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Jen Abel: How founder-led sales lands enterprise deals fast

Through counterintuitive cold outreach and vulnerable, learning-first calls; co-author scopes, navigate procurement, earn a repeatable enterprise motion.

Lenny RachitskyhostJen Abelguest
Nov 24, 20241h 16mWatch on YouTube ↗

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  1. 0:00 – 2:20

    Jen’s background

    1. LR

      (instrumental music plays) I've always wanted to create a very tactical episode on how to do sales, especially with a focus on founder-led sales.

    2. JA

      A lot of early stage founders get tripped up as they're taking late-stage sales advice. The founder is the product. You have studied, you have experienced something that most of the market hasn't even had a chance to maybe see or visualize yet.

    3. LR

      A billion SaaS tools emailing me constantly about their product, how do you get someone to even want to talk to you and be open to learning about what you're doing?

    4. JA

      So if you can focus the messaging in a way that speaks to something that is a bit of shock value, or is counterintuitive, you'll get them to continue reading. When a problem is truly being felt by the market, people will get on a call, people will respond.

    5. LR

      The next step, I imagine, is you're on the phone with them, trying to convince them to actually care. What do you do there? How do you get them to engage further?

    6. JA

      You need to be vulnerable. I would be very open and honest with where you are. "Hey, I'm an early stage startup. We have a lot to learn. Can we kind of gain your insight into, like, how this problem is manifesting on your side?" Founder-led sales is not about revenue on day one. It is about learning as fast as humanly possible to get to that pulse so that you can earn the right to sell.

    7. LR

      (instrumental music plays) Today my guest is Jen Abel. Jen is the co-founder of Jellyfish, where her and her team help early stage founders learn how to sell, do early customer discovery, and set up a repeatable sales motion. Prior to Jellyfish, Jen was an enterprise sales director at The Muse and at General Assembly, and she's obsessed with helping founders in the zero to one stage of their journey. In our conversation, we get extremely tactical and in the weeds on how to actually do sales as a founder. We talk through each step of the sales process, and Jen shares what you should be doing and saying at every step. We go through how to find your first set of leads, how to reach out to them, what to say in your message, how to structure your first sales call, how to get through procurement, and how to get that final signature. She shares actual words you should be using, and phrases, and structures, and pitfalls that most people run into at each of these steps. I've never heard a podcast episode with this much advice that you can put into practice tomorrow, and I am very excited to hear how it goes for you. If you enjoy this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube. It's the best way to avoid missing future episodes, and it helps the podcast tremendously. With that, I bring you Jen Abel.

  2. 2:20 – 8:24

    The importance of founder-led sales

    1. LR

      Jen, thank you so much for being here, and welcome to the podcast.

    2. JA

      Thanks, Lenny.

    3. LR

      What I've always wanted to do is to create a very tactical episode on how to do sales. Like, how to actually have sales conversations, how to find leads, how to close deals. Especially with a focus on founder-led sales, where founders are doing the early sales versus hiring a salesperson, which, one, I know you're a huge advocate of, and we'll talk about this, and two, you basically spend all your time working with founders and founding teams helping them learn how to do sales, how to set up their go-to-market motions, how to scale team, sales teams, how to hire salespeople. So, I am very excited to have you here to kind of create a very, like, in the weeds, hands-on episode-

    4. JA

      Yeah.

    5. LR

      ... on how to do sales. Uh, how does that sound, broadly?

    6. JA

      That, that sounds awesome, and thank you so much for having me, Lenny. I mean, it's a true pleasure to be here with you.

    7. LR

      It's my pleasure. Many people have recommended you come on this podcast. I'm excited we're doing this. Let me start with just this kind of question around founder-led sales. Maybe just briefly explain what that term means and then talk about why this is so important, why this is the way you recommend companies start doing sales.

    8. JA

      Founder-led sales is really that first milestone that a startup goes through on the commercial side, right? Which is how do I go out and get my first few customers? M- some people might say zero to one, which is, uh, t- how do I get my first million? Others might say, you know, how do I go out and get my first 10 customers? It's all kind of in the same vein. And founder-led sales is really, really, really important because in the very, very, very early days, when there is no brand equity, when there is no marketing engine running, when there is limited to no reference ability, the founder is the product, right? 'Cause the product m- is still, could be abstract, could be, you know, an MVP or really, really early, you know, um, in its really early formation. So the founder is the product, and when people say, "Well, what does that even mean?" It means that you are a subject matter expert on something highly specific. You have studied, you have experienced something that most of the market hasn't even, um, had a chance to, um, maybe see or visualize yet. So you have this, like, novel insight that you are building a business around, and it's that novel insight, and the way you see the world that gets the market excited, right? In absence of a product. And that's actually happens even before you even show the product. So founder-led sales is how do you bring the founder's vision into the world and have the market... And understand what part of the market accepts it, and then what part of that vision are they accepting? So it's aligning the founder's vision with the market reality.

    9. LR

      (instrumental music plays) This episode is brought to you by Brave Search. Brave Search is the private, independent search engine that doesn't bias or censor results. Brave Search and its Answers with AI feature are available for free to all users on desktop and mobile devices. With Brave Search, you get real answers faster, served from their own independent index of the web. Their AI search engine can give lightning fast, incredibly accurate results for almost any question. But Brave isn't just AI answers, it's also a powerful traditional search engine with real innovations versus big tech options. It fights bias and SEO spam. It brings a cleaner results page with fewer ads, Reddit threads in the search engine results page, powerful local results, and even community driven ranking options. Tired of Big Tech's same old list of links? It's time to try Brave Search. Visit brave.com/lenny to get started. That's brave.com/lenny.This episode is brought to you by Vanta. When it comes to ensuring your company has top-notch security practices, things get complicated fast. Now you can assess risk, secure the trust of your customers, and automate compliance for SOC 2, ISO 27001, HIPAA, and more with a single platform, Vanta. Vanta's market-leading, trust management platform helps you continuously monitor compliance alongside reporting and tracking risks. Plus, you can save hours by completing security questionnaires with Vanta AI. Join thousands of global companies that use Vanta to automate evidence collection, unify risk management, and streamline security reviews. Get $1,000 off Vanta when you go to vanta.com/lenny. That's V-A-N-T-A.com/lenny. And this is counter to what many founders hope is, "I'm just gonna hire a salesperson, they'll handle sales. I'll build a thing. I'll, I'll wait for them to find deals." And this is... Like, a lot of, a lot of people think this way, right? And this is... Founder-led sales is the movement of just, like, "No, no. You should be doing the sales for a long time as a founder."

    10. JA

      Absolutely. I mean, it is the competitive advantage. Like, I don't think people realize how much of a competitive advantage the founder-led sales motion is for three kind of specific reasons. One is, is that the founder is the visionary. No one's gonna be able to speak to it like they can. No salesperson. Really, no non-founder. The second is that they are the highest kind of order on the... In the hierarchy of the startup, right? It's the founder. So when the market... The market is excited to talk to a founder 'cause they usually know something that the market doesn't know and they wanna learn, and maybe they want to experience something differently. So being able to speak to the person that's running the vision, speak to the person that's crafted the vision. And then that third piece is, is that the founder can, you know, can see something budding in a conversation that a salesperson won't be able to see, right? And it's those budding moments, that's where all the gold lives, and I don't think a lot of founders realize that. Their day one market vision is never the same vision that takes them to product market fit, and I say that all the time. It's these, like, little budding moments where it's like I was able to get to that budding insight 'cause I went deeper and deeper and deeper and deeper through these calls and these conversations to fully refine how we wanna go out and sell

  3. 8:24 – 12:01

    The steps of a sales cycle

    1. JA

      it. And only a founder's gonna be able to see those things.

    2. LR

      I love this 'cause this connects really well with a episode I just did with the CMO of Wiz and the founders went through this exactly. They had all these convers-... They had 10 to 15 conversations a day for weeks, and then they're, like, realizing nobody... "People keep telling us this is... They like it, but no one's buying, no one's excited enough to want to actually move forward." And that was... Only happened 'cause the founders were on these calls.

    3. JA

      Yeah. And the... Yeah, I mean, the other thing too is that it becomes a game of telephone. It's like, "Hey, this sale- salesperson says that no one cares about this." What do you think the first thing the founder's gonna say is? It's the salesperson. So much easier to say that than, you know, "Is it me? Is it my vision?" So it also kind of brings the accountability, uh, closer to, um, the pulse where decisions are made.

