EVERY SPOKEN WORD
85 min read · 17,049 words- 0:00 – 2:49
Introduction
- LRLenny Rachitsky
So we're gonna do something really unique with this conversation, basically go through the enterprise sales life cycle step by step. Let's set this up.
- JAJen Abel
Let's start with how do I even get the first meeting? We're in this flood the zone moment of everyone trying to break into the enterprise, but, like, what exactly are you solving for them as a problem? That's level one, but most importantly, the alpha, and it needs to be different.
- LRLenny Rachitsky
Step two is basically running the intro call.
- JAJen Abel
This is the most important call out of all of them. This is what I like to do. Super informal. Don't show them a demo. Don't show them slides. Focus on them. Have a one-on-one dialogue for 30 minutes. The whole game is to slow down to go fast. And by the way, do not bring a recorder to this call.
- LRLenny Rachitsky
What are the benchmarks for how often you get through each of these stages?
- JAJen Abel
The win rate for enterprise is usually around 30% to 35%. If your win rate is higher than that, your price is too low.
- LRLenny Rachitsky
What are some signs that your salesperson is not doing a great job?
- JAJen Abel
The most successful salespeople are not trained salespeople. Fastest way to commoditize yourself is to go into some sales script. Budget authority need timing, like, that should be in the back of your brain. You never actually ask those questions.
- LRLenny Rachitsky
What percentage do you think are just doing it wrong?
- JAJen Abel
90%.
- LRLenny Rachitsky
Wow.
- JAJen Abel
Like, it's literally so fun. People read these sales books, go to these sales trainings. They try and take someone else's game and run with it, and it never works that way.
- LRLenny Rachitsky
Most people think the sales process is five steps, and we're already in step 10, [chuckles] and we're not even done.
- JAJen Abel
The worst thing you can do in the sales process is...
- LRLenny Rachitsky
Today my guest is Jen Abel. This is her third time on the podcast. For those that don't know Jen, she's co-founder of Jellyfish, GM of enterprise sales at State Affairs, and most importantly, is the person that I've learned the most from about the art and science of enterprise sales. In our first conversation, we went deep on founder-led sales. In our second conversation, we focused on the $1M to $10M enterprise sales playbook. And in this conversation, we do something I've never seen anyone do on another podcast. We go step by step through the full enterprise sales cycle. Most people think this is a five-step process. It turns out it's closer to 15 steps. Most people ignore a bunch of these steps that you'll hear about. We go through everything that you need to know at each step to significantly increase the odds that you close your deals. This episode is incredibly tactical and specific. You will learn a ton. I did for sure. Like I say in the episode, I always get so energized and just excited to sell something after talking to Jen. You will feel the same way after this conversation. I'm so thankful to Jen for sharing so much alpha with us. Before we get into it, don't forget to check out lennysproductpass.com for a free year of the hottest and most beautifully crafted AI products in the world, available exclusively to Lenny's newsletter subscribers. With that, I bring you
- 2:49 – 5:54
Why Jen is giving away her enterprise sales playbook
- LRLenny Rachitsky
Jen Abel. [gentle music] Jen, thank you so much for being here. Welcome back to the podcast, a very rare third visit to the podcast. How does it feel?
- JAJen Abel
Round three. Super excited to be here, Lenny.
- LRLenny Rachitsky
I'm even more excited. So we're gonna do something really unique with this conversation. I've never done anything like this before. We're gonna basically go through the enterprise sales life cycle step by step. You'll talk about this, but many people think it's, like, five steps. You talk about how it's actually something like 15 steps.
- JAJen Abel
Yeah.
- LRLenny Rachitsky
A lot of people ignore a lot of these steps. And the idea is I wanna create a very concrete and, um, tactical playbook-
- JAJen Abel
Mm
- LRLenny Rachitsky
... for how to do enterprise sales.
- JAJen Abel
Okay.
- LRLenny Rachitsky
We've had conversations-
- JAJen Abel
Give away my secrets.
- LRLenny Rachitsky
I'll-- Let's-- That's the goal. Just, just suck 'em all out and make everybody amazing at sales. It'll be great.
- JAJen Abel
Awesome.
- LRLenny Rachitsky
Um, and you know, this touches on just, like, why, why I think the podcast is really helpful to people and just the Valley vibe, even though you don't live in the Valley, just, like, there's so much win-win-win in helping people learn these things. You know? It may feel like, "Why is she giving away all these things?" Uh, but maybe, actually, let me ask you that. Just, like, why, why do you share these things?
- JAJen Abel
Well, it's so interesting 'cause there's so much art to this that even if you gave someone a 15-step playbook, there, there's so much of a, a feeling that you have to go off of. Like, sales is, sales is one-on-one, right? You're, you're dealing with a variable, which is another individual, and if you ran the same flow every single time, it's gonna probably not hit one out of every four times 'cause everyone's different. Like, some people like to joke. Some people like the small talk opener. Others wanna jump right into it. Some are technical. Some are not technical. You know, so everybody's so different that even if I gave-- even as we go through all these 15 steps, while it's 80% of it, the other 20% is obviously the art of, like, how you make someone feel. Do they feel heard? Did you make it fun? Did you tell a good story? I mean, that's also a huge part of this. Too much to cover today, so we'll stick to the, we'll stick to the roadmap of, like, how to close these deals. But I think the interesting thing about enterprise sales is even if you're selling a hu-- the-- If you sell a $100,000 solution, it is the same exact process to sell a million dollar solution. So it-- that's why, uh, i-it's, i-it's an interesting process because the enterprise organizations are more sensitive to the process you take them through from a sales motion than they almost are with demoing the product.
- LRLenny Rachitsky
Amazing, and I'll just give a plug for if people want to continue learning, your Twitter feed is just the best.
- JAJen Abel
Yeah.
- LRLenny Rachitsky
You share all this stuff constantly.
- JAJen Abel
Yeah.
- LRLenny Rachitsky
And I think you, you talk about there's, like, rational reasons to share this stuff, but I think there's-- it feels like there's just, like, I just need to get this stuff out.
- JAJen Abel
Yes.
- LRLenny Rachitsky
People need to-
- JAJen Abel
It's like a diary, and it also helps me, like, keep it in my mind too.
- LRLenny Rachitsky
Right.
- JAJen Abel
It's like my own education, yeah.
- LRLenny Rachitsky
I, I know exactly what you mean. That's why I started writing. I started-- I was just like, I just wanna remember this stuff myself.
- JAJen Abel
100%.
- LRLenny Rachitsky
I'm just gonna share it and crystallize
- 5:54 – 9:11
Example: selling AI legal tech to SpaceX
- LRLenny Rachitsky
it.
- JAJen Abel
Yeah.
- LRLenny Rachitsky
Okay. So before we get into the steps, let's set this up. What are some things people should know? What's kinda like the case study, what we're gonna be-
- JAJen Abel
Yeah
- LRLenny Rachitsky
... using here?
- JAJen Abel
Yeah. Let's use a company like SpaceX, right? Recently, you know, has seen massive news pressings. It, uh, you know, everyone's probably targeting them, right? So it's gonna be a hard logo to go in and, and win. Um, they are a technical organization, but I think what we do is target a non-technical team. So we're gonna, like, really get into, like, the nuance of this. So let's do SpaceX. Why don't we pick legal? Let's have some fun with legal. The interesting thing about legal, it's the largest budget line item in the enterprise, uh, uh, kind of budget, right? Sometimes three to four times other budgets, and it's forever. There's always more money for legal.
- LRLenny Rachitsky
[laughs] That's why there's so many legal AI startups. I get it now.
- JAJen Abel
100%.
- LRLenny Rachitsky
Amazing. And I, I'll just add, the reason, like, the reason I love to have you on this podcast is I o- I've left both of our previous conversations so just, like, fired up about selling. I just, like, I have nothing to sell, but I'm always feeling like I wanna sell something now. I feel like I've learned all these things. It feels so fun-
- JAJen Abel
You are-
- LRLenny Rachitsky
... doing sales after talking to you
- JAJen Abel
You're a master. You're actually a master at this. Sales is marketing.
- LRLenny Rachitsky
All right.
- JAJen Abel
Marketing is sales to some extent, right? And-
- LRLenny Rachitsky
All right. Am I crying?
- JAJen Abel
You, you do that, you do that better than a lot of people.
- LRLenny Rachitsky
I feel like you're using some sales technique on me to make me feel good about myself. [laughs] Okay, anything else before we get into step one of the sales enterprise-
- JAJen Abel
No, I think this is good
- LRLenny Rachitsky
... s- sales cycle. Okay.
