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20Sales: Inside Ramp's Sales Playbook: How to Build a $1.7BN ARR Sales Machine with Max Freeman, SVP Sales @ Ramp

67m 59s

20Sales: Inside Ramp's Sales Playbook: How to Build a $1.7BN ARR Sales Machine with Max Freeman, SVP Sales @ Ramp

In this episode of 20VC, Max Freeman, SVP of Sales at Ramp, shares granular insights into building one of the fastest-growing sales organizations in the world. Freeman explains his philosophy of hiring investment bankers and other mispriced talent, arguing that sales is fundamentally an engineering and data infrastructure problem. He details how Ramp pays above market rate for sellers who book four to six times the meetings of standard SDRs, and how the company built internal tools like OATS and Ramp Revenue to automate outbound research and unlock seller capacity. Freeman emphasizes decomposing candidate quotas during interviews, testing whether candidates were true producers or order takers, and requiring them to reconstruct wins and losses in detail. He advises sellers to prioritize market size, talent density, and founder quality over equity or title when choosing where to work. The conversation covers onboarding bootcamps, compensation design for new products, verticalization timing, sales cycle compression through rigorous qualification, and forecasting discipline. Freeman also discusses Ramp's customer success organization, the value of brand marketing on sales cycles, and his personal growth areas as a leader, including resisting the urge to personally intervene in every important deal.

