84 minutes of enterprise sales alpha | Jen Abel

So, we're going to do something really unique with this conversation.

Basically, go through the enterprise sales life cycle step by step. Let's set

this up.

Let's start with how do I even get the first meeting? We're in this flood 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

problem? That's level one, but most importantly, the alpha and it needs to be different.

Step two is basically writing the intro call.

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

minutes. The whole game is to slow down to go fast. And by the way, do not bring a recorder to this call.

What are the benchmarks for how often you get through each of these stages?

The win rate for enterprise is usually around 30 to 35%. If your win rate is higher than that, your price is too low.

What are some signs that your salesperson is not doing a great job?

The most successful sales people are not trained salespeople. Fastest way to

trained salespeople. Fastest way to commoditize yourself is to go into some sales script. Budget, authority, need,

sales script. Budget, authority, need, timing. Like that should be in the back

timing. Like that should be in the back of your brain. You never actually ask those questions.

What percentage do you think are just doing it wrong?

90%.

Wow.

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. Most people think the sales process is five steps and we're already in step 10 and we're not even done.

The worst thing you can do in the sales process is today my guest is Jen Ael. 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

enterprise sales. In our first conversation, we went deep on founder sales. In our second conversation, we

sales. In our second conversation, we focused on the1 million to $10 million 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

sales cycle. Most people think this is a five-step process. It turns out it's

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

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

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 lennisproass.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

newsletter subscribers. With that, I bring you Jen Ael.

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?

Round three. Super excited to be here, Lenny.

I'm even more excited. So, we're going to do something really unique with this conversation. I've never done anything

conversation. I've never done anything like this before. We're going to 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. A

lot of people ignore a lot of these steps.

And the idea is I want to create a very concrete and um tactical playbook for how to do enterprise sales.

Okay, we've had conversations secrets all let's go. Just just suck them all out. make everybody amazing at sales.

out. make everybody amazing at sales.

It'll be great.

Awesome.

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-winwin in helping people learn these things, you know, it may feel like why is she giving away all these things? But

maybe actually let me ask you that just like why why do you share these things?

Well, it's so interesting because there's so much art to this that even if you gave someone a 15step 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

another individual. And if you ran the same flow every single time, it's going to probably not hit one out of every four times because everyone's different.

Like some people like to joke, some people like the small talk opener, others want to jump right into it, some are technical, some are not technical, you know. So everybody's so different

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 road map of like how to close these deals. But I

think the interesting thing about enterprise sales is even if you're selling a the if you sell a $100,000 solution, it is the same exact process to sell a million-doll

solution.

So that's why it's 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.

Amazing. And I'll just give a plug for if people want to continue learning, your Twitter feed is just the best.

You share all this stuff constantly.

Yeah. 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. People need to it's like a diary and it also helps me like keep it in my mind too, right?

It's like my own education. Yeah,

I know exactly what you mean. That's why

I started writing. I started I was just like I just want to remember this stuff myself. I'm just going to share it and

myself. I'm just going to share it and crystallize it.

Okay. So before we get into the steps, let's set this up. What are some things people should know? What's kind of like the case study of what we're going to be using here? Let's use a company like

using here? Let's use a company like SpaceX, right? Recently, you know, has

SpaceX, right? Recently, you know, has seen massive news pressings. It, you

know, everyone's probably targeting them, right? So, it's going to be a hard

them, right? So, it's going to 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 going to like really get into like the nuance of this. So, let's do SpaceX. Why don't we pick legal? Let's

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 kind of budget,

right? Sometimes three to four times

right? Sometimes three to four times other budgets and it's forever. There's

always more money for legal.

That's why there's so many legal AI startups. I get it now.

startups. I get it now.

100%.

Amazing. And I'll just add the reason like the reason I love to have you on this podcast is I 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 want to sell something now. I feel like I've learned all these

now. I feel like I've learned all these things. It feels so fun.

things. It feels so fun.

Sales.

You're a master. You're actually a master at this. Sales is marketing.

Marketing is sales to some extent, right? And

right? And All right. You do that better than a lot

All right. You do that better than a lot of people. I feel like you're using some

of people. I feel like you're using some sales technique on me to make me feel good about myself. Okay. Anything else

before we get into step one of the sales enterprise?

No, I think it's just good sales cycle.

SpaceX and targeting the legal function and then like a 100K, let's say deal.

And to your point, it's the same process whether it's 100K a million. And I will add a plug for a

a million. And I will add a plug for a previous episode. You talk about why you

previous episode. You talk about why you want to be at least 100K something as a deal to be a a real enterprise company that will that will survive because the

ROI and the and just the whole economics of that stuff, but we won't get into that.

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Okay, step one, where does where does it start? How do you start selling someone

start? How do you start selling someone on your product?

It's a great question. So, I think we'll start with like how do I even get the first meeting? How do I even engage with

first meeting? How do I even engage with these people?

There is so many there's so much nuance as you target as 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 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

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 want to solve for at the organization. It has to go beyond

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.

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? Because

bringing in a net new tool, okay, is risky. No one wants it. So if we're

risky. No one wants it. So if we're targeting the chief legal officer and the N minus one, you get two sent two two to three sentences max.

Okay, that might be through an email LinkedIn, that might be through a phone call, that might be through an event, um or that might be through some marketing capability. Most most sea level

capability. Most most sea level executives don't respond to marketing.

They might see your brand, they're not going to respond to a marketing campaign, okay? They will respond

campaign, okay? They will respond one-on-one. And the best individual to

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,

the founder. Even if you're a series B, series C, right? It is the founder should be ecstatic to want to get in front of the chief legal officer at

SpaceX. I think any founder that is um

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 or enterprise sales lead to target the N minus one and you do what you call this I call it the the pincher model because you're going after two different

people and trying to get them together.

It's actually called the pinser 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 these are the two layers you want to be targeting in landing that meeting because if you go any further than that

you risk they're not going to 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 because now

right? Which is super risky because now you're learning about user value, not executive value. And a $100,000 deal

executive value. And a $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.

