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

Max Freeman is SVP of Sales at Ramp. He joined the company as its first sales hire. By 2025, he was leading more than 300 salespeople, helping build Ramp's sales organisation from the ground up. Ramp's latest reported revenue exceeds $1.7BN, with a valuation of over $40BN. AGENDA: 00:00 Inside Ramp's Sales Playbook 05:00 How Do You Find Exceptional Sellers—and Why Bankers Make the Best? 18:00 How Do You Build an Outbound Machine That Scales Beyond Your SDR Team? 24:00 How Do You Shorten Sales Cycles Without Slashing Your Price? 27:00 How Should You Pay Your First Reps—and Incentivise New Products? 34:00 How Do You Onboard Reps Who Can Actually Sell? 40:00 How High Should Quotas Be—and How Long Should Reps Get to Ramp? 44:00 How Do You Drive Customer Expansion and Forecast Revenue Accurately? 54:00 How Do You Grow as a Sales Leader Without Taking Over Every Important Deal?

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

• 0:00Speaker 00

  There'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.

• 0:30Harry Stebbings?

  I 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,

• 1:12Harry Stebbings?

  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 to close the deal. 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 10 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.

• 1:56Harry Stebbings?

  They help the fastest-growing companies like Cognition, Ramp and Clay close deals in hours, not weeks. 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 conversation sharper. Our friends over at OneMind have a hot take. The B2B GTM model we've been using for, well, 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.

• 2:41Harry Stebbings?

  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 one mind, M-I-N-D dot com. While OneMind helps you sell smarter, Framer helps you build faster.

• 3:24Harry Stebbings?

  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.

• 4:08Harry Stebbings?

  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?

• 4:45Speaker 00

  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.

• 4:54Harry Stebbings?

  Well, that's great because I was totally BSing. He said you're 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, I, we don't do prep calls. No, Harry's far too old and arrogant for a prep call. But you, 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?

• 5:20Speaker 00

  So not only bankers, but I think there's a lot of mispriced assets on the market where their resume will not suggest the true alpha. But let's, 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, 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.

• 6:01Speaker 00

  And I think the third, for our business, you know, we're, 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 TMTIP 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.

• 6:46Speaker 00

  He runs a massive piece of the business. Sam Buck runs a massive piece of the business. He came from Goldman.

• 6:51Harry Stebbings?

  I spoke to Sam before this show. He was fantastic with suggestions. My question to you is, I can literally feel the pain of founders listening going, really? How on earth do you afford these investment bankers? How do you afford these investment bankers?

• 7:07Speaker 00

  Yeah. So the, 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. 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.

• 7:31Harry Stebbings?

  You book 40 to 50 meetings? What is the expectation on meeting bookings, really?

• 7:36Speaker 00

  It depends by segment. Obviously, the, the further up market you go, the numbers are, 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.

• 7:48Harry Stebbings?

  In a given month?

• 7:49Speaker 00

  Yes.

• 7:50Harry Stebbings?

  That's not very much, dude. 50 meetings in a given month for an SDR?

• 7:55Speaker 00

  You 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.

• 8:04Harry Stebbings?

  No, because when we were chatting before, I said like Dagnan, Chris Dagnan 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.

• 8:13Speaker 00

  Those are, those are account executives that are taking seven actual meetings, like the closers.

• 8:19Harry Stebbings?

  Ah.

• 8:20Speaker 00

  Not the top of funnel that's like booking the meetings for the sellers to then take.

• 8:24Harry Stebbings?

  Do you not expect even like the low ACVs to be doing way more than 12? These are small businesses, like startups, like.

• 8:30Speaker 00

  I'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.

• 8:44Harry Stebbings?

  That's what I'm talking about?

• 8:45Speaker 00

  Yes.

• 8:46Harry Stebbings?

  That was the disconnect. So there are people doing 10 to 12 calls a day?

• 8:49Speaker 00

  Absolutely. There are some sellers at Ramp that are on 15-plus calls in a given day.

• 8:53Harry Stebbings?

  Okay, that's what I'm talking about. And, and sorry, they are AEs or SDRs?

• 8:57Speaker 00

  Account executives, AEs.

• 8:59Harry Stebbings?

  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 that tech company is 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 through.

