stay at the number one spot. So they'll take they'll take tons of You know, uh swings. to continue to stay in the number staying in the number one spot's 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.

8:57 That's where I get 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 where um not a 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.

9:15 Or go learn from like logos that don't necessarily carry a lot of weight. the ones that carry all the weight are the ones that are willing to take a shot and wanna help. Right, because um they also want to be a part of they also want to be able to it dictate the roadmap. Now it's the founder's job to decide. what what can be done and what shouldn't be done. But their voice

9:37 Takes you a hundred thousand dollar deal into a milliн dollar dial. In a very short period of time. Mm-hmm. It will literally guide you there. So

9:46 When someone says hey, go after Startups it's just short sales cycle. Yeah, they're like that that makes sense. I totally get that. It's a very it's very easy to decide define the decision maker. It's very easy you don't you have to go through procurement. But in the age of 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 wanna get to the enterprise as fast as humanly possible.

10:12 Just so folks understand what we're talking about here, uh when you say tier one, what's a good way to think about what tier one looking? Tier one is like your Walmart, your McDonald's, your Nvidia, your Tesla, your ExxonMobil, your Um United Healthcare. The logos that like

10:28 are the leader in their space. And um You know, 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 like the chevrons and the Mobile and the Walmarts as a startup.

10:45 Co 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 like say you're going after Walmart. I know this is like Not like a five Second answer, but just

10:57 How would someone approach finding someone at Walmart to sell to? First of all, make sure the founder's involved. Right, they love everyone loves talking to a founder. So like Don't and There's

11:09 We'll start with let's get the founder involved as fast as humanly possible. The second is you need to vision cast. You need to sell to a gap, don't sell to a problem. There's a very big difference between problem selling and gap selling. Problem selling is highly specific.

11:25 More technical than not. And it's the it's the way that every salesperson is gonna 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.

11:40 Which is They are here. Here's where we can take you. You know that that image where it's like m uh Mario or Mario? Mario Mario. And then there's like the mushroom and then there's like Mario on Blast.

11:52 And everyone's like don't sell the mushrooms, sell Mario and Blas. Well that's exactly what it's saying. It's It's about selling the opportunity. That's what gets the tier one logos excited and that is the best thing for a founder to sell, selling the vision versus the problem. And

12:09 Also it's 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 gonna go to bat for that. What's an example of a vision cast in a company you've worked with, just to make this real? Like what does it 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 um a way of working that no one else can do.

12:32 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 ex like

12:50 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. It's they didn't do much. They You know, they didn't sell all we we're doing fiber cable connection connectivity.

13:07 We're giving you one second of alpha before everyone else. It's it's more of like that ability. And that's not problem selling, that's opportunity selling. I like this phrase 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 uh you know that image? Yeah, and it the person that made that image uh originally was Kathy Sierra, if you remember her. Do you remember?

13:29 So there's this person, Kathy Sierra. She's from back in the day. This was a big Uh I don't know, the lesson she taught is You want to not sell your people on like a feature or product you want to sell them on

13:40 Uh uh them becoming a superhero. Yeah. That's they are 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 superior is how this alpha will help you become more successful. And that's why founders are so good at selling because they they're they naturally go to vision selling and vision casting versus

13:57 A typical trained salesperson is Find the problem. Um Uh You know, ask these questions and it just kills the vibe. It just feels like you're talking to a salesperson.

14:08 Right, it's like what's your script? And it's like that's not vision selling, that's like playbook selling and that 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. It's about training data. Like And look at them look at how the market's reacting to it. Right, it's all it's all opportunity and it's all um

14:28 Yeah, it's all about the alpha. So just to make it more concrete for people, say I'm 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 dynamo faster than everybody else.

14:44 Is that a big enough vision? to cast. I think it may be more of like you'll be able to actually hire the 10X engineers that you don't necessarily have access to because they want to be able to use this type of tool. It's about the getting letting them get better th letting them get differentiated talent. Right. Or That's probably more of what I would anchor to of like

15:08 This is the n the ten X engineers. Use cursor. You don't, do you want access to ten X engineers? Mm. 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 especi I think s especially technical folks. Like I'm not a technical person, but I would imagine that they're not going to go to

15:29 you know, they don't like to go to these corporations'cause they're forced to use some like incumbent Incoming tools. Going back to the Going after these larger companies. I asked your uh colleague Justin what he

15:42 What he sees you do that most impacts the success that teams have with their sales process. And there's a bunch I'm gonna touch on, but one is Uh Most founders are insecure about asking for large A C Vs for charging or they

15:55 The way he put it is most founders would rather get Ten ten K deals. than lose nine and get one one hundred K deal. Talk about your advice there and what you see. There are in the very early days.

16:08 People will discount till the cows come home'cause they think that's the way to get a deal done. Right. The best the best Best clients are not going to do that to you. 'Cause they they n the th they like of that's a qualification criteria, right? Which is like if they're sitting there nickel and diming you being like

16:25 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 When I say I'd rather get one hundred thousand dollar deal than ten ten thousand dollar deals. I'd rather have one rock star client.

16:42 that's gonna help me figure out the next stage of where this is going. Then ten 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 gonna distract me. So This is why I love enterprise sales is

17:00 They're not gonna 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 gonna it's gonna impact them in a way that they're gonna make it successful. That's what I love about enterprise sales. They have the resources to ensure

17:17 that it gets implemented'cause Most of in today's day and age, if people are not using the tool, you just get rid of the tool. Right. So they're gonna want to make sure whatever they bring in, what they go to bat for Remember they they get a good they go to bat. Once every two years.

17:33 Maybe once every three years. You've got to make it feel incredible. You've got to make it feel like they're gonna be a superhero going back to it. Otherwise, what's the point? Because the way Enterprises are structured. Is it is

17:48 It is designed today. to make it hard to buy because they wanna 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. It and it gets to This is gonna change the way we work.