Wow. This is there's going to be fractals of questions and things 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 going to try to summarize a

things. I'm going to try to summarize a couple of these tips and then I have a follow-up question. Okay. So tip one is

follow-up question. Okay. So tip one is go after either the exact. So, in this case, it' be general counsel, head of legal sort of person or N minus one.

Love that way of describing it. Maybe a

VP. Uh, you want to 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 for them.

Love that. Um, and it sounds like they're still like here's the problem we solve for you, but here's like really the alpha we unlock.

Correct. Because 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 going to make we're going to alleviate, you know, the the time it takes to do X activity. That's not big enough. They

activity. That's not big enough. They

want like they're like a founder two of their own business unit. Like you got to sell the vision and what are these people going to how are they going to get to the next stage? um whether with their influence, get more budget, get

more people um however they want to define that.

Yeah. So it it sounds like you don't want to like they want to win and to win you need something unfair unfair advantage. That's exactly what you're

advantage. That's exactly what you're pitching. That's exactly right. Yep.

pitching. That's exactly right. Yep.

Okay. And then this Pinsir move I so the idea here is for the exact say chief legal officer general counsel foundry needs to reach out. Yep.

And then this AE reaches out to the N minus one contact and you do this, you go from both directions.

Y and I imagine the goal is one of them at least responds.

That's correct. And then and then 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 going to 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 going to bring in my founder. Could

we see if your boss might want to be a part of this, too? It's that parody of um of uh kind of rule.

Yeah. Uh and they might be like, "Wait, I've heard of that. I think I heard that name before because I got this other email."

email." Exactly.

May not remember.

Okay. Two questions. Um how do you find this N minus one person? Any just

tricks? Is it just sitting on LinkedIn kind of figuring out? And then two is any channel recommendations these days?

Like what's the best way to try to contact these people? So I'll use you can ask you can spar with open AI and anthropic to like let them do the quick scan of like hey I'm looking to target

the chief legal officer of SpaceX and their deputy who are possibly people I should be targeting and then go off that and do your own gut check and search from there but usually they'll give you

the the the proper names. Now here's the interesting thing about this. Everyone

is probably also targeting those people.

Okay? And this is why you need to be, and we talked about this in other episodes, it needs to feel so different and it needs to be about alpha. And if

you don't have executive value, meaning you cannot get an executive exc excited by your value proposition, then you probably shouldn't be moving up into the enterprise doing a top down strategy.

Got it. Okay. And then in terms of trying to reach out to them, any tips?

Is it like the tools there to do to figure out their number, whatever?

They're all so unique. Cold calling

works.

Again, it depends on the role. You're

not going to cold call a highly technical person, but a non-technical person like it works. Email, LinkedIn,

Twitter.

Are there tools to find these emails and things? Like, is there something you

things? Like, is there something you recommend?

Yeah, you can get like there's a ton of tools that do uh that do enrichment. Um

I also like I'll try like LinkedIn first and say, "Hey, I shot you a note on on LinkedIn. I just want to make sure you

LinkedIn. I just want to make sure you got it." Like most people don't check

got it." Like most people don't check that on a daily basis, but yeah. I mean

you you have like um len list and all sorts of these enrichment tools that can give you the email but I think the number one thing is assume they are

getting hit with hundreds of emails how are you going to message your storyline to stand out and that's that's not easy to do and that's really why I think having going back to our first episode

why founder led sales is so important to figure that piece out. So that was my next question is what are some examples of two to three sentences if you have some in your head maybe even from your current job that that you think are good

examples of this two to three sentence pitch.

Yeah I think it comes down to like what is the differentiator to what you were offering not even like what do you do 10x better because to them it still sounds like a commodity. How are you

rethinking the business model? How can

you help them rethink the way that they're structuring their team? We're in

this like flood the zone moment of like everyone trying to break into the enterprise and the number one thing that breaks into the enterprise is like oh the way I'm modeling my business unit here's how I

should be thinking about it in the age of AI and it needs to be different it can't just be like oh like we'll help you reduce the number of resources here

like no no no like how are they going to show needlemoving impact to their COO CEO you if they were to bring it to the board meeting like what would they say

about the product this product will allow me to do what that's like the litmus test is this a pitch that you iterate on over time because it's pro you know you're probably getting some percentage of people responding so okay so the advice is like keep try to refrain this

that's exactly right awesome okay anything else on the first reach out before we get to the next step no I think that's good okay okay let's do it I started shaking your head before you said it in case

people are confused okay uh step two step two is basically running the intro call 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

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 super informal. Don't show them anything. Don't show them a demo. Don't

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

them. Have a one-on-one dialogue for 30 minutes.

Okay? Now, again, if they're bringing in a seuite executive, you better have your founder join that call as well. I don't

know any founder that wouldn't want to be in the room with a Fortune 100 seuite executive. So, make sure you bring in

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 out.

Okay, like super brief. Hey, this is how I typically open. Hey, I'm going to keep this super informal. I don't even know if we need a full 30 minutes. Put them

on the back for 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 want to 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?

first. Give yourself the edge, right?

Because if the more information you are receiving before you speak, the more you can frame it and and tighten it to what they specifically care about. So

and they also aren't like sitting there now listening to a pitcher like everybody.

Yeah. Exactly. Now they're talking. Now

they're conversing. Now it's like, okay, now it's fun. Now this person's not pitching me. I'm in a conversation and a

pitching me. I'm in a conversation and a dialogue. Okay. So now you're talking to

dialogue. Okay. So now you're talking to them and they usually they usually do a very brief over and they're like, "Hey, um, we didn't get a chance to look up the chief legal officers 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

blah." Okay, okay, great. They usually

don't give you much. So they say, "Okay, interesting." Like how are you thinking

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?

2027? Like does anything need to change?

Like ask does anything need to change?

Because again, what they're going to usually default to is what conversations have have happened above them and have been transcended down. So the change is usually dictated

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

all. And that's when they start to open up. And again, you don't want to be too

up. And again, you don't want to 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 inhouse and rely less rely far less on external law firms, right? Because

now we have more tools and capabilities.