    4. LR

      It's interesting how similar this is to product building, where there's this idea that a founder kind of top down can tell the team what to build and it's this very waterfall cycle, when in reality, the idea of the product and feature is just, like, step one, and then there's actually building it, testing it, talking to customers about it that actually turns that initial seed of an idea to the real thing that people want.

    5. JA

      Totally.

    6. LR

      Okay, so the catch-22, I don't know if that's the term here. The challenge is... Okay, so great. Founders should be doing sales. Most founders have never done sales. They just wanna build product. Uh, you know, they're, like, mostly product people, design people. Like, sometimes there's founders that are salespeople. Rarely is that the case in my experience. So, doing sales, very hard. Not something that comes naturally to a lot of people. A lot of people are very afraid of it. So with that, let's get into how to actually get better at the sales process. I think a nice, uh, framework for how we can go through this is basically first talk, let's talk about the sales cycle, like the steps, the key steps of a sales cycle.

    7. JA

      Yeah.

    8. LR

      And then we'll just go through each step-

    9. JA

      Yeah.

    10. LR

      ... and help people learn some tactics to get through-

    11. JA

      That sounds great.

    12. LR

      ... each of those conversations. Okay.

    13. JA

      Yeah.

    14. LR

      Cool. So what's the simplest way to think about, like, the steps of a sales cycle?

    15. JA

      The traditional sales stages that most CRMs are even set up as is, like, you have your intro call. Um, you have your second call, um, which sometimes could be the demo depending on, like, the stage of market you're selling to. Then you have your third call, which is gonna be more about, like, walking through a proposal, a scope of work, um, uh, maybe going deeper into the demo to contextualize it to everything you've learned. The fourth call is going to be, um, getting their feedback and kind of co-authoring that scope of work even further. The fifth call is going to be around probably an introduction to procurement. And then, you know, selling into procurement in itself is its own little sales cycle, but that's... We could talk about that in a sec. And then post-procurement, it's gonna be obviously getting that signature, um, and knowing who the actual signatory is 'cause sometimes it's not even the business unit. It's sometimes legal, CFO, procurement themselves. So just understanding who that is.

    16. LR

      Okay, great. So let's walk through each of these steps. So I love, I love that they, like, each call has its, like, traditional goal. Uh, demo, proposal, then co-authoring, and then procurement and then post-procurement. I love how, uh, consistent everybody is.

    17. JA

      Yeah, it's, um... Well, it's also, it's interesting 'cause it's also predicated on their buying process as well. Um, so if they're really used to bu-... Like, if they're very mature in their buying process, um, they actually might guide you to what the steps are. But, um, you know, most startups are turning non-consumers into consumers. So-... that's why this kind of fits well.

    18. LR

      Got it. So I

  4. 12:01 – 16:47

    Tactics for effective cold outreach

    1. LR

      think... So there's this intercall step, so kind of starting about where it begins. I think where p- a lot of people struggle most is, like, getting anyone to even pay attention, like even want to talk to them. Like, why I... A billion SaaS tools emailing me constantly about their product. So maybe we start there, just, like, how do you get someone to even want to talk to you and be open to learning about what you're doing?

    2. JA

      Yeah. And this is why that founder-led sales pitch is so important. One is, when it's coming from the founder, it's an entirely different weight, right? You're like, "Oh, interesting. This founder is reaching out to me. Okay. I'm, I'm gonna, I'm gonna, I'm gonna seek to go a layer deeper, um, knowing who, who is sending me this note." The second piece is this is why it needs to... That novel insight, that, that technical insight, that business model insight that you've uncovered needs to lead here, right? Because people are inspired by a new way of thinking. Something hi- usually something counterintuitive, something that's really different. I really try and stay away from better, because that's really hard to define. And better to some- better means something different to everyone, right? So if you can focus the messaging in a way that speaks to something that is a bi- has a bit of shock value, um, or is counterintuitive, you'll, you'll get them to continue reading. So first and foremost, I usually like to open it with is- which is, "Why is this relevant for me in my role? Like, why are you reaching out to me?" So first and foremost is relevancy. I think that matters even more so than personalization right now, 'cause I think it's so easy to personalize anything, and it can also come off cross as really stressed when you're like, "Hey, I noticed you were on, you know, such and such, you know, podcast," and that was when they were previously, like, two roles behind, right?

    3. LR

      Mm-hmm.

    4. JA

      So I always say relevancy, if you can get to relevancy, that's the most important piece. The second most important piece is really getting to that level of differentiation or counterintuitive nature. Um, so say something that would, like, literally make them say, "What?" Or, "That makes no sense." Not... Maybe not that makes no sense, but, like, "What?" Or, um, "How could that be?" Or, "I've never thought about it that way," or, "I actually don't fully understand what they're saying, but there's something there that's interesting." Right? Like, get them to, like, pause for a minute. And ca- and the most important piece is getting this done where if they get it on their mobile phone, which everyone i- is looking at their mobile phone and on email, they don't have to scroll. So usually three to four sentences max.

    5. LR

      Mm-hmm.

    6. JA

      That also... That's how a founder writes. That's how an executive writes if you're, you know, selling top down. Um, but most importantly, leave them wanting more. Don't say everything. Don't even talk about the solution. Talk about the problem that you want to solve and why, and why it needs to be solved or why it's not good enough today. So those are the, kind of the four main components, just to reiterate. Relevancy, bring some level of counterintuitive or really different approach to the conversation, focusing in on a problem that's predicated to them, and really concise.

    7. LR

      I love this. Is there an example you could share that helps make this even more real of maybe an email you helped with?

    8. JA

      Sure.

    9. LR

      And by the way, this is, like, email and LinkedIn, I imagine, is where you're communicating mostly?

    10. JA

      Uh, LinkedIn, email. You would be shocked to hear this, but cold calling.

    11. LR

      Mm-hmm.

    12. JA

      I n- never used to do this. It is one of the most... Uh, the interest rates on cold calling are a lot higher than email in many cases.

    13. LR

      S- so it's c- calling, email, cold email, and LinkedIn DMs. Is that the three channels generally?

    14. JA

      Yeah. Those are the three, yeah, the main ones.

    15. LR

      Cool. Yeah. Is there an example? It doesn't have to be, like, word for word, which you've-

    16. JA

      Yeah.

    17. LR

      ... done or people have done. But just how do you... Yeah.

    18. JA

      W- actually, our first three y- years were built on cold email, right? Before we actually, like, had clients, before we actually, you know, um, got word of mouth from the founders we worked with, I cold ca- I cold emailed the first 20 customers we had at Jellyfish. And the, the line I used in there was, "Zero to one sales talent doesn't exist. That's why I want to have a conversation with you." So that was kind of like that leading, like, "Wait, what? Um, what does that even mean?" And what I would do is tie that tor- to them in some respects, right? Like, you know if they've recently raised the seed or series, they're where they are in that journey. But I would lead with that and then tie it into, like, "Hey, I noticed you're looking to target, you know, X, Y and Z," um, "based off of, what, your website. Like, I'd love to have a conversation with you."

    19. LR

      And that first piece is the relevance. Here's why this is relevant to you.

    20. JA

      Yeah.

    21. LR

      Yes.

    22. JA

      And then I say, like, "Our belief at Jellyfish is zero to one sales talent doesn't exist. That's why we built this model."

    23. LR

      Awesome. Okay.

    24. JA

      Yeah.

    25. LR

      And you kept it really short. So it's relevance, counterintuitive, keep it really short, and then... What's the fourth piece?

    26. JA

      The fourth piece is just make sure it's concise so that you don't have to scroll on, on mobile phone.

  5. 16:47 – 20:20

    Conversion rate vs. win rate

    1. JA

    2. LR

      While we're on this topic, what's a good conversion rate of these sorts of cold outreaches?

    3. JA

      The conversion rate is interesting, 'cause everyone's so focused on conversion rate. I get that in the beginning. Until you have some wins, you have to, you have to focus there. But I just want to reverse engineer it backwards a bit once you kind of have this, and I'll talk about it in a sec, which is win rate. Win rate is if I got Lenny on a phone call and he went through the sales process and I signed him up, and I spoke to 10 Lennys and only, you know, Lenny R. was the one that, um, that signed, that's one out of 10. That's a 10% win rate. Okay? So if you have a really high win rate, let's say 30 or 40%, you actually don't need as high of a conversion rate on the outbound because you know if you get someone in the funnel, the throughput is very healthy. If your win rate is really low, you need that conversion rate to be much, much higher, because you need more and more and more at bats. So conversion rate is a funny thing. In the beginning I get it, 'cause you don't have cust- you don't have a lot of customers going through the pipeline yet, but it is... There's... People focus on it, um, in a little bit of a false sense because interest rate truly is also dictated by win rate. Um, so I just want to kind of, like, specify that.