18:05 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 ten Kish kind of

18:21 Opportunities for For a bunch of reasons. One is It might be giving you a false sense of success and product market fit. Uh to those companies are maybe not as innovative and will lead you in the right direction.

18:33 Three is are probably discounts, just like your product and your pricing is just gets thrown off. Yeah. And also like But you don't really get taken seriously for ten K. You get way more taken seriously for a hundred K. It's much harder to get a hundred K 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

18:54 Getting the deal done. Пизюно. That they are bought in. You know that you can now ensure w what kind of value do they want to unlock. And maybe you have an opportunity to turn them into a user, which to me in today's day and age

19:10 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 the advice here basically if you're trying to build a successful B to B company. Uh everybody should be

19:24 Aiming towards these hundred K sort of deals, is there a world where you can be successful with ten Ks for a long time? If you have a super high win rate in a massive market. 'Cause all you have to do is reverse engineer the math. If you need to j if you need to generate a hundred million dollars in revenue How many 10 K deals do you need? And the expansion on a ten K deal.

19:44 Is in parallel to that. Right? Where can you go? Ten to fifteen if you're that's a that's fifty percent growth. Right? Much easier to go to a hundred K to five hundred K because they want more bodies or they want more value out of you.

19:58 For an enterprise, they'd love to get more out of an existing customer. You're already trusted. So it's also about you know, the type of company you are, if you're venture backed, you can't be selling ten thousand dollar deals to the enterprise. You'll get killed. Or or Y you've already lost the game.

20:14 'Cause you're playing a small business game in in the wrong sector. Have you seen startups you've worked with succeed in that ten K, twenty K bucket? Or is it really, really rare? If they're going after the enterprise? Yeah.

20:25 Yes, if it's the first three months and then after three three months it turns into a fifty K and then a hundred K and it ramps up quickly, sure. That makes sense'cause you got your foot in the door and it gr and you can expand it. Exponentially. Um in a healthy manner. I think that that's fine. Ten thousand dollars a year.

20:42 Then going to twelve, then going to fifteen, 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. Ten K, we'll do twenty K. That's crazy to consider a hundred K. Yeah, that the i the math will break and Also the a really good sales person. Your commission on a ten K deal.

21:02 You're not gonna get a great salesperson. They're gonna want to do they're gonna wanna be anchored to like, how can I sell a two hundred fifty thousand dollar deal? 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 a hundred K, five hundred K. Yeah. Absolutely. And again, this is about playing that enterprise game.

21:23 If you're trying to sell a if you know you're a small business If you're s 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 P L G.

21:41 And an and 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 w and then they sell them. the small business pricing for three users to Walmart.

21:57 Very, very hard now to go from those three users that you just priced them at a small bus in a small business way. turn turn that into a hundred K'cause now it's documenting 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 executive

22:17 high level value. So that you can get that so you can get someone. 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've just ruined your enterprise game because you're anchoring to a small business price. So this is why like when you bleed these two games

22:37 It's very, very, very dangerous because These are really smart companies. They're gonna say, Well, wait a second. I just paid nine thousand dollars last year and now you wanna charge me ninety thousand dollars. Well, what's the step change in value? What's the different what's the ten X value I'm now getting? That's super hard to prove. So the tip here is uh your initial price will really

22:57 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 charge more or like what would you recommend? It is enterprise companies are very used to l a land, when I say like the first initial contract, just somewhere between seventy five K and a hundred and fifty K.

23:19 Very used to that. In fact, that's probably where you want to start because you also want to understand where can you grow from this. Start contained. Don't say A hundred and fifty K and sell the farm. Say it's a hundred and fifty K. Here's who's gets access. Here's the value we're gonna deliver.

23:34 And um here's where we're going over time. You also want them to know here's what here's how 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 terms of where this is going. If you come in at ten thousand dollars

23:52 It's so even if they want to bring you in and want to spend a hundred K for with you They have to be able to defend that. And now they see a ten thousand dollar it's just it g it can get really messy. Especially'cause a lot of them are using AI now to understand like contracts. So they're gonna quickly, Oh, wait.

24:09 You spent a thousand dollars with Lenny and now Lenny's asking you for a hundred K. Great. Just just help me understand why. Or defend it. I could totally see Chat G V T being like Mm, this is interesting. Used to be exact one K, now it's hundred K. What might be going on here?

24:22 Totally. But people don't realize, you know, how danger how Again Know the game you're playing and Don't

24:32 Be sloppy about it. So your advice here is really interesting. It's Uh there's the land there expand. Expand as uh very important but the landing May screw your expanding because it sets the wrong reference point. Thousand percent. That's exactly right. You said it better than I did.

24:48 And so you may see like Matt like in theory, if you land a ten K go to a hundred K, that's like an amazing NRR. Everyone's gonna be really impressed. Yeah. Well buy into that. It's gonna feel absurd and wrong and something like that. Unless it's defendable. All it needs to be is defendable. But who can really defend that's very hard to defend a ten X Ten X jump, they're gonna wanna see fifteen X value.

25:09 Mm. 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

25:18 Build the thing. What's your advice on when to start finding design partners, how to find design partners, what a good relationship looks like. Design partners are incredible. They're the hardest logos to upsell, meaning go from design partner to full rolled out customer. So like

25:34 Don't expect these people to be your million dollar pipeline. Expect these people to be the guide. To help you understand. Um Maybe design partners could be

25:46 you know, a technology company in the in the Fortune one thousand. So th 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 close are usually Like technology based. Right.

26:03 They they get it. Um and they also are excited about, you know, advancing the org and also giving the team and ability to have that start up feel. So like you know, if you're a large massive corporation like

26:16 Uh Stripe. Right. The stripe doesn't get that startup vibe as much, like that fifty person startup vibe, but like this can be a gift. to give them that lens and give them that voice and give them that like excitement.