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 you're trying to understand like how mature is this thought, right? Okay. So now they're

thought, right? Okay. So now they're they're going in and they say they can't really answer that fully because 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 want to 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 want to structure their team. So now you're getting all of

their team. So now you're getting all of this information about where they want to go, right? How 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

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 to that. Do not bring a recorder to this call. Do not record the call. They will not be open. They

the call. They will not be open. They

will not be vulnerable. It might assume it's being recorded because I think everyone kind of operates under that assumption right now. But for the benefit of yourself, do not have a

recorder present. Okay? like off the

recorder present. Okay? 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 or like what do you want to own or like what's the chronological like keep digging digging dig 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 other. 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

pitch. Okay. I will confirm every single conversation I have this 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

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.

That last part seems really hard to adjust and make up like here's what you're focusing on and here's how product is going to solve that problem for you. So that's kind of where that

for you. So that's kind of where that art and skill comes in.

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 another call. The

most successful salespeople are not trained salespeople. That's why founders

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?

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.

What percentage of the time are you just like, "Okay, this isn't actually going to help you that much." So, just we'll share we're up to Okay, you're nodding that happens.

One I would say two to three out of every four calls there's something real.

One there's something real.

Yeah, there's something real. 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 going to 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

talk to. Okay. Um and your job is also to quickly um quickly disqualify someone. And it's probably one in every

someone. And it's probably one in every four calls.

Awesome.

Simply because of maturity.

Cool. So you don't have to have this like intense pressure to nail it on every call and here's the here's the pitch. Okay. Awesome. What I also want

pitch. Okay. Awesome. What I also want to comment on is this idea of like getting them to share a bunch. It may

feel tricky like you're tricking them into sharing all this, but really they have problems they want to solve and you're there to help them solve a problem. And so why would they not want

problem. And so why would they not want to just like, okay, here's what we need help with. Here's the problem. Here's

help with. Here's the problem. Here's

our priority. Their job is to their job is to buy solutions to these problems, right? That's why they have budgets,

right? That's why they have budgets, right? Um so that's why the the and the

right? Um so that's why the the and the the fastest way to commoditize yourself is to go into some sales script like budget, authority, need, timing like that should be in the back of your brain. You never actually ask those

brain. You never actually ask those questions.

Cool. Okay. So the core kind of lesson here is focus on learning and extracting their priorities. And what I felt as you

their priorities. And what I felt as you push them to get more real and and like really pressure test how big of a deal are these? Why are this why is this

are these? Why are this why is this important?

Because you want them to ask you those questions cuz that's when you know you're building a relationship. Like I

like I had a client last week say to me, "What's the biggest learning your team has had this year?" Like every product needs to get better. Every product has a bug. Every product, you know, isn't able

bug. Every product, you know, isn't able to do X or Y um as well as they said.

And they're and I'm like that's a really good I'm like that's so funny. We just

had a conversation about that and I she was like thank you for sharing that's they just want to know you're vulnerable because then it doesn't feel like it feels less like sales.

I imagine um priorities for a lot of companies these days is saving token costs.

I know classically you don't want to focus on lowering costs as a sales pitch. This is the cheaper option. Yeah.

pitch. This is the cheaper option. Yeah.

Thoughts on if that just comes up a bunch. We just like legal we just need

bunch. We just like legal we just need to save costs.

Yeah. So, in pricing, their job is to there's going to there's usually going to be two motions. I need the lowest cost way to do X because it's low on the totem pole and I really don't care if

it's 60% of the way there. No one's

getting fired over it. I'd rather just save budget or you're solving a problem that you can charge, you know, 250 500k

land because the pro because it is a um uh high risk if you're dealing with legal, there's high risk to it, right?

Missing information, being delayed on something, um uh not having people understand the importance of some new

regulation or or law.

um uh not being buttoned up. Um so I think for if you every organization looks differently right like marketing needs to have needs to prod you know

marketing and sales it's very clear that number numbers drive them for legal it's probably they they need to stomp out risk.

Awesome. So yeah basically this comes back to the idea of alpha and upside.

The more you can be in that bucket the more you can charge the easier everything gets.

Okay. Uh, anything else before we get to step three?

No, I think for step one like that that that is the most important meeting and I feel like people just spend so much time talking about themselves and miss all the competitive advantage to win the deal.

Yeah, your point about how as a buyer it's so like low pressure at that point.

You're just exploring and so I could see why people come into it like cool, let's learn. Let's see if this versus you're

learn. Let's see if this versus you're in the funnel like oh I gota actually make a decision. I'm gonna have to let them down if I don't want this.

Yeah, that's like dating.

Yeah, like their openness to share more start to clam up a little bit more. But

we'll talk about how to make sure that doesn't happen, too.

Amazing. Okay, great. Great

foreshadowing. Okay, so step three is writing a follow-up intro call.

Yes. Okay,

so usually right now the stages that most people have is intro, demo, proposal, contracting, you know, close one or close loss.

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

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 you lost your

leverage to like organize that group and rally them. But more importantly, it you

rally them. But more importantly, it you never want it to feel like one person's baby, right? If you're selling to that

baby, right? If you're selling to that director or that VP, you need to make sure that that executive feels like they're part it's part of their baby and they're helping craft and they have their fingerprints on it. And vice

versa, like you want the seuite if they they want they want their the actual users to feel like that they were bought in on this, too. Okay? So, you want to make this to be and this is the tricky

part. You want it to you there's going

part. You want it to you there's going to be someone that's going to champion it and get the deal done, but you got to make it feel like a group effort. Okay? So, the person that you

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 seauite executive or um one step removed. I say champion, mo most champions are one step removed. But

let's just say the sea suite executive has delegated this now to the champion to to to navigate. Okay. for that demo call. Now with now before you do the

call. Now with 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

call. I think that there is a great opportunity to get to, you know, support you guys. This call should be 15

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 want to make sure we have the right people in the room and I'm demoing the

right things. Can you help me understand

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 we when we demo to this group at this point I want this question to be asked. can you ask this question in the

asked. can you ask this question in the meeting because I want them to understand the value and they'll be like I'm actually going to ask this question because it's going to 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 are 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

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

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 just mapped out the story line with an internal partner on their end and now you're now you have the names of the right people. Now

you're going to 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.

hour. The demo should be an hour. Okay.

