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

24:41You 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. The last age 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.

25:17I 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 high and sales teams. Think outside the horse. I repeated this to myself and it didn't become clear to me. So it didn't 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? 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.

25:51And 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 sales recruiting that fast horses run together. I'd 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, then 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.

26:26It's a pretty good outcome. But if you have a 10X better product and a 10X better sales rep, you can achieve a 100X outcome. And the best sales people in my experience rarely fit the mold of what great sales people should look like. And I'm not even talking about myself and my challenge getting into Silicon Valley. The best sales people 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. Why, what were they? What did they have? What did they not have that made them not fit in the rubric?

26:59What made them that way? For one thing they didn't come from the right companies or they didn't have the right linked in 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 H's but they're also going to have creativity Can you take duct tape chewing gum in a zoom link and McGiver a seven figure closed one deal? That takes creativity. I've seen people do it. It's extraordinary. Not everyone has that. Are they adaptable? The two first sales people at RAM. The first one now leads half the sales in SDR teams.

27:35The second one is Chief of Staff to our CEO. They're adaptable. You're hiring people not for what they can do today, but people who have enormous growth potential. That's how you get a 10X outcome. But how do we determine what that 10X is? If we go to the interview process, Yes, say we've let them into the interview process despite not being the traditional fed. But therein, we're sitting down with them. What questions do we ask? How do we know if that tann 'axes? 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?

28:09What 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, I can see all of the gears turning, and I can test them as well in that setting.

28:48and 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 give it really quickly? Go, the fast harsh mark. It happens in real life, though. I'm much rather it happened in an interview than with a real prospect. 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 there are 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.

29:27How do you think about that pitch yours product versus pitch something they know much better? 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 a call to 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. Would you rather a rep that you're hiring has experienced selling that level of ACV or has experienced selling to that segment of market in terms of finance tools?

30:04For me, I think it's about selling enterprise deals, so that value, the 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, 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. To what extent do you hand hold younger apps in these large deals like, because you can't just let them run free?

30:46To what extent do you do the kind of mental mentee going to all together? 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. Alright, I can't be in every deal and every place and every call at the same time.

31:22So 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, 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 burners on simmer and not on high, so it's not a catastrophic wound. If we're start up hiring, what does that process look like? Is it like, first interview, get to know you, the why, second to case study, what does that process look like step by step, do you think? So for me, I want to be able to qualify quickly.

31:56Is 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. back, you're working with other people internally and externally.

32:27So 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. We will 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 high -end and price sales teams? And how did that change how you I've certainly made mistakes. I think sometimes when you assume their experience, if you assume their fit 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.

33:06I'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. 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.

33:41What are some of your biggest lessons and pieces of advice to founders on giving the right comp structure for those early sales repires. 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 sales person, 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 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.

34:42But 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. 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, but in whatever four months in. Clearly, I was just shit at setting quota, to be honest. I didn't know what was going to happen. How do you advise founders on how to set quotes to accurately and efficiently? 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.

35:20Is 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 Felma 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.

35:58The other thing that's really critical here is pipeline generation. If you have a massive amount of pipeline, you are 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. Do you think traditional sales outbound is dead? And why does no one in sales want to do traditional outbound anymore? traditional outbound is the most important thing Harry. And if you're not doing it, you are doing sales wrong.

36:32And 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 throughout reach the founder that I mentor. He peed jeed into me. He called message 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.

37:06We're not trying to sell them something that they don't need. 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 calling. So glad to hear. People run away from things that are painful and our bound 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 and bound. Going back to the kind of integration in 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?

37:38I 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.

38:19I do think there's benefit as well to giving them what I'd call T -Ball opportunities. So if you're an 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. What are the biggest red flags that you traditionally see in the first 30 days? I think people often say higher -false, I think we probably agree higher -slow -fire -false. If we agree with that, what are the big red flags of the like, okay, you need to step in and do something.

38:56I recognize that not everyone is a type 8 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 or an attitude issue? You need to understand that if you want to try to fix it.

39:30And in some cases, you're right. It's higher 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 powerful, efficient, and grow their career. How do you see the real quality of a candidate? What I mean by that is, like, I've have had selfies 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 nothing deal and it was probably stunned by a credit card almost.

40:02Like, how relevant is deal attribution to you and determining in quality of candidate. I'm just too interested that. 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?

40:38Did they generate that deal themselves? Was it self -source? Or did an SDR make a cold call? And that's how it happened? Or did marketing generate the lead? And it came inbound. In terms of what I'm 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 do them, who's invited, who sets the agenda, I'm an at least age founder, educate me. 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.

41:12And 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 lost. 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.

41:48That's a painful experience for everyone. You don't wanna be living like that. What are the biggest reasons that you lose today? 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.

42:21And 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. Final one I promise, I'm just firing like interest questions. I love it. But it's like when you do antiproxails really well, it's this tailored boutique feeling for the customer. How do you do the handoff between sales wrap and antiproxails leader to customer success team, customer experience team, without it feeling like, oh good luck, often wrong. Yeah, if you're doing it badly, it's, hey, I'm handing you off over here.

42:59See 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 NCS, now you feel more comfortable moving forward with us, and when you do, you already have this relationship formed with the team you're going to be working with to make you successful.

43:42Should CS also get commissioned if their broad and pre -sales being concluded, and a part of that closing mechanism. 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. It's ultimately by helping to bring in a deal and seeing that adoption happen, they are going to be compensated for it. Mark, I've just so enjoyed this.

44:16I'm going to do a quick fire around 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 quick fire around 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 the fundamentals cold calling cold emailing that pipeline generation qualification champion building getting to the eb it'll never change what sales tactics have died a death It pains me to say it, but I think in -person meetings, it's not that it's died.

44:48I 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. Really, so even from knowledge, sex, figure, and price deals, human interaction, in -person, is not required. But 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. Does the CEO always have to be involved in sales to some extent?

45:23If you have Amazon moving to, that's a bowl one, but Amazon moving to ramp with 500 ,000 employees, does Eric still need to be getting on a jet? 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 What would you say is the biggest mistake founders make when hiring sales teams? 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. Well one piece of advice on the flip side of the table Would you give to a sales leader starting a new role today?

46:01Always 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 higher 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? What would you best like to change in the world of sales today, Mark? The perception of it. There's science behind great sales. It's not some parlor trick. Sales is often deeply misunderstood by those and other rules. And I think if you step back and look at all of the process behind it, there's real science.

46:33How 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 fate. 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 final one my friend what one company sales strategy have you been most impressed by recently? 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.

47:07Starlink's performance has been especially impressive given they fly under the radar, which is on for a company that dots the skies. I love that net totally agree with you. Oh, this has been such a joy to do. Thank you so much for doing this and I've loved having you on. My pleasure Harry, thanks so much. I absolutely love that and if you want to see the transcript for the show's day, 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 it today, you might remember in our amazing episode with Maggie Hotch, she mentioned a tool she could not live without called Pocus.

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48:35It's the one place sales teams can go to prospect, manage active deals and get the insights if 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 sales loft, and so can you. It's the new way to sell. Find out more at salesloft .com. As always, I sir appreciate all your support. My conway to bring you an incredible episode with Tom Tunger's discussing his new, incredible We'll fund theory ventures.