26:28 Um that they you know, don't get as a larger company. But they're g those are great types of logos to be you know, early design partners because one, they want to make sure they're on the they're they continue to stay on the that Cutting edge.

26:42 But two is They are Um To try and build something without that guidance is really, really, really hard. Because they're not using it.

26:54 So you need that that you need that user feedback. And you also need to tie that to the executive value. Right. So it it 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 roll out customer, such huge Such a huge win.

27:15 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.

27:25 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 design partner. I want a little skin in the game to get you to pone it. Here's where we want to go. And you'll get a you'll get a discount because uh you you were in it in the beginning, but I'm setting the framing.

27:40 Here's where we want to go with pricing, here's where we are today. you'll always have thirty percent concession in perpetuity because you were there with us on day one. So again, it's not about you know, asking for ten thousand dollars and then not expecting that design partner to upsell and keep it flat because there's no growth there. It's a flat You know.

27:59 It's about Get in that early design partner, set the framing, own the framing, and let them know where you're going. Again. hundred thousand dollars to these large l logos. If they want it.

28:10 It's very easy for them to get it done. There's this 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

28:21 Uh like there's obvious there's like the obvious companies that everyone's always trying to get these days. Open AI and Anthropic and Stripe, I think, is one. And Uh, any advice for just like 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 a logo that is deemed You know, um Startup friendly.

28:41 I or or You know, in that world. And then I think it's the person. Right, like Is this person excited to give feedback? Does this person

28:50 buy in to where we're going. Do they see this world differently with like us? Do they buy are they in locks up with the founder vision? Are they excited to To use a tool that's Janky.'Cause it is janky in the beginning.

29:04 But they know 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

29:18 I think a lot of salespeople 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 partner. Design partner even full roll out. And it's so so important to tell them

29:39 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.

29:55 One of the Biggest fears I think founders have is having a company pull basically 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 fill fixing their specific problems Any advice on just how far to go with one company?

30:10 That is the founder's job. The founder's job is to have a clear Vision. And do not let anything d delineate from that.

30:19 It's important to take feedback in terms of what is the market's reality. But like it is the fountain. This is why being a founder so hard. It is the founder's job to interpret that. Because a lot of feedback you get is this is the old way this is they're 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

30:43 Here's where we're going. This is why we're not doing that. I hear you, but here's why we're not gonna do that, because this we're gonna completely change the way you do this. That is the founder's job, and I think You know, I We did a bunch of design partnerships. Uh you know

31:00 Late last year. And There was a lot of feedback given. A lot of feedback given. But the founder had such clarity with where he wanted to go.

31:13 That he was like eighty percent noise, twenty percent, had I not asked this question. Like I wouldn't have gotten that gold in terms of where they are today. And like it's that eighty twenty role where eighty percent of what they're gonna tell you is probably going to be not related to where you want to go or based off of the old way, but that twenty percent Of like

31:32 Oh, I did not think about it that way. That drives everything. Have you seen a design partner pull a company come in the wrong direction, just kinda screw their Their path. Have you seen that, or is that is that pretty rare? No, I think that that I don't think it's that rare. Um,'cause we hear people complain about it all the time.

31:47 But I think it's more of an excuse. Coming back to this question of going after the enterprise versus S and Bs and again uh early advice you gave is uh there's no don't go in between. Either pick.

31:59 uh SMB small company which Uh, I know you said there's million way to just to kind of Differentiate what this means, but Uh what I guess I I think of employee numbers like you know like under some number over a thousand is maybe enterprise. Is that like a a good way to think about just like Yeah, I mean it depends. Are you selling per seats or are you selling um You know, based off of usage.

32:20 Or are you selling off of like I think it also depends on the pricing model a little bit. I I look at headcount too because it's just like it's just such an easy way to think about it. 'Cause you can also gauge usage off that and a bunch of other things. Um But sometimes like the small companies, like I think we're gonna see a lot more. Like

32:41 a lot more larger companies become smaller because of AI. Not like significantly smaller, but But also like high margins allow them to experiment more too. That's such an interesting point you're making there, that like the the way we designate enterprise versus S B like may 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

33:02 when people are deciding I'm gonna go enterprise versus I'm gonna sell to startups. Like Y C companies are the are the typical example they sell to their own Y C batches. I need just broad advice of picking. Okay, you go we go enterprise versus no, let's actually go startup. I think it's about and I read this somewhere and I I wholeheartedly agree with it because I've seen it live. I think it's about like what game does the founder

33:25 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 led. Or are they a bit more um

33:40 You know, un really understand how large corporations work. and really excited to deliver on a hundred thousand dollar 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.

33:59 Described that way. I think about linear Which Started very startup E? And my

34:06 Take is they did that because Changing the weight work is really hard. And they're That was like let's start with companies and grow with them and over time that becomes the default. Any reaction to that?

34:16 I think that it it sounds like That that's a great way it'll work because that's a technical tool, right? So that you need to have the right You also need to have the right infrastructure to sell, right? Like I think Slack. I mean look Slack and the Microsoft teams are still battling it out at the enterprise.

34:33 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? Um the thing with open AI and and Is like they didn't have to connect to anything. Uh say more about that.

34:46 So like the the value people were people were bringing their own use cases to it. Right. And they don't it's not like they they in well they can ingest and they've built that.

34:58 It's a brand new thing. And they started They started, I think. I I I 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.

35:17 And it's and it's much easier to get into the enterprise when you're like, We won't even touch your data. Won't even touch it yet. Just Drop like Use it to solve problems.