Now, you can ask before this meeting, do we want to 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? Um or should we just do the group demo? Like, they know their

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 want to bring in someone else before the big group. If they're like, "No, no, no.

big group. If they're like, "No, no, no.

this is something we want to, 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 want to go into pre-demo? Do we want to assume they

into pre-demo? Do we want to assume they checked off pre-demo or do we want to do group demo?

How often does that pre-demo happen?

If you're I mean, I try and push for it because again, it's just more intel.

Yeah. So, let's say let's assume there's a pre-demo.

Okay. So now you have a new colleague on the phone and you could say, "Hey, I'm going to for five minutes I'm just going to catch you up on the the things that I just learned from soand 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

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 problem. Or worse, a enterprise

problem. 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. You're either a

people?" Don't do it. You're either a checkbox and you don't want you want to 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.

Enterprise deals are one on this feels so close to who we are. It feels like it was built specifically for me. That's

the whole game.

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

conversation. It also feels like a lot of this process is you getting alpha from the team. I don't know if alpha is the right word, but No, it is. It's information edge. Yeah.

It's the information edge that whoever I'm up against is not getting and you have to assume in in the enterprise, you're always up against something. You're up against not doing

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, right? Most likely the incumbent. But it's so crazy to me how

incumbent. But it's so crazy to me how many people just like spew out a pitch with like no you also have to make an

informal and fun like you need to you know um people also buy from people they like right I love how so far at least it feels very

doable not that difficult feels like I could do this uh absolutely and and it doesn't feel like it takes that much time to do any of these steps so far it's like a call learn some stuff think

about 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?

Yeah. So I will I spend so much time thinking about what read in between the lines of what they were saying and that's when I will follow up like those

those kind of pre preun 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 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

prompting. It's the whole It's like prompting humans at this point, right?

Like go deeper and deeper and deeper and the answers you're going to get are just going to get so much more refined. The

whole game is to slow down to go fast.

All of this should be should be within a 90day sales cycle based off of their maturity.

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.

Or you're stuck at you just sold the enterprise on a $15,000 solution, which goes you where do you how do you expand that? The whole game is expansion. If

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.

Okay. So, just to kind of quickly summarize, we're at step one, landing the meeting.

Yep.

Then running the intro call. Then

there's this follow-up intro call which you pointed out is often ignored and a big opportunity to improve the demo. I love the way you describe the

demo. I love the way you describe the demo. It's kind of this carrot that

demo. It's kind of this carrot that you're holding that you can use a little bit to kind of extract more.

Yeah. And then there's step four is prepping the pitch and framing the demo.

Yeah.

Um is there more to share there?

No, I think I think we're at the point where it's like, okay, now you're running a big demo, right?

Cool. Yes.

So now you have you now you have all of the people involved in the demo. You

might have somebody that's involved from their AI team that's going to support some some roll out. 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 now you're running the

it. Okay, so now you're running the demo. Now you're before that demo on

demo. Now you're before that demo on that on one of those calls, who are all these people? What do they care about?

these people? What do they care about?

And what should I avoid? Like 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

forward. Now it's now they now this is like a great star for them of like, I found this amazing tool. It's going to 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

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? I 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 going to be people that were not a part of any of these calls. Okay? Your job is to take a

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

are. Here's why we are doing what we are doing. And it's fully in their frame.

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 this was built for us." Sorry for my French.

Now they're now they're like leaning in being like, "Okay, all right. Somebody,

this is very aligned with what we need."

Because they have no idea. You've talked

to all these people. No idea. Learn what

their challenges are.

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

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.

She was like, "Wow, these guys are good." Okay. All right. These are So now

good." Okay. All right. These are So now you could, you know, let them talk. Let

these net new people talk. Be like,

"Hey, I know you I know we haven't had a chance to speak. Like, what do you want to get out of the demo today? I want to 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 cuz 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 I don't know if we want to 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? Because 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 like

it's it's stuff that is is doable. I

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bank. banking services provided through Choice Financial Group and column NA members FDIC. How do you deal with

members FDIC. How do you deal with someone that's just kind of taking things off track or or just talking too long? I imagine that's just like, you

long? I imagine that's just like, you know, a skill in an arc, but just any tips there.

The good news is is that most senior people, like the people that you're going to 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

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 an executive level. Um now of course

executive level. Um now of course there's sometimes where there's people that meander. You could say, "I love

that meander. You could say, "I love this conversation. Can we park it

this conversation. Can we park it because I actually want to 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.

Awesome. So there's kind of two people that might be leading this. Might be the founder if you're still doing founder sales. could be the AE VP of sales that

sales. could be the AE VP of sales that VP of sales. Yep.

Okay. As say you're say you're not the founder and you're and you're the VP of sales or and leaving 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 I should release everything?

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 going to be demoing, why they're going to be demoing it, and how they're going to open it?

The demo looks different every single time. Every single time. I don't think

time. Every single time. I don't think I've ever run a demo and it looks the same. This is like when everyone comes

same. This is like when everyone comes back to like, okay, what's the scaled playbook? What's the scaled approach

playbook? What's the scaled approach with this? When you're selling $100,000

with this? When you're selling $100,000 minimum, right? Again, it's the same

minimum, right? Again, it's the same effort is selling a million dollars. So,

it could be selling a million dollar deal.

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 got to take a

be different. You've got to take a different approach. It is not cram the

different approach. It is not cram the pitch down their throat and hope that they want to buy something.

Feels like a job AI will not replace anytime soon from here.

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

right? Like do you vibe with this person? I mean I've I've definitely

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

that's okay. It was just that happens. It's such an in a point

that happens. It's such an in a point I've never heard before. This idea of when you're demoing, demo kind of as narrow a slice of the product as you can that addresses their 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.

Or let them guide you like can it also do this and 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 want to feel like it was built for them and that um it's

different and they get alpha and get alpha.

Okay. Uh so step six uh you call the post demo discussion.

Yes.

Also something you say everyone ignores.

Yes. Talk about that.

Okay. So as soon as the demo closes, you are texting the woman or the gentleman or whomever that has helped guide you to this point. How do you think that went?

this point. How do you think that went?

Can we grab can I call you in like five minutes? I just want to I want like a

minutes? I just want to I want like a fresh debrief.