• 9:17Speaker 00

  Yes, I love this. I obsess over this topic. So I am a huge fan of Moneyball and you have to treat go-to-market recruiting like Billy Bean. There is so much alpha in finding what companies have grown revenue in a significant way. I'm talking north of nine figures, but have done that despite having a low NPS score. Why is there so much alpha in this? A few things. You have to create a lot of your own demand. If you're the fifth or sixth best player in your market, the inbound funnel, that's not very fruitful. You got to go make it happen. Two, you have to navigate a lot of complexity in your cycles. There's probably a lot of weak reviews on third-party publications, whether that's G2, Capterra.

• 10:01Speaker 00

  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 Ramp, that is where the magic is going to happen.

• 10:17Harry Stebbings?

  If you were to name a company.

• 10:21Speaker 00

  I can't give away the secret sauce. I'll name one. I'll name one. Six cents.

• 10:25Harry Stebbings?

  Because they have a low MPS products, maybe not great.

• 10:29Speaker 00

  Correct.

• 10:29Harry Stebbings?

  But close good customers.

• 10:32Speaker 00

  Exactly. In fact, just yesterday, one of our top enterprise sellers sent me an 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. I was like, oh, we get that 10 to 20 times a month at Ramp. You've just been selling shit products.

• 10:55Harry Stebbings?

  When 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 happened down to order taking?

• 11:24Speaker 00

  Yeah, you have to decompose their number. And so, okay, you did, you did 2 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, 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, 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

• 12:08Speaker 00

  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.

• 12:31Harry Stebbings?

  What 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. But blame deflection can also be genuine. How do you determine like good versus bad on, on that sort of one?

• 12:48Speaker 00

  Totally. But you should be able to suss that out early enough in the, 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.

• 13:15Harry Stebbings?

  So I've done pretty well in this set of questions. I'm running through this hypothetical 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?

• 13:27Speaker 00

  Yeah. So you definitely have to 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. Two, the prospective company in question. Are you doing your research? Do you know what's going on? Have you read their 10K? 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

• 14:09Speaker 00

  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.

• 14:16Harry Stebbings?

  And 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?

• 14:28Speaker 00

  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.

• 14:50Harry Stebbings?

  Why the market?

• 14:52Speaker 00

  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 even 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

• 15:33Speaker 00

  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% a year, who cares? You're making the wrong trade.

• 15:52Harry Stebbings?

  So with the greatest of respect, so people that like go and working 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.

• 16:05Speaker 00

  I feel the same way because exact, yes, that's exactly my point.

• 16:09Harry Stebbings?

  Yeah, it's like the John Sculley, you know, the Apple moment. You're really going to spend the rest of your life selling flavored water?

• 16:16Speaker 00

  That's it. Unless you have the belief and the conviction that this could turn into something that rivals Salesforce, sure, by all means, go swing for the fences, but it's hard.

• 16:27Harry Stebbings?

  Totally get you. So sorry. Number one was market. What was number two and number three?

• 16:30Speaker 00

  Talent density.

• 16:32Harry Stebbings?

  Talent density.

• 16:33Speaker 00

  On the current roster. And then third, founders.

• 16:36Harry Stebbings?

  Okay. And so talent density, if we just unpack that, is that just how good the team is? What does that actually mean?

• 16:41Speaker 00

  You 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, the IOI gold medal Olympic track, that, 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.

• 17:09Harry Stebbings?

  That's a pretty solid engineering team to start with, isn't it? Youngest kid to ever graduate from MIT. Gosh. Okay, fine. My four weeks at university are really making me feel guilty now. That's why we're sellers, Max.

• 17:26Speaker 00

  That's right. That's right. I went to state school, baby.

• 17:29Harry Stebbings?

  Yeah, there we go. Okay. So that's talent density. I get that. And then the third is founders. And when we say founders, like, can we unpack that a little bit? Cause 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?

• 17:49Speaker 00

  That's totally fine. I think we're going to see more and more of that as a lot of engineers who 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, 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 problem when you break it down. It's a data infrastructure problem. It's a math problem. And so you

• 18:33Speaker 00

  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.

• 18:49Harry Stebbings?

  I'm so sorry. What is an oats program? Why is it a data infrastructure problem? Why is it a maths problem? Can you just help me understand this? Seriously?

• 18:58Speaker 00

  Yeah, 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 Oates 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 market, 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.

• 19:43Speaker 00

  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.

• 20:06Harry Stebbings?

  If 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?

• 20:13Speaker 00

  No, 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.

• 20:28Harry Stebbings?

  What 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?

