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

“Is exactly what this is all about, which is they sell this service, they come in, and then they introduce, hey, look at what this startup is doing over here. You might want to give them a shot. The problem with channel partnerships and why I don't believe them is there are a hundred of you on this list, right? And you're expecting them to sell it on your behalf. Biggest no-no. They're not vision casters. They're not visionaries. They're consultants. But it goes all towards like go find. I remember startups saying, oh, I'm going to go win over Accenture and then have them disseminate me into their clients. And I'm like, as if that's a workable strategy.”
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, I think that a lot of companies, a lot, sorry, a lot of folks that serve the enterprise, they have a butt in a seat in their office. Like you look at these large consultancies like McKinsey, they're not in their headquarters, they're in their client's office all the time. And the other interesting thing, and proof of this is how many people go to a Deloitte or an Accenture and expect them to be a channel partner.”
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. And they don't even need to know at first that software is doing it. Could be the magic part, which is like, guys, we literally, we are literally doing this with our technology.”
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
“Alan Tier, this forward deployed engineer. That's exactly what they're doing, right? Like, Know it's there's you know, there's a lot of companies out, like I'm sure OpenAI, and this is what someone told me, they were in and talking to CTOs and helping them better understand how AI and their organization can better work together. And it was them coaching them and educating them, whether they did it for free or not, I don't know, but they got their foot in the door. They started to build trust and then it gets adopted.”
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
“Now, the idea is that 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 serving you versus the human?”
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
“Enterprises, the number one thing they buy services. They know how to do it. It's super easy. They do it all of the time. It's like the most consistent thing they do. It's their largest budget item, right? External resources, consultants, whatever. They have a very immature way of understanding the problem, or they've never purchased technology to solve it to some extent, right? One, you are doing something that's never been done before, which is like. Know rare in today's day and age, or they might just be like laggards on the journey. So you have to decide, is this someone you really want to be working with? And if so, selling them as service, even though the technology is powering it on the back end, is the fastest way to get your foot in the door. It's what they know how to buy.”
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
“Or, hey, we're going to run an event and we want you at the forefront of it. We want you to be a speaker. Huge value, right? So it's like all of these additional things that add value beyond just the product, but are all part of the product and the vision, right? You know, everyone keeps thinking the product is just what goes into their hand. The product is pricing. The product is the opportunity, the framing, and not letting them compare you to something else. And I know we talked about that on our first call, which is as soon as you become a comparison, as soon as you become one of three that they're testing out, you've already sort of lost. It's all about differentiation. And it's all about here's what you will be able to do tomorrow because of how we're going to serve you today.”
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
“We're selling X tool. We can build out this specifically for you over the next year and integrate it because I know that you would have spent X number of dollars on engineering resources or you wouldn't have gotten an engineering head internally to do this. But we're just going to leave it to you. You got to give us a year to build it out. Again, you're not letting them sidetrack you too much. You're kind of containing it. We'll do that for you at no additional cost. That's huge value.”
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 I personally believe that Small business sales is really a. I used to think it was more science than art, right? It was more like, you know, figuring out what didn't work, running experiments, testing and validating, which I do believe. That's to get to like foundations. Like where do we play? What do we want to do? Like that early, early, early, zero to one from one to 10, I think it's more of an art. Which is how do I take my learning and how do I package it up where I own the framing, I can speak to very specific alpha, I can vision cast and where I better understand the problem over time better than the market does. And it's all about deal. And it's sometimes about giving away things that don't really cost much to you but are super expensive for them. For example,”
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
“Or Microsoft co-pilot. So I don't hear much about anthropic, to be honest. So that might be more of like a small business startup-y, I don't know, or it's a different part of the organization that's using it.”
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, like the value people were people were bringing their own use cases to it, right? And it's not like they, well, they can ingest and they've built that. That's a brand new thing. And they started. They started, I think, this is someone told me this. So, this is this could be hearsay, but I believe that they had, they were already speaking to CTOs even well before they released to help them explain where this is all going and get their buy-in. And it's much easier to get into the enterprise when you're like, we won't even touch your data. We won't even touch your shit. Just drop, like, use it to solve problems. And then we can build trust and then start to integrate and connect the pipes. But like part of the challenges with selling in the enterprise, they're like, all right, well, let's connect all your consumer data and the, whoa, that's extremely risky. So you have to start small and low risk, which is like, hey, here's what is the subset of consumers that churned. Let's figure out how we could have made them happier or whatever it be. So that data is lower risk.”
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
“Think that it sounds like a great way to 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 Microsoft Teams are still battling it out at the enterprise. I think it's also like how you plug in and how you integrate and do they even have the right systems to support you. The thing with open AI and is like they didn't have to connect to anything.”