- JAJen Abel
SpaceX and targeting the legal function.
- LRLenny Rachitsky
And then, like, a 100K, let's say, deal.
- JAJen Abel
Yeah.
- LRLenny Rachitsky
And to your point, it's the same process whether it's 100K, a million.
- JAJen Abel
Correct.
- LRLenny Rachitsky
And I will add a plug for a previous episode. You talk about why you wanna be at least 100K something as a deal-
- JAJen Abel
Yeah
- LRLenny Rachitsky
... to be a, uh, a real enterprise company that will l- that will survive.
- JAJen Abel
Yeah, right.
- LRLenny Rachitsky
Because the ROI and the, and just the whole economics of that stuff, but we won't get into that. This episode is brought to you by our season's presenting sponsor, WorkOS. What do OpenAI, Anthropic, Cursor, Replit, Sierra, Clay, and hundreds of other winning companies all have in common? They are all powered by WorkOS. If you're building a product for the enterprise, you've felt the pain of integrating single sign-on, SCIM, RBAC, audit logs, and other features required by large companies. WorkOS turns those deal blockers into drop-in APIs with a modern developer platform built specifically for B2B SaaS. Literally every startup that I'm an investor in that starts to expand upmarket ends up working with WorkOS, and that's because they are the best. Whether you are a seed stage startup trying to land your first enterprise customer or a unicorn expanding globally, WorkOS is the fastest path to becoming enterprise ready and unblocking growth. It's essentially Stripe for enterprise features. Visit workos.com to get started or just hit up their Slack where they have actual engineers waiting to answer your questions. WorkOS allows you to build faster with delightful APIs, comprehensive docs, and a smooth developer experience. Go to workos.com to make your app enterprise ready
- 9:11 – 18:44
Step 1: Landing the meeting
- LRLenny Rachitsky
today. Okay. Step one, where does, where does it start? How do you start selling someone on your product?
- JAJen Abel
It's a great question. So I think let's start with, like, how do I even get the first meeting? How do I even engage with these people? There is so many, there's so much nuance as you target, as, uh, you know, as we're using the case study of SpaceX today. You have the top of the rung, right, which is the, the general counsel, the head of legal, uh, the chief legal officer. They c- all kind of have slightly different titles, but they all carry the same weight, which is, like, who's the, who's the lead of the team? And then underneath that you have a bunch of people that carry a VP title, carry a director title, maybe just say lawyer on their LinkedIn. So you have to do the work to figure out, what is my entry point? And there's only two entry points: starting at the very, very tippy top, meaning going direct to the decision maker, the chief legal officer; or finding the individual that would be maybe one step removed, okay? I personally, other people would argue with this, I personally would not be targeting anybody else. It is the executive themselves or an N-minus-one, okay? So let's talk about, like, why. In order for an enterprise deal to move forward, you need to have this extremely compressed storyline that lands immediately to the objective that they wanna solve for at the organization. It has to go beyond just an AI mandate. I think every company today has an AI mandate, and I know everyone is an AI tool, but, like, what exactly are you solving for them as a problem? That's one. That's level one. But most importantly, the alpha. What does this executive uncover and unlock by bringing in a net new tool? 'Cause bringing in a net new tool, okay, is risky. No one wants it. So if we're targeting the chief legal officer and the N-minus-one, you get two sen- two, two to three sentences max, okay? That might be through an email LinkedIn, that might be through a phone call, that might s- be through an event, um, or that might be through some marketing capability. Most ch- most C-level executives don't respond to marketing. They might see your brand. They're not gonna respond to a marketing campaign, okay? They will respond one on one, and the best individual to one on one to a corporate executive is the founder. Even if you're a Series B, Series C, right? It is, uh... The founder should be ecstatic to wanna get in front of the chief legal officer at SpaceX. I think any founder that is, um, you know, building something really meaningful knows the importance, important role of that. Second is you can get your enter- your, um, AE, your enterprise sales lead to target the N-minus-one, and you do what you call this, I call it the, the pincher model 'cause you're going after two different people and trying to get them together. It's actually called the pincer model, which is start at the very, very top, find that kind of floor, and work in between them. Okay? So you're, so these are the two types of r- these are the two layers you wanna be targeting in j- landing that meeting, 'cause if you go any further than that, you risk they're not gonna be able to communicate your storyline. It's a game of telephone, right? And now you're learning from someone that is not near the budget or the executive discussions, right? Which is super risky, 'cause now you're learning about user value, not executive value. And $100,000 deal needs a executive sponsor to sign off on it to allocate the budget, and this is why you need to start at these, this, these two layers only.
- LRLenny Rachitsky
Wow. This is, there's gonna be fractals of questions and things [chuckles] to dig into with each of these steps. Uh, this is amazing. I love how, just how specific and tactical you are with all of these things. I'm gonna try to summarize a couple of these tips, and then I have a follow-up question. Okay. So tip one is go after either the exec, so in this case it'd be general counsel, head of legal sort of person, or N-minus-one.
- JAJen Abel
Yep.
- LRLenny Rachitsky
Love the way you're describing it. Maybe a VP. Uh, you wanna pitch them two or three sentences in like a text or email or in a, at a conference. Uh, and the key is to focus on the alpha, like the way, what your product will unlock-
- JAJen Abel
Yeah
- LRLenny Rachitsky
... for them. Love that. Um, and it sounds like there's still like a, here's the problem we solve for you, but here's like really the alpha we unlock.
- JAJen Abel
Correct. 'Cause it, for an executive to bring something in and be the sponsor and like share this and disseminate this down their, down the, down their command, they, they need to stand behind something beyond, "Hey, we're gonna make, we're gonna alleviate, you know, the nu- the time it takes to do X activity." That's not big enough. They want like, they're like a founder, too, of their own business unit. Like you gotta sell the vision, and what are these people gonna d- how are they gonna get to the next stage, um, whether with their influence, get more budget, get more people, um, however they wanna define that.
- LRLenny Rachitsky
Yeah. So it s- sounds like you don't wanna ... Like they wanna win, and-
- JAJen Abel
Yeah
- LRLenny Rachitsky
... to win you need something unfair, unse- unfair advantage.
- JAJen Abel
That's exactly right.
- LRLenny Rachitsky
That's what you're pitching.
- JAJen Abel
That's exactly right.
- LRLenny Rachitsky
Yeah.
- JAJen Abel
Yep.
- LRLenny Rachitsky
Okay. And then this pincer move, [chuckles] I love this. So the idea here is for the exec, say chief legal officer, gr- general counsel, founder needs to reach out.
- JAJen Abel
Yep.
- LRLenny Rachitsky
And then this AE reaches out to the N-minus-one contact-
- JAJen Abel
Yes, exactly
- LRLenny Rachitsky
... and you do this, you go from both directions.
- JAJen Abel
Yep.
- LRLenny Rachitsky
And I imagine the goal is one of them at least responds.
- JAJen Abel
That's correct. And then, and then y- because you're only one step removed, they'll usually loop in that next person and, or you can say, the founder could say, "Hey, I'm gonna loop in my so-and-so colleague. Who on your team should we also include?" Or the, uh, an enterprise executive could say, "Hey, I'm gonna bring in my founder. Could we see if your boss might wanna be a part of this, too?"
- LRLenny Rachitsky
Mm-hmm. [chuckles]
- JAJen Abel
'Cause it's, it's that parity of, um, of, uh, kind of role.
- LRLenny Rachitsky
Yeah. Uh, and they might be like, "Wait, I've heard of that. I think I heard that name before-"
- JAJen Abel
Exactly
- LRLenny Rachitsky
... "because I got this other email."
- JAJen Abel
Exactly.
- 18:44 – 30:00
Step 2: Running the intro call
- LRLenny Rachitsky
are confused. Okay, uh, step two. Step two is basically running the intro call.
