#1220 Javier Ramírez Lugo | Million Dollar Sales Secrets Revealed

Javier Ramírez Lugo is the founder of Cuota. He has had an incredible experience doing sales at Zenefits, Rippling, and WeWork. He is one of the most experienced and insightful people I have ever talked to about sales, and I always learn something every time we speak. This conversation breaks down how you as a founder or a salesperson can get better, how you can drive revenue, processes, hiring, firing, how to manage, and other hacks & tricks. ======================= Pomp writes a daily letter to over 250,000+ investors about business, technology, and finance. He breaks down complex topics into easy-to-understand language while sharing opinions on various aspects of each industry. You can subscribe at https://pomp.substack.com/

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:02Anthony Pompliano?

  What's up everyone? This is Anthony Pompliano. Many of you know me as Pomp. You're listening to the Pomp Podcast, which is my effort to find the most interesting people in the world and sit with them for hours while I ask questions in an effort to learn. So it would mean the world to me if you would subscribe to the show on your favorite audio platform, watch episodes on YouTube, and tell your friends and family about the podcast. My goal is to help millions learn from the world's most interesting people. So let's get into today's episode. Javier Ramirez Lugo is the founder of Quota. He has had an incredible experience doing sales at Zenefits, Rippling, and WeWork. He is one of the most experienced and insightful people I've ever talked to about sales, and I always learn something every time we speak.

• 0:46Anthony Pompliano?

  This conversation breaks down how you as a founder or a salesperson can get better. How can you drive revenue? What are the processes? How do you hire? How do you fire? How do you manage? And what are some of the things that you can do that are little hacks and tricks? Here is my conversation with Javier Ramirez Lugo.

• 1:06Speaker 01

  The action's on the court. And as the official beer sponsor of the NBA, Michelob Ultra is getting fans closer to the game with a chance to win courtside seats, merch, and more. Visit michelobultra.com/courtside to enter. Michelob Ultra Courtside, 26 to 27. No purchase necessary. Open to US residents 21+. Begins on October 1st, 2026 and ends on June 30th, 2027. Multiple entry periods. See official rules at michelobultra.com/courtside for free entry, entry deadlines, prizes, and details.

• 1:34Anthony Pompliano?

  Anthony Pompliano runs Pomp Investments. All views of him and the guests on his podcast are solely their opinions and do not reflect the opinions of Pomp Investments. You should not treat any opinion expressed by Pomp or his guests as a specific inducement to make a particular investment or follow a particular strategy, but only as an expression of his personal opinion. This podcast is for informational purposes only.

• 1:58Anthony Pompliano?

  All right, guys. Bang, bang. I thought a great place for us to start this conversation is the idea of founders. So they start a business. Everyone wants to build a business, but they don't realize that not only are you the founder, the CEO, probably the engineer, but also you have to be the salesperson. And sales is this thing that everyone kind of feels like is something they don't want to do, but like, how do I get customers? How do I drive revenue? And so let's just start with like, when the founder has to do the sales, what have you seen as the best practices? Or what are the things that they can do to increase the odds of success as that first salesperson?

• 2:26Speaker 02

  Great question, Paul. Thanks for having me, first of all. But I think that the best founders that I've worked with throughout my career have a phenomenal way to do sales. They have the most passion. They've built the product. They know how to do it. But essentially what they do is, you know, get in front of the right customers through the proper channels. So what does that mean? In a world of founder-led sales, you're juggling a lot of things, as you say. The CEO has to find a way to get in front of customers where they live. And where they live means, you know, if you're selling into engineering, you're not necessarily going to call an engineer because they don't typically like to talk on the phone. But let's say if you're, you have an HR product, you're going to find a way to build a good email sequence

• 3:08Speaker 02

  or maybe LinkedIn presence that is going to help you get in front of them. The second thing is, you know, a lot of founders educate themselves, right? So, sales has a stigma, as you say, but it is the forcing function for growth for any type of business. So the founders that understand that and that are truly seeking to, one, get feedback and two, help somebody solve a problem, usually happen to be the most successful in this domain early in the company.

• 3:36Anthony Pompliano?

  And so when they're going and finding where those people are, like, walk me through the process. So let's just say that we built a piece of software and we're trying to sell to engineers.

• 3:44Speaker 02

  Sure.

• 3:45Anthony Pompliano?

  How do I go figure out where are the engineers? Do I just like go talk to a bunch of them online and say like, hey, what do you do all day? And figure it out that way? Or like, is there a process that's repeatable that people could say, okay, if I built a company or a product, how do I find where my customers are?

• 3:57Speaker 02

  Yeah. So there's a couple of avenues. And what most people will do is if you come out of Y Combinator, for example, there's a network. So you try to find the low hanging fruit, who you know, what What distribution, you know, channels you can get easiest to. But also what a lot of companies will do is find a target list. And the process to finding that target list is really part of ideating your go to market strategy. Which means like, here's who I think I can solve a problem for. That usually is the person or the buyer persona. And then the ideal customer profile, which means the person or the business that that operates, you know, within that person. Today, it's much easier than it was 10 years ago to find access to those, let's say, lists of people.

• 4:39Speaker 02

  Companies like Apollo, Lucia, Apple Market, Sales, ZoomInfo, or SalesLoft. Will give you access to a data set that is aligned with what you've decided is your target buyer. And then from there, what's important is how do you build the right copy? Or how do you get in front of them in a way that is interesting? And that's differentiated because there's so much noise nowadays. Everyone's doing emails. Everyone's sending, you know, kind of outreach messages through LinkedIn. So it's really finding, you know, kind of that sweet spot in that honest message coming from a CEO. And maybe perhaps going to to another founder that has that problem.