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Speaker 1There's three categories of performance in sales. One, you are God. Two, I don't know yet. Or three, you're fucking fired. We'll pay 2x what a standard SDR is going to make. But guess what? You get to book 40, 50, 60 meetings, which is four to six times what a standard SDR has to book. There are some sellers at ramp that are on 15 plus calls in a given day. You have to treat go-to-market recruiting like Billy Bean. Sales is very much an engineering problem when you break it down. It's a data infrastructure problem. It's a math problem.
Speaker 2I have had enough. I've had enough of podcasts being fluffy. I want them to be granular, and I want to learn very specifically how to excel across different disciplines. 20 Sales takes you inside the world of the best sales leaders. Today, we're joined by one of the fastest growing companies in the world's SVP of sales, Max Freeman, to understand how to think about onboarding, how to think about acquiring the best talent. By the way, he thinks bankers make the best sales leaders. How to think about retention. How to think about incentivizing sales reps with new products. All of this and so much more in what is one of the most granular and detailed shows on how to build a sales machine. But before we dive into the show today, today I want to tell you about how the first AI law firm, Crosby, helped us close a big sponsor. As you know, some of the biggest companies in the world advertise on 20VC. My British dulcet tones clearly convert well. I was working to close this big sponsor, and they wanted to get through legal review quite quickly. Crosby turned red lines around in three hours and caught major issues that would have caused us serious problems in the future. Crosby combines AI, some of the best engineers in the world, from companies like Ramp and Stripe, and some of the best attorneys in the world from top ten law firms. Customers get the best of both worlds. An elite human attorney reviews every contract, but they move incredibly quickly, returning red lines in under four hours. They help the fastest growing companies like Cognition. Crosby, for instance, is the only one in the world who is able to close a deal in less than a few hours. Learn more at Crosby.ai/20VC. If you want to redline NDAs, MSAs, DPAs, and any other procurement contracts faster, go to Crosby.ai/20VC. It's speed that you can really trust. While Crosby keeps your numbers sharp, OneMind keeps your customer conversations sharper. Our friends over at OneMind have a hot take: the B2B GTM model we've been using for the last 20 years is collapsing. Predictable revenue isn't so predictable, and buyers are just tired of explaining themselves at every handoff between SDRs, AEs, CSMs, and support. You feel it in your board reporting. Your sellers feel it in their coverage. Your buyers feel it as they wait for answers. Well enter OneMind and their GTM superhumans: HubSpot, Alteryx, and ZoomInfo are just three of the tech companies using OneMind's superhumans to qualify buyers. Ride along with sales reps and coach customers. Whether you're ahead of target, or under pressure to increase bookings ahead of hiring, or behind on target even, and need every rep to hit quota, OneMind is the solution. See for yourself at OneMind.com, that's OneMind, M-I-N-D, dot com. While OneMind helps you sell smarter, Framer helps you build faster. When a new landing page turns into a pile of tickets and handoffs, Framer helps your team move faster. Framer is the AI website builder that helps creators, teams, and businesses ship production-ready sites faster than ever, while getting every detail right. Prompt, inspect, edit, and publish in one place, at a whole new pace. Agents and humans work in tandem. Agents bring speed and scale, you bring taste, judgment, and control. The work lands on the canvas and stays editable. Build custom code components, manage CMS content, optimize SEO, and audit for issues all in one place. Enterprise-grade hosting, security, and 99.99% uptime SLAs, trusted by leading brands like Perplexity and Miro. Learn how you can get more out of your site, from a Framer specialist, or get started building for free today, at Framer.com/20VC, for 30% off a Framer Pro annual plan. That's Framer.com/20VC, rules and restrictions may apply. "You have now arrived at your destination." "Max. I am so excited for this, dude. I think when people think of the fastest-growing companies, they do immediately think of Ramp. Eric told me that the entire revenue accumulation was down to you, and so no pressure, but the next hour is going to be a lot of treasure trove of wisdom, okay?"
Speaker 1"I love it. I'm fired up, and I think I'm getting too much credit for that. There's amazing individuals on the go-to-market team at Ramp, and I feel very lucky."
Speaker 2"Well, that's great, because I was totally BSing. He said you were a total douche. But moving swiftly to the show, a sales team is nothing without the people in it. And when we were chatting before this, we don't do prep calls. No, Harry's far too old and arrogant for a prep call, but you made me do a prep call, and I'm so glad you did, because you said that you like hiring bankers and turning them into sellers. Why?"
Speaker 1"So, not only bankers, but I think there's a lot of mispriced assets on the market where their resume will not sell. They will not suggest the true alpha. But let's start with bankers. So, in building the early go-to-market team at Ramp, we brought on quite a few investment bankers, and now they're running pretty large pieces of the business. Here's why I have an affinity towards doing this. One, bankers are programmed to work. The concept of a nine-to-five is completely foreign to these folks. Two, they have intelligence, and they have business acumen and a lot of horsepower that is not always found when hiring for sales talent. And I think the third, for our business, we're selling into the office of the CFO. And so, in the earlier stages when we didn't have brand recognition, no one knew who we were as a company, being able to call a CFO cold, tell them, 'Hey, I just quit my job at Goldman TMTIB to join this credit card business,' that packed a very compelling punch for us. I think those were the tangible benefits. Maybe the last additive component that I think is important is, I didn't have time. In early, sales teams don't have time to teach folks, this is how you use lean language in a cold call. This is how you use appropriate grammar in a cold email. We had to be executing, and so bringing on folks like that helped de-risk a lot of that. So we were just in pure execution mode. And now today, you know, Mike Weber, we pulled him from Citi. He runs a massive piece of the business. Sam Buck runs a massive piece of the business. He came from Goldman.
Speaker 2I spoke to Sam before this show, and he was fantastic with suggestions. My question to you is, I can literally feel the passion. I can feel the pain of founders listening, going, "Really? How on earth do you afford these investment bankers? How do you afford these investment bankers?"
Speaker 1Yeah. So the bet we took early on was to actually pay way above market rate for this talent. But in return, we were going to expect way above market rate when it comes to output. And so we'll make the unit economics work. But guess what? You get a book, 40, 50, 60 meetings. Which is four to six times what a standard SDR has to book.
Speaker 2You book 40 to 50 meetings? What is the expectation on meeting bookings, really?
Speaker 1It depends by segment. Obviously the further up market you go, the numbers are lower and we're looking for quality. But down market, we still have SDRs that are booking well above 50 meetings in a given month. In a given month?
Speaker 2Yes. That's not very much, dude. 50 meetings in a given month for an SDR?
Speaker 1You have to book a meeting with intent. There has to be qualification rigor. There's a lot that goes into it that takes precision. I think you're understating this.
Speaker 2No. Because when we were chatting before, I said Chris Dagnon is like, "Oh, you can't do more than seven." And you were like, "Oh, people do way more than that. They do like 10 in a day."
Speaker 1Those are account executives that are taking seven actual meetings,
Speaker 2like the closers.
Speaker 1Not the top of funnel that's booking the meetings for the sellers to then take.
Speaker 2Do you not expect even the low ACVs to be doing way more than that? No. I expect the low ACVs to be doing way more than 12. These are small businesses, like startups.
Speaker 1I'm talking about SDRs specifically. On the AE side, yes, of course, they're taking more than 12 meetings in a given week, especially down market with the low ACVs. Our inside sales reps, our commercial reps, they're taking 10 to 12 calls in a given day.
Speaker 2That's what I'm talking about. Yes. Okay. That was the disconnect. So there are people doing 10 to 12 calls a day? Absolutely. Okay. Okay. So they are AEs or SDRs? Account executives. AEs. They're doing like eight to 10 a day. Great. There is another component though to teams, which is we can't just have IB. They've got to come from some tech company. And there are tech companies where it's good to hire from versus bad to hire from. And I'm not asking for explicit names, but like profiles for me as a founder to think
Speaker 1through. Yes. I love this. I obsess over this topic. So I am a huge fan of Moneyball. And you have to treat. I'm a huge fan of Moneyball. There's probably a lot of weak reviews on third party publications, whether that's That's G2, Capterra. So you got to be dialed in to advance opportunities. And three, you're usually priced at a premium compared to other players in the market that are priced significantly below you. So if you can be the number one or two seller there, you come into a system like Rant, that is where the magic is going to happen.
Speaker 2If you were to name a company.
Speaker 1I can't give away the secret sauce. I'll name one. I'll name one.
Speaker 2Sixth Sense. Because they have a low NPS, products maybe not great. Correct. But close good customers.
Speaker 1Exactly. In fact, just yesterday, one of our top enterprise sellers sent me a email from a customer that said this huge review that they sent internally. They want to offer a case study. And we didn't even prompt them at all. And Alex had said, I've never seen this in my 15 years of sales. And so I go, we get that 10 to 20 times a month at Rant. You've just been selling shit products.
Speaker 2When you're trying to determine greatness in a candidate in terms of where they've come from before. How do you unpick whether it was truly them or whether they were just an order taker? You can have two different situations. One, they're just an order taker, which isn't very difficult. Or two, they're at Twilio and they sign up Uber and they sign Uber when it starts and then it expands into what it becomes and they get the credit for that. How do you determine true quality versus happen, dance or order taking?