- JAJen Abel
Yes. Okay. This is the most important call out of all of them, okay? Because you are setting the tone with how they think about you, how they respect you in your role, in your craft, and the information they will tell you on the first call, they will clam up moving forward because it starts to feel like a sales process. So, all of the information edge you can gain as a seller is on this first call, okay? So, keep it ... And this is, this is what I like to do. Super informal. Don't show them anything. Don't show them a demo. Don't show them slides. Don't ... Like, focus on them, have a one-on-one dialogue for 30 minutes, okay? Now, again, if they're bringing in a C-suite executive, you better have your founder join that call as well. I don't know any founder that wouldn't wanna be in the room with a Fortune 100 C-suite executive, so make sure you bring in your founder, uh, if, if you have that person on. But let's say you had the N-minus-one, you had, like, the VP on. Okay. Like, super brief, "Hey," and this is how I typically open, "Hey, I'm gonna keep this super informal. I don't even know if we need a full 30 minutes." Put them on the back foot, like, "Oh, this person's not trying to take up my time. All I would like to do is swap intros, and if it makes sense, we can always get on another call and go much, much deeper, but I just wanna better understand, like, who you are, and I'd love to share what we are doing and why I specifically reached out to you." So I say, "Would you like to go first?" Always let them go first. Give yourself the edge, right? Because if, the more information you are receiving before you speak, the more you can frame it and s- and tighten it to what they specifically care about. So-
- LRLenny Rachitsky
And they also aren't, like, sitting there now listening to a pitch or like, "Oh, I'm being sold to."
- JAJen Abel
Yeah, exactly. Now they're talking. Now they're conversing. Now it's like, "Okay. Now it's fun."
- LRLenny Rachitsky
Yeah.
- JAJen Abel
"Now this person's not pitching me. I'm in a conversation and a dialogue." Okay. So now you're talking to them, and they usually, they usually do a very brief opener and they're like, "Hey, I'm," uh, we didn't get a chance to look up the chief legal officer's, uh, at SpaceX, obviously this is just a case, but, like, whoever that person's name is, you know, "I oversee the legal team and blah, blah, blah." Okay. "Okay, great." They usually don't give you much, so then you say, "Okay, interesting. Like, how are you thinking about, um, like, do you guys have an AI mandate going on at the organization? Like, how are you thinking about the existing way you guys are doing work? Like, what are you looking for going into 2027? Like, does anything need to change?" Like, ask them, "Does anything need to change?" Because, again, what they're going to usually default to is what conversations had h- have happened above them and have been transcended down, so the change is usually dictated from the top, which is great. So, like, what needs to change going into 2027 that you did in 2026, or maybe not at all? And that's when they start to open up. And again, you don't wanna be too pointed of, like, anchoring them towards your product, because again, the more they speak, you can start to, like, pull on the strings that matter. So they could say something along the lines of, you know, I'm making this up at this point, but, "We are really looking to figure out how to bring more of this work in-house and rely less, rely f- far less on external law firms, right? Because now we have more tools and capabilities." Be like, "Okay, like, is there a measurement to that right now? Like, how are you guys, like, what does that look like internally in terms of, um, if you've done that successfully in 2027?" And then they'll say, you, uh, you're trying to understand, like, how mature is this thought, right? Okay, so now they're, they're going in, and they say they can't really answer that f- fully. Okay. Like, why is that important now? Like, why didn't you, why not wait another year? I mean, you guys have so much going on. You just had this massive IPO. Like, what's, what's causing the team to wanna reshape this or, or rework the way that they're, um, managing internally? And that's usually the moment of, like, where they start to really, um, guide you in terms of, like, how they wanna structure their team. So now you're getting all of this information about where they wanna go, right? H- Now, when you talk about what you do, now you're the vehicle to get them there, right? And so the, I try and spend maybe 10 minutes, the back 10 minutes explaining what we do and just keep asking them questions. Be like, "Oh, that's so interesting." Like, "What an exciting role to be in." Be like, "Okay, full disclosure," right? And by the way, I take a step back for that. Do not bring a recorder to this call. Do not record the call. They will not be open. They will not be vulnerable. They might assume it's being recorded, 'cause I think everyone kind of operates under that assumption right now, but for the benefit of yourself, do not have a recorder present, okay? Just be like, "Off the record, between the two of us talking right now, of what you just shared, like, what really matters? Like, what, what, like, a- or, like, what do you wanna own? Or, like, what's the chronological..." Like, keep digging, digging deep because the more you dig, the deeper you go, the more information they give, okay? Now, you can't sit there and just pepper them with questions. This is that, that art piece of, like, how open is this person? Some people are poker faces, some people are not. You will be able to go much deeper with some and not deeper than others. You just have to, um, improv, okay? But after you now have that intel and you can now understand, "Okay, here's the frame I'm going to take," now you can give them the pitch, okay? I will confirm every single conversation I have, the s- the storyline that I tell looks slightly different. I do not have a scripted pitch or frame for any call because it feels artificial. They feel it. It feels like you're putting them into a square box. Um, the best thing you can do is listen actively and then Feel confident enough to, to craft the pitch around what they just shared for you.
- LRLenny Rachitsky
That last part seems really hard to-
- JAJen Abel
Yeah, it's very hard
- LRLenny Rachitsky
... adjust and make up, like, here's what you're focusing on and here's how our product is gonna-
- JAJen Abel
Yeah
- LRLenny Rachitsky
... solve that problem for you. So that's kind of where that art and skill comes in.
- JAJen Abel
That's right. In enterprise sales, it's so, so hard to hire for because the more someone is trained in sales, the less natural it feels. I know this is counterintuitive, and we spoke about this on one o- another call. The most successful salespeople are not trained salespeople. That's why founders are so good at this. Like, they don't give themselves enough credit. What are they not good at? Probably following this process. What are they great at? Pulling out information, pulling on strings, getting people excited by vision. No one can do that better than they can.
- LRLenny Rachitsky
What percentage of the time are you just like, "Okay, this isn't actually gonna help you that much, so let's just-
- JAJen Abel
Oh
- LRLenny Rachitsky
... we'll share what we're up to"? Okay.
- JAJen Abel
Yeah.
- LRLenny Rachitsky
You're nodding that happens.
- JAJen Abel
One, I would say two to three out of every four calls, there's something unreal.
- LRLenny Rachitsky
Oh, wow.
- JAJen Abel
One out-
- LRLenny Rachitsky
There's nothing real.
- JAJen Abel
Yeah, there's something real.
- LRLenny Rachitsky
Okay.
- JAJen Abel
One out of every four calls I'm like, "Listen, based off of the maturity of where you guys are and where we are, it's too much of a gap. Like, I'd love to revisit this in a year, like, once you guys have a chance to, like, solve for X, Y, or Z." The, that's such a great question about the qualification. Most people are not gonna be qualified, not because necessarily you're talking to the wrong person, because if you're in an, if you're an enterprise executive or enterprise account executive, your job is to know who to talk to, okay? Um, and your job is also to quickly, um, quickly disqualify someone, and it's probably one in every four calls.
- LRLenny Rachitsky
Awesome. Okay.
- JAJen Abel
Simply because of maturity.
- LRLenny Rachitsky
Cool. So you don't have to have this, like, intense pressure to nail it on every call and-
- JAJen Abel
Yeah
- LRLenny Rachitsky
... here's the, here's the pitch.
- JAJen Abel
Yeah.
- 30:00 – 36:30
Step 3: Running a follow-up call
- LRLenny Rachitsky
great foreshadowing. Okay, so step three is writing a follow-up-
- JAJen Abel
Yes
- LRLenny Rachitsky
... intro call.
- JAJen Abel
Yes.
- LRLenny Rachitsky
Okay.
