The Exchanges

Q What are the biggest red flags that you traditionally see in the first 30 days? I think, you know, 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, ok, you need to step in and do something?

A Yeah, I recognize that not everyone is a, 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, 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 a matter of, 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. Um, and in, in some cases, you're, you're right. It's, it's higher slow and fire fast. If someone can't make it, the merciful thing to do is, is to let them go so that they can go to a place where they can be, uh, really, um, you know, powerful, efficient, and, and, and grow their career.

AI assessment note: “if someone is not asking a lot of questions, if they're not vocal”

Q I think we all learn a lot from making mistakes. I know I've made many, uh, in my time. Um, what are the biggest mistakes you've made in terms of hiring for enterprise sales teams and how did that change how you think?

A I've certainly made mistakes. I think sometimes when you assume their experience, Uh, if you assume their fit, uh, based on where they've been or what they've accomplished in their career, uh, you, you put yourself in a, in a very risky situation where when they come in, if you haven't tested for that, they may fail. Uh, 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, of your runway and six months of your time on someone who, who isn't a fit.

AI assessment note: “when you assume their experience, Uh, if you assume their fit”

Q Now we have a lot to dive into, but I want to start with actually the move, uh, to ramp and leading ramps enterprise sales team. So how did you make your way into the world of enterprise sales and how did you most recently come to lead ramps enterprise sales team?

A Yeah, it's a great question, Harry. Uh, I came to the world of enterprise sales from the world of wine. Uh, I recognize that's not the typical journey one makes, uh, but it is my own story. Uh, so I was working in, in Massachusetts, uh, 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, uh, a SaaS business back then, uh, knowing nothing about SaaS, mind you, uh, but built a cloud-based company with, uh, with tools in the cloud specifically for, uh, for the wine industry. Uh, bootstrapped it. We had paying customers. Uh, it was a wild, incredible experience. Uh, after a few years, ultimately I did decide to, to wind down that business. Uh, my wife and I moved out to Silicon Valley when she took a role with a little startup in Mountain View called Google. I don't know if you've heard of them. Uh, and so, uh, so I found myself, uh, out here in Silicon Valley and I said, okay, I'm going to be an account executive now again for, for SAS companies. And I, I sent my resume out to about a hundred companies, and the response was, well, there was no response. Literally could not get an interview. More than a hundred resumes sent out. I had founded my own company that was a SaaS…

AI assessment note: “I came to the world of enterprise sales from the world of wine.”

Q And I absolutely love that in terms of the focus on logos. In terms of kind of going back to that single sales rep hire, Jason Lampkin 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?

A The way that I think about it Is I'm looking for salespeople who can provide 10 X growth, not one X or 1.5 X. And when you find someone who can provide that 10 X 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, I, I think if you are at scale, uh, 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 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.

AI assessment note: “in those early days... you need to be grabbing the best talent when you can.”

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

A Traditional outbound is the most important thing, Harry, and if you're not doing it, uh, 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. Uh, the founder that I mentor, he PG'd into me. He, he cold messaged me. Without that, I wouldn't be mentoring him. Uh, 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. Uh, and ultimately we feel good about it because we're providing a solution for them that helps them. We're not trying to, you know, to sell them something that they don't need. We're actually helping them. And so if you think of it from that standpoint, uh, 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.

AI assessment note: “Traditional outbound is the most important thing, Harry, and if you're not doing it”

Q sold Twilio to Uber when they were a tiny startup is probably the best deal in enterprise history now, and it transformed, obviously, from a startup to an enterprise deal, um, but at the time it was a nothing deal, and it was probably stunned by a credit card, almost. Um, how, like, how relevant is deal attribution to you when determining quality of candidate? I'm just too interested there.

A It's why you need to ask those why questions, Harry. Uh, some companies are, 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? But you need to dig in to understand, uh, you know, 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?

AI assessment note: “you need to dig in to understand, uh, you know, did they do all of the work?”

Q 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?

A 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, right? 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, uh, 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 in every place and every call at the same time. Uh, no matter how much gong gives me visibility into all of it, uh, I can't do it. So I need to give you the tools to succeed, uh, when I'm not there. And I need to be in the boat with you and, and, and teach you and, and mentor you throughout that process. But what I've also found, and I, and I, I helped build enablement in my, in my former company as well. What I found is 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 burner's on simmer and not on high, so it's not a catastrophic wound.

AI assessment note: “make sure the burner's on simmer and not on high, so it's not a catastrophic wound.”

Q Yeah. I mean, you, you're the master of also being a cold outbound being the enterprise leader you are. You must also self analyze that what was wrong with your approach and why did that happen?

