00:04:11 · Peter Ahn
And his question was, who is your biggest customer? I kind of like, for a split second, I was thinking about Box. Oh my gosh. He's asking me this. And if I say our largest customer is 2,000 employees, maybe I'll lose the deal. Right? Because NBC was 42,000 employee. But what I decided was, you know what? I've built a relationship. I'm gonna be honest throughout the entirety of this deal cycle. And I told them, Lenny, our largest customer is 2,000 employees at National Geographic. They are similar in terms of use cases because they also have a lot of large media files, but we don't have yet a Fortune 500 customer. So you would be the first Fortune 500 customer to sign with Dropbox. He said, thanks. Okay. That makes sense. And then he kinda rushed off because his car was already there, so I couldn't really get a reaction from him. We ended up actually closing that deal. It was our first three year multimillion dollar contract. It was a big deal. And he told me weeks later, he said, Peter, that was the right answer when you told me who your biggest customer was because I like to take risks and I'm an innovator. And he said, I like to be the first patient, meaning that he wanted to be at the forefront of buying Dropbox for business. And so that memory is seared into my mind because a lot of sales training is about, oh, you need to show credibility. You need to show that you're impressive. But there's moments where you also need to be just very brutally honest because honesty always wins, transparency always wins, and enterprise sales is a trust exercise. The other lesson of that story is that you need to seek out innovators if you're a startup or you're an underdog. You need to align align with buyers who have that mentality that Lenny had because
00:05:55 · S0, S1, S2
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00:06:47 · S2, S3, S4
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00:07:47 · Peter Ahn
[00:07:47] S5: If he was looking for credibility, like we had a 100,000 license deal, we would have lost that deal. But there were moments throughout that deal where I knew he was an innovator, where I knew it was exciting for him to work with the startup. And so that's the other lesson is, like, to think about how are you aligning with innovators because most people are followers. And so in an enterprise sales cycle, you need to be able to filter for the ones who are not followers, but the ones who are leaders from the buying side. So the way Dropbox celebrated is there was, like, a company wide email from Drew. There was just a whole bunch of excitement because it was, like, the largest deal by magnitudes. And so I remember just, like, having a really great time that Friday getting to, like, hug Drew. Right? Why it wasn't an important milestone is because everybody... I think even Drew felt like NBC wasn't gonna close. Every time I saw Drew, the CEO of Dropbox in the bathroom, he would ask me how's NBC going almost as a joke. He'd be like, oh, how's NBC going? And I would always tell him, oh, it's going. You know? And it was, you know, probably, like, eight or nine months of that. And so when it closed, I think he also was surprised. He was like, I built this consumer brand, end user technology, and here's a multimillion dollar deal. I think even a lot of the people who are working on the deal were surprised. I mean, even I was a little bit surprised. Right? Because we didn't have that much enterprise functionality. Box had a list of, like, 50 things that was specifically enterprise, and we were a consumer brand being like, oh, we just launched single sign on, which is one of the most basic enterprise functionality. It changed the internal company's feelings about selling to businesses. Sometimes you just need a proof point to really show people that this is actually possible. So I think really good tech salespeople are able to convince buyers that their technology is from the future, but can solve problems today in the most effective way. So if I were starting at a company fresh, what would I do, like, first day? Let's call it, like, the first weeks, like, the first month, what I would focus on in trying to understand the product on a deep, deep level.
00:09:45 · Peter Ahn
Like, my goal in the first month of joining joining a technical company is how can I get to the level of a sales engineer in terms of understanding what's under the hood? Because I want to become an expert in that field as quickly as possible. So it's a lot of reading outside materials, reading documentation, asking the engineers or product managers how things work. Even if the questions feel like they're stupid, I'm always asking them because I wanna understand when I get questions from customers how to respond. Right? So that's how I treat the first month. After that, obviously, then you gotta start putting points on the board. You gotta attract customers. You gotta close customers. So, to your question of how do you actually approach customers? Today, what I suggest a lot of founders and sellers do is give something of value first to the prospect before you ask for a meeting. You know, let's say, for example, one of the pain points is how to do sales. Instead of saying, do you wanna get on a call to learn about sales? I would say, hey. I wrote something about three mistakes salespeople make. Do you wanna see it? And inevitably, a certain number of people are gonna raise their hands and say, yes. I wanna see that guide. Then you send that, and the goal is to get them to research you, research your company, learn something from the actual guide that you sent, and then you've built a certain amount of rapport and trust. Because as I said, enterprise sales is a trust building exercise. And so once you've built a little bit of trust, then you can say, hey. By the way, do you wanna get on a call? And so I think this authentic, genuine approach to providing value first before you ask for a meeting is really critical in the early, like, outbound stages. So so that's one way. There's a lot of companies too that have users already. Right? One of my clients, Elicit, they already have over 2,000,000 users, users, but they've never sold into enterprise. So in that world, it's slightly different. Right? You're you... Reaching out to users, but you're still trying to provide value and you're saying, hey. I know you signed up for our product six months ago. I'd love to get on a call to show you a few more things about the product, talk to you about where we're headed, and get your feedback. So in that
00:11:48 · S0, S1, S2
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