- JAJen Abel
Okay. So usually right now the stages that most people have is intro, demo, proposal, contracting, you know, close one or close loss, right? There's five stages. They're very basic. People usually go from an intro call straight to a demo, okay? The demo is your carrot in the process. Everyone wants to see this amazing thing you just spoke about, okay? So there's, your job is to make sure that when you do that demo, the formal demo, you have the right people on the call because if you don't One, it's you lo- you lost your leverage to, like, organize that group and rally them. But more importantly, it, you never want it to feel like one person's baby, right? If you're selling to that director or that VP, you need to make sure that that executive feels like they're pa- it's part of their baby and they're helping craft it and they have their fingerprints on it, and vice versa. Like, you want the C-suite, if they, they want, they want their, the actual users to feel like that they were bought in on this too. Okay? So you wanna make this to be, and this is the tricky part, you want it to, you, there's gonna be someone that's gonna champion it and get the deal done, but you gotta make it feel like a group effort. Okay. So the person that you had the intro call with, that's who you built the rapport with. That, that's your, that's your champion at this point, whether it's the C-suite executive or, um, one step removed. I say champion, m- most champions are one step removed, but let's just say the C-suite executive has delegated this now to the champion to, to, to navigate. Okay. For that demo call, now w- now before you do the demo, get on another call with them. "Hey, I had so much fun on our first call. I think that there is a great opportunity to get to, you know, support you guys." This call should be 15 minutes, by the way. Okay. "I'd love to do a demo, but before we do the demo, I wanna make sure we have the right people in the room and I'm demoing the right things. Can you help me understand from the conversation we had earlier, and as I'm walking you through, now I'm walking you through the product, what do you think would resonate with the team?" Now you're collecting more intel, okay? Now they're the, now it starts to feel like, "Oh, great, I get, now they get to put their fingerprints on this." So it's like, okay, if we, when we demo to this group, at this point, I want this question to be asked. Can you ask this question in the meeting? 'Cause I want them to understand the values. And they'll be like, "I'm actually gonna ask this question 'cause it's gonna resonate more." So now you're building this demo alongside this internal executive, and none of your competitors are doing this. No other startup you're competing with is taking these extra steps. You now have the alpha of the intel they're giving you from these conversations, and now they feel part of this journey. Okay? Now they trust you. So it's like, okay, so now you're spending 15 minutes trying to figure out, okay, or 30, right? Sometimes they won't give you that much more time, but ask for 30, is probably, do 15, and say, "Here are the five different things we can, we can go into. From our first conversation, it sounds like these two things matter, but let me show you all five." And then they might say, "Okay, I want you to do those two that we spoke about, but I also want you to show this because this is also part of our mandate, and this will make it feel holistic." Okay. So now you've just mapped out the storyline with an internal partner on their end, and now you're, now you have the names of the right people. Now you're gonna, to close that call, "Great. Is there a time we can look at everyone's calendar and put this on the, on the calendar?" Make the meeting an hour. The demo should be an hour. Okay. Now, you can ask before this meeting, "Do we wanna do a pre-demo to, um, maybe someone else on your team that would be excited by this before you race to the group demo? Um, or should we just do the group demo?" Like, they know their organization better than anyone else and, like, how pressing this need is. Now, if they're less mature in knowing if they want something like this, they probably wanna bring in someone else before the big group. If they're like, "No, no, no, this is something we wanna, you know, really move into," they probably are ready to go into a group. So you just need to figure out where they are on that maturity arc of their decision. Okay. So now you have, do we wanna go into pre-demo, or do we wanna assume they checked off pre-demo, or do we wanna do group demo?
- LRLenny Rachitsky
How often does that pre-demo happen?
- JAJen Abel
If you're, I mean, I try and push for it 'cause again, it's just more intel.
- LRLenny Rachitsky
Yeah.
- JAJen Abel
Um-
- LRLenny Rachitsky
So let's say, let's assume there's a pre-demo
- JAJen Abel
Okay. So now you have a new colleague on the phone, and you could say, "Hey, I'm gonna, for five minutes, I'm just gonna catch you up on the, the things that I just learned from so and so. What can you add to that? What do you think?" Do you see how you're just collecting more and more intel along the way? So now you're building the business case for them. Now they feel like they're buying, not being sold to. Okay, so now you have two or three people at this point already excited for the big group demo. The worst thing you can do in the sales process when you move into demo is just go into one straight demo with no prep. Or worse, a enterprise organization might reach out to you because they're going through a due diligence process to say, "Hey, we'd love to see what you guys have built. Will you present this to four or five people?" Don't do it. It, you're either a checkbox, and you don't want, you wanna remove yourself from being a checkbox, or two, you're about to demo your product with no competitive intel. Like, you just lost the deal at that point.
- LRLenny Rachitsky
Oh, man.
- JAJen Abel
Enterprise deals are won on, "This feels so close to who we are. It feels like it was built specifically for me." That's the whole game.
- LRLenny Rachitsky
Amazing. I love how, just how much alpha not only you're sharing with us, like there's, it's like, it feels like the theme of this is alpha, just like the alpha we're getting from this conversation. It also feels like a lot of this process is you getting alpha from the team. I don't know if alpha's the right word, but what you're saying-
- JAJen Abel
No, no, no, it is. It's information edge. Yeah, it's the information-
- LRLenny Rachitsky
Mm
- JAJen Abel
... edge that whoever I'm up against is not getting.
- LRLenny Rachitsky
Mm.
- JAJen Abel
And you have to assume in the enterprise you're always up against something. You're up against not doing anything at all, or you're up against a competitor who, who does some, or an incumbent, right? Most likely the incumbent. But it's so crazy to me how many people just, like, spew out a pitch with, like, no ... You, you also have to make it informal and fun. Like, you need to, you know, um, people also buy from people they like, right?
- LRLenny Rachitsky
I love how
- 36:30 – 38:36
Step 4: Prepping the pitch/frame for demo
- LRLenny Rachitsky
so far at least it feels very doable, not that difficult. Feels like I could do this.
- JAJen Abel
Yeah. Absolutely could.
- LRLenny Rachitsky
Uh, and it, and it doesn't feel like it takes that much time to do any of these steps so far. It's like a call-
- JAJen Abel
Yeah
- LRLenny Rachitsky
... learn some stuff, think about it. Is there any, like, times ... time buckets that we, that aren't obvious of, like, where you spend, like, a bunch of time on your own thinking about something.
- JAJen Abel
Yeah. So I will, I spend so much time thinking about what, reading between the lines of what they were saying, and that's when I will follow up. Like, those, those kind of pre s- pre-run calls before a big demo, like, I'm ask- I'm clarifying all those questions. Like, "Hey, I know you said this, like, did I interpret that correctly? Like, is that, is that the priority?" Like, and then again, they'll go deeper. Like, the more [laughs] the more you infer the questions you ask, it's almost like you just have to keep prompting. It's the whole, it's like sh- prompting humans at this point, right? Like, go deeper and deeper and deeper, and your, the answers you're gonna get are just gonna get so much more refined. The whole game is to slow down to go fast. All of this should be, should be within a 90-day sales cycle based off of their maturity.
- LRLenny Rachitsky
To some people listening, this may sound like a lot of work. I imagine that this is what separates companies and products that win deals versus not. You know, you could have a better product, you could have a better price, a lot of things, but just not executing in this way through the sales process is probably shooting yourself in the foot.
- JAJen Abel
Or you're stuck at, you just sold the enterprise on a $15,000 solution, which goes, you c- what do you, how do you expand that? The whole game is expansion. If you're not going from 100K or 250K to 350 or 500 the following year, it's not an enterprise motion.
- LRLenny Rachitsky
Okay. So just to kind of quickly summarize where we're at, step one, landing the meeting.
- JAJen Abel
Yep.
- LRLenny Rachitsky
Then running the intro call. Then there's this follow-up intro call-
- JAJen Abel
Yep
- LRLenny Rachitsky
... which you pointed out is often ignored-
- JAJen Abel
Yep
- LRLenny Rachitsky
... and a big opportunity to improve the demo.
- JAJen Abel
Yep.
- LRLenny Rachitsky
I love the way you described the demo as kind of this carrot that you're holding that you can use a little bit to kind of extract more.
- JAJen Abel
Yep.
- 38:36 – 46:45
Step 5: Running the demo
- LRLenny Rachitsky
And then there's, step four is prepping the pitch and framing the demo.
- JAJen Abel
Yep.
- LRLenny Rachitsky
Um, is there more to share there? Or do we-
- JAJen Abel
No, I think, I think we're at the point where it's like, okay, now you're running a big demo, right? You're run-
- LRLenny Rachitsky
Okay, cool.
- JAJen Abel
Okay?
- LRLenny Rachitsky
So, yeah.
- JAJen Abel
So now you have-
- LRLenny Rachitsky
Step five
- JAJen Abel
... you now, now you have all of the people involved in the demo. You might have somebody that's involved from their AI team that's gonna support some, some rollout. You might have somebody, like, you want all of the people involved in this decision at that table for the demo. That's how important it is to not rush it, okay? So n- now you're running the demo. Now you're, before that demo on that, on one of those calls, who are all these people? What do they care about? And what should I avoid? Like, the, the, the person that you've now built this relationship with can give you all of the intel. At this point, they want this to go forward. Now it's, now they, now this is, like, a great star for them of, like, I found this amazing tool, it's gonna solve our problems, and now I get to put my name on it alongside one or two other people, right? So for that demo, just make sure you know exactly who's involved, what these people care about, and what does a successful demo look like for them? Uh, just ask them. Be like, "Hey," people do demos all the time. Like, "What looks good? 30 minutes of a discussion, maybe 10 minutes of showing? 10 minutes of discussion, 40 minutes of in the product? Like, what, you tell me, like, what the, the organization likes." And on that demo, there's gonna be people that were not a part of any of these calls, okay? Your job is to take a step back and restart with, "Here's who we are. Here's why we are doing what we are doing," and it's fully in their frame. You now have all the context to put this in their frame. So now for these net new people, they're like, "Holy shit, this was built for us." Sorry for my French. Now they're, now they're, like, leaning in, being like, "Okay, all right. Somebody d- d- this is very aligned with what we need."