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 it's about, and I read this somewhere, and I wholeheartedly agree with it because I've seen it live. I think it's about like, what game does the founder best understand? Are they like an incredible marketer and have some like competitive edge for how they can win a massive audience? I would say go S&B and marketing led? Or are they a bit more 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?”
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
“Know based off of usage, or are you selling off of like, I think it also depends on the pricing model a little bit. I look at headcount too because it's just like an easy way to think about it because you can also gauge usage off that and a bunch of other things. But sometimes like the small companies like. I think we're going to see a lot more like. Lot more larger companies become smaller because of AI, not like significantly smaller, but also high margins allow them to experiment more 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
“No, I think that I don't think it's that rare because we hear people complain about it all the time. But I think it's more of an excuse.”
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
“There was a lot of feedback given, a lot of feedback given. But the founder had such clarity with where he wanted to go that he was like 80% noise, 20% 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 80-20 rule where 80% of what they're going to tell you is probably going to be not related to where you want to go or based off of the old way, but that 20% of like, oh, I did not think about it that way. That drives everything.”
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
“Is the founder's job? The founder's job is to have a clear vision and do not let anything delineate from that. It's important to take feedback in terms of what is the market's reality, but like it is the founder, and this is why being a founder is so hard. It is the founder's job to interpret that. Want you to build this because it's the old, that's how they're traditionally expecting to do that. It is not here's where we're going. This is why we're not doing that. I hear you, but here's why we're not going to do that because we're going to completely change the way you do this. That is the founder's job. And I think, you know, we did a bunch of design partnerships. Late last year and”
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
“Oversell everything, yeah, design partner, even full rollout. And it's so so important to tell them, here's where we are today. Here's what we cannot do, which is just as important. It builds trust. Here's what we will allow you to do in the next six months. Do you want to be on this journey with us? And it's really ugly right now. Barely anything exists, but like we would love your voice to be a part of it.”
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 they have to be part of a logo that is deemed. Startup friendly or in that world. And then I think it's the person excited to give feedback. Does this person buy in to where we're going? Do they see this world differently like us? Do they buy, are they in locks up with the founder vision? Are they excited to use a tool that's janky? Because it is janky in the beginning. But they know, they know that where this can go can be incredible. So 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. Think a lot of salespeople oversell it. I 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.”
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
“Such a huge win for the market, for you, for your team, and also for your investors, because it's the hardest customer to actually truly convert. They've been it when it was messy. They got a really, they usually got a low price point. But if you, again, frame it, say, listen, I would love for you to be a design partner. I want a little skin in the game to get you to pony. Here's where we want to go. And you'll get a discount because you were in the beginning, but I'm setting the framing. Here's where we want to go with pricing. Here's where we are today. You'll always have 30% concession in perpetuity because you were there with us on day one. So again, it's not about asking for $10,000 and then not expecting that design partner to upsell and keep it flat because there's no growth there. It's a flat, you know, it's about getting that early design partner, set the framing, own the framing and let them know where you're going. Again, $100,000 to these large logos.”
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
“Don't get that startup vibe as much like that 50 person startup vibe, but like this can be a gift to give them that lens and give them that voice and give them that like excitement that they don't get as a larger company. But those are great types of logos to be early design partners because one, they want to make sure they're on they continue to stay on the cutting edge. But two is they are To try and build something without that guidance is really, really, really hard because they're not using it. So you need that, that you need that user feedback. You also need to tie that to the executive value, right? So it's actually a lot, it's very hard to do. But if you can come out of it and upsell a design partner to a full rollout customer, such huge”
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
“Design partners are incredible. They are the hardest logos to upsell, meaning go from design partner to full rollout customer. So like don't expect these people to be your million dollar pipeline. Expect these people to be the guide to help you understand maybe design partners could be a technology company in the Fortune 1000 so that they're used to experimenting. They're used to technology. They're used to, they were once a startup, so they get it. Those make really good design partners. Most of the design partners that I've closed are usually like technology based, right? They get it. And they also are excited about, you know, advancing the org and also giving the team an ability to have that startup feel. So like, you know, if you're a large massive corporation like Stripe, right? Stripe.”
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
“Unless it's defendable, all it needs to be is defendable, but who can really defend? That's very hard to defend a 10x jump. They're going to want to see 15x value.”
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, even if they want to bring you in and want to spend 100K with you, they have to be able to defend that. And now they see a $10,000, it's just, it can get really messy, especially because a lot of them are using AI now to understand like contracts. So they're going to quickly say, oh, wait, you spent $1,000 with Lenny, and now Lenny's asking you for $100K. Great. Just help me understand why or defend it.”
