How to Become Great at Startup SalesㅣPeter Ahn

Name: How to Become Great at Startup SalesㅣPeter Ahn
Duration: 16 min 44 s
Description: This video is about the perspectives and sales philosophy of Peter Ahn, an elite enterprise seller and leader behind Dropbox and other startups that have gro...

EO16:44Added Aug 31, 2026

This video is about the perspectives and sales philosophy of Peter Ahn, an elite enterprise seller and leader behind Dropbox and other startups that have gro...

Watch on YouTube →

Contributed by 刘嘉琪

Transcript

00:00One of the things that is really important to understand in sales,
00:03it's a give and take relationship.
00:05Give something of value first before you ask for a meeting, gain their trust first.
00:11Oftentimes, a lot of founders, they go way too broad
00:13and you can't sell the world if you're a startup.
00:15Emailing is getting very, very noisy.
00:17So you have to be a lot more intentional about thinking about
00:20where are people talking about the problem you solve.
00:23So I think really good tech salespeople are able to convince buyers
00:27that their technology is from the future,
00:29but can solve problems today
00:32in the most effective way.
00:33Hi, my name is Peter Ann
00:34I'm a Korean American tech sales coach.
00:37I specifically help startup founders and salespeople
00:40learn sales in a genuine authentic way,
00:43while gaining confidence in their approach.
00:45I started at Google straight out of college,
00:47and then from there I went to Dropbox in the early days,
00:50helped them form their first enterprise sales motions,
00:53and was able to close their first ten large enterprise deals.
00:57I've coached over 100 startups,
00:59Figma is an example of a company where I helped them
01:02when they were around 20 people,
01:03to figure out their early enterprise sales motions
01:05companies like elicit in the AI space bezi they sell in the 3D design space.
01:10And there's then companies like Twingate, who started off as a client of mine,
01:14and then I joined full time.
01:16I really enjoy kind of the technical sales aspects,
01:19because I think that's where like the hardest challenges are
01:21and where the most skeptical buyers are.
01:29There's one moment
01:30when we were trying to sell NBC Universal at Dropbox,
01:33when my champion and executive sponsor,
01:36his name is Lenny Bloom, he was the VP of
01:39Identity and collaboration at NBC.
01:41After a day of doing vision talks,
01:44having him meet with our founders Drew and Arash,
01:47I was escorting him out of the Dropbox building.
01:50And remember our main competitor was box,
01:53and they had recently closed a deal with General Electric,
01:57and I think they were marketing that deal as
01:59having sold over 100,000 licenses.
02:02So this was a big, big deal.
02:04So we were already nervous about it from the Dropbox perspective,
02:07because our biggest deal was a 2000 license deal
02:10on the enterprise side,
02:11as my champion and exec sponsor from NBC was getting in the elevator,
02:15he looked at me and he said, hey, Peter, I just have one more question.
02:18And his question was,
02:19who is your biggest customer?
02:21I kind of like for a split second
02:23I was thinking about box.
02:25Oh my gosh, he's asking me this.
02:26And if I say our largest customer is 2000 employees,
02:31maybe I'll lose the deal
02:32Because NBC was 42,000 employees.
02:34But what I decided was, you know what?
02:36I've built a relationship.
02:38I'm going to be honest throughout the entirety of this deal cycle.
02:41And I told them, Lenny,
02:42our largest customer is 2000 employees at National Geographic,
02:46They are similar in terms of use cases because they also have a lot of large media files,
02:51but we don't have yet a fortune 500 customer.
02:54So you would be the first fortune 500 customer to sign with Dropbox.
02:58He said thanks. Okay, that makes sense.
03:00And then he kind of rushed off
03:01because his car was already there,
03:02so Icouldn't really get a reaction from him.
03:04We ended up actually closing that deal.
03:07It was our first three year multi-million dollar contract.
03:09It was a big deal.
03:10And…
03:11he told me weeks later he said, Peter, that was the right answer.
03:14When you told me who your biggest customer was,
03:17because I like to take risks
03:19and I'm an innovator.
03:20And he said, I like to be the first patient,
03:22meaning that he wanted to be at the forefront of buying Dropbox for business.
03:27And so that memory is seared into my mind
03:31because a lot of sales training is about,
03:34oh, you need to show credibility.
03:35You need to show that you're impressive.
03:37But there's moments where you also need to be just very brutally honest.
03:41Because honesty always wins, transparency always wins,