- LRLenny Rachitsky
Because they've no idea you've talked to all these people and-
- JAJen Abel
No idea you've talked to all these people
- LRLenny Rachitsky
... learned what their challenges are and priorities.
- JAJen Abel
They're like, they're leaning in, being like, "This feels different." Now this is also the whole part of, like, it's being different. Not only is your product different, not only is your pitch different, the way you're going through the sales process is different. So it's like, wow, these guys are good. Okay. All right. These are ... So now d- y- you could s- you know, let them talk. Let these net new people talk. Be like, "Hey, I, I know you, I know we haven't had a chance to speak. Like, what do you wanna get out of the demo today? I wanna make sure I focus for you." Now you're leaning a little bit more into these net new people so they feel the love, okay? And then when you demo the product, 80% of the value comes from 20% of the product, and you have learned on these previous calls what that 20% is. Do not demo everything unless there is some reason to. Because now all of a sudden this tight frame, this tight narrative you've just crafted and spent all this time with just gets thrown out the door 'cause it's like, "Oh, well, I wouldn't use that. I wouldn't use that. Well, everything she just shared, that's really only over here," and you could just blow the whole thing up. And the amount of times enterprises are like, "Hey, I'm not g- I don't know if we wanna spend this much money for half the tool, that we wouldn't use half the tool," now all of a sudden you've just unraveled all the work you've just done. Enterprise sales is super, super, super tight project management and super, super tight narrative and framing. Owning that frame. Owning that frame to exactly who these people are. And that's why this role is so hard, okay? 'Cause it's a lot of improv, and it's a lot of leaning in, and it's a lot of reading in between the lines. But, uh, like, it's, it, it's stuff that is, is doable. I mean, it's just psychology.
- LRLenny Rachitsky
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- JAJen Abel
The good news is, is that most senior people, like the people that you're gonna, that you're, you're doing your outreach to, it's very hard to get to that title if you're, like, verbose and long-winded and, like, take things off track. So that's the good thing about being, going after executives is those people are, like, really dialed in. Like, no one takes a meeting off track at, at an executive level. Um, now of course there's some times where there's people that meander. You could say, "I love this conversation. Can we park it? Because I actually wanna spend another call just dedicated to that." And if that, if that, if that needs to happen, then of course you can run with it.
- LRLenny Rachitsky
Awesome. So there's kinda two people that might be leading this. Might be the founder-
- JAJen Abel
Mm-hmm
- LRLenny Rachitsky
... if you're still doing founder-led sales. Could be the AE.
- JAJen Abel
Yep.
- LRLenny Rachitsky
Could be a VP of sales that-
- JAJen Abel
VP of sales, yep.
- LRLenny Rachitsky
Okay. As, say you're n- say you're not the founder and you're, and you're d- the VP of sales or an AE leading this. As a founder, what are some signs that your salesperson is not doing a great job up to this point? What are just, like, smells of like, "Hmm, I should really evaluate this person?"
- JAJen Abel
I would say, like, what is the timeline from intro call to demo? How many conversations have happened between those two, between those two buckets of, like, when people advance stages in the sales pipeline? Can the salesperson articulate exactly what they are gonna be demoing, why they're gonna be demoing it, and how they're gonna open it? The demo looks different every single time. Every single time. I don't think I've ever run a demo and it looked the same. This is, like, when everyone comes back to, like, okay, what's the scaled playbook? What's the scaled approach with this? When you're selling $100,000 minimum, right, again, it's the same effort as selling $1 million, so it could be selling a million dollar deal. It, it is, it's hard. You're, you're cracking some of the largest logos that every single startup goes after. You've got to be different. You've gotta take a different approach. It is not cram the pitch down their throat and hope that they wanna buy something.
- LRLenny Rachitsky
Feels like a job AI will not replace anytime soon from what I'm hearing here.
- JAJen Abel
No, I, yeah, I don't, I do not, um, I'm not worried about AI replace, because there's so much about it that's just human, right? Like, do you vibe with this person? I mean, I've, I've definitely taken intro calls with a person, probably did not appreciate with how I ran it, and that's okay. It was just, it happens.
- LRLenny Rachitsky
S- it's such an in- uh, a point I've never heard before, this idea of when you're demoing, d- demo kind of a- as narrow a slice of the product as you can that addresses their s- priorities and needs. Because to your point, they may feel like, "Why do we need all this stuff? We just want this one problem," and that's shooting yourself in the foot.
- JAJen Abel
Or let them guide you. Like, "Can it also do this?" And you can be like, "Oh, it's so funny you say that. We just released this." And now all of a sudden it feels like it's, again, built for them. They wanna feel like it was built for them and that, um, it's different.
- LRLenny Rachitsky
And they get alpha.
- 46:45 – 48:59
Step 6: Post-demo debrief
- JAJen Abel
And get alpha.
- LRLenny Rachitsky
Okay. Uh, so step six, y- uh, you call the post-demo discussion.
- JAJen Abel
Yes.
- LRLenny Rachitsky
Also something you say everyone ignores.
- JAJen Abel
Yes.
- LRLenny Rachitsky
Talk about that.
- JAJen Abel
Okay. So as soon as the demo closes, you are texting the woman or the gentleman or whomever that has h- helped guide you to this point, "How do you think that went? Can we grab, can I call you in, like, five minutes? I just wanted to, I want, like, a fresh debrief." They will give you, and be like, raw reaction, "I know you haven't spoken to anyone. What do you think? How do you think that went? Do you think we need to go deeper with anyone?" Before anyone, like, solidifies kind of everything that's said, like, where, where did, do you think we lost somebody? Where do you think we did well? Um, is there someone we need to spend more time with? There's always someone in the organization that's gonna kill a deal. There's always somebody. You need to protect that as much as possible and make sure everyone is aligned and excited by what this is. And again, the more intel you collect on these people, because again, if for some reason someone goes quiet for two weeks or three weeks, you can now prompt with, "Hey, I know you guys are in, still c- in the process of, like, thinking through if this makes sense. Do you think it's worthy if I found 15 or 20 minutes with said individual to just, like, hear their thoughts? And, and maybe we can, and maybe we can, um, approach this a little bit more closely with how they would wanna see it."
- LRLenny Rachitsky
So you're just always looking for ways this might explode and not work. And, and this person that you're working with, would, uh, would you call them, what would, um, what was the term you used for them? The, um-
- JAJen Abel
A champion
- LRLenny Rachitsky
... the champion.
- JAJen Abel
Yeah.
- LRLenny Rachitsky
Yeah. And they're-
- JAJen Abel
'Cause a champion can also be an executive, right?
- LRLenny Rachitsky
Yeah.
- JAJen Abel
Or C-suite.
- LRLenny Rachitsky
And they may, and they're, like, excited at this point, in theory, very excited for this to work out.
- JAJen Abel
Yes.
- LRLenny Rachitsky
Like, they're on your, on your side.
- JAJen Abel
Yes.
- LRLenny Rachitsky
They're not trying to ... Yeah.
- JAJen Abel
And, and I define champion as who's the individual that really wants this to come to life, that's like, was there from day one. Not necessarily, like, the person that sh- like, the C-suite executive could be the one shepherding this well, but they need to make sure that the people below them are bought in.
- LRLenny Rachitsky
Okay. Anything else around the demo or the post-demo discussion before we move on to the next step?
- JAJen Abel
No, I think we're good.
- 48:59 – 1:03:44
Step 7 through 9: Preparing for and running the pilot
- LRLenny Rachitsky
Okay. So the next step, uh, you call identifying ... pilot move forward process
- JAJen Abel
The best thing you can do, assuming that you've built an incredible solution, right? If you're, if you're, if you're now this far in, right, you usually have something that they, they allow them. Now you can control the, the timeline of it. "Hey, I want you guys to go in for two to three days," these specific users. And don't put the, do not put your C-level executive into the product. They're not the user, okay? Who are the users of this? I want them to experience the magic and the power of what this is, okay? Ru- don't char- you could charge them for a pilot if it's an extended period of time, but I'd rather forego the money and do a two to three-day pilot so that at least I can control the sales cycle a bit more. Okay. But again, if they ask for a month and there's a good reason for it, do charge for that, but I usually would, I'd rather, I'd rather go in for two to three days and, and let them see if they can get the value from it, if they can. Sometimes I understand that there needs to be some level of configuration and, you know, extensive onboarding that needs to happen, but is there a sandbox where they can assess the value, um, now even if it's not on their own data?
