The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
00:42:32 · Harry Stebbings, Max Freeman
[00:42:32] S1: Because it tells you... People think... Like, my partners 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 [00:42:49] S0: smart question to ask, Rafaan. 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, mister 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. [00:43:39] S1: Can I ask you? You've mentioned Dagnon quite a few times. Dagnon 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?
00:43:55 · Max Freeman
[00:43:55] S0: I have like a slight spin on that. But look, 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, look, think there's a lot of value that that team drives for us. And while that might work 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, 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 perfectly at the onset, it's going to be increasingly difficult to earn your way into selling more products over time.
00:45:30 · Harry Stebbings, Max Freeman
[00:45:30] S1: 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? [00:45:52] S0: 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 5% delta across the entire business. And so [00:46:11] S1: When you've been biggest delta, what did it not see?
00:46:11 · Harry Stebbings, Max Freeman
[00:46:11] S1: When you've been biggest delta, what did it not see? [00:46:15] S0: Nothing. Because we're at we're at the law of large numbers at this point. Years ago, before we've had the discipline in our revenue operations function, 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 gonna 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 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 because a lot of sellers are going to use emotion. They told us we're a vendor of choice. Well, guess what? They haven't even kicked off legal or info sec. We've got three days left in the quarter. So I think really holding everybody accountable in that way is how I describe it. [00:47:14] S1: How often do you do pipe review, Max?
00:47:14 · Harry Stebbings, Max Freeman
[00:47:14] S1: How often do you do pipe review, Max? [00:47:16] S0: 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. [00:47:41] S1: So with Pipe reviews, who comes? Who gets the invite? [00:47:44] S0: 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 gonna do as a unit to derisk and try 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? [00:48:20] S1: When you lose, why do you lose?
00:48:20 · Harry Stebbings, Max Freeman
[00:48:20] S1: When you lose, why do you lose? [00:48:22] S0: 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 gonna 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. [00:48:52] S1: 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, I don't know, Boston Red Sox shirt or whatever you Americans watch sports.