20Sales: Why You Should Never Hire a VP Sales First, How To Create Urgency in a Sales Process, How to Do Traditional Outbound 10x Better, Why Revenue Doesn't Matter with Your First Customers | Mark Goldberger, Head of Enterprise Sales @ Ramp

Mark Goldberger is Head of Enterprise Sales at Ramp, the fastest-growing corporate card and bill payment software in America, and recently named Most Innovative Company in North America by Fast Company. Prior to joining Ramp, Mark was the first enterprise rep at TripActions (now Navan), where he helped bring in more than $100m of ARR as an IC and sales leader. Before TripActions, Mark worked at Highfive, a video conferencing company since acquired by Dialpad. In Today's Episode with Mark Goldberger We Discuss: 1. From Wine Industry to Sales Leader: How Mark made his way into the world of enterprise sales having been in the wine industry? Mark sent out 100 CVs for his first sales role, why did they not respond? How should companies think differently about the people they hire? What could he have done better with the outreach? What does Mark know now that he wishes he had known when he entered the world of sales? 2. The Sales Playbook and Why You Should Never Hire a Sales VP First: Why does Mark believe that you should never hire a Sales VP as the first sales hire? What does Mark mean when he says product-customer-fit is more important than product-market-fit? Why does Mark believe that revenue does not matter with your first customers? If revenue does not matter, what should you be trying to get out of them? When should the founder handover sales to either a junior or more senior hire? 3. How to Hire 10x Sales Teams: The Process: How does Mark structure the process for hiring 10x sales reps? What questions are most revealing in identifying a 10x sales rep? How do they respond? Why does Mark want candidates to pitch his own product back to him? How does Mark make the hiring process more challenging to really test the quality of candidates? What is the core difference between losers and winners in sales? 4. Discounting, Champions, Creating Urgency: Why does Mark not like discounting? Where do many sales teams use it poorly? How does Mark like to create urgency in a sales process? What works? What does not? How can sales reps know whether they truly have a deal champion within a buyer? What is the right way for sales reps to ask to meet the exec buyer? When is the right time to ask to meet the exec buyer? What are some clear signs that you are not speaking to a decision-maker? 5. Building a High-Functioning Sales Org: What is the right way to do deal reviews? How often? Who should be invited? What is the right way to do sales onboarding for all new reps? Why is traditional outbound still the most important thing in a sales process? Why do so many people get pipeline qualification so wrong?

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

• 0:00Speaker 00

  You don't need product-market fit in order to sell an enterprise, especially as that first seller. What you need to find is product-customer fit. Those first sales, I don't think about revenue as being important. In no circumstances do you really want to bring in a VP of Sales before you have a seller.

• 0:17Harry Stebbings?

  This is 20 Sales with me, Harry Stebbings, and I started these vertical themes for 20 VC because I thought founders really needed to be advised by the best operators in these specific verticals: sales, product, and growth. Our sales discussion today is so actionable and hands-on. I absolutely love doing it, and I'm thrilled to welcome Mark Goldberg, Head of Enterprise Sales at Ramp, the fastest-growing corporate card and bill-payment software in America. Prior to joining Ramp, Mark was the first enterprise rep at TripActions, now called Navan, where he helped bring in more than $100 million of ARR as an IC and then Sales Leader. And then before TripActions, Mark worked at Hi5, a videoconferencing company since acquired by DialPad. But before we move into the show today, you might remember in our amazing episode with Maggie Hott,

• 1:01Harry Stebbings?

  she mentioned a tool she could not live without called Pocus. What is Pocus? Well, Pocus is a revenue data platform that makes it easy for go-to-market teams to analyze, visualize, and action data about their prospects and customers without needing engineers. Pocus helps companies like Miro, Webflow, Loom, and Superhuman focus their sales and success teams on the highest priority opportunities by surfacing insights at the right moment so reps can take action quickly. Pocus gives you a 360-degree view into product usage, empowering you to act on insights and fill your funnel efficiently. Sales teams save 10-plus hours per week digging through data to surface millions of new revenue opportunities. Learn more about why top PLG businesses

• 1:45Harry Stebbings?

  trust Pocus as their revenue data platform by visiting pocus.com/demo. And SalesLoft is the leading sales engagement platform, helping sales teams drive more revenue with the modern revenue workspace. It's the one place sales teams can go to prospect, manage active deals, and get the insights they need to coach seller performance, forecast with accuracy, and find out what steps to take to close more deals. Some of the world's leading companies like Google, Shopify, and Stripe all love a new SalesLoft, and so can you. It's the new way to sell. Find out more at salesloft.com.

• 2:25Speaker 02

  You have now arrived at your destination.

• 2:28Harry Stebbings?

  Mark, I am so excited for this. I heard so many great things from so many former colleagues of yours and current colleagues of yours. So, thank you so much for joining me today.

• 2:36Speaker 00

  Harry, my man, it is so good to be here. Thanks so much for having me on the show.

• 2:40Harry Stebbings?

  Now, we have a lot to dive into, but I want to start with actually the move to Ramp and leading Ram's enterprise sales team. How did you make your way into the world of enterprise sales? And how did you most recently come to lead Ram's enterprise sales team?

• 2:53Speaker 00

  I came to the world of enterprise sales from the world of wine. I recognize that's not the typical journey one makes. So, I was working in Massachusetts as a salesperson for a wine distributorship while I was going to business school. And upon graduating, it was the Great Recession. Not a great time to leave a good-paying job for an unpaid internship somewhere. So, I actually founded my own company. I bootstrapped a SaaS business back then, knowing nothing about SaaS, mind you, but built a cloud-based company with tools in the cloud specifically for the wine industry. Bootstrapped it. We had paying customers. It was a wild, incredible experience. After a few years, ultimately, I did decide to wind down that business. My wife and I moved out to Silicon Valley when she took a role

• 3:36Speaker 00

  with a little startup in Mountain View called Google. And so, I found myself out here in Silicon Valley, and I said, "Okay, I'm going to be an account executive now, again, for SaaS companies." And I sent my resume out to about 100 companies, and the response was, there was no response. Literally, could not get an interview. More than 100 resumes sent out. I had founded my own company that was a SaaS company. I had always been a top performer in sales, and yet, no one was interested in even interviewing me. It was a frustrating experience. It was a humbling experience. But ultimately, as someone who has already had a giant chip on my shoulder, it drove me to go out there and perform.