35:26 And then and then we can build trust and then start to integrate and and connect the and connect the pipes. But like Part of the challenges with selling in the airprise is that you're like All right, well let's connect all your consumer data and like in the whoa. That's extremely risky.

35:41 So you have to start small and low risk, which is like Hey. Here's what is the subset of Um consumers that churned. Let's figure out how we could have made them happier or whatever it be. So that data's lower risk.

35:55 Um 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.

36:07 I don't know if you've been seeing kinda their their growth. Open AI is very consumer. First. An anthropic is more and more winning on on B to B. I I saw this chart recently where they're like overtaking

36:17 Open AI now. On on B to B. Uh I don't know any reaction there of just like these two different approaches. I don't because most enterprises I'm talking to mention Gemini. Oh, interesting.

36:28 Yeah, or uh co uh Microsoft Copilot. Um So I don't hear much about Anthropic to be honest. So that might be more of like a small Business startup.

36:39 I I don't know. Or or Or or it's a different part of the organization that's using it. Yeah, that that's a whole discussion or bundling right there of

36:48 Like Slack and Teams and then just yeah, Gemini just kinda 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.

37:03 Oh yes. Talk about That So I personally believe that small business sales is really a

37:13 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. Um uh, you know, testing 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.

37:33 From one to ten. 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.

37:44 I can speak to very specific alpha. I can um Vision cast. And Where I

37:53 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

38:09 It's sometimes about giving away things that don't really cost much to you but are super expensive for them. For example Hey, we're selling X tool. We can we can build out this we can build out why 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.

38:34 But we're just gonna leave it to you. You gotta give us a year to build it out. Again, you're not You're not letting them sidetrack you too much or kind of Containing it. We'll do that for you at no additional cost. That's huge value.

38:46 Right. Hey, we're gonna run um We're gonna run an event and we want you at the forefront of it. We want you to be a speaker. Huge value.

38:55 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, right? You know, everyone keeps thinking the product is just what goes into their hand. The product is pricing. The product is The um

39:12 The opportunity, the framing. And not letting them compare you to something else. And I know we talked 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.

39:27 It's all about differentiation. Right. And it's all about here's what you will be able to do. Tomorrow because of of Of how we're gonna serve you today.

39:39 So along those lines that remind me in our first chat, you actually made this uh point that I've never heard anyone else make, which is that services are a really good way to start getting into companies that were Uh most founders here are like no don't just like Don't do manual stuff for the company. Build a product that you can scale.

39:55 Your advice is the opposite, actually start with cell services. Talk about that. Enterprises the number one thing they buy services. That's they know how to do it. It's super easy. It's they they like they do it all of the time. It's like the most consistent thing they do. It's their largest budget idl I don't. Right, external resources, consultants, whatever. If they have a very immature way of understanding the problem

40:18 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 like

40:30 you know, rare in today's day and age. Or Um, they might just be like Laggards. On the journey.

40:37 So you have to decide, is this someone you really want to be working with? And if so selling them a 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 they w it's what they know how to buy. Now

40:53 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 you why do we get you to come in? and leverage the tool that's been powering this the whole time. and move this more into technology sir t technology serving you versus the human. Wow.

41:12 I think this will blow a lot of people's minds. Alan here, this forward deployed engineer. That's exactly what they're doing. Right, like You know, it's there's 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

41:29 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 d 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 that 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.

41:48 We are using software to do it and then over time, oh, you could just do this yourself. You know, it'll cost you less. You can scale this. Yeah, that's right. Um 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.

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42:49 All in one easy to organise tab. Like I mentioned earlier, I use Coda every single day. and more than fifty thousand 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.

43:06 To try it for yourself, go to coda.io slash Lenny today and get six months free of the team plan for startups. That's C O D A.io slash Lenny. To get started for free and get six months of the team plan. Coda.io slash Lenny. There's a lot of talk these days about this. uh idea forward deployed engineers, something Valentir was really famous for just

43:27 Uh 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 you know, I think that that um A lot of

43:42 companies, a lot sorry, a lot of Um folks that serve the enterprise, they they have a s they have a butt and a seat in their office. Like you look at these large consultancies like McKinsey, they're not in their headquarters, they're in their clients' office all the time. And the other th interesting thing is and a and proof of this is How many people go to a Deloitte or an Accenture and expect them to be a channel partner?

44:02 This is exactly what this is all about, which is They sell the service, they come in and then they introduce Hey, look look at the 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 is there are a hundred of you on this list. Right, and you're expecting them to sell it on your behalf.

44:21 biggest no no. They're not vision casters. They're not visionaries. They're consultants. But this is that goes all towards like Go f you know, I remember startup saying, Oh, I'm gonna go, you know win over Accenture and then have them

44:35 disseminate me into the their clients and I'm like As if that's a workable scrap. Yeah. Okay. You know what might be helpful is let me try to summarize some of the

44:45 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 ten million error. And then I want to ask you just what's most different about these two stages, but let me share this first. So

44:58 Uh advice one is go for tier one logos earlier than you think you should. Because they're early adopters. They uh can move fast, they can pull you in the right direction. And the exciting cesters, too.

45:10 Mm. Yeah. Uh. For sure. And other and other leaves are going to get. And other and other, you know, talent. Future employees. Yeah, exactly. So the counterintuitive uh insight here is you think they will move slow and be too busy. But in they are actually the early adopters.

45:28 Yeah, they have to maintain that number one spot. Um, 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 pure referenceability too. And the point about them being the early doctors, like the people that join the stripes and open AIs and Anthropics 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.

45:53 I'm screaming with myself, aren't I? That's kinda funny. But yeah. That's a good sign. So two is uh ideally try to price closer to about a hundred K, like seventy five to a hundred. fifty ish K is what you said most enterprises are used to buying. So instead of starting Or even sticking with ten K.