    4. LR

      Yeah.

    5. JA

      But-

    6. LR

      That's a really good point.

    7. JA

      I would say, if you're tar- if you're doing a win rate of around, you know, 15 to 30%, and you need to carry, oh, I don't know, um, a million dollar quota, right, um, I would say a healthy conversion rate from outbound probably sits around, you know, when it's mature, around 5 to 7%. Sometimes it could be 2 to 3%. Sometimes I've seen 8 to 15%, 'cause it's coming from the founder and they're solving a really heartfelt problem. So interest rate is also predicated on the problem that the founder has decided they wanna solve for, and their insight on that problem. And everyone wants to keep going back to, "Well, email rate is really low. Email doesn't work anymore. LinkedIn, you know, I'm not getting the connects I want." Yes. Yeah, you can argue that the game has changed a little bit, but when a problem is truly being felt by the market, people get on a call, people will respond. And there, you know, if I can compare two engagements at a time that were running, I see one where it's a 2% interested rate, and then I'm, I'm seeing another one that's actually a 12% interested rate, and we're doing nothing different. The only thing that's different is the insight that the founder has on the market, which is a hard pill to swallow, and I know that's hard to hear too.

    8. LR

      And those are two different companies selling different things, or it's-

    9. JA

      Two different companies-

    10. LR

      ... selling similar things?

    11. JA

      Two different companies selling to, um, two different markets, but like, they're not fundamentally drastically different markets.

    12. LR

      Got it. But one's like-

    13. JA

      Yeah.

    14. LR

      ... basically got more product market fit essentially.

    15. JA

      That's exactly right. So everyone can keeps coming, c- always comes back to like, "We have this sales problem, we have this sales problem, we have, you know, an outbound problem." And yes, there could be some technical things going on that you need to look at, like maybe you've blasted... You, you leveraged Clay and you blasted 1,000 people and now your domain health is, you know, been impacted. But the vast majority of the time, maybe you're just not saying anything interesting at all, maybe the problem you're looking to solve just isn't widely felt, maybe the perspective you have needs another level of refinement because you're just not getting

  6. 20:20 – 23:06

    The time it takes to find product-market fit

    1. JA

      those bites.

    2. LR

      Mm-hmm. I feel like this question you just touched on is something a lot of founders are always wondering, "Is this product not the thing people want? Is it my sales skills?" I guess is there... I imagine this is a very difficult question to answer, especially quickly. I guess is there anything there that's like, more likely because of this it means your product isn't something anyone's want, versus you're not doing a good job selling it?

    3. JA

      Remember that, um, amazing chart you drew where it talked about the length of time it took?

    4. LR

      Mm-hmm.

    5. JA

      I think you picked the top 25 startups, um-

    6. LR

      For product market fit, timelines for product market fit.

    7. JA

      Product market fit. Yeah, that-

    8. LR

      Yeah.

    9. JA

      ... amazing image that I think has been re-shared more times than anything I've ever seen. It's interesting because if you look at... I was looking at this closely the other day, if you look at the top section where the, um, the time to product market fit is consolidated, and you go all the way down to like the Airtables and the Figmas, which-

    10. LR

      And Notion.

    11. JA

      ... took a long time to get to product market fit. If you think about the earlier ones which were, um, it was like GitHub that had product market fit pretty quickly, um, uh, the SOC 2 compliant company, um-

    12. LR

      Vanta.

    13. JA

      Van- Vanta. I, there's like this, this thing in my head and I haven't fully validated it but I'm gonna share it with you which is, did they start with the market problem first and then build the product? 'Cause they, they knew who their market was right off the bat. Versus an Airtable and a Figma that I think started with a technical insight and then were trying to find their market.

    14. LR

      I think that's absolutely right. Vanta, the way they approached it, Christina, she, uh, was like searching for a pain. She was obsessed with talking to everybody about a pain-

    15. JA

      Yeah.

    16. LR

      ... that they needed solved and then she just, like, built it in spreadsheets. So she started with the market very much so.

    17. JA

      And I think product market fit, when you start with the market first, it's accelerated, but I will say this, I think that it's also capped on the upside, because you're starting with the market. Versus the Airtable and the Figma which started with the technical insight and has kind of uncapped upside. But one is certainly riskier than the other, right? Starting with a product is a hell of a lot riskier. And this is where I come back to like, so many people will say, "How do you, you know, how, how did you get funding and not know who your market is?" And it's like, because if they do find it, that's a really, really, really big win, right? Versus, I think if you start with the market first, you could potentially get a good win but is it more capped?

    18. LR

      Mm-hmm. Interesting.

    19. JA

      I don't know. It's just a thought. It was just, you know, I, I was staring at your grid for so long 'cause I was like, "There's something here." And like-

    20. LR

      Yeah.

    21. JA

      ... I kept coming back to, you know, those were more like, I kept kind of breaking it down to like market versus product.

    22. LR

      Yeah, I love this. I think there's definitely something there. There's also like horizontal versus like a very specific-

    23. JA

      Totally.

    24. LR

      ... problem

  7. 23:06 – 30:58

    Identifying and engaging prospects

    1. LR

      you're solving.

    2. JA

      Yeah.

    3. LR

      Okay, so you mentioned Clay and you kind of nerd sniped me there of just like, what tools are, do you find useful? And it kind of makes me think about like finding leads, which is kind of going backwards through the sales process but it might be okay. So maybe let's spend time there just like, what do you recommend to founders to find, find the good leads, the, uh, Glen Gary, Glen Ross good leads?

    4. JA

      So I say before you buy any tool, don't even think about tools. I feel like people get s- turn everything into this complicated mess with all of the tools that they start integrating and then, you know, they're engineers, I get it. So they now, they start to engineer these, um, these sales tools together, and you know, then they blast their market and now they have fif- 5,000 notes out in one day and their domain takes a hit. So I think before you even overthink about the tools right now, can you manually find 30 people that you want to spend 15 to 20 minutes writing a rock solid note to? Are there 30 people that you are deeply excited to learn from, that you are willing to invest 15 to 20 minutes to write a really thoughtful note? Let's just start there.So, leave some questions. One, are they even discoverable? How hard is it to find 30 people? What have you noticed across those 30 people? Are there anything, any, um, interesting insights? Maybe it's the size of the team they work on, maybe it's the industry they're in, maybe it's the length of time they've been in their role, maybe it's, um, their pre- their previous roles in their career. Like, what, is there, are- are there some commonalities? There's always some level of a commonality, usually, in most cases. Okay, so now you're starting to collect some parameters. Just by doing this excel- exercise, you're starting to collect some parameters around who you wanna learn from and sell to. Now, if you send out those 30 notes and they're, you know, you wrote them specifically and, you know, you spent good quality of time on it, and you've, you know you've hit them on email, you've hit them on LinkedIn, maybe you've even tried to call them, maybe you've tw- sent them a Twitter DM. You know, pulled out all the stops. How many people respond? One? Five? Zero? Right. If it's zero, that begs the question, do you now want to do another 30 in a very similar fashion? Do you wanna change the messaging a little bit? It, now it forces these, like, natural experiments. Or, do you wanna maybe go after a different role? So it forces you to answer these questions in a very manual way before you even think about, you know, integrating and spending time on tools. And then you get to a point where it's like, "Okay, now I'm starting to get some learnings," and now I've realized, okay, it's this group of people. I've spoken to maybe two or three, now I wanna go out and actually build a campaign to now talk to the next 10 to 15 people in that group. Truncate this as much as you can, because I think people focus so much on volume in the beginning. Even if you're selling down market, mid-market enterprise, volume comes once you've identified it and know the parameters. Parameters then allow you to do really strong enrichment with a CLAY. You now know the types of questions to give it. If you're not asking it the right questions, these enrichment tools, these sales tools, will g- will- l- y- yield nothing.

    5. LR

      Mm-hmm.