• 4:17Harry Stebbings?

  You're the master of also being cold outbound, being the enterprise leader you are. You must also self-analyze. What was wrong with your approach, and why did that happen?

• 4:26Speaker 00

  There's fault on both sides. I think there's a challenge from software companies and sales leaders thinking too small inside. Out of a box in terms of the profile of who they're looking for. And there was also a challenge on my approach, not having lived in this world. It was a world that was foreign to me and I needed to find my way in. Ultimately, after a couple of months, I connected with a terrific recruiter and ultimately taking a position with a video conferencing company called Hi5. It was backed by General Catalyst and Lightspeed, was competing against Zoom. And this was before the pandemic when selling video conferencing was maybe a little bit harder. Ultimately ended up getting recruited by Trip Actions, now called Navan, and was their first enterprise account executive and really built the enterprise go to market there.

• 5:10Harry Stebbings?

  You mentioned the time at Navan in such a transformational and kind of hypergrowth time for the company. What are one to two of the biggest takeaways for you from that time? And from being the first enterprise sales leader there, what have you taken with you to your time now as Ramp?

• 5:24Speaker 00

  The first lesson that I really took away, and this comes from when I was an IC, an enterprise account executive there. I built up a massive amount of pipeline the first six to nine months. I had eighty seven opportunities in my name, Harry. And if you know anything about enterprise sales, that's way too many opportunities. But I started to close deals about month six. And what I recognized was you don't need product market fit in order to sell an enterprise, especially as that first seller. What you need to find is product customer fit. And so when you have a huge amount of pipeline like that, you can really prioritize it and focus on the accounts that match best

• 6:05Speaker 00

  with the vision that you're building toward and where their required capabilities match with your core competencies. So when you focus on that twenty percent, that's going to drive eighty percent of your outcome, amazing things happen. And I closed about thirteen million dollars of revenue that first year.

• 6:20Harry Stebbings?

  My, my question to you is, you said there about kind of product customer fit. I love it, I get it, but we have those eighty six companies. What do we do then? What does product customer fit actually mean? Help me and help sales leaders and reps understand that.

• 6:33Speaker 00

  Yeah, so it, it goes down to something that I built later on, qualification methodology, I called Lean Pivot Walk. And essentially, what you're trying to do is understand, hey, if the boxes that they're looking to check are the boxes that we check really well, you should lean in, you should be going after that opportunity, full force. If what they're looking for is something that is not even on your roadmap and wouldn't be on your roadmap for the next five years, you need to be honest with yourself. So many reps out there have happy ears and just because someone wants to meet with them, they think, hey, they've got an opportunity. You need to be honest and be able to walk away and qualify that deal out. And then there are other opportunities where maybe you check some of the boxes and not others. And is

• 7:17Speaker 00

  there a world where they're willing to have two different solutions, one for the rest of the world and maybe one for North America? And so you start to understand these dynamics and you can play off of them and ultimately close a lot of business that way.

• 7:29Harry Stebbings?

  You said that you can get product customer fit without having product market fit. I'm really intrigued. Does the salesperson need to be the one to create the sales playbook? Or does the founder need to be? How do you think about that question in terms of the product market fit question as well?

• 7:45Speaker 00

  Yeah, for product market fit, I think that is driven more by the founder, being out in the field, talking to customers, talking to prospects, really understanding their pain points and being able to dive in at that level. But when you think about sales and a sales playbook, I think that's originating from the salesperson. And in some businesses, the founder is that first seller. In other businesses, you want to hire a junior salesperson to go out there and figure things out. But in no circumstances do you really want to bring in a VP of Sales before you have a seller, because they're going to come in with the preconceived notions that ultimately might not mesh with your particular business model.

• 8:23Harry Stebbings?

  I always think hire the more senior, because then they can build the team around them rather than hire the junior and then bring in a more senior who then adopts a team that they didn't actually hire. How do you think about that challenge?

• 8:35Speaker 00

  I think about it a lot, but where I come from, ultimately, if you have a sales leader who's coming in, they have a playbook in mind. They have processes in mind, they have sales tools in mind, and that Playbook might not mesh with the product that they're actually selling. It might not mesh with the people in that organization. And so when you try to jam that square peg in the round hole, you ultimately create thrash. And for an early startup, you can waste a lot of cycles and a lot of time having the wrong people in the wrong position.

• 9:10Harry Stebbings?

  And he has a really good point. I think you said that there's sometimes for a founder where they need to lead the case. When it is the founder leading the case, what are the signals that they need to hire the first junior sales rep? Often it's like a million in ARR is touted as the number, which I think is bullshit because it means little. What are the signals that the founder needs to make that first hire, do you think?

• 9:33Speaker 00

  I think they should make that first hire as soon as they have a product that they really want to be testing out in the market. I think it's a lot sooner than a million ARR, to be honest. Those first sales, I don't think about revenue as being important. The revenue or the currency that matters in those first sales are the logos. You need to be acquiring logos. You need to be able to say, hey, this company works with us. That gives you credibility when you're trying to make that sale for revenue. You want their feedback, you want the case study, you want them to be a reference for you. That matters a lot more than revenue in those early days.

• 10:07Harry Stebbings?

  In terms of going back to that single sales rep hire, Jason Lemkin says about the importance of hiring two at a time so you can really determine quality and compare. Do you agree with that or do you think one works just as well?