03:45and enterprise sales is a trust exercise.
03:47The other lesson of that story
03:50is that you need to seek out innovators.
03:53If you're a startup or you're an underdog,
03:54you need to align with buyers
03:57who have that mentality that Lenny had,
03:59because if he was looking for credibility, like we had 100 000 license deal,
04:05we would have lost that deal.
04:06But there were moments throughout that deal
04:09where I knew he was an innovator,
04:11where I knew it was exciting for him to work with a startup.
04:14And so that's the other lesson is like
04:16to think about how are you aligning with innovators?
04:19Because most people are followers.
04:21And so in an enterprise sales cycle,
04:23you need to be able to filter for the ones
04:25who are not followers,
04:26but the ones who are leaders from the buying side.
04:28So the way Dropbox celebrated is
04:30there was like a company wide email from drew.
04:33There was just a whole bunch of excitement
04:35because it was like
04:36the largest deal by magnitude.
04:39And so I remember just like having a really great time
04:41that Friday, getting to like, hug drew, right?
04:44Why wasn't an important milestone is because
04:46everybody, I think even drew
04:48felt like NBC wasn't gonna close.
04:50Every time I saw drew, the CEO of Dropbox, in the bathroom,
04:54he would ask me, how is NBC going?
04:56Almost as a joke.
04:57We're like, oh, how's NBC going?
04:58And I would always tell them,
04:59oh, it's going, you know.
05:02And it was, you know, probably like 8 or 9 months of that.
05:05And so when it closed, I think he also was surprised.
05:08He was like, I built this consumer brand and use your technology.
05:11And here's a multi-million dollar deal.
05:14I think even a lot of the people who are working on the deal were surprised.
05:17I mean, even I was a little bit surprised, right?
05:20Because we didn't have that much enterprise functionality.
05:23Vox had a list of like 50 things that was specifically enterprise,
05:27and we were a consumer brand being like,
05:29oh, we just launched Single Sign On, which is one of the most
05:32basic enterprise functionality.
05:34It changed the internal company's feelings about selling to businesses.
05:38Sometimes you just need a proof point to really show people
05:42that this is actually possible.
05:44So I think really good tech salespeople are able to convince buyers
05:48that their technology is from the future, but can solve problems today
05:52in the most effective way.
05:56So if I were starting at a company fresh, what would I do?
05:59Like first day, let's call it like the first weeks.
06:01Like the first month.
06:02What I would focus on in trying to understand the product
06:05on a deep, deep level,
06:06like my goal in the first month of joining a joining a technical company is
06:10how can I get to the level of a sales engineer
06:12in terms of understanding what's under the hood?
06:15Because I want to become an expert in that field as quickly as possible.
06:19So it's a lot of reading outside materials, reading documentation,
06:23asking the engineers or product managers how things work, even if
06:26even if the questions feel like they're stupid.
06:28I'm always asking them because I want to understand
06:30when I get questions from customers
06:32how to respond, right?
06:33So that's how I treat the first month
06:35after that, obviously.
06:36Then you got to start putting points on the board.
06:38You got to attract customers, you got to close customers.
06:41So to your question of how do you actually approach customers
06:45today, what I suggest
06:47a lot of founders and sellers do is give something of value first to the prospect.
06:52Before you ask for a meeting.
06:53you know, let's say, for example, one of the pain points is how to do sales.
06:57Instead of saying, do you want to get on a call to learn about sales,
07:01I would say, hey, I wrote something about three mistakes salespeople make.
07:04Do you want to see it?
07:05And inevitably, a certain number of people are going to raise their hands and say,
07:09yes, I want to see that guide.
07:10Then you send that, and the goal is to get them to research you,
07:14research your company, learn something from the actual guide that you sent,
07:17and then you've built a certain amount of rapport and trust
07:20because as I said, enterprise sales is a trust building exercise.
07:22And so once you built a little bit of trust, then you can say, hey, by the way,
07:26do you want to get on a call?
07:27And so I think this authentic, genuine approach to providing value first
07:30before you ask for a meeting is really critical in the early like outbound stages.
07:34So so that's one way there's a lot of companies too
07:37that have users already