    6. JA

      So, it all comes back to even before you start your sales call, you need to make sure you're asking the right questions with, "Am I re- engaging, or do the people that, um, I wanna learn from or sell to, am I even messaging them in the right way? Are they even the right person?" And the only way you can do that is by actually truncating these little experiments.

    7. LR

      I love how tactical that is. And what I love is even, like, one of your nuances you mentioned is can you even find them? Like, this gives you a signal of how are they... Like, you're gonna have to have hundreds of these and ho- thousands of these eventually. Like if you, 30 is hard, and when you're impossible, you're in trouble already.

    8. JA

      Totally.

    9. LR

      Yeah.

    10. JA

      And it w- it w- it was funny, I was talking to someone today that said they wanted to, they had a target segment of like high net worth individuals, um, that they wanted to go out and, and serve. I'm like, "How do you find those people?"

    11. LR

      Mm-hmm.

    12. JA

      Like, no one's, you know, is our, I, I guess, uh, when you get to a certain level, your net worth may be public. I don't know. But, you know, that stuff's ha- it's very hard to have certain parameters that are undiscoverable. And then if they're undiscoverable, and it requires you getting on a call to understand if they are a fit, that does impact conversion rates. Not necessarily a bad way, but you now you need to kind of dr- bring that back into the math equation, which is like, "Okay, if I speak to 10 people, I know two o- two out of these 10 will, will be qualified, but I don't know which of those two out of 10." Well, that means you probably need more of those numbers.

    13. LR

      Mm-hmm. Okay, so to quickly recap a few of the key things that I've written down as we're talking. So, if you're just trying to figure out who to reach out to, make a list of 30 potential prospects that you think are good fits that would be excited about what you're building. Spend 15 to 30 minutes writing them each an email.

    14. JA

      Mm-hmm.

    15. LR

      Do these emails have to be really short the way you described previous?

    16. JA

      I would say the shorter, the better.

    17. LR

      Okay.

    18. JA

      But like, would you respond to that? Like, if you got this email, would you respond it?

    19. LR

      Got it.

    20. JA

      One of a, a great little tactical test is on Gmail, you can co- you can highlight the message and then have it replay it back to from a, an audio perspective.

    21. LR

      Oh, wow.

    22. JA

      Um, you'd be shocked how many notes I've changed when it replays it back and I'm like, "Oh, that sounds really passive aggressive." You know? (laughs)

    23. LR

      Interesting.

    24. JA

      Yeah.

    25. LR

      And, and so you also share the structure for how to reach out to folks, so let me just-

    26. JA

      Yeah.

    27. LR

      ... share that again, and that applies to this initial email too, but it sounds like as you automate, you want to make it more precise and focused and not, like, but basically they're not as customized as you start reaching out to more folks.

    28. JA

      Totally.

    29. LR

      So it's, uh, start with something, here's why this is relevant to you. Like, you're looking for salespeople in this market. Uh, here's something that's unexpected or surprise, like zero to one salespeople don't exist. Um, keep it short, and then I always forget the last one.

    30. JA

      Um, f- focus on the problem.

  8. 30:58 – 34:14

    Nailing the first phone call

    1. JA

    2. LR

      Okay. Amazing. So, we talked about how to find, figure out who to go after, how to pitch them to get them to want to talk. The next step, I imagine, is you're on the phone with them trying to convince them to actually care. What do you do there? How do you get them to engage further?

    3. JA

      One is, you need to be vulnerable. You're an early stage startup, okay? The market, we're at a point now where the market is smart, right? Like I always assume that the buyer I'm speaking to is highly educated and knows way more than I do. So just, just have that perception because what I've learned is, a lot of the market will play dumb and, uh, you can get yourself caught pretty quickly. So, when you speak to them, I would be very open and honest with where you are. "Hey, I'm an early stage startup. We are deeply passionate about solving this specific problem. We have a lot to learn. Here's how we are thinking about it from a problem priority perspective. Can we, can we kind of gain your insight into like how this problem is manifesting on your side?" And then o- let th- let them open up. Now you have them, one, talking about the problem. Now you're getting the intel about their perception of the problem, and if it, is it even a problem. When you say you're early stage and there's still a lot to be done, it is easier to be honest. If you tell them you have a fully baked ready to go product, they're not gonna give you honest feedback. It's very hard to give, to say to a founder and look them in the eyes and say, "Hey, we built this product. Can I show you what it is?" You're just gonna get someone that's gonna say, "Oh, this is great. This is wonderful." But when you're vulnerable and when you tell them it's not fully built yet, even if it is, even if it is, you will get more raw and honest feedback.

    4. LR

      Mm-hmm.

    5. JA

      Because it is easier to tell someone, "Hey, before you make this mistake, I actually don't care about that." If you've already built it, they're not gonna give you that feedback. So you, uh, the, the further you suggest you are, you're actually gonna hamstring a lot of the intel. Hamstring yourself on gaining a lot of the intel. So that's like one counterintuitive thing that I think a lot of founders don't realize.

    6. LR

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  9. 34:14 – 38:08

    Buying vs. selling

    1. LR

      So I had April Dunford on the podcast a while ago, I don't know if you-

    2. JA

      She's awesome.

    3. LR

      ... amazing. And her last book, it actually has the opposite advice, but I think I know why, which is she focuses on later stage companies.

    4. JA

      Mm.

    5. LR

      And her advice is, the buyer... She has this really interesting insight that it's harder to buy software now than to sell it because there's so much to consider and your job, your job is on the line if you make a mistake. It's easier just to be like, "Forget it. I'm just gonna go with what we have today. I don't wanna put my, my ass on the line for buying this new thing that someone's trying." And so her advice is, you actually have to educate the buyer on the market and, "Here's what's happening, here's where things are going, and here's why I think this is the future." But I think, again, I think that's focusing on later stage stuff, like...

    6. JA

      100%. And that's a good, that, you raise such a good point, Lenny, which is late stage sales and early stage sales-

    7. LR

      Mm-hmm.

    8. JA

      ... are very, very different.

    9. LR

      Mm-hmm.

    10. JA

      And I think that's where a lot of early stage, um, founders get tripped up is they're taking-

    11. LR

      Mm.

    12. JA

      ... late stage sales advice from an inve- usually coming from an investor or they've maybe hired a salesperson that's, you know, focused on more mature sales. Um, but, but I think she is spot on. Buying is just as hard, if not harder than selling right now. 'Cause who wants to make a mistake? And also, who wants to go through switching costs?

    13. LR

      Mm-hmm.

    14. JA

      Oh, it's so painful.

    15. LR

      Yeah. I think the other really important point here that you're making is that part of this initial sales experience of founder-led sales is not sell as much as you can, it's to learn what people want, right? And so, I love that you're sharing, "Here's how to get the best possible feedback, not necessarily close the most deals."

    16. JA

      Totally. And founder-led sales is more about... Is not, is not about revenue on day one. It is about learning as fast as humanly possible to get to that pulse so that you can earn the right to sell. We- There's this concept, um, that I talk about which is like you're going out to run sales to collect the research, right, which is what founder-led sales is, and then you, um, have sales for revenue which is that post founder-led sales stage.

    17. LR

      And like the, your milestone that you suggested of like how far to take founder-led sales, you said like around a million ARR, right?

    18. JA

      Yeah. It, I think it's about like, it should... Some people say 500, some people say a million. I think it's w- like if you get to 500K really, really fast, then I think-

    19. LR

      Mm-hmm.

    20. JA

      ... absolutely you can move out of it.... if you get to, um, 500K really, really, really slow, you might not want to get out of it right away. You haven't reached that, like velocity point yet.

    21. LR

      Awesome. I have a post that we'll link to that has actually numbers and when all these big startups-

    22. JA

      Ooh.

    23. LR

      ... moved from founder-led sales. It's in that same-

    24. JA

      Yeah.

    25. LR

      ... series about product market fit. Um, there's two stories this makes me think of, I'll share real quick. One is Sprig. Their, they shared a story of they, uh, First Round Capital led their first round and their partner there is just like, "We will not let you hire a salesperson until you hit a million ARR. We're gonna help you, like we're gonna have salespeople helping you through it, but we're not gonna let you hire someone." (laughs) And he was really happy about that. The other is, uh, Zip, which just raised like a two point in a half, $2.3 billion valuations procurement company that I was lucky to be an investor in, and their first founder-led sales motion was they just reached out on LinkedIn to heads of procurement and just leaned into what you're saying even more, which is just, "We just want your advice on this product that we're building. Would, just tell us what problems you have." Like, it was very advice-oriented versus like, "We want to sell you this thing."