• 10:19Speaker 00

  The way that I think about it is I'm looking for salespeople who can provide 10x growth, not 1x or 1.5x. When you find someone who can provide that 10x level of growth, they're a rare find. To find two at the exact same time and to be able to recruit them and have them join at the same time is an exceptionally rare opportunity. If you do find them, by all means, you should hire them. You should hire them as fast as you can, whenever you can. But ultimately, if you are at scale, it's easier to hire, hey, two salespeople at a time. You're going from 20 reps to 30 reps to 40 reps. Great, hire a.

• 10:59Speaker 00

  An incoming class, but in those early days where each additional player is going to have so much impact, you need to be grabbing the best talent when you can.

• 11:09Harry Stebbings?

  I spoke to the best talent when I could, who worked with you. And so I have a lot of information about that. You are so brilliant, Mark. So I want to dig into some of the areas where you're techs. And I want to start with deal champions and multi-threading in particular. I think it's something that people universally still do badly, actually. How do you confirm you have a deal champion in a cycle?

• 11:30Speaker 00

  There is only one way to know if they really are a champion for you. You have to test them. And the way that you test them is asking them to take you to the executive buyer. Now, that can result in two things. One, they have the power and influence to be able to take you to the EB. Typically, that's a CFO, especially today. If they have the power and influence to do it and they're willing to take you there, help present with you, you need to be in that meeting on your behalf, they're selling internally, you've got a champion. If they say no to you for whatever reason, it means one of two things. Either they don't have the power and influence to take you to the executive buyer, in which case you're dealing with a coach or just a stakeholder in the organization who really is not going to be meaningfully important for you.

• 12:12Speaker 00

  Or you haven't earned the right yet to have them take you to that CFO or to that EB, in which case you have more selling to do.

• 12:20Harry Stebbings?

  What is the right way to ask without seeming slimy or like you're asking for too much?

• 12:26Speaker 00

  You need to set that expectation from the start. Literally in the first meeting where I walk through a pitch deck, I share with them why we exist, what we're solving for, and what it's like to be working with us. And from everything from implementation and onboarding to, hey, part of our sales process is we're going to want to have an open dialogue between your executive team and our executive team. This is not a typical vendor customer relationship, but it's a partnership. And so we want to make sure there's that open dialogue so that what your CFO cares about, our CEO listens to.

• 13:03Harry Stebbings?

  When's the right time in the deal cycle to ask to go to the executive buyer? Because you don't want to do it too soon where it's like, what? Oh, we've just met, Mark, and I'm not quite ready for that. But then you don't want to do it too late. When's that time?

• 13:14Speaker 00

  You need to be able to get to the executive buyer. There's a lot of different ways you can get there, too. It's not just through a champion. You can leverage your network, you can leverage your board members, you can leverage your executive team to back channel into that executive. Typically, you want to be able to get some kind of a business value assessment where you're agreeing on what the value is that we can provide for an organization. And at that point, you're going to go with your champion and present those findings to the CFO or to the executive buyer.

• 13:44Harry Stebbings?

  What should you provide your champion to make sure that they're equipped to sell your case best to the executive buyer on your behalf, but when you're not there?

• 13:53Speaker 00

  The phrasing of that question scares the shit out of me, Harry. And the reason why is that you need to be in that meeting. There is not a world that I would ever be comfortable living in where I want to outsource my job to a champion and a prospect that is living very dangerously on the edge. I know a lot of salespeople who will take completely wholesale what a champion says. Hey, my CFO doesn't meet with anybody. My CFO is too busy. I will be the one to talk to them on your behalf. We can't have that because what happens when the CFO asks you that question, Mr. or Mrs. Champion, that you don't know the answer to? What happens when they question these numbers? Or they ask about implementation? Or have you talked to these different stakeholders? And you don't know the answer?

• 14:38Speaker 00

  We have to be in that room with you.

• 14:39Harry Stebbings?

  Yeah, Mark, what a terrible question. Gosh, silly. No, thank you for clarifying that. And by the way, do ridicule any questions. I love this. You mentioned the importance of multi-threading there and bringing in the executive buyer. It's important that sales reps and sales teams see around corners. What are some ways that sales reps can get better at seeing around corners during a deal cycle?

• 15:02Speaker 00

  A lot of people tend to wear rose-colored glasses. They get happy ears, as I mentioned before. People are meeting with them, they're excited. Rose-colored glasses people are great fun at parties, but they make for shit sellers. You need someone who is a lot more skeptical, who questions everything. That you see around corners is you ask the hard questions. You run toward the danger and what scares you not away from it. So Harry, what are the reasons why you're going to lose this deal? What happens if your champion leaves? What happens if the CFO says this, that, or the other? If you ask yourself all of these questions and any possible way you could potentially lose this deal,

• 15:44Speaker 00

  now you have a map of all of the things that you potentially need to overcome. And in the worst case, you're overcoming objections that might not actually take place. And in the best case, you're really prepared for when that punch inevitably comes.

• 15:58Harry Stebbings?

  I think it's also actually incumbent a little bit on the founders to create an environment of safety where people feel they can ask the tough questions and then bring that information back and not be terrified. Because I think often it's fear that makes happy is multiply. I do want to ask you, I think kind of sales qualification is a big problem and people still suck at it. When you look at sales qualification today, how do you coach and train young sales reps? And what do you see as the biggest mistakes that people make in sales qualification today?

• 16:23Speaker 00

  I think the biggest mistake that people make from sales qualification standpoint is really not going deep enough. They'll ask discovery questions and then that first level of discovery question has been completed and they're already selling their solution. You need to go deep. You need to do some significant discovery where you get to secondary, third level pain and really let someone stew in that pain. I'll give you an example, Harry. You're on a run this weekend and you scratched your arm, right? So I ask you about that and find out, hey, you know, yeah, it kind of stings. Maybe you need a Band-Aid, I don't know. Is there blood there? We start to dig in and find out, hey, you've got some serious pain. What happens if you don't address that pain right now? Maybe it'll get infected.