Speaker 1Yeah, you have to decompose their number. And so, OK, you did. You did two million. That's that's great. How much of it was inbound? How much of it was outbound? How much of it was expansion? How much of it was sourced by your founder? How much of it was from existing opportunities that you inherited? And then you really have to drill down such that you can spot and figure out if someone is bullshitting you. And then to get even more deep into testing their acumen around sales, it's all right. Talk to me about two deals. You have to make them reconstruct them chronologically. The best candidates give so much texture and like you're really trying to figure out, well, how did you advance this? Well, what was it? Were you articulating business value? Was it some workflow that you tied to a business outcome? They'll know that. And if they can't describe that, not a good sign. The inverse is also true. You want to understand. Talk to me about a deal that keeps you up at night. Why did you lose it? If they can't unpack why they've lost an opportunity, was it they were single threaded? They didn't build a champion. There was no business value. The product wasn't good enough. They didn't qualify well enough. Like figuring that out and testing for it is actually incredibly important in an interview process.
Speaker 2What if I said to you, hey, I get you. One of the decision makers is friends with a competitor. And that's why I kind of hate it, but I also get it. Blamed deflection can also be genuine. How do you determine like good versus bad on that sort of.
Speaker 1Totally. But you should be able to suss that out early enough in the cycle and you should confront it head on. Hey, Harry, I know you're evaluating us and another competitor. I see you have a shared board member. With that competitor, is that going to get in the way of this decision? Like, how are you actually evaluating it? Is it on its merits or is it not? A seller should be able to articulate and communicate that to me. They shouldn't find out about that at the final second after they've rallied all of these internal resources to take a deal through a cycle.
Speaker 2So I've done pretty well in this set of questions. I'm running through this hypothetical, uh, interview process with you next step. Do I need to do a demo? Do I need to do some form of case study with you? What happens next in our process?
Speaker 1Yeah. So you definitely have to do that. Do what we call a business case, which is assuming the role of a seller at ramp and you have to go through a discovery call. We'll give a prompt in advance and we really test for three things. Those three things are ramp as a business and as a product to the prospective company in question. Are you doing your research? Do you know what's going on? Have you read their 10 K things of that sort? And then the third is just selling fundamentals. Do they have executive presence? Can they get second and third level discovery questions? Can they quantify pain? Can they articulate the value? And then more than anything, not to oversimplify, would I buy a product from this person? If I can't say that with conviction, I'm not going to hire them. I feel the same way about hiring leaders. If I'm trying to hire a leader and I don't think I would work for that person, I wouldn't make the call.
Speaker 2And so you sit down with me and you realize that you would buy from me and you do want to work with me. What does the offer stage look like? What do you look for in how I respond to equity versus title versus comp?
Speaker 1I have so many. I have so many thoughts on this. It so depends on where you are in your career. If you're a seller looking to join an early stage company, thinking about equity, cash and comp is actually the wrong, the wrong thing to index on. The right thing to index on is the market, the talent density, the business and the founders. Why the market? Because there's structural advantages if you pick a business that can continue to find growth vectors. Right. In my ramp story, I was a mid-market account executive. I quit my job to become an SDR all over again at ramp. And people looked at me like I had 20 heads. The reason why I did it, though, is the market had unfair structural advantages. The card business, it's a trillion dollar plus a year market expense. Same thing. Bill payments, multi-trillion dollar a year market. Travel, multi-trillion dollar a year market. Banking, multi-trillion dollar a year market. So you don't have to be a good business to find a way to grow just given those dynamics. The fact that. You have the market leading product. You have the most talent dense engineering roster that looks more akin to that of a lab, that of a SpaceX. You're going to win. And so because of that, that's where you get the career acceleration. Like if you care about, oh, I want the VP title and I want a ton of equity, but you're going to go work at a mediocre business that might grow 20, 30 percent a year. Who cares? You're making the wrong trade.
Speaker 2So with the greatest of respect, so people that like go and work in like AI sales tools. I'm like, really? You're doing like AI revenue forecasting. I'm not being a dick, but I'm just being honest. I feel the same way because exact. Yes, that's exactly my point. Yeah. It's like the John Scully, you know, the Apple moment. You're really going to spend the rest of your life selling flavored water.
Speaker 1That's it. Unless you have the belief in the conviction that this could turn into something that rivals Salesforce. Sure. By all means, go swing for the fences. But that's hard.
Speaker 2Totally get you. So sorry. Number one. Number one was market. What was number two and number three? Talent density. Talent density. On the current roster. And then third, founders. Okay. And so talent density. If we just unpack that, is that just how good the team is? What does that actually mean?
Speaker 1You know, working in sales, you want to be the beneficiary of having killer engineers. And so first engineers that I met at Ramp were otherworldly. It's like the youngest person to ever graduate from MIT. Someone that had already built and sold a business to Apple in his dorm room at Stanford. You know, the IOI gold medal, Olympic track. That's what you want to underwrite. And then the fact that Eric and Kareem had already built and sold a business to Capital One. That doesn't happen by accident.
Speaker 2That's a pretty solid engineering team to start with, isn't it? Youngest kid to ever graduate from MIT. Gosh. Gosh. Okay, fine. My four weeks at university are really making me feel guilty now. That's why we're sellers, Max. That's right. That's right. I went to state school. Oh, baby. Yeah, there we go. Okay, so that's talent density. I get that. And then the third is founders. And when we say founders, can we unpack that a little bit? Because we see a rise of engineering-led founders who suck at sales, definitely haven't built out a sales playbook, definitely don't have really much clue about sales. How would you think about that as a potential founding team to join?
Speaker 1That's totally fine. I think we're going to see more and more of that as a lot of engineers are looking to go start their own AI native businesses. I think you need to test for. A few things. Are they seller-friendly? And I'll explain an example of what that might mean. And then two, their willingness to engage and be involved in taking feedback such that the product can mature and become sophisticated enough to meet the demanding needs that sales will face. I'll go deep on the first example. Being seller-friendly, what does that mean? Well, will your technical co-founder give you engineering resources to help build the machine? Sales is very much an engineering process. When you break it down, it's a data infrastructure problem. It's a math problem. And so you need to build the systems to help give you leverage and automate such that you can create a ton of capacity. And I give a lot of credit to Kareem early on with providing engineering resources to myself to build out our OATS program super early on in the business.
Speaker 2I'm so sorry. What is an OATS program? Why is it a data infrastructure problem? Why is it a math problem? Can you just help me understand this seriously?
Speaker 1Yeah. So outbound used to primarily be a writing and a calling problem. I think increasingly it's becoming an engineering problem. In late 2020, early 21, even before the rise of AI, we built our own internal infrastructure to help automate a lot of our outbound. And that's what OATS is an acronym for, Outbound Automation Team. And so let me break this down. So the team was understanding what I was doing to go to my office. How I was creating signals inside of accounts. And the signals could be unbounded. It could be a new hire, just joined the business. It could be, I went to the same university as this person. We have overlapping investors on our cap table. And that was very manual. You know, you got to build the templates. You got to find the contact data. Why is our sales team doing that? They should be focused on just speaking with the customer and helping solve their business problems and getting ramp deployed. And so. our team of engineers, built a lot of automation to do the list scraping, do the email outreach. And it was incredible. I'm so sorry.
Speaker 2If I'm a founder, then listening to this, wanting to do the same, what do I do? I tell my engineers to get Zoom info?
Speaker 1No, that's part of it. You tell one or two of your top engineers that, hey, we could build the coolest product in the world. It doesn't fucking matter if it doesn't get into the hands of paying customers. And so we need to obsess over growth as it's existential for our business.
Speaker 2What are we solving for here? I don't get it. Are we solving for finding new leads or for outreach to them? How do we handle the integrations of whether it should be an email or a LinkedIn message?
Speaker 1Yeah, you're solving for coverage, right? In the early innings of your business, you're not going to have an army of go-to-market talent. You might have three to a half a dozen of folks that are responsible for outbounding. Guess what? If you do that manually, maybe you could get a couple hundred emails out. Maybe you could make a hundred dials. That's not enough. Especially in markets today where the TAMs are becoming more and more unbounded, you need leverage. And so the problem you're solving for is coverage and brand awareness and getting your name out. You just can't be dependent on sellers to do that.
Speaker 2Do you not think you have efficacy reduction, in other words, less efficient outbound with scale versus if I sent 20 really, really great messages that are researched, thoughtful, included a joke about our alma mater, and a picture of a. Me and my mom walking on the weekend, my efficiency would be through the roof. A genuine asking, not telling.