• 20:39Speaker 00

  Yeah, 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, like maybe you could get a couple hundred emails out. Maybe you could make 100 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.

• 21:11Harry Stebbings?

  Do 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 me and my mom walking on the weekend, my efficiency would be through the roof. A genuine asking, not telling.

• 21:33Speaker 00

  That 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.

• 22:09Harry Stebbings?

  Do you have engineers in sales permanently? This isn't like a one and done sales tool build.

• 22:14Speaker 00

  We 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.

• 22:23Harry Stebbings?

  What's a good response rate when you're sending outbound in a tool like this?

• 22:28Speaker 00

  Response 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. It's like you could 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. It's a

• 22:50Harry Stebbings?

  And so it's how many you convert to a meeting?

• 22:52Speaker 00

  Yeah. And that should be just a hair under 1%. I think is really, really strong standard. So for every 100 emails you're sending, those convert to one, that's, that's great.

• 23:02Harry Stebbings?

  How 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?

• 23:24Speaker 00

  Yeah, I think 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, you know, 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.

• 24:08Speaker 00

  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.

• 24:16Harry Stebbings?

  One of the reasons I like verticalization of sales teams is what it does to sales cycles. Often the messaging is better, it's more accurate, the value props 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?

• 24:35Speaker 00

  The 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 infectuate change? And are they reasonably committed to doing this within a 12-month period? If you could check those boxes, yes, swing, swing at it.

• 24:52Harry Stebbings?

  How 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?

• 25:02Speaker 00

  Yeah, 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 this person, is Harry going to bring Susan into the call? Okay, great. You may have a champion, you may have someone that can infectuate change.

• 25:47Speaker 00

  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.

• 25:55Harry Stebbings?

  So I love that and Susan would love to come. One thing that's really, it's 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, you know, four bucks per card or four bucks per seat or four bucks per unit of whatever we're selling. I'm going to need it at two. Are you going to be able to meet me there, Max? Biggest device on discount.

• 26:16Speaker 00

  We haven't even 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's 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.

• 26:33Harry Stebbings?

  But so you, 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.

• 26:41Speaker 00

  Yeah, I think like early on in the conversation, if we're coming to discuss economics and pricing after call one, that's, that's usually a, 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, like for sure, maybe I'll, I'll engage that way and we'll discount to get the deal in the door. But up market, no, you have to co-author business value assessments. Like 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?

• 27:23Speaker 00

  And if you could mutually agree to that, you could circumvent any pricing concessions because hopefully you're driving seven figures in value creation.

• 27:32Harry Stebbings?

  Speaking of driving seven figures in value creation, we're going to go back to this like beautiful interview process because I've impressed you so much. You're so excited for me to join Ramp day one and you want to give me a job. And it's time for comp design, okay? Compensation design. Can you help me? How do you advise founders on comp design for the first AE and the first SDR?

• 27:55Speaker 00

  I usually advise to not have a comp plan. I usually advise to do 100% OTE for at least the first two quarters. You just don't know what you don't know. And I've actually seen founders get into some trouble where they make a quota that gets blown out in the first six months and it's, holy shit, I owe this seller multiple six figures. I've seen the inverse happen as well, where you arbitrarily finger in the air. Oh, I think this person could close this amount or I think this person can book this many meetings and it's not attainable. And then you're struggling to get momentum and it's a tailwind going.

• 28:29Harry Stebbings?

  And then confidence gets hit and confidence is hard to regain once lost, I find.

• 28:34Speaker 00

  Correct.

• 28:34Harry Stebbings?

  I've seen it though, where even when they do, okay, I'm making up numbers. Say they close 250, but you set me 500. 250 would have actually been okay. It was solid, like decent, not a bad start. But because it was half of what you set, I feel like I'm really bad.

• 28:49Speaker 00

  That's right. And in some ways, there's, there's a little bit of benefit to that where, you know, if you get the right person, they've got a fire lit under them and they feel like they're not meeting expectations. There's some healthy angst, but it depends on the archetype that you bring in.

• 29:03Harry Stebbings?

  So just pause, so we're 100% OTE. When does that change? And how do we then instigate a different discussion around correcting that plan?