• 17:08Speaker 00

  And now instead of a Band-Aid, maybe you need antibiotics. And if you don't do that, what's the risk to you? Shit, maybe my arm's gonna fall off or I'm gonna have to get it amputated. Well, now this little scratch that you weren't really thinking about is a painful festering wound that you really need to address. Hey, turns out I've got a Band-Aid, Harry, and I can solve this for you right now. You have to be able to go Deep on that pain and qualify, what is it that this person or this organization needs? From a solution standpoint to solve their pain? And if what they need is what you have, great, you've got that match, you should lean in. But if what they're looking for is something that's completely different than what you provide, you need to be able to walk away. Again, it comes down to that lean pivot walk. You can do med pick.

• 17:53Speaker 00

  Med pick is incredibly enlightening from a qualification standpoint. It's me and my team. I don't want a med pick filled out. I actually want you to come in and we're going to do an act of discovery together. And I'm going to ask you about your deal. I'll ask you about this opportunity. What's going well?

• 18:07Harry Stebbings?

  What's med pick?

• 18:08Speaker 00

  What's med pick? Are you kidding me? Med pick is is an incredibly important qualification methodology. It's really how you understand the deal dynamics. You can look up the definition afterward, but basically it's an acronym. And what we want to find out are what are the metrics that are important? The economic buyer, the decision criteria, the decision process, paper process, implicated pain, not just pain. We want to understand the implications of it. Your competition as well as your champion. That's what med pick stands for. Ultimately, it's an act of discovery. Harry, what do you like about this deal? What gives you pause? Are there any red flags you've encountered? Okay, if I could give you a magic wand, Harry, what are the five things you would want to know or see happen here that that you don't know?

• 18:53Speaker 00

  Or haven't happened yet? Great, now we've got an action plan for what to do. Let's go out there and do it.

• 18:59Harry Stebbings?

  I love that. And I'm also very ashamed that I haven't heard of this before. I love any acronym. As a VC, it's what feeds my soul. But I do want to ask, okay, so we're going through this qualification process and I am leaning in. Okay, I'm excited for what you've got to sell, but I'm not quite converting. What do you do to create a sense of urgency in a sales cycle to get someone over the line?

• 19:20Speaker 00

  It comes down to pain, Harry. If you don't have enough pain, there's not a world where I can get you to have the urgency you need, short of discounting, and that kind of cheapens what we all do. What I would suggest is you've got to go back to first principles. You've got to go back to discovery. And if you, Harry, don't have enough pain. I need to find someone else in the organization who has that burning pain. I need to find other people and build ground swell. Again, this comes down to multi-threading and pipeline generation. You want to get as high and as wide as you can in an organization because the only thing better than having a champion is having multiple champions.

• 19:57Harry Stebbings?

  Does that mean that you would advise founders not to do discounting?

• 20:00Speaker 00

  I think that discounting is an expectation that's built into procurement teams. It's built into the way that sales operates today. I think some organizations lean on it very heavily, whereas others are able to sell the value and really hold the line more. The more pain that you find and the more your solution matches with the pain that you're solving for, the less you need to discount.

• 20:22Harry Stebbings?

  A lot of people say, hey, we'll give you the discount or we'd love for you to give us a customer referral and allow you to use your logo. How do you, as a startup, ask a prestigious company, hey, can we use your logo for validity? What's the right way to do that without sounding needy and startup-y?

• 20:39Speaker 00

  Yeah, so one, I don't ask for it. The assumed close there is really important. As part of working with us, we want to support our customers. We love to show off the great companies that are working with us. And so we're going to have your logo on our sales materials, on our website. That's part of what we do. Oh, we don't allow companies to do that. Okay. It was great chatting with you. Good luck finding a solution that is going to solve for the pain that you have today. You have to have confidence around it, Harry.

• 21:05Harry Stebbings?

  Do you feel enough people do have confidence in sales today?

• 21:07Speaker 00

  No, not at all.

• 21:09Harry Stebbings?

  Why is that?

• 21:10Speaker 00

  It's a great question. I think when you're a junior sales rep, when you don't have as many bats, you see things all the time that are new to you. And that's scary. As a junior salesperson, hey, I'm encountering something I've never seen before. I don't know where this path will take me. When you've done hundreds of deals like I have and you don't have that much hair left on your head and what is there is graying quickly. You have what, and one of my mentors, Carlos Delatorre, he had a great colorful phrase for it. It's called scar tissue. And scar tissue is also known as pattern recognition. And the more pattern recognition you have, the better you're able to combat that. Because Instead of living in your head and having to analyze every single decision and every single thing you do,

• 21:55Speaker 00

  you can actually live by instinct. You've seen it before, what the proper response is.

• 22:00Harry Stebbings?

  You mentioned your mentor there being Carlos. What do you think sales leaders can do to better mentor this younger, less confident cohort? To be their best selves. I spoke to some of your mentees. What does great sales mentorship look like and require stage, you think?

• 22:14Speaker 00

  I think the key to mentorship is helping people see their blind spots. So I'll give you an example. I know you spoke to a founder of a Y C company who I mentor. He actually reached out to me in a cold LinkedIn message and it cut through the noise and I responded to him and I've been excited to work with him and his team, but he's not a sales professional. And so he's going through this deal cycle and I shared with him, what are his blind spots? He thinks he's got an opportunity here. What happens if it doesn't work out? Does he want to have all of his eggs in that basket? No, you got to build more pipeline, right? So I'm helping him as an example to see around his blind spots and ultimately to be able to close more opportunities.

• 22:58Speaker 00

  With other reps, with other people, the dynamics can change, the buttons you need to push will change, but ultimately you're helping to make them more well-rounded.

• 23:07Harry Stebbings?

  I do want to talk about hiring this young talent, which as we said, needs more confidence and needs a lot of mentoring, but can still be brilliant. In terms of hiring, we need to know what great looks like. And you said to me before that it's about the four Hs. Success in sales is the four Hs. I'm loving the acronyms today, Mark. What are the four Hs?

