How to Become Great at Startup Sales

In this interview, Peter Ahn, a Korean American tech sales coach who helped build Dropbox's first enterprise sales motion, tells the story of winning Dropbox's first Fortune 500 contract with NBC Universal by being honest about the company's small customer base instead of hiding it. He draws out what that deal taught him about seeking buyers who want to be first, learning a product at sales-engineer depth before selling it, and leading with value before ever asking for a meeting.

Hi, my name is Peter Ahn. I'm a Korean American tech sales coach. I specifically help startup founders and salespeople learn sales in a genuine authentic way, while gaining confidence in their approach. I started at Google straight out of college, and then from there I went to Dropbox in the early days, helped them form their first enterprise sales motions, and was able to close their first ten large enterprise deals.

I've coached over 100 startups. Figma is an example of a company where I helped them when they were around 20 people, to figure out their early enterprise sales motions. Companies like Elicit in the AI space, Bezi, they sell in the 3D design space. And there's then companies like Twingate, who started off as a client of mine, and then I joined full time.

I really enjoy kind of the technical sales aspects, because I think that's where like the hardest challenges are and where the most skeptical buyers are. There was one moment when we were trying to sell NBC Universal at Dropbox, when my champion and executive sponsor, his name is Lenny Bloom, he was the VP of Identity and Collaboration at NBC.

After a day of doing vision talks, having him meet with our founders Drew and Arash, I was escorting him out of the Dropbox building. And remember our main competitor was Box, and they had recently closed a deal with General Electric, and I think they were marketing that deal as having sold over 100,000 licenses. So this was a big, big deal.

So we were already nervous about it from the Dropbox perspective, because our biggest deal was a 2000 license deal on the enterprise side, as my champion and exec sponsor from NBC was getting in the elevator, he looked at me and he said, hey, Peter, I just have one more question. 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 2000 employees, maybe I'll lose the deal, because NBC was 42,000 employees. But what I decided was, you know what? I've built a relationship. I'm going to be honest throughout the entirety of this deal cycle.

And I told him, Lenny, our largest customer is 2000 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 kind of 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 multi-million 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 with buyers who have that mentality that Lenny had, because 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 a startup. And so that's the other lesson: 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 magnitude. And so I remember just like having a really great time that Friday, getting to like hug Drew, right? Why was 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 is NBC going? Almost as a joke, he'd say, oh, how's NBC going? And I would always tell him, oh, it's going, you know. And it was, you know, probably like 8 or 9 months of that. And so when it closed, I think he also was surprised.

He was like, I built this consumer brand and use your technology. And here's a multi-million 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, like my goal in the first month of 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 want to 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 got to start putting points on the board. You got to attract customers, you got to 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.

Before you ask for a meeting, let's say, for example, one of the pain points is how to do sales. Instead of saying, do you want to get on a call to learn about sales, I would say, hey, I wrote something about three mistakes salespeople make. Do you want to see it? And inevitably, a certain number of people are going to raise their hands and say, yes, I want to 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 built a little bit of trust, then you can say, hey, by the way, do you want to 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 that's one way. There's a lot of companies too that have users already. One of my clients, Elicit, they already have over 2 million users, but they've never sold into enterprise.

So in that world it's slightly different, right? You're 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 world, you could ask for the call straight up because you're a PLG company, but you still have to understand what will get them excited to join the call, right? And typically it's something that is a new advancement in the product. Or sometimes, other incentives. You know, you have to think about adding value before asking for time.

Don't try to sell things first. Try to provide value around a pain point you think somebody has. Gain their trust first. So discovering customers, I think first starts with defining who your customer is. Oftentimes a lot of founders, they go way too broad and you can't sell the world if you're a startup.

The first thing I get founders to do is write down, you know, what's the company size that's ideal? What's the title? You know, what is the revenue if that's important? What's the technology that they use? Maybe you find that people who are on AWS are really good for your technology. Write everything down in detail and then map that to some of the modern tools that are out there today.

So everybody's familiar with LinkedIn Sales Navigator. Clay.com is a new tool. There's all these platforms where you can actually match your ideal customer profile and look for contacts. And then once you do that, then it's a matter of figuring out from the list of contacts how do you reach out to them. And that's where kind of my methodology around like provide value and then ask for a meeting comes into play.

The last thing to keep in mind, I think that's really important is there's a lot of talk about emailing people. Emailing is getting very, very noisy. So you have to be a lot more intentional about thinking about where are people talking about the problem you solve? Is it a conference? Is it LinkedIn? Is it Reddit? Is it Twitter?

So then there's this whole strategy around how are we actually taking a multi-channel approach to find people where they're already talking about the problem? Sometimes it could be like a Slack community too. And then from there you figure out the messaging and get into the execution path. 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.

One of the things that is really important to understand in sales, it's a give and take relationship. If you want your buyer to divulge information that is private to them, or that might be sensitive or something that they're uncomfortable sharing, you also need to be able to mirror that and show that. A lot of great salespeople are able to do this. This goes back to honesty.