Speaker 1That is a concern. You have to make the system recursive to actually understand what is yielding results such that it optimizes over time. And so if you're just relying on automated emails that are going out and out and out, that's irrelevant. You have to constantly be A-B testing and pulling in what's actually going to yield the best results. And then guess what? You still allow for manual outreach from your sales team because they, to your point, if you're going to. Send 20 unbelievably curated notes, the likelihood of those getting responded, sure, it is higher. And then the system can identify that, take that feedback, pull it in and start actually doing it at scale.
Speaker 2Do you have engineers in sales permanently? This isn't like a one and done sales tool build.
Speaker 1We have a growth engineering team. Yeah, I think there's at least half a dozen engineers that truly obsess over building products for go-to-market.
Speaker 2What's a good response rate when you're sending outbound in a tool like this?
Speaker 1Response rates over time since the acceleration of AI have actually regressed pretty meaningfully. But response rate isn't the right metric to index on, it's meeting response rate. Because you can get a 5% response rate, but if they're saying, "Please never email me again," or "Opt out," or "Fuck off," that's not directionally helpful. And so it's how many you convert to a meeting? Yeah, and that should be just a hair under 1%, I think is really strong standard. So for every 100 emails you're sending, those convert to 1%, that's great.
Speaker 2How quickly do you verticalize your sales team? Because all of this can become better, more efficient, more accurate with verticalization. Hey, we've got clients including British Airways, Delta, and Ryanair. Oh, wow, okay, we're targeting the travel industry, and specifically airlines. Do you see what I mean? When is the right time, and how do you think about that?
Speaker 1Yeah, I think the right time to verticalize your business is when you're sending outbound emails. When is the right time to verticalize your business is when you need to pull the lever to inflect conversion. I think companies actually verticalize far too early, especially if you have a huge addressable market. You're in land grab market share mode. And so I think verticalizing the business may actually be counterproductive to doing that. But as you own more and more of the market, I think this is arbitrary, but I'd say 3% to 5%, guess what? The total amount of opportunities you can go after starts to become contained. And so the lever that you need to pull is you need to be able to convert leads to close one at a higher clip. And so I think that is the moment when you start to verticalize, you know, looking at companies that I think have done this moderately well, the Oracles, the Workdays, the SAPs of the world, that's exactly what they've done.
Speaker 2One of the reasons I like verticalization in sales teams is what it does to sales cycles. Often the messaging is better, it's more accurate, the value prop is kind of clearer, and I just see a compression in the sales cycle. When I see that verticalization, what are the biggest lessons you have on how to compress sales cycles?
Speaker 1The best way to compress sales cycles is qualifying with more rigor. So upstream, you need to understand, does this person have the influence to actually effectuate change? And are they reasonably committed to doing this within a 12-month period? If you could check those boxes, yes, swing at it.
Speaker 2How do you determine that actually? Because a lot of people like to have ego and say they're very important. And a lot of people will like to please you and say, yes, they'll do it fast. How do you actually determine it?
Speaker 1Yeah, you've got to test them. The way to test them is if they're not in the C-suite or they don't have a VP title, you have to know who their boss is in the org chart. And so if you've had an unbelievable call and you've earned the right to pull in another stakeholder, you have to ask for it. And there's a subtle way to do this where it's seemingly a give to get. Hey, Harry, today was awesome. I have a lot of conviction that we can solve this problem for your business. We're going to knock this demo out of the park. I'm going to bring on a bunch of my technical resources. In an effort to bring them onto the call, my ask would be that you bring Susan, your VP of procurement, into this next conversation. You'll know right then and there. Is Harry going to bring Susan into the call? Okay, great. You may have a champion. You may have someone that can effectuate change. If not, oh, why aren't you? Are you just window shopping? Do you not have a relationship with your boss? Do you not actually do this? So it's a really good way to test that out.
Speaker 2So I love that. And Susan would love to come. One thing that's really important for us right now is just cost controls. And so, Max, can you help me out here? You're saying that you're charging $4 per card or $4 per seat or $4 per unit of whatever we're selling. I'm going to need it too. Are you going to be able to meet me there, Max? Well, Harry, we haven't
Speaker 1even determined technically if this is going to fit for your organization. And so, look, we can figure out economics. I think once you see how this product is going to transform and change your business, it's going to be a lot more financial impact back to 20 VC than trading two bucks.
Speaker 2So you don't engage on discounting because so many founders say to me, I just don't know how to do it. I want to close the deal, but they want a 20% discount.
Speaker 1Yeah. I think early on in the conversation, if we're coming to discuss economics and pricing after call one, that's usually a bad sign. It's not a sophisticated buyer on the other end, unless it's super down market and you're talking to a 10 person. Startup founder, and you're trying to one call close for sure. Maybe I'll engage that way and we'll discount to get the deal in the door. But upmarket, no, you have to co-author business value assessments. You really have to understand what are they trying to solve and what does the total cost of ownership look like? Are you trying to get a margin win? Are you trying to make your accounting function more efficient and give yourself FTE leverage? And if you could mutually agree to that, you could circumvent any pricing competition. I think that's a really good point. advise against one at a time do we always shed one or do we sometimes keep the most how do you
Speaker 2mean like if someone isn't performing well by nature of having two one will always perform worse than the first how often do you keep them both versus get rid of
Speaker 1one it depends if someone is just complete outlier destroying the other seller yeah you probably need to shed that person if it's a 10 to 20 delta you have to you have to go deeper and unpack it like what why why is this person winning more like what structural advantage might they have is it pipeline that i gave them is a pipeline that came from our cap table is it something else do they know the product better are they more motivated do they give a shit and the other person doesn't like this is this is on the founder to go
Speaker 2ascertain so for the 100 ot sorry going back to that that's for sdrs does that change when we're doing comp
Speaker 1design for a's no it's for it's unilateral across early early
Speaker 2the big mistakes you think founders make when they're doing comp design because again like we have challenging nuances like when you have new products you want to incentivize them more you want to encourage bonuses for selling more of those but i don't want to then have a load of people sell all of that and none of the core how do you think about that i have so many thoughts on
Speaker 1this depends on stage first if you're an early stage founder you're probably still trying to take one product to market and you want to focus on that you really need to understand your icp said another way it's so much more valuable to have 20 customers that are raving and thrilled about one single product offering than you in a half-ass way serving six customers on multiple products that aren't as thrilled you need to get the tailwind going of case studies references and positive momentum across your business later stage though like where ramp is today incentive design is incredibly important and i think it's i think it's existential to over incentivize new products to get off the ground and so thinking through 2x to 3x quota retirement for new products you got to get the again you have to get the momentum going such that you earn your way into more multi-product customers more case studies more momentum when
Speaker 2you get a higher wrong max what do you not see that you should see so like for me sometimes i'm i'm quite overtly aggressive it's very innate i'm intense and i'm gonna kill competition and i'm gonna salivate over it and i'm happy to talk about that the quiet killers i don't find as easy sometimes to uncover that would be the talent that i miss and i try and correct for that when you make a mistake on hiring what do you miss that you should
Speaker 1see people in sales especially leadership naturally tend to interview well they are sellers by trade they know how to say the right things they know how to respond extremely quickly in the interview process to show that they are urgent and can follow up ruthlessly i think the the only mistakes that we've made are over indexing on pedigree and coming from you know the big name brands and not truly understanding two things one do they have the agency to do that or do they have the agency to do that or do they have the agency and do they possess the figure it out x factor where they do not need to be dependent and reliant on so many different internal resources and then two which is related are they going to go all in are they going to have a deep obsession with working at rant like it has to become their identity and if both of those things aren't ascertained crisply in the interview process it could come out and it's it's sometimes the wrong
Speaker 2hire chad pete said on the show legendary sales leader he said that young people just don't want to work and that there is a different appreciation for they want to work from home they want work life balance they want mission they get burnt out they want kombucha is he right i love chad he's a
Speaker 1beast i love degnan too that was a fun show um i think he's right it's a bit provocative but there are plenty of young professionals that do want to go all in and you have to find them and it's on you to build the culture internally and i think that's what we need to do and i think that's what we need to do and i think that's what we need to do and i think that's what we need to do and i think that's what we need to do and i think that's what we need to do and i think that's what we need to do and i think that's what we need to do and i think that's what we need to do and i think that's what we need to do and i think that's what we need to do and i think that's what we need to do and i think that's what we need to do and i think that's what we need to do and i think that's what we need to do and i think that's what we need to do and i think that's what we need to do and i think that's what we need to do and i think to that. Like, look, if you want to work remote, you want to make calls for four hours a day, other ICs in the business are just not going to let that permeate throughout our org.