- LRLenny Rachitsky
So this isn't yet the pilot. This is just, like, prepping for the actual-
- JAJen Abel
Correct
- LRLenny Rachitsky
... pilot.
- JAJen Abel
So, so there's two different pilots you can run.
- LRLenny Rachitsky
Mm-hmm.
- JAJen Abel
A pilot that does not require their data to be in the product to get the value, or a pilot that you want to charge for because they need to see, um, some level of, like, integration on their end for the whole product to actually work, right? Like, I understand that those are two very technical things. Um, let's talk about something that they can get in two to three days and it's a pretty, pretty much of a light lift. Time box it to two or three days. Don't make it two weeks, okay? I've done this enough times to say people will go in usually for half a day and get what they need out of it, okay? Shorten your sales cycle by two weeks by doing two to 48 or 72 hours. Now, if you need something a bit more integrated and it, and it's a, a far more technical solution, what I'd highly recommend is do it for a month or two months, charge them for it, and then use that, that fee that you charged them for and credit it back to them if they move forward, okay? If they're willing to pay, that is a huge, huge signal, especially if you're about to put in all this work. They have no problem paying for it. It's usually probably gonna come out as services anyway, 'cause it's like a, it, it, they're not buying technology, they're buying the services to go through it. Um, and also make it a credit on the back end. Don't ... Start the relationship up, shift. Start the relationship off on a good foot.
- LRLenny Rachitsky
I'm definitely feeling the feeling [chuckles] I feel when we chat is, like, I just wanna find something to sell. This feels really-
- JAJen Abel
[laughs] It's fun. It's so fun
- LRLenny Rachitsky
... fun. Yeah.
- JAJen Abel
Like, it's literally so fun. People, I think people read these sales books, go to these sales trainings, and they, they, they ma- they try and take someone else's game and run with it, and it never works that way. Like, no one taught me this. I was just like, "Okay, if I collect more intel than the competitive set, that will be my special sauce."
- LRLenny Rachitsky
And it's, like, more fun that way. You're building a relationship more. You're chatting more often. You're not trying to just, like, uh-
- JAJen Abel
Yeah, speed run
- LRLenny Rachitsky
... it feels more real.
- JAJen Abel
Yeah.
- LRLenny Rachitsky
Yeah. Okay, a couple questions here. One is this idea of the two to three-day pilot. How do you convince them you only get two to three days? 'Cause that feels tough.
- JAJen Abel
So I would say here, this is what we typically do. Who are the three or four people we wanna put in and assess the, assess the value from a user perspective? Okay. Make sure it's your person, right? As- assuming that it's no, or, or the person closest to the C ... Don't put your C-suite executive in it. They're not gonna, they're not gonna go into the product. And then two or three other people, okay? And I want you to say, "We're gonna do two or three days. I'm gonna onboard you each differently. We're gonna do two or three different, like, onboard sessions before those two or three days, and I want you to go in and I want you to do these three specific tasks." Be very, very thoughtful and explicit and descriptive with what you want them to do, okay? Here's how we're gonna measure success. Define that with them. Define that with, co-author that. And that's no different than the thing that's a little bit longer where you require that integration and, um, and build out. Co-author it with them. What does success look like? What are the specific things they should be doing? They should not just be logging in and meandering. That puts the work back on them. Your job in sales is to take all the work off their plate, 99% of it.
- LRLenny Rachitsky
And help them discover the magic really easily.
- JAJen Abel
Help them discover the magic, and also continue to ... You might have one of those users that's like, "Oh, I didn't like it." Great. Of, in that three-stage process you just... What did, what didn't you like? What wasn't clear? What wasn't obvious? Where did you get lost? The tighter it is, the less people get lost, the mo- the more, um, grounded it feels and the more consistent the experience is. You don't want people having different experiences.
- LRLenny Rachitsky
Okay, so just to make clear the steps involved here, 'cause we've gone through, I think, three kind of around the same.
- JAJen Abel
We've gone through so much, yeah. [laughs]
- LRLenny Rachitsky
We've gone through so much, so we're kind of on step nine. So there's, uh, step seven, which was identifying the pilot move forward process. A lot of people ignore just, like-
- JAJen Abel
Yep
- LRLenny Rachitsky
... who that person is and what the steps are. Then there's prep for the pilot, and then there's run the pilot.
- JAJen Abel
Run the pi- exactly.
- LRLenny Rachitsky
So we've kinda talked through all these things.
- JAJen Abel
Now-
- LRLenny Rachitsky
Is there anything else on... Yeah.
- JAJen Abel
For prep for the pilot, the one thing I wanna say is, okay, before we put everyone in, let's work backwards of if this is successful, how do we get this deal through? Okay. Because you go-
- 1:03:44 – 1:04:49
Why the standard five-stage CRM pipeline doesn’t work
- JAJen Abel
are for. That's not the stages you take a client through. Like, those are just the broad buckets. Um, and I think a lot of people use those buckets to say, "Okay, I've ... There's about five different meetings that need to happen," when it's like, no, there's, like, three meetings, maybe up to five meetings in each of those buckets that are critical, um, to get the deal done. Now, we're, we're still speaking at it at a very macro level. Like, you know, obviously selling a million dollar deal, you wanna have more of those upfront meetings. Um, and you wanna make sure you know who the executive sponsor is and all that. You always wanna know who the executive sponsor is. But, like, for 100K deal, you probably can accelerate it a little faster, again, ensuring that they're qualified.
- LRLenny Rachitsky
I know you've worked with a lot of founders and salespeople over the years. What percentage do you think are just doing it wrong in that way and treating it like this five-step process?
- JAJen Abel
90%.
- LRLenny Rachitsky
Wow.
- JAJen Abel
Yeah. Because e- en- like, enterprise sales is, it's, it's, it's mirroring their buying process. It's trying to control their buying process. It's not plopping these people into your sales process.
- LRLenny Rachitsky
Amazing.
- 1:04:49 – 1:07:48
Step 10: Post-pilot session
- JAJen Abel
Yeah.
- LRLenny Rachitsky
Okay, let's keep going. Step 10, post-pilot session.
- JAJen Abel
Yes. Um, you can send a survey. They might wanna send a survey. Get the intel. Or one-on-one to each of these users and say, "Hey," or let your champion ... I mean, there's a few ways you can do this. Or you can have your champion internally discuss and say, "Hey, how was that?" Okay? You need to make sure that you are mirroring their experience, right? From a technical perspective, like how much time did they spend in the product? Did they run into any bugs? What were they using the most of? Because you need to be prepared of, like, going into that call to say, "Hey, I know we gave the, I know we gave everyone those three things, but most people only spent it on two. Why?" And that might be okay. But you, but, like, you don't want them to be like, "Oh, well, you know, we wish it did this." Well, yeah, but no one spent time on that. We do do that, but no one spent time on that. So you just need to control also that you're capturing what they did in those pilots and making sure that you're syncing up. Or you could go to your champion and be like, "Hey, I know so-and-so logged in for, like, 15 minutes today. They didn't get past step one." Don't tell them what they're doing. You shouldn't even need that. But, like, they didn't get past step one. Do you wanna, can you check in on them and making sure, like, they're having a good experience? Like, use your champion to, like, again, they've invested so much time into you, guide them with where they should be focused as well. Because at the end of the day, getting a deal done at the enterprise, it is set up to have as much friction as possible, right? There's the people that will kill the deal, then you gotta deal with procurement, then you gotta deal with legal, then you gotta deal with finding the executive sponsor, right? Which usually comes in the very top of the funnel, but there's so much friction to get a deal done. The project management and the individual on the inside, that's your key.
- LRLenny Rachitsky
So funny. So many ways it could all fall apart.
- JAJen Abel
Yep.
- LRLenny Rachitsky
Um, what I was gonna say is it feels like many people would naturally, like, they don't wanna, they wanna avoid confrontation. They won't want to say, "This is not gonna be ... We don't want this." They're gonna probably be like, "It's fine. It's, yeah, it's good. Oh, yeah, everything's great."
- JAJen Abel
It's like PCs.
- LRLenny Rachitsky
[laughs] That's right. That's right. And so it feels like a lot of this process is to, like, pull out.
- JAJen Abel
Yes.