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 is enterprise companies are very used to a land when I say like the first initial contract to assist somewhere between 75K and 150K. Very used to that. In fact, that's probably where you want to start because you also want to understand where can you grow from this start contained. Don't say $150K and sell the farm. Say it's $150K. Here's who gets access. Here's the value we're going to deliver. And here's where we're going over time. You also want them to know here's what we plan to do roughly in year two, year three. I know it's hard to look that far out, but like plant the seed with them in terms of where this is going. If you come in at $10,000.”
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
“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, it's very, very, very dangerous because these are really smart companies. They're going to say, well, wait a second. I just pay $9,000 last year and now you want to charge me $90,000. Well, what's the step change in value? What's the difference? What's the 10x value I'm now getting? That's super hard to prove.”
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
“Let's say you're PLG and a big company like Walmart comes to and is like, hey, can we get access for three of our users? And they're like, this is so exciting. And then they sell them the small business pricing for three users to Walmart. Very, very hard now to go from those three users that you just priced them at a small business in a small business way, turn that into 100K because now it's documented what they're actually paying for this. So you're stuck. You've kind of like anchored yourself to this price. Not to mention, like, what's the, how are you going to unlock the executive high-level value so that you can get that, so you can get someone executive to buy in and stamp this as well. Otherwise, it's just going to be throwing it on the credit card. 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
“Yeah, absolutely. And again, this is about playing that enterprise game. If you're trying to sell, if you're a small business, if you're in the small business place and an enterprise company comes to you and is like, I like this, ensure that you structure it for an enterprise. Don't play the small business game with an enterprise company.”
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, the math will break and also the really good salesperson, your commission on a 10K deal. Not going to get a great salesperson. They're going to want to do, they're going to want to be anchored to how can I sell 250,000 deal? How can I sell a half a million dollar deal? That's the type of person you want.”
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 going after the enterprise. Yes, if it's the first three months and then after three months, it turns into a 50K and then 100K and it ramps up quickly, sure, that makes sense because you got your foot in the door and you can expand it exponentially in a healthy manner. I think that that's fine. $10,000 a year than going to $12,000, then going to 15, the math will break.”
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 have a super high win rate and a massive market because all you have to do is reverse engineer the math. If you need to generate $100 million in revenue, how many 10K deals do you need? And the expansion on a 10K deal is in parallel to that, right? Where can you go 10 to 15 if you're that's that's a 50% growth? Much easier to go to 100K to 500K because they want more bodies or they want more value out of you. For an enterprise, they'd love to get more out of an existing customer. You're already trusted. So it's also about the type of company or if you're venture-backed, you can't be selling $10,000 deals to the enterprise. You'll get killed or you've already lost the game because you're playing a small business game in the wrong sector.”
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. And also, like, you don't really get taken seriously for 10 Get way more taken seriously for 100 cases. Much harder to get 100k deal Like an executive use needs to be involved. I'd much rather have an executive sign off on something and spend two more months getting the deal done because you know that they are bought in. You know, you can now ensure what kind of value do they want to unlock. And maybe you have an opportunity to turn them into a user, which to me in today's day and age with our generation being the ones that are now the executives at these corporations, this is native to them.”
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
“Really, really want. Gets rid of the mediocre, you know, I think this would be good, and it gets to this is going to change the way we work. It's going to impact our ability to capture some form of alpha however you want to define that for them. And it's sticky because of 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
“They're not going to do the hard work of bringing you in if it's not critical or if it's not, when I say critical, it's not going to impact them in a way that they're going to make it successful. That's what I love about enterprise sales. They have the resources to ensure that it gets implemented because in today's day and age, if people are not using the tool, you just get rid of the tool, right? So they're going to want to make sure whatever they bring in, what they go to bat for. Remember, they go to bat once every two years, maybe once every three years, you've got to make it feel incredible. You've got to make it feel like they're going to be a superhero going back to it. Otherwise, what's the point? Because the way enterprises are structured is it is designed today to make it hard to buy because they want to make sure whatever you're bringing in.”
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
“There are in the very early days People will discount till the cows come home because they think that's the way to get a deal done, right? The best, the best clients are not going to do that to you because they like, that's a qualification criteria, right? Which is like, if they're sitting there nickel and diming you being like, no, 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 I say I'd rather get $100,000 deal than $10,000 deals, I'd rather have one rock star client that's going to help me figure out the next stage of where this is going than 10 or maybe five that are a good fit, five that are not. And I still have to serve those five that are not a good fit. And that's going to distract me. So, this is why I love enterprise sales.”