• 5:12Anthony Pompliano?

  So plenty of founders will say like, okay, it's time for me to do sales. Let me write up this like six paragraph email that explains exactly what I do. Tells you every single detail you need to know. In my experience, like actually maybe just sending like, hey, we did X. It'll save you money. Do you want to talk? Right? Like three sentences.

• 5:30Speaker 02

  Yeah.

• 5:30Anthony Pompliano?

  Actually may have a better response rate. How do you think about copy and like how professional to be? Whether the emails should be like really beautiful and have, you know, a bunch of images and things like that. Or they should just be plain text. Like we're starting to get into the nitty gritty of actually, you know, reaching out to these people. But like, what have you seen is either best practice? Or what is the process at which people can figure out and test to get to what works for them?

• 5:53Speaker 02

  Yeah, that's a great question. And I love that you say that because I'm sure you want to be spoken to in the way that you speak to others. Right? And as a founder, you probably or your CEO of all the businesses that you have, you don't have time to go through like a sophisticated, like lengthy message. And you're going to get lost. So like the longer messages usually don't have the best conversion rates. What messages usually are most successful is When you understand the person on the other end of, you know, kind of the email. So if you're writing to a CEO, like, think like a CEO would like to be spoken to. Right. And to your point, simplicity, hey, which by the way, is one of the most successful subject lines in the history of like email prospecting. Because it seems like it's personal. It's coming from someone that you may want to have a conversation with.

• 6:38Speaker 02

  And then you go straight to the point. Like, you don't need to say, like, hey, we just went to the Y C. We raised all this money. Like, you lost me at that point. And all of that is, is sort of the structure that you use for posting online, for doing copy for newsletters. It's, it's really that hook at the beginning to say, like, how can I help you? Or we built this. Should we talk?

• 6:59Anthony Pompliano?

  And then when you get someone and they respond, how much of this is the founders getting on phone calls? Can it be done over email? Like, what do you see in terms of, okay, I put out all this bait. I got a couple of bites now, right? Like, what is the process from that point?

• 7:14Speaker 02

  Yeah. So I, I think it really depends on the stage of the company and also like the size of the deal. Right? So if it's an early stage company, the founder benefits from being part of any type of conversation. I want to know what the market wants and I want to know what type of feedback everyone is giving me with regards to what I'm trying to solve for. So I guess to directly answer your question, like a founder would want to be on every single call, like in the early days. And, you know, if you have any other like sales staff, sure, you can have them maybe qualify that opportunity in a, in a light way. But, you know, try to get as much information as possible and answer them as quickly as possible. So you can, you know, kind of get the ball rolling and, and get into the sales process itself.

• 7:55Anthony Pompliano?

  And then when they are in that process, they're obviously learning, right, from potential customers. How much of this is just like the founders are passionate about what they're doing and they're good? Versus they should have scripts and they should practice and they should kind of have what I'll consider a more intentional sales process, even though it's still just the founder doing the sales themselves.

• 8:16Speaker 02

  I love that question because it's where a lot of founders miss out on the most. And I'll explain why. Typical founders are more on the technical side, right? They're the ones that can code. They have a lot of sophistication from a technical capacity. They don't necessarily have that much exposure or experience on the commercial side. So they try to over engineer sales. And when you over engineer sales, you sort of lose that human component. And you know, in selling, what you want to do is have a human connection, ask the right questions, understand the other guy and make sure that you have a product that can solve their problems. And that simplicity is sometimes forgotten. And when people try to do scripts too early on, you know, they sort of miss out on a lot.

• 8:59Speaker 02

  The basic thing that I can think of, you know, that most early stage founders will do is sure, they'll have an agenda, they'll have a structure and a process. But the beauty is in the questions that you can ask them to understand like where they stand, what they need, and based off that, then you tell them about your product with their needs in mind.

• 9:16Anthony Pompliano?

  So ask questions.

• 9:18Speaker 02

  Yes.

• 9:18Anthony Pompliano?

  Have them tell you the answers to the test before you take the test is basically the, the big lesson.

• 9:23Speaker 02

  A hundred percent. And, and I mean, it's sort of like, people joke about this, but it's like a seller has like two ears and one mouth, so you're supposed to listen more than you actually talk. There's, there's a ratio within like, you know, kind of sales enablement, that's the talk to listen ratio. And supposedly it's like, you know, if, if you listen more than what you talk, you have a better percentage of closing the deal, which is a huge, you know, kind of breaking of a misconception because people historically think that the best sellers are the ones that don't shut up and it's the, the complete opposite.

• 9:51Anthony Pompliano?

  And when you're asking these questions, how much of them are, I'll call it open ended questions, like, hey, tell me about your problem, right? And just kind of sit back and listen versus it is questions that are very specific. What is your budget for this specific type of product? What is the timeline to make a decision? Like, is there a combination of open ended and kind of more direct questions? Or is there, uh, each one's different? Talk to me about like the types of questions that people are asking.

