YouSaid · the spoken record

Jen Abel

lines on the record: 104
first: 2025-11-09
most recent: 2025-11-09
sittings or episodes: 1
sources: podcast

Every line below is reproduced as it was said and linked to the record it came from. Nothing here is summarised or generated. Directory · Search · Corrections

“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 citizens and corporations an inside peak into like what's actually going on inside the state capitol building. State policy has way more impact on you than federal policy. Federal policy has written more about.”
2025-11-09 · Lenny's Podcast · "Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel · IDENTIFIED FROM THE TRANSCRIPT · source
“Twitter. Every new learning or mishap, I put red on Twitter. So it's like my personal diary and super responsive on Twitter DM.”
2025-11-09 · Lenny's Podcast · "Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel · IDENTIFIED FROM THE TRANSCRIPT · source
“I think Jason Lempkin 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've actually heard a lot from him too. Like the 50-50 thing. Or a higher two salespeople, he's spot on Failure rate's actually probably higher than 50%.”
2025-11-09 · Lenny's Podcast · "Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
2025-11-09 · Lenny's Podcast · "Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel · IDENTIFIED FROM THE TRANSCRIPT · source
“Oh, that's awesome. What a great plug for him right there. Yeah, those three would be great. I know they're all men, but.”
2025-11-09 · Lenny's Podcast · "Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel · IDENTIFIED FROM THE TRANSCRIPT · source
“You get into the minds of people that 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 link to that because that was a great piece. I actually learned a ton from it. I love Gavin Baker. Super nuanced 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?”
2025-11-09 · Lenny's Podcast · "Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel · IDENTIFIED FROM THE TRANSCRIPT · source
“Gringy's like, you know, bringing your AI recorder into a call. Like, that's cringy. But sending 15 notes to people that you can deliver serious value to, like, don't be afraid. And don't be afraid to ask the hard questions. Be different. This is the whole game is about, oh, this feels different. That's what people want access to. And yet everyone commoditizes themselves. Like they try and mimic whatever, you know, they try and mimic, you know, a forward deployed engineer. Just rename it. You don't have to use the same nomenclature, you know, like. Everyone gets excited by 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.”
2025-11-09 · Lenny's Podcast · "Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel · IDENTIFIED FROM THE TRANSCRIPT · source
“This stuff is really hard. It's very hard. Like 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. Like you can't be afraid to.”
2025-11-09 · Lenny's Podcast · "Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel · IDENTIFIED FROM THE TRANSCRIPT · source
“This is why it's cell to the alpha. 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.”
2025-11-09 · Lenny's Podcast · "Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel · IDENTIFIED FROM THE TRANSCRIPT · source
“If it was just a database list and it was just about figuring out the right messaging and then, you know, emailing folks. Would have known by that by now.”
2025-11-09 · Lenny's Podcast · "Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel · IDENTIFIED FROM THE TRANSCRIPT · source
“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. It's all, it's so weird to say it's all VAT. 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 found this insight from somewhere. What's the next adjacent ring of people that would buy into that?”
2025-11-09 · Lenny's Podcast · "Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel · IDENTIFIED FROM THE TRANSCRIPT · source
“Versus like you go to, you know, some lower end enterprise company and they're like, wait, what do you do? I can't even comprehend. Also, the most strategic people, some of the most strategic examples are at these tier one logos. That's why they're tier one, because 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 constant, it's like this compounding thing.”
2025-11-09 · Lenny's Podcast · "Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel · IDENTIFIED FROM THE TRANSCRIPT · source
“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 who I'm going to go to after I close those logos because they get excited by those logos. So it's just like experience of like, you know, you land You land a Walmart, you're going to go to the rest of the industry and say, hey, we're working with Walmart.”
2025-11-09 · Lenny's Podcast · "Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel · IDENTIFIED FROM THE TRANSCRIPT · source
“The thing about AI tools is they're all pulling from the same databases. So I'm like, I want to email someone not in the database that's getting hit by a million folks. I want to take a backdoor in, not the front door where everyone else is trick-or-treating, you know?”
2025-11-09 · Lenny's Podcast · "Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel · IDENTIFIED FROM THE TRANSCRIPT · source
“I don't believe in playbooks. I believe that there's a feel to it. Like I emailed a chief legal officer at a hedge fund once. And he responded to me because I wrote to him on Saturday. I knew he wasn't going to be busy. I made it one sentence. And it was like tweaked for him.”
2025-11-09 · Lenny's Podcast · "Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel · IDENTIFIED FROM THE TRANSCRIPT · source
“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 my own horn, obviously, but like I've been successful in sales. And the most successful salespeople can't explain why they're good at 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? Very, very hard to define. How are you become a good engineer? Very, very hard to define.”
2025-11-09 · Lenny's Podcast · "Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah. So it's like if I'm talking to someone up here, I might say, quick question, like QQ. 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 lowercase. 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 $100,000. It's actually a million dollars at the end of the day because $100,000 deal if you play your cards right turns into a million dollar deal over three to five years.”