• 29:11Speaker 00

  Data, typically this would take, it depends on what segments you're going after. But if you have cycle times that are less than six months, you should have enough data in the system to figure out, okay, this person has been in seat for two months. They've ramped for the first 90 days. We're seeing stage progression here. We have reason to believe that pipeline is going to be X. Let's make a quota that is both ambitious and somewhat reasonable based on the data that we have. And you should never hire one seller or one SDR at a time. Because the problem is, how are you going to benchmark their performance? How do you know if they're good? Are you going to benchmark them against yourself as the founder? I don't think that's reasonable. Also, as a founder, if you're going to be spending time onboarding a seller, that's laborious, that's expensive. Do it in pairs.

• 29:54Speaker 00

  And there's competition, there's collaboration, they're not lonely. I strongly advise against one at a time.

• 30:01Harry Stebbings?

  Do we always shed one or do we sometimes keep the most?

• 30:04Speaker 00

  How do you mean? Like if someone isn't performing well?

• 30:07Harry Stebbings?

  By nature of having two, one will always perform worse than the first. How often do you keep them both versus get rid of one?

• 30:14Speaker 00

  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 why, why is this person winning more? Like what structural advantage might they have? Is it pipeline that I gave them? Is it 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 ascertain.

• 30:46Harry Stebbings?

  So for the 100% OT, sorry, going back to that, that's for SDRs. Does that change when we're doing comp design for AEs?

• 30:53Speaker 00

  No, it's for, it's unilateral across early, early go to market teams. Yeah.

• 30:57Harry Stebbings?

  Wow. What are the big mistakes you think founders make when they're doing comp design? Cause 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?

• 31:17Speaker 00

  I have so many thoughts on this. Depends on stage. First, if you're in 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.

• 31:59Speaker 00

  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 gotta 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.

• 32:19Harry Stebbings?

  When you get a hire wrong, Max, what do you not see that you should see? So like for me, sometimes I'm quite overtly aggressive. It's very innate and I'm intense and I'm going to fucking kill competition and I'm going to 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 see?

• 32:48Speaker 00

  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 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?

• 33:30Speaker 00

  Are they going to have a deep obsession with working at Ramp? 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 hire.

• 33:43Harry Stebbings?

  Chad Pete said on the show, legendary sales leader, said that young people just don't want to work and that there is a different appreciation for it. They want to work from home, they want work-life balance, they want mission, they get burnt out, they want kombucha. Is he right?

• 34:00Speaker 00

  I love Chad, he's a beast. I loved Eggnan too, that was a fun show. 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 to make sure people want to come into the office every single day. We have younger sellers in their career that badge in on Saturdays and Sundays. Nobody's asking them to do that. But if you create that culture, it's super infectious. And the beauty of that culture is it sniffs out people that do come in that don't want to adhere 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.

• 34:44Harry Stebbings?

  Help 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?

• 34:53Speaker 00

  So 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, on point one, in the age of AI, and especially as the next generation of buyers sit in seat, they have what I would describe as bullshit repellent. They are direct, they could get answers quickly. And so the expectation is if they're talking to a seller, they need answers quickly too.

• 35:37Speaker 00

  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 need to know the two. Like one is going to be super high level, they are trying to drive positive business outcomes. 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.

• 36:20Speaker 00

  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 to be as perfect as possible for the buyer in question.

• 36:35Harry Stebbings?

  Do you have a bootcamp where you go through these stages?

• 36:38Speaker 00

  We do.

• 36:39Harry Stebbings?

  Can you walk me through that? Like how long is it? Who leads it? What materials are there like?

• 36:44Speaker 00

  Yeah, 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, you know, self-guided skills that our enablement team has created across all of 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, it's existential that you perform well.

• 37:26Speaker 00

  Otherwise, your ability to ramp and become a successful seller is contained.

• 37:31Harry Stebbings?

  How long before I start speaking to clients or customers on my own?

• 37:35Speaker 00

  Two to four weeks, depending on your segment. We try and make it as quick as possible.

• 37:39Harry Stebbings?

  And I'm going to be listening to a load of gong calls before that to really try and understand the cadence, the language, the pattern.

• 37:45Speaker 00

  Absolutely, 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 responsible for 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, new hires onboarding.

• 38:21Harry Stebbings?

  It's one of those ones which sounds obvious, but is hard. When you are a leader to like delve down into, I didn't mean it awfully, but it's kind of like intern batches in venture funds where you're like, of course, everyone wants to help young people, but like I got to close the big fucking whale of a deal.

• 38:36Speaker 00

  A hundred 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.

• 39:00Harry Stebbings?

  What percent of first calls do you think you're impressed by versus disappointed by?

• 39:06Speaker 00

  Seventy, 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 thirty 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 in our leader and we're going to talk about it.