• 10:15Speaker 02

  I, I mean, it sounds like you know about this, but, uh, the earlier in the sales process, the more open end that you want to be because the, the tactical thing is that you can't interrogate. interrogate a buyer, right? They're going to feel interrogated and they're going to say like, you're wasting my time or show me the product, right? So let's go. So what you want to do is sit down and pick five open-ended questions that can give you as much information as possible. And so, for example, help me understand what are your, you know, kind of short-term goals in terms of revenue, right? So if I'm selling a product that impacts, you know, let's say, top-line revenue, I want to, I want to understand like how they're going to get there and what challenges or what's in the way. And I give them a question that can give me as much information

• 10:56Speaker 02

  as possible, so I can use it to my advantage when I am talking about the product later down the road.

• 11:02Anthony Pompliano?

  So I put out bait, I get bites, I get on the first call, I do a great job, I shut up after asking my open-ended questions, I get a bunch of information, and then I say, okay, I'm going to send you follow-up information.

• 11:14Speaker 02

  Yep.

• 11:14Anthony Pompliano?

  What the hell am I supposed to send, right? Again, this is just the founder. We don't have a sales team yet.

• 11:18Speaker 02

  Sure.

• 11:18Anthony Pompliano?

  So is it, uh, here's a link to a demo? Is it a presentation? Is it a signup form? Like, what is kind of the best practice there? And then, as a second part to this, what do I do if they don't respond?

• 11:32Speaker 02

  Yeah, yeah.

• 11:32Anthony Pompliano?

  The, uh, hated follow-up, you know, hell that you get kind of thrown into. What is the best practice for a founder?

• 11:39Speaker 02

  So a lot of that is, is a result of not doing a good job on the first call. And let me explain. So when you go on a first call and you have an okay conversation, you show them the product, and you sort of see that the person is not as excited, that's when you go into murky waters. And I'll tell you why. Because what typically happens is that you'll end the call with something like, hey, thanks for your time, you know, let me send you some follow-up information, I'll check in with you in a couple of weeks. That is where you get into the deal-chasing territory, which is not a good place to be. Now, what you want to do is, if you have a good call, which you're asking the right questions, and there is mutual interest, you want to propose the next step before you leave the call, right? And my best practice

• 12:22Speaker 02

  is usually like have something on calendar for your next meeting, so you avoid the, they went dark, or like, they're stuck in my CRM after my first call and I can't get a hold of him. Because you want to make sure that there's like that mutual benefit, but also you're driving the deal to the next place. But assuming that you did a great job with presenting an opportunity that, you know, is something that will provide value to them.

• 12:45Anthony Pompliano?

  And let's say that you do have that calendar invite set up. This happened to me before and I was like, I don't know what to do.

• 12:50Speaker 02

  Yeah.

• 12:51Anthony Pompliano?

  And then they, hey, I gotta reschedule.

• 12:52Speaker 02

  Okay.

• 12:53Anthony Pompliano?

  And then you basically get another one and then they reschedule again. It almost feels like they're using the reschedule as a way to keep kicking the can down the road.

• 12:59Speaker 02

  Sure.

• 13:00Anthony Pompliano?

  What do you suggest in terms of actually being able to be effective in follow-up without annoying people?

• 13:05Speaker 02

  Yeah, so there's a couple of tactics. I'll go back to how well you execute that first call. I think, you know, if you execute that right call, you can find out ways that they actually have some sort of urgency. So going back to my revenue example, if they're trying to get to an X number of revenue by, let's say, the end of the year, the sooner you guys start working together, the sooner I can help you get to that goal. Right? So what I tried to find out in the first call is that, you know, kind of urgency lever. So I can keep it in mind as regards to follow-up. So you're saying like, hey, if you want to get this implemented, let's say by August 31st, in order for us to do that, we need to make sure that we go through X number of steps. And instead of being annoying, what I'll do is I'll remind them of what happened in that call.

• 13:49Speaker 02

  Like, hey, listen, I think we had a great conversation. Just want to make sure I'm not being the annoying sales rep. But understanding that you have a goal or deadline, doesn't make sense to, you know, have a call sooner than instead of two weeks later down the road. Right? That's one. The second one is I'm a big fan of something that's called the call between the call. So when you call someone and assuming they answer, between the scheduled calls, that person is not necessarily prepared to have a conversation with you. So naturally and humanistically, they will give you the honest answer. Right? So you call them and say like, hey, Pomp, you know, I know we have a call, you know, kind of next Thursday. You know, give me a sense of, you know, kind of how you felt about the product. You know, does this really align with what you're looking for?

• 14:32Speaker 02

  And hopefully in that scenario, you tell me like, listen, you're good, but you know, you're a little bit out of budget. And then we can, you know, know what to address at that situation.

• 14:40Anthony Pompliano?

  Got it. And so are you calling them on their cellphone or like just trying to catch them off-guard essentially?

• 14:45Speaker 02

  Pretty much. I mean, it's, um.

• 14:48Anthony Pompliano?

  Well, whatever the tactics are, tactics are, right?

• 14:50Speaker 02

  Yeah.

• 14:50Anthony Pompliano?

  And so when you're calling though, is it just like, you know, hey, Steve, hey, Mary, uh, I got two seconds. You know, I just want to hear what you thought about the product? Or is it something that is much more kind of polished? Like, how do you normally approach those calls?

• 15:03Speaker 02

  It has to be as human and as like straightforward as possible. So if I'm calling you to say like, hey, Pomp, you know, what did you think about, you know, kind of my product? I, you know, I'm excited about this opportunity. You know, you think that we're, you know, on the right track. If, if, if, for example, I forgot to ask this question, that that's something that I'll use as an opportunity. I forgot to ask you this question on the call, but I wanted to, you know, catch you one on one. Is this something that you think is worthwhile or, you know, you see as, as getting you closer to your goals?