    26. JA

      Yeah. No, absolutely. I have this, like theory that like maybe you shouldn't hire any salespeople until series A.

    27. LR

      Hm.

    28. JA

      Right? Because seed is all about experimentation and proving out that experiment, and then obviously series A is about ext- you know, exploiting that learning, but I see so many people... I mean, early sta- hiring for early stage sales is oof. The od- like (laughs) the odds are actually more against you than, you know, trying to get your next round of funding because eh- it's just, it's truly, truly such a counterintuitive stage.

  10. 38:08 – 41:57

    Testing the questions to ask

    1. JA

    2. LR

      Interesting. Okay. So I ki- I kind of took us on a whole tangent here-

    3. JA

      Yeah, you did.

    4. LR

      ... sharing advice on how to get someone excited, so the first is when you're engaging, you're talking to the prospect and company-

    5. JA

      Yep.

    6. LR

      ... ABC, your advice is, be very honest and vulnerable about your stage, tell them you're early stage, you're building this thing, you, you deeply, you're deeply passionate about this problem, here's what we're trying to do, here's our pro- uh, priority problem, perspective and where we're focusing, and kind of get their feedback on-

    7. JA

      Yeah.

    8. LR

      ... on your approach. Cool. Uh, you were gonna go to the next tip and, and I took us off course.

    9. JA

      Testing the questions to ask, right? Like where, where is that aha unlock for you? But more importantly, where's that aha moment unlock for them? Because when they start getting their gears churning in their head about... And this is the beauty about not having a product and not showing them anything, they're visualizing in their head now. This is like a really powerful thing, right? Which is like, "So tell me how like this looks in your head, like how are you seeing this?" And they're like, "I don't know if I can see it." I'm like, "Great, we'll show you that. Great insight to know, by the way." Or like, "So I think this is how, I guess this is how it would work. Walk me through what's living in your head right now." You pick up on so much and then all of a sudden they're like, "Wait a second. We've tried solving for this and it's still not solved for." Or like, "You know what? We hired someone last year to manage this." Great understanding. Is it being measured? Is it being managed? And have they tried to solve for it? The leading indicators that you're, you're onto something here.

    10. LR

      I love this thread because this is what everyone's always like, "How do I know if my product market fit?" There's like these signals that you're talking about of signs that there's something here, like a big enough pain point where they're excited to... Basically they want to pay for it. They will pay to solve a problem. So maybe just again, say the things you notice that are signs like, okay, you have something here.

    11. JA

      So I think the first is, it has to be a growing and widening problem. No one's gonna spend time fixing a pretty fixed problem 'cause it's not necessarily really a priority anymore. It's maybe a pain in the butt, but like it's not a priority if it's not growing or widening. So gate check one is like, what is the implication? Are you measuring, are you managing this problem today? Yes or no? If they don't know, great to know. If they said no, okay, move on to the next. Like that's a, that's pretty powerful. No, we're not measuring or managing this. Okay, there's probably not much there. If it is being measured or managed, then the next question you want to get into is, how have you tried to solve for it? Is it through that headcount that you just hired? Is it through another tool? Is it just still an open gap because nothing exists yet to solve it? Like, just understand like their maturity around how they've tried to plug it. These are all like the in- that make the secret moments and intel to, um, to close that gap.

    12. LR

      That's awesome. And essentially it's like te- showing you that there's a pain here-

    13. JA

      Yeah.

    14. LR

      ... that they're, uh, they're paying attention to and are trying to solve.

    15. JA

      And what you're psychologically doing is now you're flipping them into a buyer where they're like, "Wait a second."

    16. LR

      Hmm.

    17. JA

      "Hold on, I need to bring on so-and-so on the next call." Like, they also think that this is, this is like not good enough.

    18. LR

      That's funny 'cause that's exactly what Wiz noticed is they moved from people being like, "Oh, this is cool. I like it, I like it," to, "Okay, I'm gonna pull in this person, I'm gonna pull in this person to talk about it and make sure we're..." And like they were like pulling in other people exactly as you described to, because they wanted to like make, move forward on this thing.

    19. JA

      Absolutely. And that, that's when you know there's some momentum behind it, right? Which is when they're bringing in other colleagues, whether it be the potential users, um, right? If you're reaching out to the executive or the user's like, "Hey, I, I actually wanna bring my boss onto the next call."

  11. 41:57 – 43:08

    Avoiding common sales questions and securing the second call

    1. JA

    2. LR

      Good sign. Cool. Anything else along these lines of how to get someone ex- excited/understand if there's gonna be pull there?

    3. JA

      Oh, I guess the one thing is please, please, please do not ask questions like, "What keeps you up at night? Um, if you had a magic wand, um, you know, what are your pain points today?" Uh, 'cause I can guarantee you that answer changes every single day.

    4. LR

      That's super interesting. Is there any tip for how to end one of these calls, as someone that's never done sales is like-

    5. JA

      Yes.

    6. LR

      ... "What?" Okay.

    7. JA

      Get the second call booked-

    8. LR

      Hm.

    9. JA

      ... on the first call.

    10. LR

      Love it.

    11. JA

      Pull up calendars, look at calendars, who else should be invited? It's just a natural evolution to ending the call.

    12. LR

      Great. So I have to do in 30 minutes though, right?

    13. JA

      And if they say, "Ah, you know, I'll email you."

    14. LR

      ... I could say.

    15. JA

      It's also... That's also, kind of, a leading indicator, yeah.

    16. LR

      Mm. So do you recommend not getting off the call, like, trying to avoid that? Or is it just-

    17. JA

      If they, if they won't give you time on the calendar, um, you could say, "Listen, great. Like, feel free to email me." Maybe they're just being honest and they don't have their calendar available. But nine times out of 10, it's usually, "I don't have the heart to tell you I'm not interested."

    18. LR

      Yeah. It's hard. It's hard to tell-

    19. JA

      Yeah.

    20. LR

      ... people you're not interested. Very cool.

  12. 43:08 – 45:06

    Co-authoring with customers

    1. LR

      Okay. This is amazing. Okay. Uh, so the next step, if I remember correctly, is kind of co-authoring and co-

    2. JA

      Yes.

    3. LR

      Okay, cool. Talk about that.

    4. JA

      In the early, early days, one of the biggest ways you can get folks excited is it feels like it's gonna be built specifically for them. The power of specificity, the power of being extremely focused. With that, you can literally turn a customer into a, a guide by asking them to co-author the scope, the scope of work. Um, the co-authorship piep- is in-... The co-authorship piece is important for two reasons. It helps you understand where they are on their buyer maturity. Let me explain. If they do not have an existing process or strategy to solve X problem, they can't buy technology yet, which means you need to sell them... And this is where I go back to you. You need to sell them some form of a service, right? Why? You want to be the one in there educating. You also want to get the logo. You also want to show the revenue. While it's not recurring revenue, it still shows intent, right? And I think that that's really important. Every founder I speak to is like, "Well, my investor really doesn't want, you know, service-based revenue." That's fine, but then you can also tell your investor, "Great. Should I wait 18 months to when they're ready to buy a solution and be the one that's not the one selling them 'cause someone else educated them?" Like, these are all of the implications of waiting. So yes, is service-based revenue great? No, we all know why it's not great. But it's great in the sense that it shows intent. It's great in the sense that you can call them a customer. It's great in the sense that now you can use their logo. And it's great in the sense because you are getting paid to educate them. You are getting paid to help them design their process. This is where all the power lives, right? And this is why so many AI startups a year and two years ago were going in on services contracts 'cause they wanted to set the mindset with the buyer around what

  13. 45:06 – 49:20

    Time-boxing service contracts

    1. JA

      this would look like.

    2. LR

      Is there anything you recommend to, like, time box, contain the services piece?

    3. JA

      Yes.

    4. LR

      'Cause I know a lot of companies-

    5. JA

      Such a great point, Lenny.

    6. LR

      Yeah.

    7. JA

      You absolutely need to time box this.

    8. LR

      Okay.

    9. JA

      I would time box it as 90 days, and then you, well, you can-

    10. LR

      Mm-hmm.

    11. JA

      ... say, "In the next 90 days, we'll scope where we are and, like, what you need."

    12. LR

      Mm-hmm.