They will give you and be like raw reaction. I know you haven't spoken to

reaction. I know you haven't spoken to anyone. What do you think? How do you

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 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 going to kill a deal. there's always somebody.

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 3 weeks, you can now prompt with,

hey, I know you guys are in still in the process of like thinking through if this makes sense. Do you think it's worthy if

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 want to see it.

So you're just always looking for ways this might explode and not work and and this person that you're working with would you call them um what was the term you use for them?

Champion the champion.

Yeah. Because the champion can also be an executive, right?

Yeah. And they may and they're like excited at this point in theory very excited for this to work out like they're on your on your side. They're

not trying to and I define champion is who is the individual that really wants this to come to life that's like was there from day one not necessarily like the person

that like the seuite executive could be the one shephering this well but they need to make sure that the people below them are brought in.

Okay. Anything else around the demo or the post demo discussion before we move on to the next step?

No, I think we're good.

Okay. So the next step uh you call identifying pilot move forward process.

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 time on hey I want you guys to go in for two to three days these specific users don't put the do not put your sea 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 run don't chart 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 2 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 even if it's not on their own data.

So this isn't yet the pilot this is just like prepping for the actual correct. So there's two different pilots

correct. So there's two different pilots you can run. 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

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.

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

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 charge 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 going to come out as services anyway because it's like a 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.

I'm definitely feeling the feeling I feel when we chat is like I just want to find something to sell. This is really It's fun. It's so fun. Like, it's

It's fun. It's so fun. Like, it's

literally so fun. People

I think people read these sales books, go to these sales trainings and they they they make 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."

sauce." 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 Yeah. speed rock.

Yeah. speed rock.

It feels more real. Yeah. 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 because that feels tough.

So I would say here this is what we typically do. Who are the three or four

typically do. Who are the three or four people we want to put in and assess the assess the value from a user perspective. Okay. Make sure it's your

perspective. Okay. Make sure it's your person right assuming that it's no or or the person closest to the se don't put your seuite executive in it. They're not

going to they're not going to go into the product. And then two or three other

the product. And then two or three other people. Okay. And I want you to say,

people. Okay. And I want you to say, we're going to do two or three days. I'm

gonna onboard you each differently.

We're going to 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

specific tasks. Be very, very thoughtful and explicit and descriptive with what you want them to do.

Okay, here's how we're going to measure success. Define that with them. Define

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 buildout.

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, and help them discover the magic.

Release it.

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

it." Great. Of in that three-stage process, you just what did what didn't you like? What wasn't clear? What wasn't

you like? What wasn't clear? What wasn't

obvious? Where did you get lost? The

tighter it is, less people get lost. The

more the more um grounded it feels and the more consistent the experiences. You

don't want people having different experiences.

Okay. So, just to make it clear the steps involved here because we've gone through, I think, three kind of around the scene.

So much. Yeah. We've gone through so much. So, we're kind of on step nine.

much. So, we're kind of on step nine.

So, there's step seven, which is identifying the pilot, move forward process. A lot of people ignore just

process. A lot of people ignore just like y who that person is and what the steps are. Then there's prep for the pilot and

are. Then there's prep for the pilot and then there's run the pilot.

Run the pilot. Exactly.

We've kind of talked through all these things.

Now, is there anything else? Yeah.

For prep for the pilot, the one thing I want to 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.

Ahead of time. Before doing the Yes. Ahead of it. Um I should have

Yes. Ahead of it. Um I should have clarified that this is all before before the before the people's pilots start.

This is in the pre-pilot stage. Okay.

Assuming fingers crossed a successful pilot, which I feel confident is going to be. Um one is when do we want to get

to be. Um one is when do we want to get signatures on these papers? Let's work

backwards from there. Do we think we can get this closed by the end of next month?

Yes, I do. Great. Who needs to be involved in that? like do you have a procurement lead that we should be educated in this process and they might say let's wait till after the p totally but like push them a little bit again

you're project managing it um is there a security lead we should be working with to run due diligence on the product um is there someone in legal or is there a way for me to draft the paper to make

this make sense now the one thing I'm going to take a step back on is you would have already gone through pricing discussions with them post demo

okay try to hold out on talking about pricing until post demo because you might they might assume, oh, this is three times what I'm spending and not know why it's three times, right?

Because there's all these other people that might not have been involved in those initial discussions. Talk through

pricing post-pilot once everyone's excited.

Post-pilot or post demo, right? Post demo. I apologize.

right? Post demo. I apologize.

Okay, cool. Yeah.

So, and so you basically just kind of tell them, let's we'll figure out pricing once we understand what you're looking for.

This is in the pre-pilot stage. Talk

about pricing.

Okay. Now, if they're this far along, they you like if they're really concerned about pricing, they would have brought it up by now, right? So, these

are like the little cues like, "Okay, I think I could probably push them a little bit here, right?" Or like go a little bit further. Uh two is um if they ask and they push, give them a ballpark.

Well, it depends, but like let's say it's somewhere between 150 and 250 and there's a lot of dependence on that, right? Um so, you can give them a

right? Um so, you can give them a ballpark, but work with your champion to say, "Listen, here's what the price is."

Um, you I know you know why we price it this way. Where

this way. Where before you put this in front of anybody, h how are you going to make the case?

Right? Like where are you going to cut?

How are you going to defend it? How can

I build out a slide to defend this for you and show you the ROI?

Let them. They will tell you. You don't

have to go blind into it.

And then if they come and then say, "Okay," and if they push back and they're like, "Listen, I don't know if I can go to bat for this." Be like, "I hear you. Let's let's work on this

hear you. Let's let's work on this together. How can what do you feel

together. How can what do you feel comfortable going to bat with? And can

we do a step up for year two to get to the actual full value of what we know we charge?"

charge?" And do you include the slide or the price in the demo or is that like a post demo conversation? they push you to do

demo conversation? they push you to do it, give a ballpark, but do pricing one-on-one with the individual you've been working with because they will help. They might say, "Okay, I think this is I think I think

we're all aligned." This is what's usually going to happen. There's three

answers. We're all aligned. I'm not too concerned about this.