• 15:32Anthony Pompliano?

  And then what about like identifying who the champion is internally, right? So sometimes in my experience, the champion is the decision maker. Other times they're not the decision maker.

• 15:39Speaker 02

  Yep.

• 15:40Anthony Pompliano?

  But how do you, if you've got a couple of different people you're talking to at a company, how do you kind of identify, okay, that is going to be the champion? And then how do you treat them differently than maybe you may treat other people?

• 15:48Speaker 02

  Yeah. So, great question. I think that it's more obvious than you think in a sense of like being able to ask, right? So who is, who is going to be the person that's going to sign on the dotted line? Who needs to be part of this as you're making process? Those types of questions, a lot of like sales reps or even founders in the early days, like forget or fear asking. But is that simple as understanding, you know, how do you transact and let me align to the way that you transact, right? And, and a lot of times they might just give you the answer and say like, hey, I'm going to be the one that's, you know, kind of making the decision, but we have a panel of people, et cetera, et cetera. How you treat that person is hopefully in a more personal way, right? I want to build the relationship with that person.

• 16:31Speaker 02

  And then if I'm the one being the founder calling, I will make the call to the champion. I won't make the call to the economic buyer or somebody else, right? It's tough sometimes because the champion may be the CEO. CEO is not necessarily going to be available to pick up a call, you know, 3pm on a Tuesday afternoon. So you have to be strategic about it.

• 16:49Anthony Pompliano?

  What about, um, once you've got, as a founder?

• 16:53Speaker 02

  Yep.

• 16:53Anthony Pompliano?

  The decision maker says, yeah, we're good to go. And then it gets sent to finance. Or it gets sent to compliance or, you know, the, the, uh, general counsel. There's a couple of different organizations internally usually that have to kind of touch whatever the contract is or, or review something. And now you feel like you've almost been separated from the champion being able to manage the process to like, hey, it's with finance. Hey, it's with, you know, uh, compliance.

• 17:20Speaker 02

  Yeah.

• 17:20Anthony Pompliano?

  How can you as a founder continue to help? Help move this forward without being annoying.

• 17:25Speaker 02

  Yeah, so that is very typical in enterprise sales, right? So when you're selling to a bigger organization, I think that the important thing for you to understand is that that will happen, right? So a lot of people go into these sales processes like expecting it to be signed off, you know, and that is where you lose time and where you lose momentum, right? So if I know that I'm going to have to go through legal, compliance, finance, sometimes even vendor risk, I want to start addressing those as early as possible in the sales process. So I know that I need to go down that route and that I'm going to do it in a either parallel fashion as we're like agreeing to business terms and then doing the logistical work, right?

• 18:06Speaker 02

  So sometimes what reps will do or early-stage founders is they'll create a mutual action plan. And in that mutual action plan, there's pretty much sort of a timeline of the things that we assume that need to be covered. And that actually shows a lot of preparation from like the seller's side because, you know, you want to do business with someone that knows what they're doing, right? So if someone shows up and tells me like, hey, pump, here's usually how we sell into enterprise customers. And we're able to go through agreeing on the business terms, going to committee, going to legal, going to compliance, and here are the different dates that we want to, you know, kind of agree to. What typically happens in something like that process is that you also have a date that you solve back from, right?

• 18:49Speaker 02

  So if it's going to take me a month to be in finance and we need to get the deal done, you know, within three weeks, I'm going to go back to my champion and let them know what the process is like. Cause I want to make sure that they can deliver the urgency because in both of our best interests for it to move forward. And then I use that champion to gain some velocity on the finance side, or maybe he needs to go nudge someone because being the champion also means that he can help me, you know, lobby or work the internals of that heavy or big organization.

• 19:22Anthony Pompliano?

  Now that the founder has made a couple of sales and starts to understand the process, eventually they'll say, okay, I need to hire someone. I've talked to founders and they're like, all salespeople are full of shit. They can't sell at all. And then I've talked to other founders that are like, build as big of a sales team as you possibly can. They're amazing and they all drive revenue.

• 19:39Speaker 02

  Yeah.

• 19:39Anthony Pompliano?

  The truth is probably somewhere in between.

• 19:41Speaker 02

  Sure.

• 19:41Anthony Pompliano?

  But how do you think about that first or second sales hire? Where do you find these people and how as a founder can they actually interview and kind of underwrite who's good and who may not, you know, be able to deliver on the promises that they say?

• 19:55Speaker 02

  Yeah. So the founding account executive, as I like to call it, or it's known in the industry, is one of the hardest hires to make early in a company's, you know, journey. And I'll tell you why. It's because you're going from the founder-led sales motion to starting, you know, kind of that sales-led growth motion, meaning sales is leading the charge, but you're transferring all the information from the person that built the product, that knows it best, and that actually has the most passion into someone that you want to make sure that has the same skillset or like passion for what they're selling. So this is a very non-traditional sales role, and I can tell you a lot about it because I was a founding account executive, which we can talk about more.