46:13 twenty K for too long. You need to make yourself go towards seventy five to hundred and fifty K. That's right. Yep. And if you were to sell a service,'cause I know we're talking about selling services first, prorate that over time. So maybe it's ten K a month. So they start to get used to what that pricing looks like. So this is a way to make it feel

46:31 This is like how you get to seventy five to a hundred and fifty K 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, or person will be sitting there doing this for you. Yeah, or it's a t no, it's a technology too. I mean, you can add the services. I always well Let me take that back. The service whether the services is bundled into it or not.

46:50 that some people will unbundle it, other people will say the services is a part of it. But yeah, it nets out to seventy five to one hundred fifty K. That's right. Okay. And you said that it's okay to start lower on A C Ds and deals, but you need to push fast towards a hundred K like over a few months. Yep, that's right. Like if you can get into if you can get into an enterprise for ten K in a month, which is not Doable. But if you could. And you could go from ten K to fifty K in four months through an expansion strategy.

47:18 All game, that makes sense. But it's really rare and very hard to do. And so the so th there's two different paths there. One is land cheap and grow quickly, the other is move your A C V uh average up quickly. That seems like both are that's the latter's probably the more common strategy is just keep increasing rate. The former you can get tripped up because

47:38 They could say, Okay, now give me an economical price for doing this for a hundred people. And then it all kinda evens out'cause now you're at the hundred K deal anyway. You know, but it's hard it's much there's more room for error, which is why I say k go in and try to land a hundred K. By the way, in our first chat, we talked uh a lot about the procurement process. Which is what trips a lot of people up and is really painful. And I remember I I vividly remember that conversation still.

48:04 Uh 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. Because as soon as the executive picks up a phone and tries to get a hold of like their buying group.

48:25 Things move. Right. Like when people say, Oh, I'm stuck in procurement, I'm like, Oh, that's a that could just be a qualification error and you never get out of it'cause you sold to someone too junior. Um So that's why the hundred K is such a safe zone because

48:39 Even for ten K you might have to go through procurement. So um this is like the surest way to make sure that like You don't um Listen, I've seen ten K take nine months to close. No bueno.

48:53 Yeah. So Okay. Uh 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.

49:06 In the market. By adopting software. We talked about the example of cursor, where if you adopt cursor, you're gonna draw the Ten X 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.

49:19 Um especially in the age of AI. And I know that that's we're we're moving into the next dimension. It's all about solving for a gap. It's seldom about You know Solving for a very, very specific problem because people are trying to figure out what's our AI strategy. Where are we going to go with this? What is the world gonna look like?

49:38 I want to 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 you talked you shared uh about design partners. I've just had a select them, uh Your advice is definitely have design partners because they will help you build the right thing. But as a founder, it's You need to have a clear

49:56 s vision and sense of where you want to go and not just build everything they're asking you to build. That's right.'Cause it's important to say no, right? Like Um and then 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 we're here's what we're marching towards in the next six to twelve months. Like

50:17 Yeah. Are we aligned there? If we prove if we deliver on what we say we're gonna deliver, are we aligned there? And 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 ten is no longer the founder.

50:32 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. T is a different game. Right, Vavic a different game. You need to understand how corporations buy, you need to understand how executives think. You need to better understand

50:53 simply just like what the enterprise business model is 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 ten like this person that's five years out of school with no corporate experience. Doing it again.

51:13 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, I again if the founders involved, maybe that's doable.

51:33 Um But you 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.

51:45 Right, which is like Selling the vision. Getting them excited, y 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.

52:00 And that's okay. Because Um every organization has slightly different Opportunities of where they want to go. And you have to kind of build towards that.

52:12 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 the best type of sales person because it doesn't feel like sales. It's more of the art.

52:30 This is amazing advice. What is a a common profile that you've seen be successful? Like what level of seniority, what kind of personality these traits to look for? Maybe a former founder. If you can get that. Um,'cause they're used to selling, right? They've sold investors and they've sold employees.

52:47 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 t typical salesperson and and putting them

53:04 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 this it's very hard to hire a really good enterprise sales person.

53:20 Right. Um 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 a it's a it's a It's almost like you know coming across a great founder. Right. It's it's like

53:34 You know, it's not as it's not as common as everyone expects. Um, and I think that that's true for engineering, I think that that's true for sales. And I think a lot of people uh s sales is like, oh just throw a body into it, the product will do the work. Uh advice I often hear is don't hire a kind of a senior VP of salesperson from a bigger company. Yep. Do you agree with that? How what's like two senior.

53:56 So um The bigger company thing, the m 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.

54:11 The product is just starting to get like a a case study. You probably have s maybe a few references, but it's still very, very early days. You need the market to believe the salesperson. And you need that market to know that they're trustworthy. A V P of sales at a large company, I would say Uh, they're bet they're best suit for a large company because one to ten, you're running through walls.

54:33 Right, 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 deal crafting, a lot of owning the frame. It's not necessarily selling a product, it's selling that future value. Um which a VP of sales at a large companies. It it's a very different

54:50 Um it's a different game. kind of like the S B in Enterprise. It's interesting you said when you described uh the profile of a of a grade 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 a what do you look for that tells you okay, this is a good fit for the first hire.

55:06 I actually think it's less about experience and more about the person. Like, does this person make you feel good? Do you want to buy from this person? I think Jas Jason Lemkin said that best, like, would you want to buy from this person? Can they sell you a pen? The class. Yeah, exactly. Um You know Do they do they do they mimic or mirror the market they're selling to.

55:26 Right. It's much easier to buy from someone that looks and feels like you than it does from somebody that's like You know. Yeah. Been a totally different realm. Um

55:36 And also like An executive wants to talk to another senior person. Right. They don't want to talk to someone that just graduated from college and is is selling them the new way of working. Like what do they know? So I think it's it's tricky. I would say like You know, um

55:51 Someone with no sales experience makes it feel different and special. That's what I like about it. Someone with sales experience who knows how to navigate and probably qualify better. But it's almost like the blend of those two things. And that's why you go back to like cosplaying the founder, which is like could this person You know, could this person like close a future employee?