    13. JA

      Scoping out more than 90 days... Listen, everything... So much is gonna change. Um, you might also not wanna do it anymore, so you don't wanna lock yourself up, so I would look at, like, 90-day increments. A specific example, we had a, a founder that we, um, my colleague was working with, and, um, they were selling a very specific, uh, technology to a non-traditional, like a ve-... Sorry, a very traditional industry. Um, I don't wanna be too bleeding with what it is, but a very non-tr-... a very traditional industry that's not used to working with startups or, like, necessarily plugging in a new technology right away. And they were very honest. They said, "Listen, like, we haven't changed, um, you know, vendors or partners in over, you know, five or six years. Like, I do-... I actually don't even know how we would do that today. Like, could you come in and explain to us, like, understand where our workflow is and how we would integrate this before we even consider the technology?" Which we did. We got paid a nominal amount, but we're now a customer, and now we get to set the stage for how they think about this, and then we won... they, they won the technology contract. But everyone is so focused on selling the technology really, really, really quickly. That works in markets that know how to buy that technology, have a process in place, have a strategy in place, have an implementation team in place. If it's a new technology, like AI right now, they need a strategy and process. Like, who's the human in the loop? Is it them or is it you? How do we measure success? What does success look like? What risks should we be aware of? We don't... Our legal team's not even aware of all these risks. Like, you wanna be careful because legal could immediately, and procurement can shut these things down if it seems too novel, where it's, like, foreign, um, versus they're so used to buying services, especially out market, so largest budget line item.

    14. LR

      So it's interesting 'cause most founders are very afraid of moving into services. I hadn't heard this advice before.

    15. JA

      Probably gonna get slapped for saying all this stuff, by the way, but...

    16. LR

      Well, so along those lines, like, what percentage of companies that you've worked with or see, like, do that or have to do that step?

    17. JA

      Y- you... This would be a... It's gonna be a shocking stat. So, um, I would say 40 to 50% have to sell some form of service before they can sell a technology.

    18. LR

      Wow. Of B2B SaaS companies?

    19. JA

      Of B2B SaaS. And this is... Again, this is specifically more top-down sales. But yeah, because the user and the buyer are different, which means, you know, there's user value. There's buyer value. There's all different players. There's procurement you have to go through, but yeah.

    20. LR

      And just to make it even clearer, what's an example of, like, a service that you've seen a company offer, like as... in a step?

    21. JA

      So I've seen, "Hey, can you come in and actually help me pitch this, design a custom pitch to my boss, um, as to why we should do this today?" And we-

    22. LR

      I see.

    23. JA

      ... literally got paid to build a sales pitch. Uh-

    24. LR

      Okay. So it's not necessarily providing a service. Um, it could be just helping them sell this.

    25. JA

      Yeah, it could be, it could be helping them sell in a way that, like, g-... makes you... Y- you know, you need to get some, a lot more context on their business. It can also be, "Hey, we, uh, haven't actually thought about the... a n-... a process for how we can actually deploy something like this," right? "We're currently using this technology, which we a-... we want to change from." Like, you've kind of hit this at the right time. "How would we implement, or how is it best to integrate with this tool? Um, can we get both of you guys in a room to, like, map, map this out?"

    26. LR

      Got it. So it's like-

    27. JA

      So, you c-

    28. LR

      ... consultants almost, like, um, people coming in-

    29. JA

      Yeah, it's- it's-

    30. LR

      ... to help you solve this problem.

  14. 49:20 – 51:05

    Why you should avoid demos on the first call

    1. JA

      adopt it and not have to, you know, um, create a new strategy or process, then obviously sell the technology. You don't need to be selling services.

    2. LR

      I want to come back real quick. The previous call, I wrote this note down as you were talking. Uh, you recommended not doing a demo and just talking about it broadly.

    3. JA

      Yes, on the first call.

    4. LR

      Is that On the first call?

    5. JA

      Yeah, on the first call. My fundamental belief is that the demo is a bit of the only carrot you control in the sales process, right? Once they see it, it's kind of like, you know, pitching an investor. Once they take a look under the hood, that dream- dreaminess in their eyes, you know, they're like, "Oh, I saw it." So like, leave them wanting more like th- and the demo is that, like leave them wanting more. Even when you do a demo, don't demo everything. Leave it for a second call. Get them, get like, let them invest a lot of time in you. Again, if it's qualified. I preface that, if it's qualified. But like everyone races through the sales process like, "Let's do a demo call as quickly as humanly possible." Yes. That is important down market. That is important if you're selling a $3,000 tool, you absolutely wanna be demoing as fast as humanly possible because it's a high volume game. Upmarket when you're talking about hundreds of thousands of dollars, you wanna slow that down as fast as possible because you want to, one, make sure all of the right people are in the room. As soon as there's one lead on this, and if it's like a, requires other people involved, it doesn't feel like anyone else's baby. So you want it to make it feel like the group's baby versus this one individual's baby 'cause it's very quick, y- you know, someone can easily say, "Eh, I'd rather use this tool." And then there's like this stalemate of like, nothing happens.

    6. LR

      Just to maybe reiterate, so far we've talked about getting... figuring out who to talk to, pitching them on talking to you, then having that first conversation. Maybe there's like another conversation in there to get them excited,

  15. 51:05 – 54:22

    Dealing with procurement

    1. LR

      and then there's just like getting them past the finish line, keeping everyone aligned. Is that roughly the next step or how should we think about this?

    2. JA

      Yeah. So if you are selling upmarket, right? Um, and you now need to go to procurement, who is the group involved in the buy? Like, you know, they're the professional buyers. Procurement is a very interesting function. They are very smart. Very, very smart, right? They do this for a living, like they are like professional buyers. So there's a couple things that you need to be aware of. You need to sell them as well. Like you need to really make this sound. Don't over-complicate it, don't add in jargon. Make it feel like, "Okay, I can wrap my head around this." The second piece is it's gotta feel different from anything else out there because the professional buyer, it's much easier to say, "Wait a second, we have these 17 other preferred vendors that do similar-ish work. Why don't you just go use one of them? Because oh, by the time this gets through procurement, it could be another three to four months." I've seen deals die on the vine because procurement actually suggested they go use another vendor in the system that this buyer wasn't even aware of because they didn't differentiate. They didn't, it didn't feel different, it just felt slightly better. That's how it was positioned. The third piece is when you get to procurement, you're gonna have to do all the work, right? Make their job easy.

    3. LR

      Mm-hmm.

    4. JA

      You are probably a very small piece into the very large deals that a lot of these people buy. So you're going to, you can get easily sidelined just because you're just a small, you know, a small, a small buy. So do the work for them. Literally say, "I wanna make this as easy as possible for you. Give me the forms that you need to fill out. I'll fill them out for you and you can, you know, you can do it yourself. You, you can edit them." Um, do the lift for them. If you don't, it's so easy for it to just go there and die. Another piece that's important with procurement is explaining exactly what you do and don't do because if you say you do a bunch of things and they can't really place you, they're gonna send you to the kitchen sink of contracting and MSA, which are, is gonna ask you for, you know, $5 million and an insurance policy and all sorts of other things, and like the ability to look at your book, um, at any point in time. And the reason they did that is because they can't classify you, so they just, the easiest thing to do is classify you as high risk. So like make it easy for them, make it simplified. You can also truncate your contracts, meaning let's say, um, IT is may- and you wanna ask this, like, "How long does it take to get through IT- IT due diligence?" They might say, "Oh, it's a 90-day backup. It's a 60-day backup. It's a 30-day backup." There's no backup. If there's a backup, you also don't want it to die and you want it to give an incentive, so this is when you wanna truncate contracts to a technology contract and a service contract. Service contract allows you to onboard them, get them prepped, come in and educate all of the users about what they're about to go through so that then there's an incentive to get that technology piece through. There's all these like little things to think about, and I think everyone's... You know, getting through procurement is also creative, right? Um, and knowing who you're dealing with and how to make their job as easy as humanly possible 'cause what you said and what Ap- April said is spot on, which is buying is just as hard as selling.

  16. 54:22 – 58:14

    The power of enterprise sales

    1. JA

    2. LR

      As I'm hearing you describe this, um, I feel like we might be discouraging people from selling because this feels very not fun. All these steps, all these procurement work. Anything you can say to get people to feel like-

    3. JA

      Yes. I can get people very excited by this.