• 20:38Speaker 02

  It's more a seller that wants to build, but that can overly communicate. And I'll explain why. When you're trying to find that velocity, that, you know, scalability and repeatability in the early days, when you're past the baton from the founder to a seller, you still need to report back to the engineering team. You still need to tell the engineering team, hey, listen, like, I know this is our roadmap, but what I'm hearing in the market and what people are telling me that they want is X, Y, or Z. And so you're giving, you're putting a lot of responsibility from a company's perspective into someone that's, you know, kind of external. Now, that person, because I mentioned he is a builder, must want to have that ability

• 21:18Speaker 02

  to work outside of like, you know, sales conversations or like maybe non-revenue generating activities, which may be talking to engineering. That person also must want to build and they must be willing to be in an Environment where there's a lot of uncertainty, but nothing is put together. So I'll tell you what an example of like a founding account executive that usually doesn't work. Is someone that comes from a really large organization and goes into an early stage environment. And I'll explain because in a larger organization, you have marketing, you have sales engineering. That's usually the one that's doing the presentations or the product demos. You have, you know, a brand behind you that you may not have in the early days.

• 21:59Speaker 02

  And when you put that same exact person that's used to just transacting with a team behind them. Into an early stage environment where they don't have that, you know, infrastructure or support behind them. They usually get overwhelmed and, you know, they can't perform. Right? So that's the very long answer to the first part of your question. I think that from an interview process, it has to be the founder identifying someone. That is a lot of entrepreneurial, but a lot of selling. Right? And there are many ways to catch, I get this all the time, salespeople interview well. But in reality, they don't if you ask the right questions. Right? Because they're, everyone's happy, everyone's peppy, et cetera, and whatnot. But what you got to understand is number one, like, why do you want to go early stage?

• 22:44Speaker 02

  Like, why do you want to go into like the most uncertain sales environment possible? Number two is like, what's your willingness and give me examples of like, how would you build this? And send me the examples. And then three, I usually like to do situational questions. Right? So let's say somebody called you to tell you that you suck or, you know, something along those lines. Or maybe it's a deal that I want them to walk me through because I want to find alignment to. I want to find that someone that has been in a particular sales environment can actually translate over. And if they've sold into actually the same buyer persona that this company is now selling into. That's even better because they can help us accelerate and they know exactly what to do.

• 23:25Anthony Pompliano?

  So one of the things that you're highlighting here that many people probably just don't think about until they're in it is that first sales hire, they also have to create all the sales material, right? They have to create the deck. They have to create, what is the demo going to look like? What is all of our email sequences, et cetera? And in my experience, there are some people who are amazing at sales. They hate prospecting, right? And they're like, hey, at my last job, like, just like, you know, leads showed up and then I went and I sold and I was amazing at it. But like, I don't know how to go get the leads. And there's even people who are really good at prospecting and they're like, well, I've never been on a sales call before.

• 24:01Speaker 02

  Yep.

• 24:01Anthony Pompliano?

  Right? I just went and found all the leads and gave them to somebody else. And so it really almost feels like you need somebody that can go kind of full funnel and find leads, have the materials, the system, all the follow-up sequences, et cetera. And then also be able to actually close the deal as well.

• 24:16Speaker 02

  Yep.

• 24:17Anthony Pompliano?

  How many of those are out there, right? Like, are there a lot of those people out there? Or is this actually like a pretty hard role to find?

• 24:25Speaker 01

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• 24:52Speaker 02

  It's hard. It's hard. It's a hard role to find. And you open up a question or a situation where, you know, traditionally in B2B SaaS, as you mentioned, there's the SDR that's doing the prospecting, you know, kind of full force. And there's an account executive that's just doing the demos, closing, negotiation, et cetera. I think that there is a world where the founding account executive like needs to be a full sales cycle rep. But also that the full sales cycle rep is something that is going to come and be more prevalent like in this day and age. And let me explain why. There are so many tools out there today that help you create a system to prospect that allow

• 25:32Speaker 02

  you to get access to information or leads very easily. And with AI and all the different things that we can go into, it's even easier to write good copy and to, you know, make it more personalized to that particular person. So if you create the right systems, which obviously require a level of savviness from like that individual, you're going to create your own momentum to get leads, right? And then second to that, which you see a lot of reps doing on LinkedIn nowadays, is creating your own personal brand, creating a lot of content that can, you know, give you that audience. So when you do prospect, there's a perception of like, this guy is well-known, I've

• 26:11Speaker 02

  seen you before, I want to talk to you, right? So that skillset is hard to find, right? Someone that wants to go through the, through the whole process, not only wants to, but has the tools to actually do prospecting and closing altogether. The reason a lot of companies historically will do SDR and A is because of focus. Because when you're prospecting, you're not transacting, and when you're not transacting, you're prospecting. So it's really important that like that, that first sales hire, the founding account executive has the right system, right, to, to create top of the funnel if you haven't created it yet, which again, requires a particular sales muscle. And then the

• 26:52Speaker 02

  separate sales muscle, which is like, how do I structure the sales process and iterate every day?

• 26:59Anthony Pompliano?

  As the founder, you've now hired someone, you think they're good. How can you be a good manager? And then what are the things that you could do to really fuck it up? Right? Like, like you've got the salesperson there. There's got to be some trust, right? But like, what are some of the things that are like best practices of managing that first salesperson? And then what are the things that just please avoid because you're going to make the situation worse?

• 27:23Speaker 02

  I think, you know, micromanaging for any role is what, you know, kills any sales rep. No sales rep wants to have someone on top of their stuff, you know, kind of on a regular basis. That's number one. I think that, you know, wanting the salesperson to specifically operate under a particular style is a way that you can break a rep. And I'll tell you why. Some reps are phenomenal on the phone. Some are not. And some reps are extremely good at email, some are not.