• 23:26Speaker 00

  The four Hs is something that I came up with that really is about saying the intangibles matter more than the tangibles. First H, hunger. You need to want it more than anyone else. If you don't have that burning desire to succeed, that deep need to win, that insatiable yearning to compete, you probably won't win or compete or succeed. Hunger is an incredible motivator to get you through the inevitable challenges. It's not enough to just be hungrier than everyone else. You need to be prepared to outwork them too. There's a great quote from John McMahon, who was a tremendous sales leader, and it sums it up well. "The difference between winners and losers is that losers practice until they get it right.

• 24:10Speaker 00

  Winners practice until they never get it wrong." And also applies to sports. I always think about Tom Brady when I hear that. Someone who was not the most gifted athlete of all time, but certainly the greatest professional athlete of all time, because he outworked everyone else. Watched more film than everyone, was in the gym earlier than everyone. No one would outwork him. And so he was able to rise when it mattered the most. Third H, humility. This is one that I will grant you, a lot of salespeople don't have. They come in with bravado, but I actually think humility is the approach. You need to know that no matter how much success you've achieved, there's always someone who's done more. And there are always areas you can improve. None of us are perfect, certainly not me. You need to recognize and embrace that. You need to use that to fuel your growth.

• 24:55Speaker 00

  The last H is heart. It should be table stakes, but instead it's more like special sauce. Think of it like grit, what it takes to be a champion, to be able to take a punch and keep fighting. There's a great book by Reed Hastings called No Rules, where he talks about talent density. I actually think as important or potentially more important than talent density is grit density. To have a team that just has a massive amount of grit.

• 25:17Harry Stebbings?

  I do have to ask, you mentioned there about hustle and the ability and desire to work hard on anyone else and put the hours in. You said before to me, you need to think outside the horse when it comes to hiring sales teams. Think outside the horse. I repeated this to myself and it didn't become clear to me. So can you help me out here? What did you mean by this? And how does that impact how you think about what you look for in the people you add to your sales teams?

• 25:42Speaker 00

  It's a little bit of a mixed metaphor, but let me tell you. So from a product standpoint at Ramp, we think of the legacy state as a horse and buggy. And do we want to build a faster horse and buggy? Or are we going to build an automobile? On a slightly different vein, I've heard guests of yours talk about the expression in sales recruiting that fast horses run together, right? A players attract a players. But if you want 10x productivity, you need to think outside the horse. You need a Race car, not a race horse. Let me give you an example here. If you have a 10x better product, and I hope you're investing in companies with 10x better products because they're amazing. But if you have a 10x better product and a good traditional sales rep, the best you can achieve is a 10x outcome. It's a pretty good outcome.

• 26:27Speaker 00

  But if you have a 10x better product and a 10x better sales rep, you can achieve 100x outcome. And the best salespeople in my experience rarely fit the mold of what great salespeople should look like. And I'm not even talking about myself and my challenge getting into Silicon Valley. The best salespeople I've seen in the last several companies I've been in, none of them would be hired today based on the rubric that sales leaders have. You need to think outside the horse.

• 26:53Harry Stebbings?

  Why? What were they? What did they have? What did they not have that made them not fit in the rubric? What made them that way?

• 27:00Speaker 00

  For one thing, they didn't come from the right companies or they didn't have the right LinkedIn profile or something about them would have canceled them out from even getting into the funnel from a hiring standpoint. But the best salespeople will have those four Hs, but they're also going to have creativity. Can you take duct tape, chewing gum, and a Zoom link and MacGyver a seven-figure closed one deal? Right? That takes creativity. I've seen people do it. It's extraordinary. Not everyone has that. Are they adaptable? The two first salespeople at Ramp, the first one now leads half the sales and SDR teams. The second one is chief of staff to our CEO. Right? They're adaptable. You're hiring people not for what they can do today, but people who have enormous growth potential.

• 27:45Speaker 00

  That's how you get a 10x outcome.

• 27:46Harry Stebbings?

  But how do we determine whether they're 10x? If we go to the interview process, say we've let them into the interview process despite not being the traditional fit. But therein, we're sitting down with them. What questions do we ask? How do we know if they're 10xs?

• 28:00Speaker 00

  Yeah, you need to get really intimate. You need to go deep in your interview questions. Get at the why, not just the what. So many interview questions are, what did you do next? What were you doing at that company? What deals did you close? I want to know the why. I want to know the how. I want to know them and get really deep to understand what makes them tick. What was the Reasoning behind decisions they made, not just the performance. And a great way to test this is with a challenge. So I know different organizations think about this differently. I want them to sell to me, not what they're selling today, but I want them to sell my solution back to me. Because it shows if they can do research. It shows if they can synthesize that information. I know if what they're saying is correct or not.

• 28:43Speaker 00

  I can see all of the gears turning and I can test them as well in that setting. And say, hey, I'm a CFO. We scheduled this for 45 minutes. I actually only have 10. Go. Are you adaptable? Can you take a punch? Can you pivot really quickly?

• 28:57Harry Stebbings?

  God, that's harsh, Mark.

• 28:58Speaker 00

  It happens in real life, though. I'd much rather it happen in an interview than with a real prospect.

• 29:04Harry Stebbings?

  I've had many sales leaders on the show say before, I like them to sell a product that they've sold before and they know. Because if they sell mine back to me, there's this massive asymmetric knowledge, one. And then two, if you have any form of hiring committee who are involved, they'll naturally respectfully intellectually look down on them. Because they just know way more given your experience compared to theirs. How do you think about that pitch yours product versus pitch something they know much better?

• 29:31Speaker 00

  I don't want you to be comfortable in that interview process, selling me something that you could talk about with your eyes closed while you're sleeping. I want you to have to think. I want to challenge you. It's called a challenge for a reason. I want to see if you can rise to that occasion. Enterprise sales is hard. I want to see if you have what it takes to rise up and be able to perform in that setting.

• 29:54Harry Stebbings?

  Would you rather a rep that you're hiring has experience selling at that level of ACV? Or has experience selling to that segment of market in terms of finance tools?