I don't know if I feel comfortable going to bat with this number. That's when you say, "Okay, I hear you. Let's take a step back. Let's figure out how to make

step back. Let's figure out how to make this work."

this work." Don't say you're going to discount.

Don't throw out numbers. Be like, I want you to I need your help to tell me how to make this work. Now, this is the one part where you want to put it on them because they might come back and say,

"Is there any way we can cut 20K?" And

you're like, "Oh, I would have gone much lower than that." Right? You don't want to negotiate with yourself.

But work with them. You've gotten to this point. You've shown so many people.

this point. You've shown so many people.

Everyone's excited.

This is when you know you can win them over through the um the co-authorship.

And remember, you can always do the full value in year two and sign a two-year deal.

Awesome. The expand.

Okay. So, in the pilot step, do you how many people do you give access to the pilot? Any advice there?

pilot? Any advice there?

Three. Three to four.

Okay. So, very small.

Very small. Very tight. Who are the power users? Who are the people that are

power users? Who are the people that are going to be in on a daily level? You

don't want everyone in there. You want

it to feel like they're buying into it too, not like the same people and the same, but you do want your in that one individual that's been giving you all this intel to be part of the pilot

because you want them to get you prepped for everything. So before we get to the

for everything. So before we get to the next step which is post-pilot discussion and session uh I imagine many products especially today just take a lot of

integration work and data ingestion and you know all that stuff this whole FTE emergence um thoughts there if your product is just like wow it's going to take us a month to even get you onboarded

and that's that when we when we talked about those two different pilots there's like hey we can show you the value in two to three days or it's the hey we have to show you the value in 30 days

for a 30-day value charge and credit it back to them, but know that your sales cycle is going to probably be a month longer because of that. But that's okay because you're probably charging more anyway.

Got it. And just do the work to like integrate enough to make it your price should be predicated on your sales cycle, right? Like if you can get a deal done in 90 days for 100K, do that all the time,

right? If it takes nine months to get a

right? If it takes nine months to get a deal done, you got you probably should be charging 250 300K. What are your thoughts on uh Ford deployed engineers as a part of this process just as a role?

My opinions sway back and forth like is a Ford deployed engineer there because the product's super hard to navigate or is it there because you're taking the

work off their plate?

I think people use them. I'm all about it if it's taking the work off their plate and accelerating and controlling the situation all day every day. But is

it are you using um a forward deployed engineer because your product's so gnarly and hard to hard to do like they can't do it on their own. Um it's a bad sign.

Yeah.

Yeah. I feel like like the original idea of Ford to play engineer and the Palunteer guys talk about this like the original idea was they work at a comp inside of your company building custom

software for you to solve your problems and then they figure out how to make that a a broad product they can sell to other people.

Totally. And I think that an FDE is great for an expansion for a land on okay if you're talking about like a palunteer where it's much more complex

to like I understand why they did that.

Right. But they're also charging multi-million dollar deals.

That's right.

Right. So like the the the business model structure supports that. If you're

selling a $100,000 deal and you're pulling a four deploy like your economics are it's going to get messy.

just like you will not make money if you have a full-time engineer salesperson sitting there working on this and you know I I think I also know like there's a lot of folks in like account management whose job is to service and

and up you know expand and upsell and they just take on the title of FDE so they're just another salesperson.

Yeah, it's just a nice Yeah, it's a cool title. I think the Palunteer people

title. I think the Palunteer people called uh FDs at most companies sparkling sales engineers.

That's awesome.

Yeah.

Okay. Uh, anything else on the pilot up to the pilot step before we get to the post session?

Yeah, I think because now you've talked about like the timeline to if this is successful, what does that look like?

Again, you want to run this before you put everyone in it because you might want to push out the pilot. If they're

like, hey, listen, this is probably going to be another quarter. Well, put

the people in the pilot now because now you've lost all the you need the momentum to continue. You need the steps to happen. So, use that. Hey, if this is

to happen. So, use that. Hey, if this is successful pilot, how far out are we from like a commitment from you guys?

Oh, I see. Commitment. So, there's like the commitment and also just which is equivalent to rolling it out to the company. That's exactly

company. That's exactly if they're not ready in a month to roll this out if this is a huge success, then wait on doing correct. Yeah.

correct. Yeah.

Awesome. Because you're saying you may lose that momentum and Yeah. You like you've already exhausted

Yeah. You like you've already exhausted all the stages. Um, you don't want to do that. You want the stages to align with

that. You want the stages to align with how they're thinking, but you want a project management as tightly as you can. And some it's out of your control,

can. And some it's out of your control, but yeah.

And yeah, it's not like you can push them to deploy it broadly. That's like a thing that is probably very hard to Yeah.

to shift. So, so yeah, so understanding that and working with that seems really important. Okay. So, step 10. And again,

important. Okay. So, step 10. And again,

uh, as you pointed out at the beginning, most people think the sales process is five steps. And we're already in step

five steps. And we're already in step 10, and we're not even done.

And you made this point actually before we started recording that you haven't touched on that I think is important to share this idea of that these five steps kind of emerged out of like a CRM pipeline kind of check thing. Talk a bit about that.

Yeah, so everyone knows the traditional five steps. Intro, demo, proposal,

five steps. Intro, demo, proposal, contracting, and then like closed winner or close loss, right? Those are like the the typical or maybe there's like some

variation of that. Like that's not how you run the sales. Those are buckets to understand how to understand a weighted forecast,

right? Like a proposal or something

right? Like a proposal or something midfunnel might be weighted at 50% of the deal value for the for the um for the pipeline. Something in contracting

the pipeline. Something in contracting might be weighted at 80% and something in intro might be weighted at 10%.

That's what those stages are for. That's

not the stages you take a client through. Like those are just the broad

through. Like those are just the broad buckets.

Um, and I think a lot of people use those buckets to say, okay, I'm 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 want to have more of those upfront meetings. Um, and you want to

upfront meetings. Um, and you want to make sure you know who the executive sponsor is and all that. You always want to know who the executive sponsor is, but like for a 100k deal, you probably can accelerate it a little faster.

Again, ensuring that they're qualified.

And 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?

90%.

Wow.