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, like think about there's so many people are so specific about what they're able to especially, I think especially technical folks. Like I'm not a technical person, but I would imagine that they're not going to go to, you know, they don't like to go to these corporations because they're forced to use some like incumbent incumbent tools.”
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 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. About letting them get better, letting them get differentiated talent. Or that's probably more of what I would anchor to like this is the 10x engineers use cursor You don't do you want access to 10x engineers?”
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 that's why founders are so good at selling because they naturally go to vision selling and vision casting versus a typical train salesperson is find the problem, ask these questions and it just kills the vibe. It just feels like you're talking to a salesperson. It's like, what's your script? And it's like, that's not vision selling. That's like playbook selling. And in the age of AI where a lot of it is about alpha. It's about speed. It's about getting access to information. It's about training data. And look at them, look at how the market's reacting to it. It's all opportunity and it's all, yeah, it's all about the alpha.”
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
“We have an ability to deliver alpha, meaning we have information, we have data, we have a way of working that no one else can do or is going to unlock a new way of thinking for you or an ability to deliver to a customer or an ability to solve a problem. Right now, you have an ability to access this level of information. I have an opportunity through our resources or through this gated data we have access to to get you much further upstream so that you can get information faster sooner. It's kind of like the high frequency trading that one second, that one second, they didn't talk about they, you know, they didn't sell, oh, we're doing fiber cable connectivity. We're giving you one second of alpha before everyone else. It's more of like that ability. And that's not problem selling. That's opportunity selling.”
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're selling to a leader, you need to be vision casting and you need to be selling an opportunity, right? Which is they are here. Here's what we can take you. You know that image where it's like Mario or Mario Mario Mario. And then there's like the mushroom and then there's like Mario on blast and everyone's like, don't sell the mushroom, sell Mario on blast. Well, that's exactly what it's saying. It's about selling the opportunity. That's what gets the tier one logos excited. And that is the best thing for a founder to sell, selling the vision versus the problem. And also it's what gets them to want to take a swing. Who wants to take a swing because you can do some small problem? They're not going to go to bath for 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
“First of all, make sure the founder's involved, they love everyone loves talking to our founder. So, like, don't. 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, more technical than not. And it's the way that every salesperson is going to go about it, find the problem and anchor to it.”
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
“Tier one is like your Walmart, your McDonald's, your NVIDIA, your Tesla, your ExxonMobil, your United Healthcare. The logos that are the leader in their space and their job is to stay in the number one spot.”
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 will literally guide you there. So when someone says, hey, go after startups at just short sales cycle. Yeah, that makes sense. I totally get that. It's a very, it's very easy to define the decision maker. It's very easy. 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 want to get to the enterprise as fast as humanly possible.”
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 where I get promoted. That's where I get the pat on the back because we are the world's leader in our industry. We cannot be disrupted there. So there's this running joke where 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 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 want to help, right? Because they also want to be a part of they also want to be able to dictate the roadmap. Now it's the founder's job to decide what can be done and what shouldn't be done. But their voice takes you a hundred thousand dollar deal into a million dollar deal in a very short period 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
“Exact opposite. Early adopters are those logos because they have to continue to stay at the number one spot. So they'll take tons of swings to continue to stay in the number one, stay 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”
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 a bit. That's right. And just like the power laws, I mean, if you look at the Fortune 1000 and then the kind of the lower end enterprise from there, it trails Like power laws totally exist in these large corporations. And we can't be treating everyone the same.”
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
“Low end enterprise or upper end SMB. And if you bleed those two games, you're going to lose. They're so distinctly different. So that's kind of my theory on it.”
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 there's no hybrid approach. So the best way to think about it is you have small business, which is typically can be really powered by marketing. And then you have enterprise, which is typically going to be sales-led. If you bucket them into these two very specific silos, it makes it much, much easier to understand what game you're playing. Now, when we talk about mid-market, I usually will say, are we talking about the upper end of small business 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, know you're playing the enterprise game, know the type of people you need to hire, know the type of ACV 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. So I say the mid-market doesn't exist because what is a mid-market hire? It's either”
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 fascinating because if you ask someone to describe the mid market, actually, if you ask someone to describe the enterprise, every single person has a different answer, right? It's either based off of revenue. It's either based off of market cap. It's based off of employee size. And I think a lot of people can get lost because selling to a hundred person organization is a radically different game than selling to a thousand person organization.”
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. The thing about AI tools is they're all pulling from the same databases. I want to email someone not in the database that's getting hit by a million folks. I want to take a backdoor in, not the front door where everyone else is trick-or-treating.”
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