56:13 Right. Like do they get excited about the problems they're solving internally? And the vision that they get to sell to. This actually was a a r a reader question, uh listener question from Twitter. Uh so Peter the Denet. asked how do you how do you make this first salesperson as enthusiastic about the product as you? Is there something you can do or is it more just they already are and you just leverage that?

56:36 Incentives. Salespeople love to make money. So if they if they know it's possible If they know it's possible, you'll be shocked. What people can get done.

56:49 If they see how much they could make. Amazing. Uh I imagine there still also has to be an innate Excitement about the product and the believe in it. They have to believe in the founder, but like incentives usually make the world go round. Um but yeah it

57:05 Is this person are they asking the right questions to the founder? D are they um You know, I always the best thing to do is have the founder join the first Five calls. You know after five calls that this person has what it takes. And don't be afraid to fire like

57:21 one in every two salespeople. Usually are fired. It's it's a very Yeah, it's like it's It's a very high failure rate. 'Cause you can tell pretty quickly how it's gone.

57:35 You can tell or the 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 Right.

57:45 Um, it's usually fifty fifty. So it's o fifty percent O T, fifty percent so it's uh fifty percent uh base salary fifty percent um ot e And then how much of the sale do they typically get? Say the first sale's higher? It depends on the price si the size of the deal. But in technology Uh, it could be anywhere between like eight and twelve percent. So rounds out around ten percent.

58:07 Okay. Awesome. Uh when do you hire the first salesperson is around around the one millionaire mark usually? Yeah. It's around that one million AR market and I and It's it's usually

58:18 when you have your first seven to ten customers and there's some There's some pattern recognition around it that you can that you can Sh share with somebody else. Um It's con there's some consistencies. Otherwise it's just like

58:33 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 I've I'm a ten million dollar business. I'm like in this small business space. You're zero dollars in enterprise. Mm. 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.

58:58 It's a different risk tolerance. It's a it's totally different. So don't Don't be Blind sided. when

59:06 Uh It doesn't work. There's a lot of un unlearning that needs to happen when you move into a new market. So the advice here is f make yourself sell up until around a millionaire or uh especially Uh, if you're trying to go enterprise settling 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.

59:26 Yeah. And then it you know, try and find Try and find someone that like you get excited by. Like 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 and it was hard to hire, so

59:41 Interesting. I remember I think it was Jason's advice was to hire two people immediately. So you can compare them. Do you you agree with that? Yeah, because of the fifty f fifty percent failure rate. I think that's exactly right. Um so yeah it

59:53 Even h even even a taller order go order, go find two people that are good. Um but yeah, I think that that's right,'cause You know, one and two will fail. Okay, let me ask you another reader question. From uh Hang Huang.

1:00:06 This is kind of in a different direction. Uh so he says the biggest challenge is always cutting through the noise to get that initial meeting with the right decision maker. How to even get their attention. It's the vision. What what is the opportunity that you're selling?

1:00:21 That If if they are excited by that, they will take a call. I see it all the time. And don't give away the farm, Mike. Keep it to three sentences. Right? Like

1:00:32 And this is I I know I said this on our first call, but like say something counterintuitive. They could feel different. Make it feel like they can learn from you by taking a fifteen minute call. Right. Um You know, you you see the standards of like oh like oh I came across your LinkedIn and

1:00:47 You know Are you looking to grow your business by fifteen percent? It's like that what kind of statement is that? So and this is in the in the cold email they get. Awesome. Uh so this is a this is a good segue to another reader question from Hugo Alves, co-founder of Synthetic Users.

1:01:03 He asked what's the best advice for going from healthy inbound to targeted outbound? Healthy inbound usually is a marketing led initiative. So that's a marketing game. it depends like what deal value you're selling. Are you selling a five thousand dollar deal? It's gotta be marketing led. To make that to make the engine work.

1:01:22 If you're selling a hundred thousand dollar deal, you're doing outbound day one. So again, it it breaks it into those that this is like that blending of the I see a blending of that question. It this is where are you doing small business you know, marketing led activities. Or you a sales led organization selling a hundred thousand dollar deal. And the reason this important just in case it's not obvious is you're not gonna make money if you're

1:01:44 selling people are spending time closing deals that are making ten, twenty K. Just the ROI on that won't work for your business model. That's right. Yep. Awesome. Uh by the way, let me just say, Jen, this is this is like an incredible conversation already. We've kinda th through so much this is like Exactly what I was hoping to get through. We've then s gone through so much advice that I think is gonna be so helpful to so many people. There's a there's a few things that your partner Justin also suggested I ask you about that I wanna touch on.

1:02:13 One is you have this question that you ask founders a lot that uh 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.

1:02:25 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 questions 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 this the deal done this year?

1:02:46 Like, is it possible? They'll give you the real answer. I get people are afraid to ask. Like the other side is sort of You know, if they're in it with you.

1:02:58 They don't care about that question. Right. Can't ask that question on day one. Well like if you are And we didn't talk about this, but maybe this is important. Every single enterprise

1:03:11 deal I have done. The deal is done. The deal is closed and pretty much done through text. It's not on email anymore. It is a relationship you're building with someone where if my

1:03:24 C 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

1:03:42 People will You know, turn over rocks for you. Like I have a a client at a fortune Ten company.