Yeah. Because like enterprise sales is it's it's it's mirroring their buying process. It's trying to control their

process. It's trying to control their buying process. It's not plopping these

buying process. It's not plopping these people into your sales process.

Amazing.

Yeah.

Okay, let's keep going. Step 10,

postpilot session.

Yes. Um, you can send a survey. They

might want to 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

this. Or you can have your champion internally discuss and say, "Hey, how was that?" Okay, you need to make sure

was that?" Okay, you need to make sure that you are mirroring their experience, right? From a technical perspective,

right? From a technical perspective, like how much time did they spend in the product? Did they run into any bugs?

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 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. 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 be but

they're doing. You shouldn't even be but like they didn't get past step one. Do

you want to can you check in on them and making sure like they're having a good experience?" like use your champion to

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 a people that will kill the deal then you got to deal with procurement then you got to deal with legal then you got

to 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 on the project management and the individual on

the inside. That's your key.

the inside. That's your key.

So funny. So many ways it could all fall apart.

Yeah.

Um what I was going to say is it feels like many people would naturally like they don't want they want to avoid confrontation. They won't want to say

confrontation. They won't want to say this is not going to be we don't want this. They're going to probably be like

this. They're going to probably be like it's fine. It's good. It's good. Oh

it's fine. It's good. It's good. Oh

yeah. Everything's

like PCs.

That's right. That's right. And so it feels like a lot of this process is to like pull out. 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 when you're in this is why your internal champion is so important. When they go quiet on you, that's when you know

that's why this individual and listen, this individual is going to 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 repick

this back up." That's why having someone on the inside is so so so critical.

And yeah, the easier pro the easier approach is just to stop responding and just hope that they the salesperson understands or a little not excited.

Oh man. Okay. What are like the benchmarks for like how how often do you get through each of these stages? You

mentioned like a few just like Yeah.

From demo to the stage.

Usually once a once something is qualified, meaning you're speaking to the right person, they are excited by the alpha. that they they admit that

the alpha. that 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

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 is actually probably going to surprise you. It's not 50%.

Meaning of all qu sales qualified leads or opportunities a healthy win rate is usually around 30 to 35%.

From qualified lead to qualified signed contract meaning you speak to a 100 you're closing anywhere between 30 to 35 maybe

slightly less maybe 25 to 30 that seems high actually. Yeah 25 to somewhere

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 are all the chasms. And the implication here is it's better off keeping your price high than winning more often.

Yes. Because the market talks too. The

worst thing you can do is charge somebody's friend 50 and somebody else 500k.

They talk people the market talks. You

have to assume that.

Yeah. I'm in a lot of a lot of WhatsApp groups with founders and they do exactly that. What kind of deal do you get for

that. What kind of deal do you get for this this product?

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 deals to not advance right but to a healthy win rate in the enterprise is

typically I would say between 25 and 35%. Okay, that is incredibly helpful to

35%. Okay, that is incredibly helpful to people. A I know. Uh how about like key

people. A I know. Uh how about like key stages along the way just like percentage drop off up and so it's usually like from qualified lead

to like um you're coming out of demo it's probably you'd lose half and then out of demo.

Out of demo. Yeah. And then

post demo. Yeah.

That gets you to 30%. So from demo to what was that step that you from demo to like the more you move down a little the less those numbers uh the less um wider those numbers. So like,

okay, so like let's say if you speak to um and you're doing a really good job targeting the right people, maybe

uh 70 50% of those people move to a qualified lead or 50 to 75% move to qualified lead. Of that then um another

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 good deal qualification, so say you're at the pilot stage, what percentage should you expect? Drop off

and 20 80% succeed post pilot.

Correct. Yeah. Okay. Amazing.

I find that. Yeah.

Okay. So, if you're below that, something's wrong with your pilot.

Yeah. Or you're not qualifying clearly or I see. Yeah.

You're almost doing too good a job convincing them this is the thing for them.

Correct. And the product's not there.

Correct. So, yeah, that that's where and again like smart buyers always want to do a pilot. So, just have it part of your process.

Okay, there's four more steps to go before you're done before the money's wired. Um, okay. So, step 11, papering

wired. Um, okay. So, step 11, papering prep, setting timeline for procurement.

Yes. So, you have now um spoken pre pilot about the timeline of what we're reverse engineering. Now, you're going

reverse engineering. Now, you're going to document into 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

they give them something. Here's the um kicker they're going to give us if we if we get to this date. Um there's always got to be a reason to create urgency.

And then what you want to do is say here's our paper. Send a word document.

Do not send a PDF because they're going to always redline. Always send a word document of your paper and ask the question, do you want to use our paper?

Here's a word doc version. or do you want to lift from it and do you want to 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 isn't there because they might say, "Well, in order for us to hit that time, we got to use our paper and it's not Google Docs. It's Word

Google, like Microsoft Office, Microsoft Word." Yeah. Not most of these

Microsoft Word." Yeah. Not most of these people can't access Google Docs. But

yes, and so this says postpilot feels like it's gone well. Um, you're saying the next step is here's like the contract basically get that to procurement that early

and again your internal champion is is you're working from N minus one from the exe from the executive sponsor or it's the executive sponsor themselves. You

you wouldn't have made it that they're not going to put their team into a pilot if it doesn't have legs.

And I an implication here is procurement is a way that your deal might still die even if people internally love your product.

Correct. if if you get sent to procure.

So here's here's something interesting a lot of people don't realize people will use procurement as the excuse to not want to give you um the the bad feedback. Oh, uh, I got to go talk. Oh,

feedback. Oh, uh, I got to go talk. Oh,

it procurement. It's it's it's lost in procurement orah, 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.

Start work meaning implementing rolling out people on boarding. 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

procurement. kind of getting on board with like what is it going to take to sign by the state? 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.

Yes. The best thing you can do is they're going to send you back red lines. No question. If the red lines are

lines. No question. If the red lines are extensive, okay, go ahead and accept the things that are easy. The red lines are extensive. See if you can get legal on a

extensive. See if you can get legal on a call live and just talk through them.

That will accelerate your sales cycle versus a bunch of back and forth.

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 light. Can we jump on a a live call

red light. Can we jump on a a live call and just go through them?