Speaker 2Help me understand. I'm delighted to accept your offer. Thank you so much, Max. What have been your biggest lessons on how to onboard new reps effectively?
Speaker 1So early stage, you're all locked into a room, okay? You're going through four very key components, the first of which is the product and the technology that you're selling. The second, the buyer personas that you're selling into. The third is the competitive landscape. And the fourth is just like the internal operating chaos of how your systems run and what you need to know as a seller. And so on point one, in the age of AI, and especially as the next generation of buyers sit and see, they have what I would describe as bullshit repellent. They are direct. They could get answers quickly. And so the expectation is that they're going to be able to do that. And so the expectation is that they're going to be able to If they're talking to a seller, they need answers quickly too. And so if you're not technically proficient in your product offering, you're fairly useless as a seller. The second is the buyer personas that you're selling into. This is really important. You need to know what their priorities are. You need to understand their challenges. And it differs. If you're talking to a CFO of a venture-backed software company, that conversation is going to be a hell of a lot different than if you're talking to the senior accountant of a construction business. And you the accountant might need one workflow that is tied to the month-end close that is creating a lot of laborious chaos for them. And you need to have that context switching capability. The third, the competitive landscape. We obviously play in an incredibly saturated market. A lot of players claim to do many of the same things. You need to study these businesses. You need to understand their weaknesses and you need to expose them in a diplomatic way where you're positioning your product. And you need to understand their weaknesses and you need to expose them in a to be as perfect as possible for the buyer in question.
Speaker 2Do you have a bootcamp where you go through these stages? We do. Can you walk me through that? How long is it? Who leads it? What materials are there?
Speaker 1Yeah. In the bootcamp specifically, depending on the segment, it's going to be 60 to 90 days. First four weeks is fairly rigorous with many milestones that you need to hit. Some of this is intense hands-on keyboard. Some of it is self-guided skills that our enablement team has these different topics. And then the milestones, there's a lot of rigor that goes into this. You need to complete a disco certification and you need to be excellent. You need to complete a demo certification and you need to be excellent. I like to pop into these periodically. And if you don't complete them, you don't get turned on in the router. You don't get your accounts. And so it's existential that you perform well. Otherwise, your ability to ramp and become a successful seller is contained.
Speaker 2How long before I start speaking to you? Two to four weeks, depending on your segment.
Speaker 1We try and make it as quick as possible.
Speaker 2And I'm going to be listening to a load of gong calls before that to really try and understand the cadence, the language, the patter.
Speaker 1Absolutely. You're going to be listening to gong calls. You're going to be joining live calls. You're going to be in team meetings, listening to pipeline reviews and forecasting calls and everything in between. And then guess what? After your first call, your leader is riding shotgun and making sure they're supporting you from start to finish. If you're running a big sales team and you're just dependent on enablement, you're going to die. You need your frontline leaders to lean in aggressively and also be as deep in the weeds as possible with new hires
Speaker 2onboarding. It's one of those ones which sounds obvious, but it's hard when you are a leader to delve down into it. I didn't mean it awfully, but it's kind of like intern batches in venture funds where you're like, 100 percent. Everyone wants to help young people, but I got to close the big fucking whale of a deal.
Speaker 1100 percent. But you have to do both. Yeah, of course. You have a number that you're responsible for. And so, yeah, if there's a big swing deal and you're a frontline leader, yeah, you're all hands on deck. At the same time, guess what? Your number is going to keep going up sequentially month over month, quarter over quarter as these new sellers ramp up. And so you're directly incentivized to make sure that they're coming into the system to be killers. Otherwise, you're going to be in trouble as a leader.
Speaker 2What percent of first calls do you think you're impressed by versus disappointed by?
Speaker 1Seventy, thirty. Seventy in the camp of I'm impressed. Thirty in the camp of this is just not to our standard. And so what happens in the 30 percent? I'm actually fairly in the weeds on this where I'm reviewing and watching a lot of gone calls specifically with new hires. Candidly, even more of our tenured reps. And if it's not to our standard, I'm pulling them in and our leader and we're going to talk about it. It's tough. It's a sales team that doesn't have your leader or your SVP that into the weeds holding you accountable. That's probably a bad sign.
Speaker 2Talk about holding you to account. Let's say I come out of these 90 days. OK, I'm ready. I'm unleashed in the wild. Carlos, who was the head of sales at Eleven Labs, said that they get 20 X quota. Now, it was a slightly, slightly popular clip. How do you feel about that what is like good to you and how would you advise founders listening i sort
Speaker 1of lean in the camp of degnan on this one where if you're that efficient you're probably leaving money on the table and you need more reps now i think the old school thought you know that the snowflakes and the mongos used to run of you know four to one or five to one that's too low i think depending on our segments at ramp it's anywhere from seven to twelve i think that's pretty healthy
Speaker 2it's a lot i want you to pay me more if i was doing 12 to one dude i know we might have to pay me pay me pay me double and then it'll be six to one we might
Speaker 1have to cut that part out i don't know if our uh inside sales reps actually know that uh some of them are like 14 to one are they
Speaker 2a hundred percent i think it's good you want like the hunger games of competition okay so for me it's like an early stage company though i'm in the six to ten range now is where i kind of need to be hitting to be in a you are a performance sales team i think that's right and like ramp time how long do you give me to to ramp post boot camp because obviously boot camp kind of getting my feet on the ground how long do i get to ramp
Speaker 1again it depends on the segment our down market sellers inside sales reps 60 days commercial reps 90 days mid-market four months enterprise five months and our strategic enterprise is a six month ramping schedule the reason why those ramping schedules exist in that way is just due to cycle length timing how quickly do you know if someone's not very good i think it's actually fairly simple to get a pulse check on if someone is going to be good or not i think there's a direct correlation in onboarding with sellers that are annoying and sellers that are are not and when i say sellers that are annoying they are constantly asking questions 24 7 they're very thoughtful they're talking about account strategy they want to pick your brain about pipeline and getting you to send emails on their on their behalf they want to ask you product questions and it's never ending there is a direct correlation with that person being incredible the inverse is not always true but i think the folks that are quiet not asking any questions or asking questions that any ai bot or notion bot can answer usually that's going to be weak signal
Speaker 2i totally agree i always say actually the quality of a founder is very obvious the quality of the questions the founder are going to ask is the quality of the questions the founder are going to ask is the quality of the questions the founder are going to ask is the quality of the questions the founder are going to ask
Speaker 1that's why i intentionally leave at least 10 minutes in an interview for them to fire away at
Speaker 2me because it tells you people think like my partners will often say why why are we spending so much time answering that question like because it's you don't get it i'm actually measuring them they go tell me you've got four partners is it an equal vote in the ic or how do you guys think about investment decision making that's quite a
Speaker 1exactly smart question i think about it the same way i think about an interview where i intentionally need to give them at least 10 to 15 minutes to fire away as if they're trying to sell into me and so i get some sellers who will say hey max i spoke with scott on your enterprise team i know he's number one right now the reason why i think he's doing really well is he walked me through his process here's how i think about sales and why it's uniquely very similar to what it is that scott's doing that makes me a really good fit for this role in the same way that you're breaking into an enterprise account if i'm a seller and i get on the phone with a cfo hey mr cfo i spoke with your controller these are the pain points these are the challenges here's how i think ramp can uniquely solve some of these said challenges it's the same thing that i'm trying to ascertain can i ask you
Speaker 2you've mentioned dagman quite a few times dagman always says to me like i think customer success is bullshit like it should be paid for professional services and i'm like i'm not sure if he's right do you think cs is bullshit and it should just be paid
Speaker 1for i have like a slight spin on that but look i i believe enormously in customer success as an outcome and as a result we've decided to make customer success an organizational construct in our business and they're highly technical some of them are cpas by trade they're proficient in erp and accounting systems and so it's almost an extension of the customer's accounting function in ways that are not the customer's accounting function that i don't think you can replicate with a professional services business and the economics of our product works such that we can subsidize a lot of that work and so okay i think there's a lot of value that that team drives for us and while that might work for for snowflake i don't think it's the right decision for us at ramp you kind of have to think of customer success as the economic engine that is going to drive ndr for your portfolio of customers over time and so we want to be hands-on we want to own the outcome because at the time of the initial transaction that deployment is so incredibly important because if we knock it out and we do well and we deliver value guess what we earn the right to over time sell more and more products in ramp today there's no shortage of new products we have to think through how can we thoughtfully cross sell upsell and expand all with the goal in mind of driving financial impact and operational efficiency for our customers but guess what if you don't do that you're not going to be able to sell your product you're not going to be able to do that perfectly at the onset it's going to be increasingly difficult to earn your way into selling more products over