1:03:50 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 gets done. It's relationships. And it's it's this like

1:04:05 And this is why I'm saying like structuring the deal, make it feel like you Went to bat for them. And in often ta uh in often cases you are going to bat for them. And structure it in a way that makes sense for them. You everyone kind of just tries and pigeonhole. Pigeonholing and deal structuring consistency is important for a ten thousand dollar, sub ten thousand dollar deal. A hundred thousand dollar deal it sh it could it it very commonly will look different.

1:04:31 Every time. April Dunford was on the podcast and she shared this really interesting insight that the r the reason people behave this way is the person at the company buying this thing, their ass is on the line also. Like their reputation is on the line for this thing to work out. So they want it to go really well. That's right. They've again it's that one they do this one in every three years. One in every two years, maybe one in every five years. Hell, I don't know.

1:04:53 It is not at all 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 less It changes everything. Yeah. Figma. Figma was a great example of that Slack.

1:05:08 Everything you've touched. 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

1:05:22 This is a hundred and fifty thousand dollar 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 it Yeah, it steps up.

1:05:36 Like how do we get this done so when you go to bat It's a win. They r sell them. Sell them. Do they Like

1:05:45 take it to the wrong side and like try and discount you. I've actually never seen that. Cause at that point you have a relationship. So I co authoring the pricing is so important because They need to know that that they go to bad, they can say I I got this out of them. If we get this deal done.

1:06:04 Right, so um 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 i a lot of it is co-authored. So again, if someone wants a slightly lower price

1:06:22 Give it to them, but maybe then lock them in a little bit longer. There's another point that Justin makes that uh you've touched on a bit, but it's when you hear no. The way he phrased it is Jen always talks about how no is the best answer to yes. Because now is data that you could use. Talk about that. I am a qualification crazy person. I will not get an on another call with someone because on the first call, it's either a yes or a no. There's no in between.

1:06:48 Like it is people, humans are Like We're so different and we're so unpredictable, but we're also so predictable at the same time. Right, like It's very obvious if someone is excited and wants to do something.

1:07:02 It is so obvious when someone is just trying to be nice. So I will 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 misinterpret that? And they will usually say Yeah, you're right. It's probably not a good f and then immediately great.

1:07:19 I would love to stay in touch. You've just saved a relationship and you've just saved yourself a ton of time. And the implication here is just y to your point, there's you're you're limited on time. You you don't wanna be spending time going down a rival that won't get you 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.

1:07:39 I don't use a tool. Because I believe in the manual Okay, and I'll explain why. Every single note I send is slightly different. Because like I see a picture of them and I'm like, Oh, I don't know if that's gonna land. But like

1:07:52 Ooh. They actually might appreciate this. It's weird, like Visual cues are so helpful. A picture's a visual cue. You know, looking at how long they've done they've been in the role.

1:08:02 looking how long they've been at the company. Um I use all of these little things and I don't I seldom customize a a a note. In a way that like

1:08:14 people expect, which is like that first like customized sentence, because 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. Um or the subject line.

1:08:27 Uh Yeah. So it's like um Like if I'm talking to someone like like our peer, I might be I might say like Quick question like Q Q. If I'm talking to someone that, you know, um

1:08:39 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

1:08:52 It's a 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 hear. So essentially what are you doing? You're sitting on LinkedIn finding folks to ping and then you called email them one b individually manually. It's so

1:09:14 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 Hm.

1:09:26 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 like it's it's hard to describe. Like it's a very emotional thing for me. And You know, not to not to toot my own horn, obviously, but like

1:09:44 I've been successful in sales. And the most successful salespeople can't explain why they're good at it. It just comes to them natural. It's just like an emotional Thing it's like The world's best founders. How how do you be a good founder?

1:10:01 It's r very, very hard to define. How are you become a good engineer? Very, very hard to define. So like I don't believe in I don't believe in like playbooks. I don't b I like I believe that like It there's like a feel to it. Like I emailed Like the uh

1:10:17 Chief legal officer at a hedge fund was. And he responded to me'cause I wrote to him on Saturday. I knew he was gonna be busy. I I made it one sentence. And it was like tweaked for him. Do you feel like this is gonna be the the way as AI SDRs just kind of take over and everyone's getting billions of emails that feel AI ish?

1:10:37 Yes. Mm. So I guess maybe speak more there, just like Uh

1:10:43 The is the alpha essentially. Just become human, don't automate. Yeah, I'm not sure. The thing about AI tools is they're all pull from the same databases. So I'm like, I wanna email someone not in the database that's getting hit by a million Folks.

1:10:59 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 takes a lot of time to do this to do it this way. Yeah.

1:11:12 Interesting. So you're not like sitting in clay, you're not like uh Apollo, I don't know all 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.'Cause I've been doing this for so long. I I like I have in my brain I'm like, these are my early adopters. These who 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

1:11:37 You know, you land, um I don't know. You You land a a Walmart. You're gonna go to, you know, the rest of the industry.

1:11:46 And say, Hey, we're working with Walmart. You know, um Ver versus like you go to you know some Yeah. You know

1:11:55 Laura and Enterprise. company and they're like, Wait, what do you do? What h Like I I can't even comprehend. Like they're the also the most strategic people, some of the most strategic exities 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

1:12:18 Con it's like this compounding thing. For someone that isn't gen and has all this experience, say like their 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 coming up with who we should go after

1:12:31 Should they be using these tools? Should they be hiring someone like a gen? Like I know this is what you do for companies. So you know one crowd is go hire jellyfish to help them through this, but founder. The founder. I would say The f the founder

1:12:46 This is sort of in tune with them in a way. They just have to like Find it. They it 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.

1:13:01 And it's like Some of these brands are in flow with you right now. Right? Like Um you you you found this insight from somewhere

1:13:16 Who else what's the next 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 Yeah. If it was just a database list and it was just about figuring out the right messaging and then

1:13:34 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

1:13:44 When you hit resistance, you never argue, you reframe. If someone says we already have X solution. You'll agree and 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.