• 30:04Speaker 00

  For me, I think it's about selling enterprise deals. So that value, selling to organizations that size. Because the scale is so different. I've seen mid-market account executives get promoted into enterprise in my past and flame out pretty quickly. And the reason is usually they're used to a certain level of multi-threading. Hey, I need three or four people in the deal. Now, all of a sudden, every- Everything is magnified by an order of magnitude. Can you play 20 simultaneous games of chess? It's great that you can play chess, but can you play 20 games at the same time? It's much harder.

• 30:40Harry Stebbings?

  To what extent do you handhold younger reps in these large deal cycles? Because you can't just let them run free. To what extent do you do the kind of mentor mentee going to war together?

• 30:51Speaker 00

  So you need to create space for them to fail when the stakes are low, so they can succeed when the stakes are high. You have to be in the boat with them. First of all, as a sales leader, my quota, I've got a quota, and my quota is a roll up of my reps. So number one, I'm in the boat with you because your performance is going to matter for my performance. Putting that aside, I want to see everyone on my team succeed. But I can't do the job for them, right? I can't be in every deal and every place and every call at the same time. So I need to give you the tools to succeed when I'm not there. And I need to be in the boat with you and teach you, mentor you throughout that process. But what I've also found, no matter how much you say the stove is hot,

• 31:33Speaker 00

  people still want to touch it in order to find out that it's really hot. And so it's my job to make sure the burner's on simmer and not on high. So it's not a catastrophic wound.

• 31:42Harry Stebbings?

  If we're a startup hiring, what does that process look like? Is it like first interview, get to know you, the why? Second, the case study? What does that process look like step by step, do you think?

• 31:53Speaker 00

  So for me, I want to be able to qualify quickly. Is this person of the right caliber? Have they closed the right level of deals? Do they have the right experience? Do they have the right gravitas to be able to hold themselves in an executive meeting? That is usually like a 30 minute getting to know you call. Assuming that goes well, you want to go deeper. You want to spend an hour with them. You want to really go deep. You want to ask those why questions, those how questions. Really get to understand what makes them tick. You want to have other stakeholders meet with them as well. Typically in enterprise, you're a quarterback. You're working with other people internally and externally. So how do those relationships form? Are you able to play off those dynamics? And then ultimately, yeah, you want to do a challenge with a panel of interviewees all the way up to your C-suite leadership.

• 32:38Harry Stebbings?

  We all learn a lot from making mistakes. I know I've made many in my time. What are the biggest mistakes you've made in terms of hiring for enterprise sales teams? And how did that change how you think?

• 32:48Speaker 00

  I've certainly made mistakes. I think sometimes when you assume their experience, if you assume they're fit.

• 32:56Speaker 00

  Based on where they've been or what they've accomplished in their career, you put yourself in a very risky situation where when they come in, if you haven't tested for that, they may fail. I've seen people who are extremely accomplished join organizations I've been a part of, and within six months, they're no longer in the company because they weren't able to cut it. The fit was wrong. And so you really need to test for that because the last thing you want is to waste six months of their career, of their time, and six months of your runway and six months of your time on someone who isn't a fit.

• 33:30Harry Stebbings?

  Before we dive into that integration with the existing team, which is so important during the onboarding, I do just want to close. We go through that process and we get to the deal itself of the package. What are some of your biggest lessons and pieces of advice to founders on giving the right comp structure for those early sales rep hires?

• 33:49Speaker 00

  I think when it comes especially to early sales hires, there's not enough emphasis placed on equity in sales. They give out equity for other roles, and I think equity is often something that founders don't really think of when it comes to salespeople. They really only think about cash compensation. That's the wrong approach. If you're hiring a 10x salesperson, someone who's going to be with you for a long time and drive an inordinate amount of impact in the organization, you should want to keep them for a long time. And they're going to be able to see the impact of their revenue generating activities on the company, all the way up to raising funds. And we just need to get more creative and we need to find a path forward.

• 34:31Speaker 00

  And so when you have people who can drive an impact like that and put an entire team or company on their back, you want to reward them. Cash is great. We all like cash. Sales reps are coin operated. I get it. But you want them to be bought into the long-term vision as well, and it needs to be aligned with what the company cares about.

• 34:48Harry Stebbings?

  To hit those targets, they need to have targets in the first place. How do you advise me on setting quota, especially in a year like this year where it's so fucking uncertain? I set a quota for the media company, and we're like 250% over target now, whatever, four months in. Clearly, I was just Shit at setting quota, to be honest. I didn't know what was gonna happen. How do you advise founders on how to set quota accurately and efficiently?

• 35:12Speaker 00

  You need to, in the early days, figure out what is the goal that the board is setting for you or that you're sharing with the board, number one. Is it realistic? Is it achievable? Work backward from that goal. Working backward is something that I often teach to my teams. Okay, here's the goal that we're trying to get to. If we're just driving toward it in a forward direction, we may drive off a cliff. And if you don't want to end up like Thelma and Louise, then what you need to do is work backwards so you know where the cliffs are. You know where the landmines are. You know where the traps are. And you can find, hey, is there one path? Is there no path? Are there multiple paths to get there? And then you can move forward. So if you work backward from that goal, regardless of how lofty it is, you can figure out the way to achieve it.

• 35:57Speaker 00

  The other thing that's really critical here is pipeline generation. If you have a massive amount of pipeline, you're able to qualify deeply and make sure that you're going to hit the goals that you've set for yourself. This is something that I instill in my teams. And I'm proud to say that this quarter, the enterprise team at Ramp is trending to hit more than 300% of their quota, which is pretty insane.

• 36:19Harry Stebbings?

  Do you think traditional sales outbound is dead? And why does no one in sales want to do traditional outbound anymore?

• 36:25Speaker 00

  Traditional outbound is the most important thing, Harry. And if you're not doing it, you are doing sales wrong. And the reason why is because pipeline is the most important thing, if you want to hit your quota, as we just established. And the way that you build pipeline is through outreach. The founder that I mentor, he PG'd into me. He cold messaged me. Without that, I wouldn't be mentoring him. We have so many opportunities that are in our pipeline because we did the hard thing. We picked up the phone. We sent out an email. We were persistent with it because usually it takes about five messages before someone is going to respond. And ultimately, we feel good about it because we're providing a solution for them that helps them. We're not trying to sell them something that they don't need.