Speaker 2time the hard thing about i find the expansion is forecasting it's difficult to forecast expansion number one but i find forecasting stage is like freaking impossible the volatility inherent within our ecosystem is so high growth rates we can never how do you think about forecasting today as a leader and what's your advice to founders and leaders sales leaders on how to forecast in 2026 i'm the
Speaker 1benefit of the doubt beneficiary of having an unbelievable counterpart in finance his name's asher who has built pretty ridiculous systems and models around forecasting such that they are consistently within a five percent delta across the entire business and so when you've been biggest delta what did it not see nothing because we're at the law of large numbers at this point years ago before we've had the discipline in our revenue operations function we've had the discipline in our revenue operations a lot of this was self-done by sales and there was discrepancy i think the the advice that i'd give and like the lever we pulled to make it far more consistent is guess what sellers you're not going to be compensated or quoted on your forecasting accuracy and discipline but it's part of your performance review it's coming up in one-on-ones it's coming up in your qbrs and so forecasting accuracy at the onset of the seller guess what they're they're incentivized to care the same thing with frontline leaders they're incentivized to care they're incentivized to care they're the same thing with segment leaders if you don't make it part of your performance culture i think it's going to be hard because a lot of sellers are going to use emotion they told us we're vendor of choice well guess what they haven't even kicked off legal or info so we've got three days left in the quarter so i think really holding everybody accountable in that way is is how i describe it how often do you do pipe review max gosh we do pipeline reviews once a week what's great though is i've gotten rid of forecasting calls why because it's so system driven and there was too much duplicative overlap it's just performative work theater and we don't we don't need that like every hour matters and as a leader i need to give as much capacity as humanly possible otherwise it's an expensive problem so with pipe reviews who comes who gets the invite so they are led by segment leaders all frontline leaders are on and then it's a rotation of certain ics that go through their business deals and what we try to focus on like we we don't really care that much about deals that are in a beautiful spot it's like what are the deals that are at risk of losing and what are we going to do as a unit to de-risk and try and advance i think it's also important to understand what are the deals that we've lost how do we stop the losses is it something that we could have controlled is it a product gap is it pricing is it something else when you lose why do you lose i would say the majority of the time we're losing to the status quo which is on us that's not a product gap that's a we need to look ourselves in the mirror we did not create enough urgency and you can manufacture urgency as a seller you got to latch on to a big business problem you got to find the right person internally that's motivated enough to actually make a change because it's going to impact their career they could yield political capital from it you might not get that with somebody low level you might not get that with a cfo it's like you have to be appropriately multi-threaded did we're seeing
Speaker 2brand marketing spend like never before from big brands like ramp are you seeing the effect of that as a sales team do you see the compression of that in sales cycles do you see the warmth of buyers going oh i saw you on the subway or oh i saw you on a boston red sox shirt or whatever you americans watch sports
Speaker 1yeah it certainly helps look we have a lot of hype and buzz it's hard to truly attribute this in the sense that it's a lot of hype and buzz it's hard to truly attribute this in the sense that it's a especially if we're in certain markets certain geos it's uh a way for sellers with customers and just as critically prospects in funnel to invite folks to a sporting event invite folks to our bill pay musical invite people to bespoke dinners and things of that sort and it's it's definitely showing up in cycle times in customer willingness to expand their usage of ramp it's directly correlated and it's a lot of hype and buzz it's a lot of hype and buzz it's a lot of hype and buzz it's a lot of hype and buzz it's a lot of hype and buzz it's a lot of hype and buzz it's a lot of hype and buzz it's a lot of hype and buzz it's a lot of hype and buzz it's a lot of hype and buzz
Speaker 2what would you most like to change about your internal sales process today that you haven't changed yet or can't change?
Speaker 1We've made so many iterations to optimize our sales process over time. As the models have gotten better, really predates to end of last year, early this year, we've done so much for our sellers to unlock a lot of capacity. And I'll give examples of this. Like sales is very much a conveyor belt. You're a seller. You have an initial meeting with a business. There's work you have to do prior to that meeting. You have to go perform your independent research. What does that mean? You got to go into LinkedIn. You got to go on their website. You got to go into pitch book. You got to go into all of these different third-party sources and publications. When we came to figure out the time of this labor, it's like anywhere from 15 to 30 minutes on the high end. Maybe if you're exceptional, maybe 10 minutes. When you quantify that, Harry, across hundreds and hundreds of sellers, that is a disgusting loss of productivity. And so we've built our own internal revenue operating system called Ramp Revenue that performs a lot of this pre-call research. And what's great about it is it actually bridges the talent gap. When I think about it, like what an amazing seller might do is, okay, cool. They just launched a new product. KKR just came in. They're now the new sponsor on the debt. This random person that isn't even in finance or accounting happened to use Ramp at a previous company. An average seller might neglect all of that. And so like what this system is, it's like, okay, I'm going to do this. I'm going to do this. And so what this system does is it bridges the talent gap one. So going into a call at your fingertips, you know exactly what you need to say and how to execute. And then two, the time savings, like at most, that's going to take you 90 seconds to perform your pre-call research. And so when you quantify that across all of go-to market, there's just significant capacity unlocked that I turn into extra selling days, which allows us to over time, increase quotas. Increasing quotas is more revenue back to the business.
Speaker 2Would you ever open that up to the public? One thing that we're seeing with Deal in particular and Revolut actually in some cases for their performance management software is they built these internal tools and now they're selling them. Would you, and to what extent is secret source secret versus monetizable? Because you've got Ramp rooted, don't you? You've got the open root.
Speaker 1Yeah, we've got Ramp router. So on the Ramp revenue piece, I won't speak for Eric and Kareem, but our ambitions are well beyond owning the office of the CFO. And so I can certainly see a time when we can put these other products to market. I think it comes down to timing and sequencing these appropriately such that, you know, our go-to market organization can structurally handle all of this
Speaker 2change. That's the fucker. It's not just like a product decision. Like you can't just be like, oh yeah, why don't we do Ramp revenue? It's like no, Ramp revenue actually needs salespeople to sell it, to implement it, to do customer success on it, to market it. And I think this is what people so often get wrong with enterprise, which is you can't just like give it a go. It's like you need, in consumer you can. Yeah, you flip the light switch on and yeah. Yeah, no, honestly, yeah, you can. And it's much easier. Let's see how it goes. But it's so different and it's so complex. And this is why I think people get it so wrong when they're like, oh, Astra law is going to kill Harvey and Nagora. It's like, are you serious? You think the training and deployment methods are going to be the same for open AI and for Harvey and Nagora who spent two years kissing the ass? I completely agree.
Speaker 1Completely agree. Final one.
Speaker 2Where do you fall down as a sales, leader where you feel you need to improve most? There's a lot that I
Speaker 1need to improve. I think my biggest thing that I'm working on is resisting the instinct to personally jump into every important problem. A lot of what helped me progress at Ramp was being incredibly hands-on. If there's an important deal, important customer, I'm all over it. But that only works well for a certain period of time. As your scope, gets bigger and bigger, that instinct can actually become a weakness. And so said another way, if I jump in to every deal and solve it, maybe we win the deal, but I haven't necessarily made my sales organization better. And worse, I can unintentionally teach people that when something gets sufficiently important, Max is just going to jump in and take over. That's going to become a constraint. I need to build more and more barrels inside of the go-to-market organization. Not doing my job effectively as a leader.
Speaker 2And you don't build those barrels because you're busy just in the machine.
Speaker 1I think you have to do both. Like something I pride myself on as a leader, and I force it across all of the other leaders in go-to-market is you got to be a dual threat. You got to be able to operate in the clouds. You got to be able to go toe-to-toe with me, toe-to-toe with Eric, toe-to-toe with Will and Colin. At the same time, you have to be in the trenches with your sellers. Still to this day, I'm making cold emails every single day. Are you really? Yes, I have to. And the moment that we as leaders get further and further away from the customer and what it is that our sellers are doing, I think we die. I don't think we're being helpful or adding value to our sales team. There's nothing less inspiring as a seller than taking instruction from someone that you don't believe can do the job better than you.