1:13:57 Hey I know I Listen, that problem you just described, you're 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.

1:14:10 Jen, I've gone through everything I was hoping to get through. Uh On the other hand, I feel like we could do another hour on all these things. Uh I feel like we need to do three. In uh Yeah, we need round three on the next phase and all the things that people want to dig further into. Before we get to our very exciting lightning round. Is there anything else?

1:14:27 That you wanted to touch on or share. This stuff is really hard. Um It's very hard like sales is also all about like learning very, very quickly from the rejection. The rejection is good'cause it's it's a forced learning and you never want to go through that again.

1:14:43 Um But you have to be I don't like to use the word cringe. Like you can't be afraid to Green cheese like

1:14:53 you know, bringing your AI recorder into a call. Like that's cringy. But like Sending Sending 15 notes to people that you can deliver serious value to, like don't be afraid and don't be afraid to like ask the hard questions. Be different. This is the the whole game is about, oh, this feels different. That's what people want access to. And yet everyone commoditizes themselves.

1:15:19 Like they try and mimic whatever one you know, they try and mimic you know, a forward deployed engineer. Just rename it. You don't have to use the same nom nomenclature, you know, like Everyone gets excited by the new. Because the new could be The next thing.

1:15:34 The thing that changes it all. Um So that's why I'm always like don't be better, be different. Mm. An amazing way to end it. Uh with that, Jen, we've reached our very exciting lightning round. I've got five questions for you. Are you ready?

1:15:48 Yeah. First question, what are two or three books that you find yourself recommending most to other people? I do Twitter accounts. Hm. Oh, Twitter accounts to follow. Oh. Okay. Like Lenny, the day I have time to read a book. Period.

1:16:05 Period. I would love I would love to be reading books. Cool. Twitter accounts to follow. Hell yeah. Obviously you, like you produce some of the best content, truthfully. Appreciate it. With like you get into the minds of people that like they're not even giving this insight on Twitter.

1:16:22 Um Uh Who else do I absolutely love? Um Jason Lemkin.

1:16:30 So for sales. Jason Lemkin is Awesome. Awesome follow for sales. And also he had a great, great um recording with you. So link to that because that was a great Peace.

1:16:40 I actually learned a ton from that. I love Gavin Baker. super nuanced takes, like takes a lot of like obvious statements, but like shares a lot of the non obvious Uh insight. He's great.

1:16:54 Uh Jason Cohen. Have you ever had Jason Cohen on the cast? Jason Cohen A Smart Bear, Jason Cohen. Yeah. Yeah, he's coming on the podcast and at the end of the year. So that's awesome. What a great plug for him right there. Um

1:17:08 Yeah, those three would be great. I know they're all met, but great tips. Yeah. Next question, is there a favorite recent movie or TV show that you've really enjoyed? I know you said you have time to read. This is gonna be embarrassing. Pay watch.

1:17:22 Baywatch. Yeah. A watch channel. They're so nummy. And it's like ninety classic. You watch.

1:17:30 Wow. I've never heard that one before. So this is original Baywatch with This is original Hasselhoff, David Hasselhoff, Yasmine Blee. Pamela Anderson, the original cast. Amazing. Okay, deep cut.

1:17:44 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 pre school.

1:17:58 Uh, so I can get like the daily updates on like what's going on in preschool. Um when he's not home. Amazing. I need that. Uh we get like emails and And Google Photos. I wouldn't really there's yeah, there's another one called Cla uh like Class Dojo. There's a few of them, but Playground's the one that this

1:18:14 Schools up. Love class dojo, I'm a small investor. Are you really? I am. Oh, that's awesome. How about that?

1:18:20 Uh, 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 gimme the one cent give me the bullet, not the Paragraph. Final question. I was told that by Justin that you've never read a sales book. You've just learned to do this.

1:18:41 Uh 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 most? I think Jason Lemkin has the strongest understanding of sales. His content is unbelievable. He speaks about it clearly and cleanly.

1:19:01 I would say he like and as I mentioned, like unbelievable Twitter follow. I'm a big fan of his. I've actually heard a lot from him too. Like The fifty fifty.

1:19:10 Or a higher two salespeople, he's spot on. Failure rate's actually probably higher than fifty percent. Mm. I love that guy. And he's so he's so like AI forward these days, he's just Building.

1:19:21 Uh. Complaints. It was a whole news cycle, yeah of how roughly did that. Correct. Like sometimes he says things that are like harsh but you're like, he's not wrong. Mm-hmm. Love it. I gotta get him back on the podcast. Yeah.

1:19:33 Jen, this was incredible. This was Everything I want it 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 uh a lot of happy V Cs from all the sales that will be closed as a result of the advice you shared. Two final questions, where can folks find me if they want to either work with you or or follow you online? And how can listeners be useful to you?

1:19:54 Twitter. Um I Every New learning or Mishap I

1:20:01 put right 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 double J, so J J E N underscore A B E L You did not make that easy.

1:20:16 for people to find you, but we've got I know, I know, I didn't. And the J's that from jellyfish, is that where the extra J Yeah J's and then also well someone else had the handle, so I was like, I I need my name. By the way, just tell people what jellyfish is in case that might be helpful to them. Yeah, so it's a um consultancy that helps folks in the zero to one stage. And now I'm at uh general manager of Enterprise at State Affairs, which is Basically giving

1:20:42 individu giving citizens and corporations an inside peek into like what's actually going on inside the state capital building. State policy has way more impact than on you than federal policy. Federal policy's written more about. Incredible. Uh I've 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.

1:21:01 Even democracy. Yeah. Happy deal. Jen, thank you so much for being here. Thank you so much, Line. This was a blast.

1:21:08 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 Lenny's podcast dot com.

1:21:30 See you in the next episode.

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