• 27:53Speaker 02

  Now, I cannot, it's sort of like, you know, get your job done however you can get it done like I'll respect it, but you know, many times a founder will say, no, no, you have to make, you know, a thousand calls this week. And this rep may not necessarily be good on the phone. Now, you need to know that ahead of time because if you're trying to sell to a buyer that needs to be communicated through on the phone, you just made the wrong hire. That's no, that's, that's super important as well, right?

• 28:17Anthony Pompliano?

  Yep.

• 28:18Speaker 02

  But you need to give them, you know, kind of the respect to what their style is in a sense of like, here's how you execute, but also give them the right direction. Sales is very grueling. It's intense. You get a lot of rejection. So I think that as a manager, you also have to support a lot of like your team and remind them why they're here, where they're good, because a lot of times like they will be defeated because it's, it's a grueling job with a lot of pressure, deadlines, goals, et cetera. And I think the last thing I'll say is, is, um, you know, you mentioned trust. I think that's one of the most important things. When a rep knows that they're, they're not being trusted. I mean, it's, it's a hard situation to be in, but also at the end of the day, sales is black and white. You're performing or you're not. So.

• 29:03Anthony Pompliano?

  So I've done it in the past. Somebody smarter than me told me they're like, hire two at a time.

• 29:09Speaker 02

  Yeah.

• 29:10Anthony Pompliano?

  Don't just hire one AE, don't just hire one SDR, hire two at the same time. And then in some ways, there's this like implicit competition.

• 29:19Speaker 02

  Yeah.

• 29:20Anthony Pompliano?

  So they kind of bring their A game.

• 29:21Speaker 02

  Yep.

• 29:22Anthony Pompliano?

  But there's also this like explicit, uh, almost like, um, kind of social safety net of like emotional support because you're not there by yourself trying to figure out all this. You have somebody to talk to, et cetera. Is that the best practice is to kind of hire two at a time?

• 29:35Speaker 02

  You're spot on. You're spot on. I'll tell you why. Um, you know, a salesperson is used to being around a team. When you take them out of that environment and you put them in a, in a, an environment where he's by himself, it's tough. Not everyone's built to be a lone wolf. So when you hire two, you know, you give them that social, let's say belonging, but you're also solving for, you know, performance. Sometimes when you have, um, two reps, you might see that one is better than the other or one figured it out. The other didn't. And what a lot of companies will do is they'll just hire one and say, well, this guy can't sell. He's a sales guy. We don't have a good product. That's a tough decision to make just based off the performance of one individual. But when you have two individuals and two performance, let's say, metrics that you can compare.

• 30:20Speaker 02

  It makes life a little bit more understanding to say like, well, if this guy works, like that means that we have, we have a solution. We, we can sell. How do we get more people and create a process that then we keep adding more to the process?

• 30:32Anthony Pompliano?

  When do you know when to fire them?

• 30:35Speaker 02

  Everyone has their own, you know, kind of way to do this, but usually there's like a ramp period, uh, three months. Right? So you give them soft goals. You say like, you know, by month one, you have to do what I think is 25% of your goal. Month two, you have to do 50% of your goal and month three, you're fully ramped, which means it's at the, uh, what I think you can sell, you know, you're selling that by month three. If that person hasn't, or you see that they don't have, you know, kind of the right, uh, let's say, performance with those metrics, it's time to go.

• 31:07Anthony Pompliano?

  So I'll give you a real life example. I think of how some of this gets very complex. We have a business. They're five figure contracts. Uh, they're with pretty large businesses. And we'll get verbal commitments.

• 31:21Speaker 02

  Yep.

• 31:21Anthony Pompliano?

  We're in. Send us the contract. We're very quick. We turn around the contract, usually same day, get it in their hands. A week, two weeks, three weeks. And what happens is there's internal pressure because these teams have to hit quarterly quotas.

• 31:37Speaker 02

  Sure.

• 31:39Anthony Pompliano?

  The external companies, they don't give a shit about your quota. They're going through their process.

• 31:43Speaker 02

  Right, right.

• 31:44Anthony Pompliano?

  And so one of the things that we've tried, sometimes with success, sometimes not, is to just be honest and say, hey, for internal purposes, like getting this done by the end of the uh, quarter would be really powerful for us. Like, how do we get that done?

• 31:55Speaker 02

  Yep.

• 31:55Anthony Pompliano?

  Literally, sometimes I've seen people respond back and be like, so what? Right? Like, I don't care.

• 31:59Speaker 02

  Yeah.

• 32:00Anthony Pompliano?

  But other times I have seen them say, okay, let us see what we can try to get done.

• 32:03Speaker 02

  Sure.

• 32:04Anthony Pompliano?

  How do you see kind of quarterly quotas and like the internal pressure?

• 32:08Speaker 02

  Yep.

• 32:08Anthony Pompliano?

  Is that a tool to be used externally? Or is it actually something that could hurt people when they start to kind of, you know, pull back the curtain and explain some of like the internal, you know, inner workings and they're just like, I don't give a shit.

• 32:19Speaker 02

  Yeah, that's a great question, and I think it depends how you use it. Right? So there's a little bit of finesse in how you say it in a sense of like, hey,

• 32:29Speaker 02

  you know, I have goals and our quarter is, you know, done at the end of this week. I don't want to be pushy, but you know, help me understand you think is real that we can get this done by Friday? If not, I completely understand, but I just want to make sure that, you know, I forecast this accordingly. And they'll understand, you know, and if you have a good enough of a relationship, like I think that you can do that. What doesn't work is if you come out of left field and you haven't talked to them in a while and say like, hey, you know, the quarter ends today, you think we can get this done? Like, you're probably actually hurting the deal in that case because it's like, dude, it's about self-interest. If you have that good enough of a relationship where you can be, you know, subtle about it, I think you can get the answer that you're looking for.