- LRLenny Rachitsky
"Okay, here's the concern. Here's the problem." Are there any other signs of like, okay, they're actually not interested and, like, this is not going well and I need to really-
- JAJen Abel
When your in-- this is why your internal champion is so important. When they go-
- LRLenny Rachitsky
Mm
- JAJen Abel
... quiet on you, that's when you know. That's why this individual-- And listen, this individual's gonna do you-- If they've spent enough time with you, they will call you and be like, "Listen, if I'm reading the tea leaves, we should sit on this for a minute. Let's re-pick this back up." That's why having someone on the inside is so, so, so critical.
- LRLenny Rachitsky
And yeah, the easier pro- [chuckles] the easier approach is just to stop responding and just hope that the, the salesperson understands-
- JAJen Abel
That's right
- LRLenny Rachitsky
... very little.
- JAJen Abel
That's right.
- LRLenny Rachitsky
Not excited. Oh,
- 1:07:48 – 1:11:45
What a healthy enterprise win rate looks like
- LRLenny Rachitsky
man. Okay. What are, like, the benchmarks for, like, how, how often you get through each of these stages? You mentioned, like, a few. Just, like, yeah, from demo to this stage.
- JAJen Abel
Usually once a d- once something is qualified, meaning you're speaking to the right person, they are excited by the alpha, they, they admit that there's change that needs to happen. Notice I didn't say problem, but change. People get so fixated on problems, which are important. They are important, but, like, everyone speaks to the same problem and it commoditizes you, which is why I don't like to, like, overly emphasize it. The win rate for enterprise, a good, healthy win rate, it's actually probably gonna surprise you. It's not 50%. Meaning of all qua- sales qualified leads or opportunities, we-- a healthy win rate is usually around 30% to 35%.
- LRLenny Rachitsky
From qualified lead to-
- JAJen Abel
Qualified call
- LRLenny Rachitsky
... signed contract.
- JAJen Abel
Meaning-
- LRLenny Rachitsky
Mm
- JAJen Abel
... you speak to 100, you're closing anywhere between 30 to 35, maybe slightly less, maybe 25 to 30. That seems high, actually. Yeah, 25 to-- somewhere between 25% and 35%. Why? If, if it's, if you, if your win rate is higher than that, your price is too low. There's a lot of part of the market that's just not in a maturity perspective to take you on, and that's healthy. Right? Those, those are all the chasms.
- LRLenny Rachitsky
And the implication here is it's better off keeping your price high than winning more often.
- JAJen Abel
Uh, yes, because the market talks, too. Well, the worst thing you can do is charge somebody's friend 50 and somebody else 500K. They talk. Peop- the market talks. You have to assume that. So it's-
- LRLenny Rachitsky
Yeah, I'm in a lot of, a lot of WhatsApp groups with founders, and they do exactly that.
- JAJen Abel
It's ex-
- LRLenny Rachitsky
They're like, "What kind of deal do you get for this-"
- JAJen Abel
Yeah
- LRLenny Rachitsky
... "this product?"
- JAJen Abel
That's exactly right. So the-- assume the market talks, especially at the corporate executive level, and someone might just not be ready yet, and that's okay. The amount of deals that come, that boomerang a year later of the ones that have lost, that's probably another 25%. So it is totally normal and natural for, uh, de- deals to not advance, right? But to, a healthy win rate in the enterprise is typically be- I would say between 25% and 35%.
- LRLenny Rachitsky
Okay. That is incredibly helpful to people. A, I know, uh... How about, like, key stages along the way, just, like, percentage drop-off up in-
- JAJen Abel
So it's usually, like, from qualified lead to, like, um, you're coming out of demo, it's probably you lose half, and then-
- LRLenny Rachitsky
Out of demo.
- JAJen Abel
Out of demo, yeah. And then from there to-
- LRLenny Rachitsky
Post-demo, not from-
- JAJen Abel
... five, yeah, it gets you to 30%.
- LRLenny Rachitsky
So from demo to, what was that step that you lo-
- JAJen Abel
From demo to, like, n- the more you move down-
- LRLenny Rachitsky
To close
- JAJen Abel
... the sales funnel, the less those numbers, uh, the less, um-
- LRLenny Rachitsky
I see
- JAJen Abel
... wider those numbers. So, like-
- LRLenny Rachitsky
Okay
- JAJen Abel
... so, like, let's say if you speak to, um, and you're doing a really good job targeting the right people. Maybe thir- uh, 70, uh, f- 50% of those people move to a qualified lead, or se- 50% to 75% move to qualified lead. Of that, then, um, another half move to demo, and then from there, another quarter advance beyond that. Once you're in the bottom of funnel, you usually don't lose too much from there if you're doing-
- 1:11:45 – 1:18:01
Steps 11 through 14: Navigating procurement and getting the signature
- LRLenny Rachitsky
Um, okay, so step 11, papering prep, setting timeline for pre-procurement.
- JAJen Abel
Yes. So you have now, um, spoken pre-pilot about the timeline of which we're reverse engineering. Now you're gonna document it in, in an email so that that champion that you're working with can forward that to procurement to say, "Hey, here's what we agreed to. Here's the pricing that's predicated on us getting this signed by this date. Here's the..." Give them something. "Here's the, um, kicker they're gonna give us if we, if we get to this date." Um, there's always gotta be a reason to create urgency. And then what you wanna do is say, "Here's our paper." Send a Word document. Do not send a PDF, 'cause they're gonna always redline. Always. Send a Word document of your paper and ask the question, "Do you wanna use our paper? Here's a Word doc version. Or do you wanna lift from it, and do you wanna use your paper?" It might be a lot faster to use their paper. That's why you give them the option, and that's why the timing is in there, because they might say, "Well, in order for us to hit that time, we gotta use our paper."
- LRLenny Rachitsky
And it's not Google Docs. It's Word Do- Google, like Microsoft Office.
- JAJen Abel
Microsoft Word, yeah.
- LRLenny Rachitsky
Okay.
- JAJen Abel
But not, most of these people can't access Google Docs, but yes.
- LRLenny Rachitsky
And so this says post-pilot, feels like it's gone well. Um, you're saying the next step is here's, like, the contract, basically. S- get that to procurement that early.
- JAJen Abel
And again, your internal champion is, is you're working from N minus one from the exec- from the executive sponsor, or it's the executive sponsor themselves. You, you, you wouldn't have made it th- they're not gonna put their team into a pilot if it's doesn't have legs.
- LRLenny Rachitsky
And I th- an implication here is procurement is a way that your deal might still die even if people internally love your product.
- JAJen Abel
Correct. It, if you get sent to procur- so here's, here's something interesting a lot of people don't realize. People will use procurement as the excuse to not wanna give you, um, the, the, the bad feedback. "Oh, uh, I gotta go to, oh, it, procurement, it's, it's, it's lost in procurement," or ba, ba, ba, ba, ba, right? Very easy to blame procurement. Usually procurement is like a 30-day process between the back and forth on the legal, the papering. Procurement's job is not to kill the deal. It's just to make sure that it is aligned with how they need to buy. That's their job. Procurement is the only person that can get you paid. Do not start any work till you go through procurement. Business unit leaders can't just pay you. That needs to come from the finance team who pulls from the budget. So be very careful, like do- don't start any work until obviously the papers are signed.
- LRLenny Rachitsky
Start work meaning implementing, rolling out-
- JAJen Abel
Correct. Ex-
- LRLenny Rachitsky
... people onboarding. Got it, got it, got it. Okay, amazing. Okay, so that's step 11, papering prep, setting timeline for procurement, kind of getting on board with like what is it gonna take to sign by this date? Here's a little gift you'll get if you do it by this date, free month or whatever. Okay, uh, step 12, papering review.
- JAJen Abel
Yes. The best thing you can do is they're gonna send you back red lines, no question. If the red lines are extensive, okay, go ahead and accept the things that are easy. If the red lines are extensive, see if you can get legal on a call live and just talk through them. That will accelerate your sales cycle.
- LRLenny Rachitsky
Versus a bunch of back and forth emails.
- JAJen Abel
Versus a bunch of back and forth. Get them on a call. Be like, "Hey, everything, we're 80% of the way there. I have a few questions based off of your red line. Can we jump on a ca- a live call and just go through them?" D- focus on the things that are gonna impact the business and push in on those. Let the other stuff go if it's not super important. Obviously have a lawyer look at it from your side. You're dealing with a commercial lawyer, commu- commercial legal team. Have a lawyer look at their red lines.
- LRLenny Rachitsky
I imagine most companies have a legal counsel [chuckles] to do that.
- JAJen Abel
Yes, I would hope. I would hope, so yes.