A Yeah. You know, it was, um, I, we can talk more about why it happened. And I think there's, there's fault on both sides. I think there's a challenge from Software companies and sales leaders thinking too small inside of a box in terms of the profile of who they're looking for. And there was also a, a, a challenge on, on my approach, not having inhabit, uh, lived in this world. It was a world that was foreign to me and I needed to find my way in. Uh, ultimately after a couple of months, I, I connected with a, a terrific recruiter, uh, David Hipperson at, at Betts, uh, at the time. And I ended up interviewing and ultimately taking a position with a video conferencing company called Hi-Five. It was backed by General Catalyst and Lightspeed. I was competing against Zoom, and this was before the pandemic when, when selling video conferencing was maybe a little bit harder. And, and I had a great run there for two years, ultimately ended up getting recruited by Trip Actions, now called Navon, and, and was their first enterprise account executive and really built the enterprise go to market there.

AI assessment note: “there was also a challenge on my approach, not having lived in this world.”

Q 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, right? It's like, whoa, 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?

A It's different in every deal. If, if you are, are doing a transactional sale, Uh, obviously that's going to happen a lot earlier in the process than, than in a large complex global enterprise deal. Uh, you need to be able to get to the executive buyer. Uh, 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. You want to be able to get there and understand what they care about. Listen to the YouTube videos they've posted. Listen to when they joined you, Harry on, on your podcast, right? All of these are going to provide you insight and information that's going to allow you to be more effective in, in, in asking for that meeting in an enterprise deal. Typically you want to be able to, 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, uh, you're going to Go with your champion and present those findings to the CFO or to the executive buyer.

AI assessment note: “at that point, you're going to Go with your champion and present those findings”

Q Can I ask you in terms of product reviews, what are the biggest reasons that you lose today?

A Honestly at, at, at ramp where we're not really losing. Um, I, I know that sounds, uh, that sounds self-serving where we're growing so fast. Um, we, we have an incredible product and I'm, I'm blessed to be able to, uh, you know, to, to sell this transformational, uh, platform that we have in my experience when, when deals, uh, when you do lose to competition, you can lose for a variety of reasons. Um, one, it could be price, and, and if you're selling something that's to someone who's really price sensitive and you haven't sold the value and articulated it well, uh, you can have someone come in and, and offer a product for free or offer it for a really low price, and that company may, 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, uh, 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.

AI assessment note: “Honestly at, at, at ramp where we're not really losing.”

Q Yeah. I mean, you, you're the master of also being a cold outbound being the enterprise leader you are. You must also self analyze that what was wrong with your approach and why did that happen?

A Yeah. You know, it was, um, I, we can talk more about why it happened. And I think there's, there's fault on both sides. I think there's a challenge from Software companies and sales leaders thinking too small inside of a box in terms of the profile of who they're looking for. And there was also a, a, a challenge on, on my approach, not having inhabit, uh, lived in this world. It was a world that was foreign to me and I needed to find my way in. Uh, ultimately after a couple of months, I, I connected with a, a terrific recruiter, uh, David Hipperson at, at Betts, uh, at the time. And I ended up interviewing and ultimately taking a position with a video conferencing company called Hi-Five. It was backed by General Catalyst and Lightspeed. I was competing against Zoom, and this was before the pandemic when, when selling video conferencing was maybe a little bit harder. And, and I had a great run there for two years, ultimately ended up getting recruited by Trip Actions, now called Navon, and, and was their first enterprise account executive and really built the enterprise go to market there.

AI assessment note: “I connected with a terrific recruiter... ended up interviewing and ultimately taking a position”

Q 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, like, I don't know, 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 quota accurately and efficiently?

A Yeah, you, you need to, in the early days, figure out what is the goal that the board is setting for you, or that you're, you're sharing with the board, number one. Um, is it realistic? Is it achievable? Work backward from that goal. So 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, 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, uh, you can figure out the way to achieve it. 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, I'm proud to say that this quarter, uh, the enterprise team at ramp is trending to hit more than 300% of their quota, which is pretty insane.

AI assessment note: “Work backward from that goal.”

Q 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, like, I don't know, 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 quota accurately and efficiently?

A Yeah, you, you need to, in the early days, figure out what is the goal that the board is setting for you, or that you're, you're sharing with the board, number one. Um, is it realistic? Is it achievable? Work backward from that goal. So 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, 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, uh, you can figure out the way to achieve it. 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, I'm proud to say that this quarter, uh, the enterprise team at ramp is trending to hit more than 300% of their quota, which is pretty insane.

AI assessment note: “figure out what is the goal that the board is setting for you”

Q Can I ask you in terms of product reviews, what are the biggest reasons that you lose today?

A Honestly at, at, at ramp where we're not really losing. Um, I, I know that sounds, uh, that sounds self-serving where we're growing so fast. Um, we, we have an incredible product and I'm, I'm blessed to be able to, uh, you know, to, to sell this transformational, uh, platform that we have in my experience when, when deals, uh, when you do lose to competition, you can lose for a variety of reasons. Um, one, it could be price, and, and if you're selling something that's to someone who's really price sensitive and you haven't sold the value and articulated it well, uh, you can have someone come in and, and offer a product for free or offer it for a really low price, and that company may, 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, uh, 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.

AI assessment note: “Honestly at, at, at ramp where we're not really losing.”