Speaker 2Can I ask you, what do you think Eric Kareem did to imbue a founder like mentality within you? When I talk to you now, it very much feels like speaking to a founder. I was just thinking, my gosh, I would like to poach Max. I was upfront about alternate investment. I'm like, we got to poach Max. Come on. I know that you'd be like, come on, go fuck yourself. And so my question just to you is, it's amazing. I'm giving Ramp credit here. What do you think Ramp and Eric and Kareem did? To make no offense, Max from Namely, who wasn't extraordinary, a founder.
Speaker 1I think a few things. One, a lot of exposure. When I joined Ramp, my boss was effectively Eric. I'm seeing him in sales conversations. I'm seeing him talking to investors. I'm seeing an operating out of his email inbox. It felt like I earned 50 MBAs in a nine-month period of time. That was an insane acceleration. And then two, also exposure to, investors that have seen and done this before. I'm super grateful that I get to call Dave Schneider a friend and a mentor. I've learned a lot from him. And then two, Colin, my boss, is exceptional. He's taken companies public. He's sold businesses. And so I think just being in the room has allowed me to absorb a lot of this knowledge. And two, it's forced me to figure it the fuck out. I'm naive to the fact that I have to earn this every day. If I don't perform, I could lose my job at any moment. If I'm not. If I don't end up in executive conversations with Eric, whether it's external with a customer or internal with a hot board topic, why would I still have this position? And so I think it's a combination and a sum of all parts of the founders have given me a lot of exposure. They hold me intensely accountable. And I have a healthy amount of stress and paranoia that if I don't keep delivering and I don't keep growing, the music could stop.
Speaker 2Yeah. Dave Schneider said one of the greatest lines ever to me on a podcast. He came to London. Love this guy. He says, VCs are like seagulls. They like to fly 100 feet ahead of you, look down on you, and then just take a big crap all over you. And I just say, honestly, I can't remember anything else he said. But that one line
Speaker 1really stuck with me. He had the best one line around. I forget what the topic. It was something around, how do you measure performance? How do you stack rank? And he's like, Max, there's three categories of performance in sales. One, you are God. It's so true. You know what?
Speaker 2It also taught me that when you listen to what I just said, which is like, oh, the seagull's shitting on you. It's better to be a purple cow sometimes, which is like Seth Godin. Being different is sometimes being better. Dude, we're going to do a quick fire because otherwise I could talk to you all day and you've got a quota to hit. What one sales tool could you not live without?
Speaker 1I don't know if I could say that. I'm going to say this publicly, but I'm going to. Inspect. Inspect is Ramp's internal coding agent in Harness. It feels as though I have an engineer and a sales engineer in my pocket at any given moment. Have you guys just built all your own tools? Harry, when I come to London, I'll show you this. It is insane what our sellers can accomplish with Inspect, like creating bespoke custom demos, performing any analysis on current customers' Ramp configuration. It's epic. Who's to credit for that?
Speaker 2Is that the CTO who's built the internal tooling?
Speaker 1Yeah, I give dual credit to Eric and Karim. It's just culturally in our DNA to push forward and go build. Okay.
Speaker 2You have a job offer that you know will not be rejected. You can give it to anyone in sales in the world to join the Ramp sales team. Who is it? I see your leader or anyone. Anyone. I like to back it up. I like to back a Lindquist a lot from Clay.
Speaker 1So I was literally going to say Becca or someone that's under, like I'm a big believer in finding someone that's just about to hit an insane trajectory. Again, my whole thesis on mispriced assets. There's a guy, Charlie DeMuth, who's an enterprise frontline leader at Profound. He's an animal. Every six months, I try and bring him in. Hopefully, Mark doesn't listen to this because he's the SVP of sales at Profound. What's your biggest
Speaker 2advice to a new rep on their first day?
Speaker 1You need to go all in. You need to be obsessed because if you're not obsessed, you're going to be average. And the additive thing I'd say too is be a problem solver. Don't be a problem finder. Anybody can be a problem finder at a startup. There's a thousand things on fire every waking moment. Very few can be a problem solver. As a new seller, you bring a fresh perspective. You could see there could be something structurally wrong with our process. There's something that you were doing at your previous company that might be applied to help move the business forward. That is how you're going to accelerate your career and do well. And then get, I guess, with obsession, like take fucking onboarding seriously. Pass your certifications, break into accounts, start creating a lot of your own pipeline. All the basic stuff that you'd be surprised some people neglected.
Speaker 2I'm always like, listen. Accept, blame, and deflect credit. Like the worst thing for me is like, oh, no, no, but that wasn't my fault. That was Max's fault.
Speaker 1Yep. There's nothing worse than going to your leader and saying, hey, do you have any feedback for me? That's an atrocious exercise for everybody involved. Come to the table with a point of view. Hey, I noticed this in my last two deals. Here's how I'm thinking about course correcting. I'd love to get your take. I'd love to get your advice. Am I viewing this the right way? Have you seen this play out with other sellers? That's just the mindset that you need. What do you bring to be incredibly effective in your role as a new seller?
Speaker 2I agree with you. It's a really good point because whenever they always do it to me and I'm always like, oh, fuck. I guess I should have been better at giving you performance reviews. I know. Do you know what I mean? And it makes me feel shit. You're kind of asking a horizontal question. It's not like, hey, I feel like I need help with the closing process.
Speaker 1Yes. Same with leaders. Same with leaders. Hey, do you have any feedback for me? Hey, I noticed this problem. Here's how I'm going to go solve it. Here's the cross-functional resource. That I'm going to need to bring in. If I get blocked, like, come help me.
Speaker 2Do you know what fucks me off more than anything? Intro requests is in a similar vein, horizontal. I'd love an intro to someone at RAM. I know. Someone at RAM. I can do Keith Raboy, the board member. I can do Eric Gleiman. I can do Max, the rockstar sales leader. But I don't have also a freaking clue why. So that would be helpful too. And then on top of that, you know, I get about 50 intro requests a day. Maybe if you could do a copy and paste, that might be helpful too. The horizontal shit nature of intro requests astounds me.
Speaker 1You and me both. If you're going to ask for an intro, there needs to be substance. And you need to make it so easy that they're just forwarding it to the person with the appropriate context, otherwise you shouldn't expect a response.
Speaker 2Max, I'm totally aware of the ask here, but I'd love to meet Colin. I'd love to specifically speak to him about his experience at X. I've added a message below that you can copy and paste. By the way, I totally understand if this is not possible. Huge hugs and let me know when you're in London. Yes. Final one for you. What's the kindest thing that anyone's ever done for you?
Speaker 1I have to give my wife credit. She was my girlfriend at the time. Oh, you're getting brownie points for this one. I am. Look, it was late 2020 and I basically told her what I think this could turn into. This was like four or five months into Ramp, but I was deliberate in telling her this is going to fuck up our lives, like we're going to have to make a lot of tradeoffs. I'm going to be absent in our social life. I really want to pursue this and I'm fired up about it, and she was super supportive. Still is today. Doesn't love the weekend calls, right? Yeah, I think that was that was probably the kindest thing that that anyone's done for me.
Speaker 2Wow. Well, dude, listen, Chanel solves a lot of problems. So, you know, it's OK. You know, I've learned this. I miss a lot of family shit and my mother has 30 Chanel handbags. So that's right. We both win. You know, dude, I've loved doing this. I really so enjoy episodes like this where it is granular. It's reflective. It's fun. It's everything in one. So I really appreciate it, man.
Speaker 1Me, too. This was a blast. I'm such a huge fan of yours. This is full circle moment. Actually, what's funny, I should have said this in the beginning back when I was in PR at Ramp, I always used to listen to your podcast and take anecdotes. This was all done by hand manually and reach out to the founders that you had as guests as a way to try and get them on Ramp. And so it's funny, six and a half years later that I'm sitting here.
Speaker 2But before we leave you today, today, I want to tell you about how the first AI law firm, Crosby, helped us close a big sponsor. As you know, some of the biggest companies in the world advertise on 20VC, my British phone's clearly convert. Well, I was working to close this big sponsor and they wanted to get through legal review quite quickly to close the deal. Crosby combines AI, some of the best engineers in the world from companies like Ramp and Stripe and some of the best attorneys in the world from top ten law firms. They help the fastest growing companies like Cognition, Ramp and Clay close deals in hours, not weeks. If you want to red line NDAs, MSAs, DPAs and any other procurement contracts faster, go to Crosby.ai/20VC. While Crosby keeps your numbers sharp, OneMind keeps your customer conversation sharper. Our friends over at OneMind have a hot take. The B2B GTM model we've been using for the last 20 years. It's collapsing. Predictable revenue isn't so predictable and buyers are just tired of explaining themselves at every handoff between SDRs, AEs, CSMs and support. Well, enter OneMind and their GTM superhumans, HubSpot, Alteryx, and ZoomInfo are just three of the tech companies using OneMind superhumans to qualify buyers, ride along with sales reps and coach customers. Whether you're ahead of target or under pressure to increase bookings ahead of hiring or behind on target even and need every rep to hit quota, OneMind is the solution. See for yourself at OneMind.com. That's OneMind, M-I-N-D dot com. Framer is the AI website builder that helps creators, teams and businesses ship production ready sites faster than ever while getting every detail right. Prompt, inspect, edit and publish in one place at a whole new pace. Agents bring speed and scale. You bring taste, judgment and control. Custom code components, manage CMS content, optimize SEO and audit for issues all in one place. Enterprise-grade hosting, security and 99.99% uptime SLAs trusted by leading brands like Perplexity and Miro. Learn how you can get more out of your site from a Framer specialist or get started building for free today at Framer.com/20VC for 30% off a Framer Pro annual plan. That's Framer.com/20VC. restrictions may apply.