2025-11-09 · Lenny's Podcast · "Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel · IDENTIFIED FROM THE TRANSCRIPT · source
“I don't use a tool. 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 going to land. Like, oh, they actually might appreciate this. It's weird. Like, visual cues are so helpful. A picture is a visual cue, you know, 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 seldom customize a note in a way that people expect, which is like that first like customized sentence because AI does that and everyone's doing that. So I go the opposition, which is like, remove it. And I customize it with how I frame it or the subject line.”
2025-11-09 · Lenny's Podcast · "Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel · IDENTIFIED FROM THE TRANSCRIPT · source
“I am a qualification crazy person. I will not get on 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. 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. It is so obvious when someone is just trying to be nice. So I will say to them, I'll not 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. And then immediately, great. I would love to stay in touch. You've just saved a relationship and you've just saved yourself a ton of time.”
2025-11-09 · Lenny's Podcast · "Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel · IDENTIFIED FROM THE TRANSCRIPT · source
“Will say, listen, 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. How do we get this done so when you go to bat, it's a win. They sell them, seldom 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 co-authoring the pricing is so important because they need to know that they go to bad. They can say I got this out of them if we get this deal done. 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 us.”
2025-11-09 · Lenny's Podcast · "Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel · IDENTIFIED FROM THE TRANSCRIPT · source
“That's right. Again, it's that 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 at all, they don't do this every year. It's very rare. No one likes a new tool. One, not you, not me, unless it changes everything.”
2025-11-09 · Lenny's Podcast · "Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel · IDENTIFIED FROM THE TRANSCRIPT · source
“It's going to help you, let's do it. Like these are how enterprise deals get done, it's relationships, and this is why I'm saying like structuring the deal, make it feel like you went to bat for them. And often in often cases, you are going to bat for them. And structure it in a way that makes sense for them. Everyone kind of just tries and pigeonhole pigeonholing and deal structuring consistency is important for a $10,000 sub $10,000 deal. Hundred thousand dollar deal it could very commonly will look different every time.”
2025-11-09 · Lenny's Podcast · "Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel · IDENTIFIED FROM THE TRANSCRIPT · source
“The deal is done and pretty much done through text. It's not on 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 going to get you to pick up and they know that you're going to do everything humanly possible to make sure that this is successful. 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.”
2025-11-09 · Lenny's Podcast · "Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel · IDENTIFIED FROM THE TRANSCRIPT · source
“I always say ask the questions you're afraid to because that truth is going to 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 going to get the deal done this year? Like, is it possible? Give you the real answer, like, and people are afraid to ask, but the other side is sort of, you know, if they're in it with you, they don't care about that question. Can't ask that question on day one. But like, if you are. We didn't talk about this, but maybe this is important Every single enterprise deal I have done.”
2025-11-09 · Lenny's Podcast · "Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel · IDENTIFIED FROM THE TRANSCRIPT · source
“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 $5,000 deal? It's got to be marketing led to make the engine work. If you're selling a hundred thousand dollar deal, you're doing outbound day one. So again, it breaks it into those. This is like that blending of the, I see a blending of that question. This is where are you doing small business, you know, marketing led activities or you a sales-led organization selling $100,000 deal?”
2025-11-09 · Lenny's Podcast · "Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel · IDENTIFIED FROM THE TRANSCRIPT · source
“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 it to three And this is, I know I said this on our first call, but like, say something counterintuitive, they can feel different. Make it feel like they can learn from you by taking a 15 minute call, right? You know, 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?”
2025-11-09 · Lenny's Podcast · "Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel · IDENTIFIED FROM THE TRANSCRIPT · source
“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 and two will fail.”
2025-11-09 · Lenny's Podcast · "Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel · IDENTIFIED FROM THE TRANSCRIPT · source
“Long time. Yep. And then, you know, try and find. 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.”
2025-11-09 · Lenny's Podcast · "Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel · IDENTIFIED FROM THE TRANSCRIPT · source
“And this is the common thing I hear. Well, I'm a $10 million business. I'm like in this small business space. You're a zero dollar in enterprise. 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.”
2025-11-09 · Lenny's Podcast · "Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, it's around that one million ARM mark and I, and 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.”
2025-11-09 · Lenny's Podcast · "Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel · IDENTIFIED FROM THE TRANSCRIPT · source
“It depends on the price, the size of the deal, but in technology, it could be anywhere between like 8 and 12 percent, so rounds out around 10%.”
2025-11-09 · Lenny's Podcast · "Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel · IDENTIFIED FROM THE TRANSCRIPT · source
“They have to believe in it. They have to believe in the founder. But 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 that this person has what it takes. And don't be afraid to fire. One in every two salespeople usually are fired. It's a very, yeah, it's like it's It's a very high failure rate.”