• 39:28Harry Stebbings?

  It's tough.

• 39:29Speaker 00

  It's tough, but it's right. If you join 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.

• 39:43Harry Stebbings?

  Talk about holding you to account. Let's say I come out of these ninety days, okay? I'm ready, I'm unleashed in the wild. Carlos, who was the head of sales at Eleven Labs, said that they get twenty 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?

• 40:05Speaker 00

  I sort of lean in the camp of Dagnan 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 in 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.

• 40:29Harry Stebbings?

  It's a lot. I want you to pay me more if I was doing twelve to one, dude.

• 40:33Speaker 00

  I know, we might have to cut that out.

• 40:34Harry Stebbings?

  Pay me, pay me, pay me double and then it'll be six to one.

• 40:37Speaker 00

  I know, we might have to cut that part out. I don't know if our inside sales reps actually know that some of them are like fourteen to one.

• 40:46Harry Stebbings?

  They are a hundred percent. I think it's good. You want like the Hunger Games of competition. Okay, so for me as 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.

• 41:00Speaker 00

  I think that's right.

• 41:01Harry Stebbings?

  And like Ramp time, how long do you give me to ramp? Post bootcamp, because obviously bootcamp, kind of getting my feet on the ground. How long do I get to ramp?

• 41:09Speaker 00

  Again, it depends on the segment. Our down market sellers, inside sales reps, sixty days, commercial reps, ninety 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.

• 41:28Harry Stebbings?

  How quickly do you know if someone's not very good?

• 41:31Speaker 00

  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 not. And when I say sellers that are annoying, they are constantly asking questions twenty four seven. 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 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

• 42:12Speaker 00

  or asking questions that any AI bot or Notion bot can answer, usually that's going to be weak signal.

• 42:18Harry Stebbings?

  I totally agree. I always say actually the quality of a founder is very obvious. The quality of the questions a founder asks at the end of an interview with a VC or a meeting with a VC.

• 42:26Speaker 00

  Hundred percent. That's why I intentionally leave at least ten minutes in an interview for them to fire away at me.

• 42:32Harry Stebbings?

  Because it tells you, people think like, my partners will often say, why, why are we spending so much time answering their 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

• 42:49Speaker 00

  Exactly.

• 42:50Harry Stebbings?

  smart question to ask your founder.

• 42:51Speaker 00

  I think about it the same way. I think about an interview where I intentionally need to give them at least ten to fifteen 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.

• 43:37Speaker 00

  It's the same thing that I'm trying to ascertain.

• 43:39Harry Stebbings?

  Can I ask you, you've mentioned Dagnan quite a few times. Dagnan 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 for?

• 43:55Speaker 00

  I have like a slight spin on that. But look, I, 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 I don't think you can replicate with a professional services business. And the economics of our product work 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.

• 44:36Speaker 00

  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 keyboard, 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, up-sell and expand?

• 45:16Speaker 00

  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 perfectly at the onset, it's going to be increasingly difficult to earn your way into selling more products over time.

• 45:30Harry Stebbings?

  The hard thing about, I find, 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 twenty twenty six?

• 45:52Speaker 00

  I'm the 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

• 46:11Harry Stebbings?

  When you've been biggest delta, what did it not see?

• 46:15Speaker 00

  Nothing, because we're, we're at the law of large numbers at this point. Years ago, before we've had the discipline in our revenue operations function, yeah, 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, they're incentivized to care. The same thing with frontline leaders, 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

• 46:59Speaker 00

  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 infosec, 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.

• 47:14Harry Stebbings?

  How often do you do pipe review, Max?

• 47:16Speaker 00

  Gosh, we do pipeline reviews once a week. What's great, though, is I've gotten rid of forecasting calls.

• 47:25Harry Stebbings?

  Why?

• 47:25Speaker 00

  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.

• 47:41Harry Stebbings?

  So with pipe reviews, who comes? Who gets the invite?

• 47:44Speaker 00

  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 biggest 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?

• 48:20Harry Stebbings?

  When you lose, why do you lose?

• 48:22Speaker 00

  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.

• 48:52Harry Stebbings?

  Dude, we're seeing brand 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?

• 49:13Speaker 00

  Yeah, it certainly helps. Look, we have a lot of hype and buzz. It's hard to truly attribute this in the data, but it's a surround sound for our outbound SDR team, especially if we're in certain markets, certain GOs. It's 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.