• 37:09Speaker 00

  And so if you think of it from that standpoint, what you're doing when you're picking up the phone is something that's good for you and it's good for the people that you're

• 37:16Harry Stebbings?

  So glad to hear. People run away from things that are painful and outbound can just be continuous punches in the face. And so I think it's nice to stay in the warm and cozy environment that is warm inbound. Going back to the kind of integration into the team, I think onboarding is just chronically poorly done. How do you think about the right way to onboard new sales reps into your team? And how do you do it today?

• 37:38Speaker 00

  I think it needs to be a mix of structured learning and unstructured learning, so asynchronous learning. I think there needs to be a fair amount where they're going to be shadowing the best reps on calls. I think you need to dig in with them and go deep on a daily and weekly basis. So one-on-one coaching as well. And you need to make them drink from the fire hose. I know we try to limit that as companies get larger where, hey, we're going to give them this nice cushy ramp up period, but you're going to find out a lot those first few weeks about their ability to run at pace if they can drink from the fire hose and start to synthesize that information. So I'm a big believer that the training wheels need to come off quickly. I do think there's benefit as well to giving them what I'd call T-ball

• 38:23Speaker 00

  opportunities. So if you're in enterprise, you don't want to risk some massive deal by giving it to the guy who just or the woman who just started. You need to be able to give them a smaller opportunity that's safe, that's a safe place for them to iterate and figure out the motion before they're getting into these really large, complex deals.

• 38:41Harry Stebbings?

  What are the biggest red flags that you traditionally see in the first 30 days? I think people often say hire fast, fire fast. I think we'd probably agree hire, slow, fire, fast. If we agree with that, what are the big red flags that are like, okay, you need to step in and do something?

• 38:55Speaker 00

  I recognize that not everyone is a type A personality and gregarious even in sales. But if someone is not asking a lot of questions, if they're not vocal in that first month or two, to me, that's a red flag that I want to at least dig into. It's not a sign, hey, we need to fire them because they didn't ask questions. It's, hey, are they not asking questions because they understand everything? Bravo, brilliant, go forth and prosper. Or are they not asking questions because they don't actually even know what questions to ask? And is it an aptitude issue? An attitude issue. You need to understand that if you want to try to fix it. And in some cases, you're right, it's hire slow and fire fast. If someone can't make it, the merciful thing to do is to let them go so that they can go to a place where they can be

• 39:40Speaker 00

  powerful, efficient and grow their career.

• 39:42Harry Stebbings?

  How do you see the real quality of a candidate? What I mean by that is I've had sales leaders on the show say before, the person that sold Twilio to Uber when they were a tiny startup, it's probably the best deal in enterprise history. And it transformed obviously from a startup to an enterprise deal. But at the time, it was a nothing deal and it was probably stunned by a credit card almost. Like, how relevant is deal attribution to you when determining quality of candidate? I'm just too interested there.

• 40:08Speaker 00

  It's why you need to ask those why questions, Harry. Some companies are great at product-led growth and they're selling to an organization when it's an SMB. At what point did you sell to that organization? Was it a 10-person company that grew to a 10,000-person company? Or did you sell to them net new when they were 10,000 people? Did you sell wall to wall across the entire organization? Or was it a land and expand motion? Who else was involved with you in selling that deal? You need to dig in to understand, did they do all of the work? Did they generate that deal themselves? Was it self-sourced or did an SDR make a cold call and that's how it happened? Or did marketing generate the lead and it came inbound?

• 40:48Harry Stebbings?

  In terms of like digging in on the deal and the deal dynamics there, I think deal reviews are so important, whether successful or not successful. How do you do deal reviews? How often do you do them? Who's invited? Who sets the agenda? I'm an early-stage founder, educate me.

• 41:04Speaker 00

  I think you should do a deal review for any deal that is going to be impactful toward you hitting your goal for that quarter or that year, period. And that means that you're probably doing more deal reviews than you're typically anticipating. You need to give time for that. If you're not digging in with your rep and understanding the deal dynamics, what could go wrong, what needs to happen, the various stakeholders? Have you mapped the organization? And getting really into the details? Then you're putting yourself at risk because that deal could slip. That deal could end up as a closed law. And if you were counting on that, if you were committing that opportunity, man, that is an unpleasant place to be. I can tell you, it has happened in my career a long time ago when you commit a big deal and then it doesn't come through.

• 41:48Speaker 00

  That's a painful experience for everyone. You don't want to be living like that.

• 41:51Harry Stebbings?

  What are the biggest reasons that you lose today?

• 41:54Speaker 00

  In my experience, when you do lose to competition, you can lose for a variety of reasons. One, it could be price. And if you're selling something to someone who's really price sensitive and you haven't sold the value and articulated it, you can have someone come in and offer a product for free or offer it for a really low price. And that company may grow to regret that decision, but ultimately they might make that decision. You could get outflanked. You have a champion, but you know what? They've got a champion that's more senior. And so the more senior person who's got more influence in the organization is potentially going to win. There are a variety of reasons you could lose, but you need to map the organization. You need to understand the dynamics at play.

• 42:32Harry Stebbings?

  Final one, I promise. I'm just firing my interest questions now.

• 42:35Speaker 00

  I love it.

• 42:36Harry Stebbings?

  But it's like when you do enterprise sales really well, it's this tailored boutique feeling for the customer. How do you do the handoff between sales rep and enterprise sales leader to customer success team, customer experience team, without it feeling like, oh, good luck, off to market?