    4. LR

      ... "Okay, this is worth doing." (laughs)

    5. JA

      Once you are in, you are in. Once you are in, you are now a preferred vendor.... you now have the ability to cross over into other business units. You are now the reason that, hey, if your, your competitor comes in, well you got there first. So what do you think procurement's gonna say? This is why it's so important to get into the enterprise as fast as humanly possible. While it's a headache to get through, if you, if you project manage it, i- you'll be good. If you, if you make an accountability, if you... Just like you, just like if you were to go through fundraising, right? If you've, if you've, you know, are a part of a team that had to, you know, raise money, it's no different. Right? There's always some level of due diligence. There's always you doing more of the work than them. That's just enterprise sales. But if you prove value, right, your $100,000 deal could be $500,000 next year. Your $500,000 deal could be a million dollars the following year. This is where stuff begins to compound and this is where growth, your growth journey really gets accelerated. So the beauty with enterprise is once you're in, you're in. You beat out your competitor, for a short period of time. There is a little bit of a moat there, but it's not forever. You will have intel that no one else will also have, meaning you're a part of the conversations, you have the badge, you can join the meetings. You can ask for introductions. They'll do it. Doesn't feel like sales anymore. You're now a partner. This is, this is why it's so powerful to get into the enterprise, 'cause there's so many compounding effects if you, if you put the effort in on the sales side. The return is, is insane.

    6. LR

      That was awesome. Nailed it.

    7. JA

      (laughs)

    8. LR

      (laughs) I'm excited. Just for folks that are listening, just to kinda calibrate what size of company you're talking about selling to here, like what's the size of the device you've been sharing so far, roughly?

    9. JA

      So I've been talking a lot about enterprise sales, which is, um, I would say anywhere north of 500 to 1,000 employees. Just mental model. I'm talking about enterprise sales specifically because there's so much nuance involved in it, because the user and the buyer are very different. Right? As you go down market, let's talk about small business for a second, the user and the buyer are the same person. There's no procurement. If they like what you've built, it's pretty straightforward process. In the mid-market, mid-market's a funky place, because you either are anchoring towards the lower end of mid-market, which is more upper end of small business, or you're anchoring towards lower end enterprise. Those are two very different divides. So mid-market just, if you're talking about lower end enterprise, um, again this is all relative. If you're talking about lower end small business, again your user and the buyer probably are the same person, which makes sales a lot more streamlined. But churn. Small business, challenge with small business is the churn. If they get pissed off, if they don't feel like it's good enough, they are gone, faster than you don't even realize. Right? They are... And they might not even tell you. They'll just cancel or they'll... And we always see this on Twitter, right? Like, they'll call American Express and say, "Cancel these charges. I don't wanna talk to these people anymore." Like, they're just more irrational. Uh, because sometimes it's, you know, maybe it's their money if they're a small business, right? So small business and mid-market, while sales is a bit faster, you really gotta be on the product market fit side, worried about churn.

    10. LR

      Mm-hmm. And they also go out of business at a higher rate.

    11. JA

      Exactly.

    12. LR

      And so you have that kind of churn.

    13. JA

      That churn piece too. Yeah, exactly.

    14. LR

      Yeah.

  17. 58:14 – 1:00:15

    Getting a signature

    1. LR

      Amazing. Okay. What comes next? So we're kind of in procurement at this point.

    2. JA

      Okay. So now we're at signature, right?

    3. LR

      Okay.

    4. JA

      Okay. So as you enter procurement, okay, you wanna know before you get to the next stage, who is signing this deal. Here are some examples of signers I've seen: chief financial officer, chief legal officer, the business unit head themselves, the head of procurement. You want to know who that person is so that you can literally say to the head of procurement, "Hey listen, I wanna make sure this person has everything they need when they review this to know what they're signing. Who is it and how can I, can I give you a f- a few bullets to share that you can maybe respond to that we get tight so that they know exactly what they're looking at?" I was a... This was a two y- two or three years ago, I was involved in, uh, getting a deal over procurement that was just, um, truly... It was a, a pharmaceutical company and it was very, very long process. And we got to the finish line and, uh, the CFO was the signature. And this is when I made the mistake. CFO responds back to, uh, the procurement lead who sent it to the business unit, who sent it to me and was like, "What am I signing? I don't actually understand what these people are doing. And why are we doing this?" So then she quickly said to me, "Hey listen, we need to defend this. You know, can you put together some bullets?" And I'm like, "Well, what kind of bullets do I need? What does this person care about?" And it cr- again, it had just, it created so much anxiety. And now I'm back in the bottom of the queue, 'cause she's probably, he or she is looking at the things that come in, in a, in an order of priority.

    5. LR

      Mm-hmm.

    6. JA

      So now I've elongated this by another month, um, simply because I didn't plan. So like, this is just to say like, I'm learning from my own mistake of know who the signature is, 'cause if they don't know what they're looking at, they're gonna kick it out and you're gonna lose your queue spot.

    7. LR

      So many ways to fail. And this was you selling Jellyfish or this was you working with a-

    8. JA

      This was be-

    9. LR

      ... with a company?

    10. JA

      This was me helping a-

    11. LR

      A startup?

    12. JA

      ... helping someone do it for a job. Yeah.

    13. LR

      Got it.

  18. 1:00:15 – 1:02:19

    Choosing a focus and overcoming sales challenges

    1. LR

      Oh, man. Okay. Anything else in that step that might be helpful to folks?

    2. JA

      Yes. Th- one thing to caveat is you do not get paid until you are approved by finance and procurement has a signature on the contract. Meaning don't start any work o- or if you do start work, know that there, they, there is no payment. Like the business unit can't just pay you. It's paid through a purchase order, which is paid through, by finance.

    3. LR

      Mm-hmm. So don't rely on that money-

    4. JA

      Yeah.

    5. LR

      ... unless it's finally, unless the signature's on the paper.

    6. JA

      Yeah.

    7. LR

      Uh, quick tangent. Thoughts on discounting at any-... parts of the journey?

    8. JA

      If there is a reason as to why. So, um, discounting just to get the deal over the line, you're negotiating with yourself, unless they ask for it, and then ask them to defend it, right? Like certain segments, like small business, you should leave a little bit of room for buffer because sometimes that's their own money, right? It's like their own small business. Mid-market and enterprise, there's gotta be a reason why. And ask them, be like, "Hey, so you know if I give you a 30% discount, can I remove 30% of the value?"

    9. LR

      (laughs)

    10. JA

      Like you can kind of like play it a little bit like that. I, I don't recommend it, but like that's kind of what, you know, what they're saying. Um, but I'm... Discounting is great if you're getting, if they, if they're doing something for you far and beyond. Like for example, if they're a design partner, um, if they're all- if they're gonna be a, a reference for two years.

    11. LR

      Mm-hmm.

    12. JA

      If you're, if they're gonna give you something far beyond, you know, just using the technology, then yeah, I think a discount, um, is, is a good reason to, um, give back to somebody that's giving to you, but, uh, not as like a strategy to get a deal done.

    13. LR

      Okay. Is there anything beyond this step of getting a signature, or are we done?

    14. JA

      Yeah. I hope you celebrate because-

    15. LR

      Okay, stars. (laughs) Okay, great.

    16. JA

      (laughs) Yeah.

    17. LR

      You got a signature from this whole process.

    18. JA

      Yeah. Yeah.

    19. LR

      Uh, yeah.

    20. JA

      Well, hopefully I'm not making this sound too daunting. I'm just really trying to lay out all the-

    21. LR

      Yeah, no this is-

    22. JA

      ... best ones I've made.

    23. LR

      ... exactly, this is exactly what people need.

    24. JA

      Okay.

    25. LR

      This is amazing. And your, your pep talk was really helpful too (laughs) along the way.

  19. 1:02:19 – 1:04:27

    General timelines

    1. LR

      Um, what's the general timeline for sales process like this in your experience with these 500-plus size companies?

    2. JA

      So there's three things that dictate sale cycle. One is you as the fou- like how well are you project managing it? Like for example, it's, you know, I'll say, "You know, let's have our second or third call in two weeks." Two weeks? Do a week. Why are you elongating this? You know, like keep your calls as tight as possible 'cause that shortens your sale cycle. The second is just how complex the organization is. If you're dealing with a highly regulated industry, just know it's gonna take a bit longer, sometimes 20 to 30% longer.

    3. LR

      Mm-hmm.