• 33:13Anthony Pompliano?

  Got it. That makes sense. Let's talk about kind of your transition, right? You were inside some of the fastest growing companies in the country in terms of startups. Absolutely wild places. People have heard a ton of stuff about them. Talk a little bit about those experiences, really kind of from the sales perspective and like, you know, what were the lessons that you learned and then maybe what were some of the things that you're like, okay, you know, if I go to the next business, we're not going to recreate some of these other things.

• 33:35Speaker 02

  Yeah, so, listen, I appreciate you bringing that up. I've been part of, yeah, three unicorns, Zenefits, Rippling, and WeWork. And I have too many lessons from each of them. And starting with Zenefits, Zenefits in 2014 was the fastest growing B2B SaaS company in the world. We did zero to $72 million in about two and a half years. And it was really like building a plane mid-flight. As some of the leadership would describe it and you just learn how to operate fast effectively. Right? There's, there's, you have to put in work around, you know, the performance, just like a performer.

• 34:18Speaker 02

  It's, I think, sales are, you know, kind of performers in a certain extent. But at Zenefits, I was in an environment where I had anywhere between 10 to 12 net new customer demos a day. For, for years and you learn about, a lot about selling, you learn a lot about, you know, kind of trusting yourself. But, you know, you start paying attention to the company and to the business. My background's in finance, so I, I kind of had a different perspective from like a financial perspective. And in 2014, there was a growth at all costs mentality that may or may not have been sustainable, as you and I know. And it was, it was sad because Zenefits was a very boom bust situation.

• 34:59Speaker 02

  The company, you know, after growing aggressively, becoming a unicorn in such a short period of time. Ended up having, you know, a lot of problems with like sales growth and we ended up having to lay off a lot of the team and, and that was hurtful. The lesson there is, you know, kind of operate effectively, but you know, kind of keep going. And then, of course, you know, everything that I know from B2B SaaS, like I learned there. And having a big exposure to building stuff and talking to the engineering team. Now, the second unicorn that I went to was Rippling. I was the first sales hire at the company, exactly what we were just discussing, working for Parker Conrad, who's a great friend. And I was sitting in the basement with 12 engineers and we had one SDR.

• 35:42Speaker 02

  And you learn how to have a lot of conviction, but you learn how to put yourself in a situation where you have to wear every single hat that you can think of and pull every trick out of your hat that you've used throughout your career. Right? There's nothing structured, so you have to be okay with uncertainty and know that it's going to be okay. But also, you know, be very organized about the things that you do because you have to think about revenue generating time, but you also have to think about building at the same time. And then the third company I went to was WeWork, which I thought was a very safe bet at the time. Incredible story, experience, maybe for another time, but WeWork was also a high-growth environment. And I kind of realized, and you know, looking back, that

• 36:26Speaker 02

  I've had a lot of success by saying yes to opportunities that a lot of people have said no to. And WeWork brought me to Miami, actually. Miami in 2018 was a distressed market in the eyes of WeWork because not a lot of big companies wanted to set up their headquarters here. And I signed up for it and, you know, the lesson there is, you know, I was willing to, you know, kind of get my hands dirty, stand up a team, recruit the right team to sell from Miami. And then eventually I ended up, you know, growing my responsibilities to run sales for the southeast of the United States. And that was a very different environment from my experience from selling B2B SaaS deals that ranged anywhere from 50 to 250K

• 37:08Speaker 02

  to going to WeWork where the average contract value was anywhere between $2 and $5 million. So, very different stages, very different, you know, kind of experiences and products. But common lessons, you know, in terms of sales and like the right things to do, which, you know, I carry with me for all my career.

• 37:27Anthony Pompliano?

  How did you decide to leave kind of doing sales for other people to go start your own business?

• 37:35Speaker 01

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• 38:03Speaker 02

  I always knew I wanted to be an entrepreneur, but I also noticed something that was very unique, which was I have a very unique exposure and experience that a lot of people want access to and that I can make a business out of. Coming from like my business background, I always think about hedges and not putting all your eggs in one basket and the recalcification. And I sort of build that structure with my company now. It's called Quota in a way where I can work with different companies. I can give them the value that I bring to the table, given my experience, but I'm not putting all my eggs in that one basket. And maybe it's a protection for my own self, given my past experiences, that's benefits and we work, which didn't necessarily end how I wanted them to end, right?

• 38:46Speaker 02

  And I knew that, you know, as a founding account executive, you're such an entrepreneur because you're doing so many things. And if I would have applied all those to starting my own business, I would have been successful. And so far, it's been an incredible experience.

• 39:00Anthony Pompliano?

  And then talk to me about you kind of have to do sales for yourself to then go help people with sales, right? So it's like this, like very interesting kind of meta type thing. But where have you found the best channels to get customers? Like, how have you applied some of your lessons that you know from these other businesses to your own business now?