• 42:54Speaker 00

  Yeah, if you're doing it badly, it's, hey, I'm handing you off over here. See ya. That's not the way it should go. You need to be introducing that implementation and that CS team before the deal is ever closed. Implementation, onboarding, how we're going to make you successful as a customer is part of the sales process. And so you want to bring them in to be able to walk them through what the implementation plan looks like, what does success look like? What are you trying to solve for? Where are you at today? And what does good look like? What are your goals? And once we're aligned on all of that, and there's some overlap here between the sales team and CS, now you feel more comfortable moving forward with us. And when you do, you already have this relationship formed

• 43:39Speaker 00

  with the team you're going to be working with to make you successful.

• 43:42Harry Stebbings?

  Should CS also get commission if they're brought in pre? Sales being concluded and a part of that closing mechanism.

• 43:50Speaker 00

  That's a great question. Typically, they end up being compensated in a slightly different way, which is that CS often in most organizations are going to be compensated based on adoption, at least in companies that are based on usage. Are you seeing that adoption curve? Are you seeing full adoption? So that's how they're going to get paid. So ultimately, by helping to bring in a deal and seeing that adoption happen, they are going to be compensated for it.

• 44:15Harry Stebbings?

  Mark, I've just so enjoyed this. I'm going to do a quickfire round with you now. So I'm going to fire questions at you, very much like I have been doing for the last hour, to be honest. I'm going to call it a quickfire round because I'm good at marketing and you're going to give me immediate thoughts. So let's start with what sales tactics have not changed over the last five years?

• 44:32Speaker 00

  The fundamentals, cold calling, cold emailing, that pipeline generation, qualification, champion building, getting to the EBD. It'll never change.

• 44:40Harry Stebbings?

  What sales tactics have died to death?

• 44:43Speaker 00

  It pains me to say it, but I think in-person meetings, it's not that it's died. I think it's on life support, video conferencing, digital whiteboarding, sales intelligence tools. They're all built so we can collaborate and be productive in a remote first world, but it can sometimes create this soul-crushing reality where human interaction becomes transactional instead of deep.

• 45:04Harry Stebbings?

  Really? So even for large six-figure enterprise deals, human interaction in person is not required?

• 45:10Speaker 00

  It hasn't been required the last few years. I miss it. I love it. I will take every opportunity to meet clients where they are, but I think it's a dying art.

• 45:19Harry Stebbings?

  Does the CEO always have to be involved in sales to some extent? If you have Amazon moving to, that's a bold one, but Amazon moving to Ramp with 500,000 employees, does Eric still need to be getting on a jet?

• 45:31Speaker 00

  I think so. I think with any kind of really large company trajectory-changing deal, you want not just the CEO, but you want the entire executive team to be involved.

• 45:42Harry Stebbings?

  What would you say is the biggest mistake founders make when hiring sales teams?

• 45:46Speaker 00

  I think, again, it's about trying to hire people who fit inside a box with their preconceived notions. Every time, that's going to end up biting you in the butt.

• 45:56Harry Stebbings?

  Device on the flip side of the table, would you give to a sales leader starting a new role today?

• 46:01Speaker 00

  Always look to raise the bar. Don't settle for B players. I've made that mistake myself. I now have a rule, which is that each subsequent hire has to raise the bar for the entire team. If they don't have the potential to be as good or meaningfully better than everyone else in seat, why are you hiring them?

• 46:17Harry Stebbings?

  What would you most like to change in the world of sales today, Mark?

• 46:21Speaker 00

  The perception of it. There's science behind great sales. It's not some parlor trick. Sales is often deeply misunderstood by those in other roles. And I think if you step back and look at all of the process behind it, there's real science.

• 46:33Harry Stebbings?

  How do you maintain morale when goals are missed in a sales team? It's tough because you want to maintain morale, but you don't want to create a culture of accepting failure.

• 46:42Speaker 00

  You have to start with understanding why it happened. Who's responsible? How do you ensure it never happens again? And the answer inevitably is pipeline coverage. And whose responsibility is that, Harry? Everyone's.

• 46:53Harry Stebbings?

  Final one, my friend. What one company sales strategy have you been most impressed by recently?

• 46:58Speaker 00

  I think anyone who's executing right now and exceeding their goals, outside of generative AI, which I think has a very unique tailwind, they're doing something right. Starlink's performance has been especially impressive, given they fly under the radar, which is odd for a company that dots the skies.

• 47:15Harry Stebbings?

  I love that and I totally agree with you. This has been such a joy to do. Thank you so much for doing this and I've loved having you on.

• 47:21Speaker 00

  My pleasure, Harry. Thanks so much.

• 47:25Harry Stebbings?

  I absolutely love that. And if you want to see the transcript for the show today, you can sign up for the newsletter on 20vc.com or watch the whole show on YouTube by searching for 20vc. But before we leave you today, you might remember in our amazing episode with Maggie Hott, she mentioned a tool she could not live without called Pocus. What is Pocus? Well, Pocus is a revenue data platform that makes it easy for go-to-market teams to analyze, visualize and action data about their prospects and customers without needing engineers. Pocus helps companies like Miro, Webflow, Lumen, Superhuman focus their sales and success teams on the highest priority opportunities by surfacing insights at the right moment so reps can take action quickly. Pocus gives you

• 48:06Harry Stebbings?

  A 360 degree view into product usage empowering you to act on insights and fill your funnel efficiently. Sales teams save 10 plus hours per week digging through data to surface millions in new revenue opportunities. Learn more about why top PLG businesses trust Pocas as their revenue data platform by visiting pocas.com/demo. And SalesLoft is the leading sales engagement platform, helping sales teams drive more revenue with the modern revenue workspace. It's the one place sales teams can go to prospect, manage active deals and get the insights they need to coach seller performance, forecast with accuracy and find out what steps to take to close more deals. Some of the world's leading companies like Google, Shopify and Stripe all love a new

• 48:51Harry Stebbings?

  SalesLoft and so can you. It's the new way to sell. Find out more at salesloft.com.

• 48:56Speaker 00

  As always, I so appreciate all your support and I can't wait to bring you an incredible episode with Tom Tungas discussing his new incredible fund, Theory Ventures.