    4. JA

      So like a highly regulated industry, nine to 12 months, um, on like conservative, on the conservative side. Again, if there, is there a budget? It, it's, it's tricky 'cause is there a budget line item dictated towards it yet, or are you creating budget? Um, how p- how painful is the problem, and how senior have you gone? Like if you're talking to like the SVP or C, you know, chief, uh, just you know, chief of whatever, they're pretty good about being able to like navigate the traps. If you're dealing with a director or mid-level person, they maybe have not purchased something before and like just make some internal mistakes. So it's, it's, I I always say it can range anyw- I've seen enterprise deals close in 90 days, believe it or not. Rare, but I've seen it. Um, I've also seen enterprise deals typically take anywhere between six and 12 months. Really important but. Enterprises know that the process and the length to get the deal done is what costs more than the technology itself, meaning the effort it takes to get through their, their system. That's why they're willing to spend so m- much, right? Like sometimes that's actually more expensive than the technology itself.

    5. LR

      Mm-hmm.

    6. JA

      So don't negotiate with yourself. Understand the value you're delivering, and um, but don't be crazy. Like I've seen people try and go in with a million dollar deal as a seed stage startup, like...

    7. LR

      Mm-hmm.

    8. JA

      Oh, interesting thing.

  20. 1:04:27 – 1:13:32

    Final thoughts and advice

    1. JA

      So interesting tactic. I've seen, uh, contracts in the enterprise that state that the deal cannot exceed more than 20% of the existing revenue. So there are these things just to be aware of. Like m- in most cases, like you can ask them, be like, "Is that a hard line? Like-"

    2. LR

      Mm-hmm.

    3. JA

      "... is that hard, hard line?" Or like, "How negotiable is that?" Sometimes it's negotiable. Sometimes it's like, "No, this is a hard rule. Like w- we can't..." But then it seems silly 'cause you take $100,000 deal and bring it down to $20,000. It's just like a... You know, just be careful that like you're stripping some of the value out. But like I, I, I kid you not, I've seen an enterprise deal go from it lands at 60 and it turns into 280,000 in four months. So like again, I want to encourage, yes, this is a lot of work, but the payoff is exponential.

    4. LR

      What's a good ACV to start with if you're trying to sell to enterprise to make it all worth it for your startup?

    5. JA

      I would say anywhere between 50 to 200K depending on the s- the business unit you're selling to, that's kind of like sweet spot. Like they're used to something like in that, in that realm.

    6. LR

      And this is like a startup selling ac-

    7. JA

      It's a early stage startup.

    8. LR

      ... 50K to 100K.

    9. JA

      Yep, like founder led, uh, early stage, um, yeah.

    10. LR

      Initial contract. Wow.

    11. JA

      Yeah, initial contract. I would say, okay, probably caters more towards like 50 to a 100K.

    12. LR

      Okay.

    13. JA

      But I've seen people sell 200... Aga- again, it's how big is the problem? Um, who are you selling it to? Is it the CF, the SVP that you started with and you know they've got a large budget, um, and a, it's a pretty healthy business unit? Or are you selling to, you know, um, you know, a director?

    14. LR

      If you're not able to sell your product at that price, what's your advice to teams?

    15. JA

      If you are a startup, I always ask the founder, "Did you build it... Are you, do you, did you build this for the enterprise and is that the model you wanna apply? Or did you build this for small business?" Small business is a marketing game, marketing intensive activity, right? It's high velocity, high volume, lots of dials. It's a very different game than enterprise. So h- which game do you wanna play? Let's just start there. Like which game is more attractive to the founder? Sometimes, you know, or, or who is more exciting to serve?

    16. LR

      Mm-hmm.

    17. JA

      Um, what's the storyline you wanna tell investors? You know, that, that plays a lot of it into it too. And i- do you have an enterprise product? Like are you solving an enterprise problem or do you think you're solving an enterprise problem but you're not sure yet?

    18. LR

      And your point is also mid-market is it's a rare, rarely to be successful.

    19. JA

      It's hard to start there-

    20. LR

      Mm-hmm.

    21. JA

      ... because you're, you're straddling two very different go-to-markets, right? One that's of high value, one that's of high volume. And also mid-market companies, th- this is where a lot of people don't, um...... if it requires heavy integration, they don't have those resources. That's usually outsourced to, like, an Accenture or, like, a, some of these consulting firms, or, like... A- and now you're having to rely on third parties to be involved. It gets messy.

    22. LR

      This is fascinating. Okay. I have a list of questions from the audience that, uh, you pulled from Twitter. You asked on Twitter what questions to ask you as you were coming out here, so... There's one that's very related to this, which is, someone said, "If you're still very early in pre-product market fit, but get initial validation from both small-to-medium businesses and enterprise, how do you decide which one to focus on? Is there a counterargument against starting more SMB, going upmarket over time, like most SaaS companies do?"

    23. JA

      I've seen companies successfully do in both of those motions, truthfully. Like, I, we, we know all those, right? We know people that started small business and worked their way up into enterprise and were successful. We've seen people be really successful by starting at the enterprise, like a whiz. That's more of, like, an internal question, which is like, what's... Who did you build this for? What, how, where's the problem most felt? Um, and w- which go-to-market game do you want to play?

    24. LR

      And I think that latter part is so important. Like, it sounds like... It's, why should it be what I want? It's like, what's gonna make a big business? But I think people forget, this is gonna be your life for, like, 10 years, right? Do you want to be selling to enterprises and building all the enterprise features? Would you prefer to build for small companies? The pros and cons to both, but it's important to think about the life you're creating for yourself and your team.

    25. JA

      100%. And I, like, I built my career in enterprise sales, like upper-end, mid-market enterprise sales. And yeah, that's just the game I know the best.

    26. LR

      Mm-hmm. Yeah. Uh, and that's, that's also an important part of it, just to double down on that, is like, what do you, what do you have experience doing? Not like...

    27. JA

      Uh-huh. Exactly.

    28. LR

      Yeah. Where's the opportunity? Okay. Another question that I love is, and we touched on this initially, but I think it's good to come back to this. Uh, someone said, "Customers are fascinating, well, fascinated with what we're offering from the initial calls, but response and momentum is too slow from their end. Would be great to know how to fix this."

    29. JA

      Yeah. That's a, it's tough because... Unless you're in the weeds to understand why. Is it because you're, you s- Y- I'll give you some ex- a few examples that it could be. D- Did you speak to a buyer who now is trying to sell this up to their boss, and it's just getting sidelined, and they don't know the executive value, they've just been selling the buyer value the whole time? That's one reason things can slow down. Another reason things can slow down is you haven't really framed the problem well, and the, the implica- they ha- they don't understand the full implications of why they need to solve it, so it's kinda just, like, sitting there a little bit. Um, the third is they've just been really nice, and h- it's not gonna go anywhere.

    30. LR

      My guess is it's usually the latter. Th- was that true, or, or it's kind of all over the place?

  21. 1:13:32 – 1:15:08

    Working with Jen

    1. JA

    2. LR

      Amazing. Okay, Jen, so I'm gonna cut the lightning round. I know you also have to run and do real work, so let me give you a chance to just to talk about what you do, how you help companies, and-

    3. JA

      Yeah.

    4. LR

      ... in case folks can find value in working with you.

    5. JA

      Yeah. Uh, deeply passionate about sales, as I'm sure (laughs) you, you can tell. Um, we specifically help founders through this, this pain. Um, navigating enterprise sales, mid-market sales, and really trying to crack that first million of, of ARR or sometimes even that first 500K of ARR if they move fast enough. And, you know, it is really hard. It's, it's counterintuitive to what most people think, but it can be really, really fun when we show you the way.

    6. LR

      And you described to me how it works, and I think it's important to clarify this, like, you basically embed with the team and help them-

    7. JA

      Yes.

    8. LR

      ... do this.

    9. JA

      So, um, I fundamentally do not believe in outsourcing, um, the heartbeat of the organization, which is sales. Um, so what we do is we embed alongside the founder and drive a lot of the execution, but make sure that they are the tip of the spear engaging directly with their market and learning directly from the market's mouth, not playing this game of telephone.

    10. LR

      Amazing. And I mentioned this when we were chatting, but it, uh, I think of it again, is when I was interviewing all these companies about how they started selling early on, one of the interesting threads that I heard again and again is how many of them hired, like, a coach or a consultant as a founder to help them learn to do sales, and that's essentially what you do. And I didn't even know service like this existed, so this is super cool and will point people to what you do. Uh, I also have to ask you, the question I ask everyone at the end is just, how can listeners be useful to you?

Episode duration: 1:16:04

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