• 49:54Harry Stebbings?

  What would you most like to change about your internal sales process today that you haven't changed yet or can't change?

• 50:01Speaker 00

  Oh, we'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, I'll give examples of this, like sales is, 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 PitchBook, you got to go into all of these different third-party sources and publications.

• 50:41Speaker 00

  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 area 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.

• 51:25Speaker 00

  An average seller might neglect all of that. And so like 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, 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, is more revenue back to the business and.

• 51:56Harry Stebbings?

  Would you ever open that up to the public? One thing that we're seeing with Deal in particular and Revolut, actually in some cases their performance management software, is they built these internal tools and now they're selling them. Would you and to what extent is secret sauce secret versus monetizable? Cause you've got Ramp router, don't you?

• 52:14Speaker 00

  Yeah, we've got Ramp router. So on the Ramp revenue piece, like 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 take 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 change.

• 52:38Harry Stebbings?

  That's a 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 now 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, cause give it a go.

• 52:58Speaker 00

  In consumer, you can, yeah, you flip the light switch on, yeah.

• 53:01Harry Stebbings?

  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, astral 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 OpenAI? And for Harvey and Nagora who spent two years kissing the ass.

• 53:23Speaker 00

  Completely agree.

• 53:24Harry Stebbings?

  Can I, final one, where do you fall down as a sales leader where you feel you need to improve most?

• 53:31Speaker 00

  There's a lot that I need to improve. I think my, my biggest thing that I'm, 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. You know, if there's an important deal, important customer, I'm all over it. But, you know, that, that only works well for a certain period of time. Like 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.

• 54:10Speaker 00

  And worse, I can, you know, 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. Like I need to build more and more barrels inside of the go-to-market organization. Otherwise I'm, I'm not doing my job effectively as a leader.

• 54:29Harry Stebbings?

  And you don't build those barrels because you're busy just in the machine.

• 54:33Speaker 00

  I 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-toe with Eric, toe-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 calls. I'm sending at least five cold emails every single day.

• 54:59Harry Stebbings?

  Are you really?

• 55:00Speaker 00

  Yes, I have to. And the, 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.

• 55:22Harry Stebbings?

  Can I ask you, what, what do you think Eric Karim did to imbue a founder-like mentality within you? When I talk to you now, it very much feels like speaking to a founder. You know, 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. And like, you know, I, I know that you'd be like, come on, go fuck yourself. And so my question just to you is like, it's amazing, and I'm giving Ramp credit here. What do you think Ramp and Eric and Kareem did to make, no offence, Max from Namely, who wasn't extraordinary, a founder?

• 56:03Speaker 00

  I 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 and operating out of his email inbox. Like 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. Like 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. Like 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.

• 56:47Speaker 00

  And two, it's forced me to figure it the fuck out. Like I'm not 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 buttoned 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 like I, 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 like a healthy amount of stress and paranoia that if I don't keep delivering and I don't keep growing, the music could stop.

• 57:22Harry Stebbings?

  Yeah, 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, you know, a hundred feet ahead of you, look down on you and then just take a big crap all over you.

• 57:39Harry Stebbings?

  And I just say, honestly, I can't remember anything else he said. That one line really stuck with me.

• 57:45Speaker 00

  He had, he had the best one line around, I forget what the topic, it was something around like, how do you, how do you measure performance? And like, how do you, how do you stack rank? And he's like, Max, there's three categories of performance in sales. One, you are God. Two, I don't know yet. Or three, you're fucking fired. It's so true.

• 58:06Harry Stebbings?

  You know what? It also taught me that when you listen to what I just said, which is like, oh, the seagull shitting on you.

• 58:11Speaker 00

  Yeah.

• 58:12Harry Stebbings?

  It's better to be a purple cow sometimes, which is like, you know, the Seth Godin, being different is sometimes being better. Dude, we're gonna do a quick fire, because otherwise I could talk to you all day and you've got a quota to hit. Uh, what one sales tool could you not live without?

• 58:26Speaker 00

  I don't know if I could say this publicly, but I'm going to. Inspect. Inspect is Ramp's internal coding agent and harness. It feels as though I have an engineer and a sales engineer in my pocket at any given moment.

• 58:41Harry Stebbings?

  Have you guys just built all your own tools?

• 58:43Speaker 00

  Harry, this, when I come to London, I'll, I'll show you this, it is insane what our sellers can accomplish with inspect. Like creating bespoke custom demos, performing any analysis on, you know, current customers ramp configuration. It's epic.