They can be very, very honest about their situation and be very open. And that opens up the other side to open up about their own problems too. So that's one thing. I'll give you a very tangible example. Let's say I tell a buyer like, hey, I'm a little nervous about this deal because I don't feel like I did a great job with the demo on the last call.

Do you feel that's the case? You know, that's very vulnerable, right, to say that, hey, like, I didn't do a good job on the sales call, but psychologically what happens is the other side is like, oh, Peter's being very honest and vulnerable. Let me also share with them something that is equal to that level of question or answer or information.

So I think that's one thing. The second thing is you have to be a really great listener if you want to be able to mirror people, and if you want to be able to understand people, and you also need to be able to take answers and follow the breadcrumbs and follow up with more questions that help you dig in to the root of why people are saying certain things.

I think that's the second part. The third part to build trust and EQ is you need to be really, really good at your craft. You need to understand your industry and the space really, really well. Because in this day and age, people trust experts. You're not going to be able to hold a conversation with somebody if you're surface level or if you're not able to show that you know what you're talking about or that you're an expert in your field. Those are like three tangible things.

The other thing I would say about building EQ is you just have to be around people a lot in different environments. So if I were just on Zoom calls all day, like it probably wouldn't help me with EQ, but I try to meet people for coffee. Like I try to vary things, you know, like text people, go to bars or dinners with people and, you know, like spend time around people and really understand what makes people tick, what gives them motivation, both on the personal and professional side.

That's the other thing I think with EQ is if you're in sales, you can't always be talking about your product or business. You have to have a genuine interest in the other person as a person. And if you don't have a genuine interest, that shows if you're just asking a set of questions about the weather or where they're from or how many kids they have, like those are very trained.

But the question is, what do you do with that information? And how do you actually remember people's kids' names, or remember people's hobbies and ask more about their interests? I think the reason why I was successful at sales is because, one, I have a genuine passion for technology and understanding more about the technology than my competition. And then the second thing is I'm a hard worker.

You know, Dropbox had ping pong tables, they had a cafeteria. And I never played a game of ping pong at Dropbox. Maybe I did, actually once or twice. But I always pride myself on being the hardest worker in the room. And clients notice that if you're the fastest person to reply to an email, if you're the fastest person to get back to somebody or find a solution, that is a lot of what customers are looking for because they want to understand that when there's a problem, you're going to be there.

So the other reason why I was successful in sales is because I took outlier characteristics and what I perceived to be weaknesses of myself and turned them into superpowers. I'll give a very tangible example. English was my second language. Initially, as a kid growing up, I had a stuttering problem. I was not very confident speaking English. But fast forward to today.

I teach people how to communicate, and I think I'm more effective at it because I've actually created phrases that help slow down the conversation. So when I need to buy more time to think, I have phrases like let me think about that or that's a great question, but I don't know the exact answer right now. Or can we go back to what you said in the beginning of the conversation?

A lot of these phrases were designed to help me slow the conversation down, and I think it resonates with a lot of people who are not natural communicators, because they can imagine how to authentically slow the speed of the conversation down for them. So I turned something like that into a superpower. The other thing, too, is I thought it was going to be a weakness to be an Asian salesperson because there weren't that many Asian salespeople.

But then I decided to actually lean into that and take people to Korean barbecue or karaoke bars instead of steakhouses and stuffy bars, right? So I think a lot of like putting my personality into the sales process also made me successful because it made me memorable as a seller. My vision is to teach sales to as many people who think that sales is not for them, and to get them confident in the craft, and then for existing sellers or existing sales teams, change the focus not just only on numbers and results, but also empowering individuals to feel like they have their own personality in the deal.

And so I'd love to start to educate people more on the art of sales and how important that is, and the nuance of communication in a way where people see sales as an example of how to do great business, not as an example of stereotypes or sales bro culture or something else. I do believe sales can change the world.

I think right now there's a lot of waste in technology spend, and I think a lot of people are getting convinced of the wrong things. And so I think a great way sales can change the world is if we can start making a dent in that, where people feel like salespeople are trustworthy people and not people who are trying to buy their next Ferrari.

The other way I think sales can change the world is that I do think the best salespeople are the best communicators. When you're trying to give your next speech or you're trying to connect as a diplomat with another country. I think it's sales. Like if you're good at sales, you can understand how to negotiate with countries as well, right?

If you're a diplomat. So I think like my dream would be like if other industries look at salespeople and they're like, wow, I don't want to just learn sales from this salesperson. I want to learn how to communicate, or I want to learn how to bridge the gap. I want to learn how to bridge misunderstandings. That would be like a dream: bringing sales into a noble profession.

I think the most important thing in sales is to have a confident mentality. If you're not confident, people are gonna sense that right away. And then the other thing with sales and technical sales is you have to be as close of a thought leader expert as possible to the product that you're selling, because sales is a lot about education as well.

So if you're able to confidently educate your prospects, you'll do very well in sales.