• 39:17Speaker 02

  That's a great question. And we touched on it lightly earlier, but there are three channels, let's say, that worked for me really well from a top of the funnel perspective, which I wish like every rep would know or would utilize a lot more. Number one is referrals, right? So, you know, I work with companies that, you know, I do a good job, they refer me to other customers and I ask for the referral and that, you know, kind of comes, I come highly recommended. So I have like a pretty good close rate on those referrals. Number two is your network, right? So there's, there's a, people call it the go to network. And the go to network is pretty much like, you know, where throughout your experience in your life, you know, have you made, you know, relationships that you can, you know, knock on their door and say like,

• 40:01Speaker 02

  hey, here's what I'm doing, like, how do we work together? And then the third one is content. So I like to talk a lot about content. And I've been talking a lot about content lately because what I realized Is that sales is taking a page out of, you know, marketing's book. And it's almost becoming where like a lot of B two B sales motions are becoming B to C sales motions. And I'll explain because, you know, typically you would see people marketing their product online or doing all this content online. Just to sell like a particular like, you know, let's say e-commerce product. But now you're starting to see a lot of B two B folks doing the same. Creating content on LinkedIn, sharing a lot of value, sharing their experiences. Doing it even through Twitter, doing it even through, you know, kind of Instagram.

• 40:47Speaker 02

  And I started to invest a lot in that time and obviously through like being well organized with creating content on one side. And then running the operation on the other side. I found a lot of success and interestingly enough, I never had to do outbound for my business.

• 41:02Anthony Pompliano?

  And so when you're going to like, let's say the network as an example, how much of this is, uh, hey, here's everything I do.

• 41:09Speaker 02

  Yeah.

• 41:09Anthony Pompliano?

  Versus let me just have a conversation with this person, listen.

• 41:13Speaker 02

  Sure.

• 41:13Anthony Pompliano?

  Right. And then kind of, uh, see where you can almost, um, you know, help.

• 41:18Speaker 02

  Sure.

• 41:18Anthony Pompliano?

  And that helping is really where the business gets inserted like, is it this like intentional, like that's a company I want to work with them. Here's exactly what I'm going to do for them. Like, let me go talk to them.

• 41:27Speaker 02

  Yeah.

• 41:27Anthony Pompliano?

  Or is it much more like, that seems like a business that, uh, is gonna going to continue to grow. Let me go talk to them, learn about all their problems, and then I'll come to them with a proposal for like how I could be helpful.

• 41:36Speaker 02

  That, um, it's, it's more of like, I try to be very prescriptive when I ask for something. So I know, I know my expertise. And so for example, if I see a B two B SaaS company that's series A that's doing good. Um, and then I think that they could be doing better. Uh, I'll try to, you know, kind of study up the company and find a mutual connection and then say like, hey, I think this company like could benefit from my work. The other thing that I'll mention that I forgot to mention, which is really important, a big referral partner for me is VCs. So I work very closely with VCs for a handful of reasons. First of all, I mean, you get a lot of exposure, one to many, uh, in terms of like getting access to a portfolio. But, um, not every VC has an internal sales expert.

• 42:21Speaker 02

  A lot of VCs have. Have very sophisticated operators, builders, people that have been more on the technical side of the business, but don't necessarily have like that commercial element. So I come and sort of sit on their bench and act as a, you know, kind of sales expert for those companies, which end up, you know, kind of working really well because when a VC is funding a company and they tell you like, hey, go talk to Javier. It's almost like the person that's giving you money is telling you to do something. You're probably going to go do it. Right?

• 42:49Anthony Pompliano?

  Yeah, that makes, that makes a lot of sense. What, what would you say is the biggest mistake that founders make when it comes to sales? Whether it's them doing the sales, hiring, managing the teams, like what, what's like the one thing you're like, if I could just take, have everyone take something away from this conversation, please don't do X.

• 43:05Speaker 02

  Yeah. Well, I mean, there's one that's super obvious, which is like, don't build products that people don't want, right? Because listen, pump, at the end of the day, there's a lot of people that build products that, you know, they forced the distribution. And like, if the market doesn't want it, like you're not going to have any type of product market fit or repeatability. So I think that the way to solve for that is, you know, front load your sales. And what I mean by that is like, start talking to people as many as you can. Imagine that you're doing the sales process, get feedback and understand what people are struggling with or what they're doing. And, you know, I, I've, you know, kind of experimented with an AI product ourselves that we're looking to, you know, add to our services or sell individually. And what we've done is talked to hundreds of people.

• 43:50Speaker 02

  And I don't know that a lot of founders will do that on a regular basis to say like, hey, let me talk to a hundred companies, run it like a sales process, get feedback and then build something that the market wants. Because then when you start talking about it and building content and, you know, kind of doing the prospecting, once the product is built, you're actually responding to like a true need versus like a need that is perceived from just your own perspective. So talk to more people ahead of time is, is pretty much what I would recommend.

• 44:23Anthony Pompliano?

  Where can we send people to find you on the internet or find out more about Quota?

• 44:26Speaker 02

  So I'm very active on LinkedIn. So Javier Ramirez Lugo is where you can find me. And on Twitter, Javi B2B is my handle. So you can find me there. I'm very proud.

• 44:39Anthony Pompliano?

  Pretty clear what you do.

• 44:40Speaker 02

  Pretty clear what I do. So yeah, you can check out anything that I'm doing and the companies that I'm working with there.

• 44:46Anthony Pompliano?

  Awesome. Thank you so much for doing this. I always learn something about sales every single time we talk. And anyone who's looking to learn more, I suggest they reach out to you. So I appreciate it.

• 44:54Speaker 02

  Thank you for the time, Pom. Super exciting.