Focus on the things that are going to impact the business and push in on those. Let the other stuff go if it's

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, comm legal team, have a lawyer look at their red lines.

I imagine most companies have a legal counsel.

Yes, I would hope. I would hope so. Yes.

Okay, cool. So, paper review. So, that's

reviewing basically. It's interesting

called the paper.

Um, is there like a more technical term for that? Like the

for that? Like the contract? I say paper. That's the That's

contract? I say paper. That's the That's like corpo language. Paper.

So interesting. Okay. Papering review.

Okay. Step 13. Papering procurement

process.

Yes. So this is where um we kind of talked about this. We kind of merged that conversation. This is when you are

that conversation. This is when you are getting the procurement league and that legal league on a live call to work through the questions or the things you cannot accept. Now remember,

cannot accept. Now remember, if they give you their paper, there's going to be a lot in there that you're going to need to redline.

Red line. They're expecting that.

They're just giving you the kitchen sink, right? Like if they ask for $10

sink, right? Like if they ask for $10 million of liability insurance as a smaller company, you can push back and be like, "Listen, your exposure with what we're doing is not that high." Or

maybe it might be and you need that, but you know, they're going to give you the kitchen sink. Know that it's all

kitchen sink. Know that it's all negotiable, but but pick battles. Pick your battles.

Yeah. Don't be afraid like the deal will fall apart if you see something in there.

At this point, the deal will not fall apart.

Um you just need to work closely with them to like make sure they understand where you're coming from. That's more

what it is.

Okay. Okay. And the final step, signature. Tada.

signature. Tada.

Yep.

Anything special there other than signing?

No, that's this is like the really exciting part, which is um just figuring out who the signatory is before it goes routed for signature so that you that your make sure your internal client

knows, you know, because sometimes it's the CFO. It's not the executive sponsor.

the CFO. It's not the executive sponsor.

Um and you just want to make sure you everyone knows who that individual is because if there's a delay, you just want to make sure they get pinged. Damn,

we did it, Jen. We did it. We got

through all the steps. We just signed a massive contract. Congratulations. Let's

massive contract. Congratulations. Let's

go. Steak, dinner, champagne. I don't

know what sales people do when they close a deal. Ding a bell. There's bells

often.

You know what we do? Okay, what's the next one?

That's it.

Because you're all you are in sales.

You're only as good as your pipeline.

Uh so fun. It must be the best feeling

so fun. It must be the best feeling after all this work.

It is. But then you're like, "Oh, now like literally the fuels is like 5 minutes and you're like back to work."

Yeah. And I imagine part of this is also how do we expand this deal?

100%.

Is there anything there just real quick just like how to start thinking about how this where this goes once the deal is signed?

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 want to build out you know do we want to charge for services again here's the other thing too services and I know

every company is an ARR recurring revenue focus but services is still the largest line item in budgets and so you're saying uh it's okay to offer services.

Yes. Yes.

Yeah.

Yeah. This has come up a number of times I think with Jason also Linen and and you just like the increasing like there's a rise in services being a part of software companies

to buy. It's what they know how to buy.

to buy. It's what they know how to buy.

They're so used to it. Consultants,

lawyers, you name it. Um

the the the the budget there's always budget for services.

Yeah. We talked about this last time, so we won't get too deep into it. Something

else I wanted to ask you kind of at the end here. Say you're a buyer and you're

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 want to disappoint. You don't want to drag you along. What are some things that people buying software products with working with a salesperson? How

should they communicate? What should

they be saying to kind of avoid disappointment?

Yeah, I would say as soon as humanly possible, explain why the timing is not right. It usually comes down to timing

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'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 and 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 want to start with selling the technology versus the services.

And if you talk about how it's not the right timing or not mature, I imagine the saleserson will try to prod you and push you to see if maybe you're not. So,

it's okay to just tell them what you think it's you know what 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 again you need to know if you're in a position to be able to say that.

Yeah.

But 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 because again use

out together? Because because again use the intel they've given you towards that.

And like interestingly you're talking to a lot of their competitors and you would think you have insight into okay here's what everyone else is doing in this space. Yeah, exactly. Or like, "Hey,

space. Yeah, exactly. Or like, "Hey, listen. On our first two calls, you you

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

change? No, we're just like in a weird spot. I'd be like, "Okay, listen.

spot. I'd be like, "Okay, listen.

Here's what we're going to 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 going to crush it for you.

I do not I don't want X to get in the way of that.

And there and then there's obviously they're going to 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

acquisition, right? And like bringing on net new vendors is just like not a priority right now. You just have to respect that too.

I love how this whole process a lot of listeners of this podcast are product managers, product people. It just feels very producty and product manager in terms of the organization and the step by step and just like or 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 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

points are. We're here to solve them like yeah unexpected.

We did it Jen. We did it. We going

through it all. Is there anything else?

Anything else we haven't touched on?

Anything else you want to I don't know leave listeners with before we wrap up?

We gave them a lot.

We did it.

which was the goal. Just the right amount.

Yeah.

Yeah.

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 in

conversation. Very rare these days in podcasts, which I love.

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 salesy.

What's your alpha? It always comes back to that.

Exactly.

And I know you talked about this last time, just like craft your own email and text. Don't

text. Don't don't use the boiler plate. Don't use

your AI.

Emails are living and breathing. I swear

to God that like people can read you saying the email out loud.

Yeah. Okay, Jen. Uh,

this is awesome.

This was amazing. everything I want it to be. This is going to be I'm excited

to be. This is going to be I'm excited for like the not to talk about but just like AI summary of this especially that's just going to be like step one here.

Yeah.

Uh final questions? Anything you want to plug? Anywhere you want to point people

plug? Anywhere you want to point people to and how can listeners be useful to you?

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.

Wow. And this is at state affairs.

This at state affairs.

Holy What an opportunity. Yeah. So

there's multiple roles, not just one.

Multiple roles. Yeah.

Wow. Uh you'll be paid to learn from Jen directly.

Yes. I will I will teach you everything I know.

Whoa. Okay, cool. We'll link to the job descriptions uh uh in the description if you want to check that out.

Awesome.

Amazing. Um, Jen, thank you so much for being Penny. This was awesome.

Penny. This was awesome.

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