- LRLenny Rachitsky
Okay, cool. So papering review, so that's reviewing basically. It's interesting you call it the paper.
- JAJen Abel
Yeah.
- LRLenny Rachitsky
Um, is there like a more technical term for that, like the-
- JAJen Abel
Contract
- LRLenny Rachitsky
... um-
- JAJen Abel
I say paper 'cause that's the cor-
- LRLenny Rachitsky
Contract?
- JAJen Abel
That's like corpo language, paper.
- LRLenny Rachitsky
So interesting.
- JAJen Abel
Yeah.
- LRLenny Rachitsky
Okay. Papering review. Okay, step 13, papering procurement process.
- JAJen Abel
Yes. So this is where, um, we kinda talked about this. We kind of merged that conversation. This is when you are getting the procurement lead and that legal lead on a live call to work through the questions or the things you cannot accept. Now remember, if they give you their paper, there's gonna be a lot in there that you're gonna need to-
- 1:18:01 – 1:19:18
How to think about expansion
- LRLenny Rachitsky
Is there anything there just real quick, just like how to start thinking about how this, where this goes-
- JAJen Abel
Yeah
- LRLenny Rachitsky
... once the deal is signed?
- JAJen Abel
Yeah. Um, and this is where I think the expansion comes in. You either know the products that they can expand into, like you've been through this journey before, and that's pretty straightforward, but if you are early in the journey and you're closing your first 10 enterprise customers, you need the founder involved, um, once these people are in to understand like what part of the product is, um, custom to what these people need and do we wanna build out, you know, do we wanna charge for services? Again, here's the other thing too, services, and I know every company is in ARR recurring revenue focus, but services is still the largest line item in budgets.
- LRLenny Rachitsky
And so you're saying, uh, it's okay to offer services-
- JAJen Abel
It's okay to offer services
- LRLenny Rachitsky
... as a part of.
- JAJen Abel
Yes. Yeah.
- LRLenny Rachitsky
[chuckles]
- JAJen Abel
Yeah.
- LRLenny Rachitsky
Yeah. This has come up a number of times I think with Jason, also Lemkin, and, and you just like the increasing, like there's a rise in services-
- JAJen Abel
Yeah
- LRLenny Rachitsky
... being a part of software companies.
- JAJen Abel
It's what they know how to buy. It's what they know how to buy.
- LRLenny Rachitsky
Mm-hmm.
- JAJen Abel
They're so used to it. Consultants, lawyers, you name it. Um, the, the, the-
- LRLenny Rachitsky
Yeah
- JAJen Abel
... the budget, there's always budget for services.
- LRLenny Rachitsky
Yeah. We talked about this last time, so we won't get too
- 1:19:18 – 1:21:53
How buyers can say no without wasting everyone’s time
- LRLenny Rachitsky
deep into it. Something else I wanted to ask you kind of at the end here, say you're a buyer and you're, say you're talking to Jen, and you're just like Not sure this is a fit, you don't wanna disappoint, you don't wanna drag you along. What are some things that people buying software products w- working with a salesperson, how should they communicate? What should they be saying to kind of avoid disappointment?
- JAJen Abel
Yeah, I would say as soon as humanly possible, explain why the timing's not right. It usually comes down to timing. Or why they're not mature enough to be able to, um, be in a position to ... It, it's interesting. You have to be, your organization and the team has to be structured in a way to bring on the technology. Like, there's a maturity you have to go through. Now, I know we talked about this before, where sometimes it's easier to sell the service first and then do the technology, and counsel them towards the technology. But, like, if you are in a, if your sales maturity in the enterprise is further, uh, further down the road, you wanna start with selling the technology versus the services.
- LRLenny Rachitsky
And if you talk about how it's not the right timing, you're not mature, I imagine the salesperson will try to prod you and push you to see if maybe you're not, so it's okay to just tell them why you think it's not the right time.
- JAJen Abel
Yeah, and you, and you know where you can get ... Like, I've had one, I've had clients say to me, like, "Hey," like, "I don't know if we're in a position to do this," and I've straight up said to them, "You are a liability not closing this gap." And they're, like, sometimes they just need to be like ... But again, you need to know if you're in a position to be able to say that.
- LRLenny Rachitsky
Yeah, yeah, yeah.
- JAJen Abel
But like, be like, "Listen, I know you need this. I know you need this. I'm not accepting no as an answer. How do we figure this out together?" Because-
- LRLenny Rachitsky
Yeah
- JAJen Abel
... because again, use the intel they've given you towards that.
- LRLenny Rachitsky
And like, interestingly, you're talking to a lot of their competitors, and you would think you have insight and say, "Okay, here's what everyone else is doing in this space."
- JAJen Abel
No, exactly. Or like, "Hey, listen, on our first two calls, you, you told me how important this is. Did that change?" "No, we're just, like, in a weird spot." I'd be like, "Okay, listen. Here's what we're gonna do. Let's start it a little bit smaller. Let's get in. I know, I ... You admitted that this is something that you guys need. I know that we are gonna crush it for you. I do not, I don't want X to get in the way of that."
- LRLenny Rachitsky
Mm.
- JAJen Abel
And there, and then there's obviously they're gonna be the cases where it's like, it's just not the right time. Like, they might be going through an acquisition, right? And like, bringing on net new vendors is just, like, not a priority right now. And
- 1:21:53 – 1:22:27
Why enterprise sales is a lot like product management
- JAJen Abel
you just have to respect that, too.
- LRLenny Rachitsky
I love how this whole process, a lot of listeners of this podcast are product managers, product people. It just feels very product-y and product manager-y in terms of the organization and the step-by-step, and just, like, org- just staying on top of all these little things. Like, it's so interesting how you don't think sales and product management are at all alike.
- JAJen Abel
But they're similar.
- LRLenny Rachitsky
But, but they're so similar, and it's just like you being human, like the way a PM tries to understand what your pain points are. We're here to solve them.
- JAJen Abel
Yep.
- LRLenny Rachitsky
It's like, yeah. Unexpected. We did it, Jen. We did it. We went through it all.
- 1:22:27 – 1:24:54
Closing thoughts
- LRLenny Rachitsky
Is there anything else? Anything else we haven't touched on? Anything else you wanna, I don't know, leave listeners with before we wrap up?
- JAJen Abel
We gave them a lot.
- LRLenny Rachitsky
We did. [laughs] Which was the goal.
- JAJen Abel
Yeah.
- LRLenny Rachitsky
Just the right amount.
- JAJen Abel
Yeah. Yeah.
- LRLenny Rachitsky
I'm excited for like, uh ... Oh, I was gonna say, I, I love that AI, I don't think it came up one, maybe one time in this conversation. Very rare these days-
- JAJen Abel
Yeah
- LRLenny Rachitsky
... in podcasts, which I love.
- JAJen Abel
Well, it's, it's interesting, like so many people will create, like, AI reports that they can send to their clients, or like AI imagery, or like, I don't know, you name your, your flavor. And it's like, anyone can do that. It just feels sales-y.
- LRLenny Rachitsky
What's your alpha?
- JAJen Abel
Exactly.
- LRLenny Rachitsky
It always comes back to that.
- JAJen Abel
Exactly.
- LRLenny Rachitsky
And I know you talked about this last time, just like craft your own email and text.
- JAJen Abel
Yes.
- LRLenny Rachitsky
Don't, don't use the boilerplate.
- JAJen Abel
Yeah.
- LRLenny Rachitsky
Don't use your AI.
- JAJen Abel
Emails are living and breathing. I swear to God that, like, people can read you saying the email out loud.
- LRLenny Rachitsky
Mm-hmm. Mm-hmm. Yeah. Okay. Jen, uh-
- JAJen Abel
This was awesome
- LRLenny Rachitsky
... this was amazing. Everything I want it to be. This is gonna be, I'm excited for like the [laughs] not to talk about AI-
- JAJen Abel
Questions
- LRLenny Rachitsky
... but just like AI summary of this especially, that's just gonna be like step one, two, three, four, here it is.
- JAJen Abel
Yeah, yeah, yeah.
- LRLenny Rachitsky
Uh, final questions. Anything you wanna plug? Anywhere you wanna point people to? And how can listeners be useful to you?
- JAJen Abel
Let me know if anyone has questions. I'm more than happy to go deeper into this. I would say, um, if anyone, here's a plug, if anyone is interested in enterprise sales, we are actively hiring, and I will teach you everything I know.
- LRLenny Rachitsky
Wow. And this is at State Affairs?
- JAJen Abel
This is at State Affairs.
Episode duration: 1:24:56
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