• 58:58Harry Stebbings?

  Who's to credit for that? Is that the CTO who's built the internal tooling?

• 59:04Speaker 00

  Yeah, I, I give dual credit to Eric and Karim. It's just culturally in our DNA to push forward and go build.

• 59:13Harry Stebbings?

  Okay, you 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?

• 59:24Speaker 00

  I see your leader or anyone.

• 59:25Harry Stebbings?

  Anyone. I liked Becca Lindquist a lot from Clay.

• 59:29Speaker 00

  So I was literally gonna 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, who's a, he's an animal. And I've been, every, every six months, I, I try and bring him in. Hopefully Mark doesn't listen to this because he's the SVP of Sales at Profound.

• 1:00:00Harry Stebbings?

  What's your biggest advice to a new rep on their first day?

• 1:00:05Speaker 00

  You need to, you 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, 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.

• 1:00:48Speaker 00

  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 neglect it.

• 1:00:56Harry Stebbings?

  And was like, listen, accept blame and deflect credit. Like, the worst thing for me is, oh, no, no, but that wasn't my fault. That was Max's fault.

• 1:01:04Speaker 00

  Yep. There, 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 to bring to be incredibly effective in your role as a new seller.

• 1:01:31Harry Stebbings?

  I 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.

• 1:01:38Speaker 00

  I know.

• 1:01:39Harry Stebbings?

  Do you know what I mean? And it makes me feel shit. You're kind of asking a horizontal question that's not like, hey, I feel like I need help with the closing process.

• 1:01:47Speaker 00

  Yes, same with leaders, same with leaders. Hey, um, do you have any feedback for me? Hey, I noticed this problem. Here's how I'm gonna go solve it. Here's the cross-functional resource that I'm gonna need to bring in. If I get blocked, like, come, come help me.

• 1:02:02Harry Stebbings?

  Do 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 Ramp.

• 1:02:08Speaker 00

  I know.

• 1:02:08Harry Stebbings?

  Someone at Ramp. I can, I can do Keith Reboi, the board member. I can do Eric Gliman. I can do Max, the rock star sales leader, but I don't have also a fricking 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.

• 1:02:27Speaker 00

  Yep.

• 1:02:27Harry Stebbings?

  The horizontal shit nature of intro requests astounds me.

• 1:02:32Speaker 00

  You and me both. If you're gonna 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.

• 1:02:45Harry Stebbings?

  Max, 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.

• 1:02:55Speaker 00

  Yep.

• 1:02:56Harry Stebbings?

  By the way, I totally understand if this is not possible. Huge hugs and let me know when you're in London.

• 1:03:01Speaker 00

  Yes.

• 1:03:02Harry Stebbings?

  Final one for you. What's the kindest thing that anyone's ever done for you?

• 1:03:06Speaker 00

  I have to give my wife credit. She was my girlfriend at the time.

• 1:03:11Harry Stebbings?

  Oh, you're getting brownie points for this one.

• 1:03:14Speaker 00

  I am, I, I am. Um, 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 gonna fuck up our lives. Like, we're gonna have to make a lot of trade-offs. I'm gonna be absent in our social life, but like, I really wanna pursue this and I'm fired up about it. And she was super supportive, still is today. Um, doesn't love the weekend calls.

• 1:03:46Speaker 00

  Yeah, no, I think that was, that was probably the kindest thing that, that anyone's done for me.

• 1:03:50Harry Stebbings?

  Well, well, dude, listen, Chanel solves a lot of problems, so you know. So it's, it's okay, you know? I've learned this. I miss a lot of family shit and my mother has 30 Chanel handbags, so.

• 1:04:03Speaker 00

  That's right.

• 1:04:03Harry Stebbings?

  We both win, you know?

• 1:04:06Harry Stebbings?

  Dude, I've, I've loved doing this. Um, I, I really so enjoy episodes like this where it is granular. It's reflective. It's fun. It's everything in one, right? So I really appreciate it, man.

• 1:04:18Speaker 00

  Me too. This was a blast. Uh, 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 SDR 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.

• 1:04:44Harry Stebbings?

  But 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 dulcet tones 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 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 10 law firms. Customers get the best of both worlds.

• 1:05:23Harry Stebbings?

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• 1:06:06Harry Stebbings?

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• 1:06:46Harry Stebbings?

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• 1:07:26Harry Stebbings?

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