2025-11-09 · Lenny's Podcast · "Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel · IDENTIFIED FROM THE TRANSCRIPT · source
“That's why I go back to like cosplaying the founder, which is like, could this person, you know, could this person like close a future employee? Like, do they get excited about the problems they're solving internally and the vision that they get to sell to”
2025-11-09 · Lenny's Podcast · "Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel · IDENTIFIED FROM THE TRANSCRIPT · source
“Pen the class, yeah, exactly mimic or mirror the market they're selling to, 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 in a totally different realm. 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 selling them the new way of working. Like, what do they know? So I think it's tricky. I would say like, you know, 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.”
2025-11-09 · Lenny's Podcast · "Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel · IDENTIFIED FROM THE TRANSCRIPT · source
“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. Like, would you want to buy from this person?”
2025-11-09 · Lenny's Podcast · "Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel · IDENTIFIED FROM THE TRANSCRIPT · source
“They're best suited for a large company because one to ten, you're running through walls, right? You have to figure out 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, which a VP of sales at a large company, it's a very different, it's a different game. It's kind of like the SMB and enterprise.”
2025-11-09 · Lenny's Podcast · "Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel · IDENTIFIED FROM THE TRANSCRIPT · source
“So the bigger company thing, the brand was doing all of the work. 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 salesperson and you need that market to know that they're trustworthy. A VP of sales at a large company, I would say.”
2025-11-09 · Lenny's Podcast · "Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel · IDENTIFIED FROM THE TRANSCRIPT · source
“And I know that this is like it's very hard to hire a really good enterprise salesperson, right? 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, right? It's like 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 what the product will do the work.”
2025-11-09 · Lenny's Podcast · "Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel · IDENTIFIED FROM THE TRANSCRIPT · source
“Maybe a former founder, if 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 them 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.”
2025-11-09 · Lenny's Podcast · "Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel · IDENTIFIED FROM THE TRANSCRIPT · source
“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 adapt from what you're hearing and like let that compound over time. But I always say like, can this person cosplay the founder? I think that that's the best type of salesperson because it doesn't feel like sales. It's more of the art.”
2025-11-09 · Lenny's Podcast · "Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel · IDENTIFIED FROM THE TRANSCRIPT · source
“Doing it again, unless they have some extremely 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. 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. That's okay because every organization has slightly different.”
2025-11-09 · Lenny's Podcast · "Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel · IDENTIFIED FROM THE TRANSCRIPT · source
“So 1 to 10 is no longer the founder. Maybe the founder comes in in very strategic points, but you need a really good enterprise salespeople. Taking someone from small business and expecting them to do enterprise sales, big no. It's a different game, right? Vad like a 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 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 person that's five years out of school with no corporate experience.”
2025-11-09 · Lenny's Podcast · "Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel · IDENTIFIED FROM THE TRANSCRIPT · source
“That's right, because it's important to say no, right? And that's all part of the framing, right? Which is like, here's, we want a little skin in the game, like you set the price, but 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?”
2025-11-09 · Lenny's Podcast · "Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel · IDENTIFIED FROM THE TRANSCRIPT · source
“Right, and yeah, it's pain versus opportunity. Especially in the age of AI. And I know that 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 going to look like? I want to be a part of that new world. So it's a great time to be doing that.”
2025-11-09 · Lenny's Podcast · "Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel · IDENTIFIED FROM THE TRANSCRIPT · source
“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 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, things move, right? Like when people say, oh, I'm stuck in procurement. I'm like, oh, that's just be a qualification error and you never get out of it because you sold to someone too 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 you don't. Listen, I've seen 10K take nine months to close. Yeah.”
2025-11-09 · Lenny's Podcast · "Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel · IDENTIFIED FROM THE TRANSCRIPT · source
“Just keep increasing prices. Yeah, because 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 because now you're at the 100K deal anyway, but it's hard. There's more room for error, which is why I say go in and try to land 100K.”
2025-11-09 · Lenny's Podcast · "Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel · IDENTIFIED FROM THE TRANSCRIPT · source
“Yep, that's right. Like, 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 games. That makes sense. But it's really rare and very hard to do.”
2025-11-09 · Lenny's Podcast · "Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel · IDENTIFIED FROM THE TRANSCRIPT · source
“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, 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.”
2025-11-09 · Lenny's Podcast · "Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel · IDENTIFIED FROM THE TRANSCRIPT · source
“That's right, yep. And if you were to sell a service, because I know we're talking about selling services first, prorate that over time. So maybe it's 10K a month so they start to get used to what that pricing looks like.”
2025-11-09 · Lenny's Podcast · "Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel · IDENTIFIED FROM THE TRANSCRIPT · source
“Right, they have to maintain that number one. And also all of the people that are in the number two, number three, number four spot all want to do what number one is doing. So it's also like peer reference ability too.”
2025-11-09 · Lenny's Podcast · "Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel · IDENTIFIED FROM THE TRANSCRIPT · source