Podcast Summary

Key Points:

  1. Max Freeman, SVP of Sales at Ramp, argues that sales is fundamentally an engineering, data infrastructure, and math problem rather than just a writing and calling problem.
  2. Ramp deliberately hires investment bankers as sellers because they are programmed to work hard, possess strong business acumen, and can credibly cold-call CFOs, though they are paid above market rate and expected to book 40 to 60 meetings monthly.
  3. Freeman advocates treating go-to-market recruiting like Moneyball, targeting mispriced talent from companies with weak products or low NPS where top sellers have proven they can close good customers despite poor tooling.
  4. Interview processes should decompose a candidate's quota attainment by inbound, outbound, expansion, and inherited pipeline, and require them to reconstruct won and lost deals chronologically to test real sales acumen.
  5. When evaluating job offers, sellers should prioritize market size, talent density, and founder quality over equity, title, or compensation, because structural market advantages drive career acceleration.
  6. Ramp built an internal Outbound Automation Team (OATS) and a revenue operating system called Ramp Revenue that automates pre-call research, bridging the talent gap and unlocking massive seller capacity.
  7. Sales cycles compress through rigorous qualification, testing whether champions can bring in senior stakeholders, and co-authoring business value assessments rather than engaging in early discounting.
  8. Ramp's onboarding bootcamp lasts 60 to 90 days with mandatory discovery and demo certifications, and frontline leaders must be deeply involved rather than relying solely on enablement teams.

Summary:

In this episode of 20VC, Max Freeman, SVP of Sales at Ramp, shares granular insights into building one of the fastest-growing sales organizations in the world. Freeman explains his philosophy of hiring investment bankers and other mispriced talent, arguing that sales is fundamentally an engineering and data infrastructure problem. He details how Ramp pays above market rate for sellers who book four to six times the meetings of standard SDRs, and how the company built internal tools like OATS and Ramp Revenue to automate outbound research and unlock seller capacity.

Freeman emphasizes decomposing candidate quotas during interviews, testing whether candidates were true producers or order takers, and requiring them to reconstruct wins and losses in detail. He advises sellers to prioritize market size, talent density, and founder quality over equity or title when choosing where to work. The conversation covers onboarding bootcamps, compensation design for new products, verticalization timing, sales cycle compression through rigorous qualification, and forecasting discipline. Freeman also discusses Ramp's customer success organization, the value of brand marketing on sales cycles, and his personal growth areas as a leader, including resisting the urge to personally intervene in every important deal.

FAQs

Bankers are programmed to work, have strong business acumen, and can credibly cold-call CFOs early on. Ramp pays them above market but expects four to six times the output of a standard SDR.

Down-market SDRs can book well above 50 qualified meetings per month. Account executives typically take 8 to 12 calls per day, depending on segment.

They decompose the candidate's number by inbound, outbound, expansion, and inherited pipeline. They also make candidates reconstruct won and lost deals chronologically to test sales acumen.

Candidates must show research on Ramp and the prospect, demonstrate selling fundamentals, quantify pain, and articulate value. Ultimately, the interviewer must believe they would buy from the candidate.

Prioritize the market, talent density, and founders over title or short-term equity. A huge market with strong talent and founders offers more career acceleration.

OATS stands for Outbound Automation Team, which automates list scraping, email outreach, and signal detection. Sales is treated as a data infrastructure and math problem to increase coverage and seller capacity.

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