07:39One of my clients elicit they already have over 2 million users,
07:43but they've never sold into enterprise.
07:44So in that world it's slightly different, right?
07:47You're reaching out to users, but you're still trying to provide value.
07:50And you're saying, hey, I know you signed up for our product six months ago.
07:53I'd love to get on a call to show you a few more things about the product.
07:57Talk to you about where we're headed and get your feedback.
07:59So in that world, you could ask for the call straight up
08:02because you're a plg company, but you still have to understand
08:05what will get them excited to join the call, right?
08:08And typically it's something that is a new advancement in the product.
08:12Or sometimes, you know, you know, other incentives,
08:15you know, you have to think about adding value before asking for time.
08:17Don't try to sell things first.
08:19Try to provide value around a pain point you think somebody has.
08:22Gain their trust first.
08:24So discovering customers, I think first starts with defining who your customer is.
08:29Oftentimes a lot of founders, they go way too broad
08:32and you can't sell the world if you're a startup.
08:34The first thing I get founders to do is write down,
08:37you know, what's the company size that's ideal?
08:39What's the title?
08:41You know, what is the revenue if that's important?
08:43What's the technology that they use?
08:45Maybe you find that people who are on AWS are really good for your technology.
08:49Write everything down in detail and then map that
08:52to some of the modern tools that are out there today.
08:54So everybody's familiar with LinkedIn Sales Navigator.
08:56Claycomb is a new tool.
08:58There's all these platforms where you can actually
09:01match your ideal customer profile and look for contacts.
09:05And then once you do that, then it's a matter of figuring out from the
09:09list of contacts how do you reach out to them.
09:11And that's where kind of my methodology around like
09:14provide value and then
09:15ask for a meeting comes into play.
09:17The last thing to keep in mind, I think that's really important is
09:20there's a lot of talk about emailing people.
09:22Emailing is getting very, very noisy.
09:24So you have to be a lot more intentional about thinking about where are people
09:28talking about the problem you solve?
09:29Is it a conference? Is it LinkedIn?
09:32Is it Reddit? Is it Twitter?
09:34So then there's this whole strategy around how are we actually taking a multi-channel approach
09:39to find people where they're already talking about the problem?
09:42Sometimes it could be like a slack community too.
09:44And then from there you figure out the messaging and get into the execution path.
09:48So I think really good tech salespeople are able to convince buyers
09:52that their technology is from the future, but can solve problems today
09:57in the most effective way.
09:58One of the things that is really important to understand in sales,
10:01it's a give and take relationship.
10:03If you want your buyer to divulge information that is private to them,
10:08or that might be sensitive or something that they're uncomfortable sharing,
10:12you also need to be able to mirror that and show that.
10:15A lot of great salespeople are. This goes back to honesty.
10:19They can be very, very honest about their situation and be very open.
10:23And that opens up the other side to open up about their own problems too.
10:27So that's that's one thing. I'll give you a very tangible example.
10:30Let's say I tell a buyer like, hey, I'm a little nervous about this deal
10:34because I don't feel like I did a great job with the demo on the last call.
10:38Do you feel that's the case?
10:39You know, that's very vulnerable, right, to say that, hey, like,
10:42I didn't do a good job on the sales call,
10:44but psychologically what happens is the other side is like,
10:48oh, Peter's being very honest and vulnerable.
10:50Let me also share with them something that is
10:53equal to that level
10:55of question or answer or information.
10:58So I think that's one thing.
10:59The second thing is you have to be a really great listener if you want
11:03to be able to mirror people, and if you want to be able to understand people,
11:07and you also need to be able to take answers and follow the breadcrumbs
11:11and follow up with more questions that help you dig in to the root
11:17of why people are saying certain things.
11:19I think that's the second part.
11:20The third part to build trust and EQ is you need to be really,
11:24really good at your craft.
11:26You need to understand your industry and the space really, really well.
11:29Because in this day and age, people trust experts.
11:31You're not going to be able to hold a conversation with somebody
11:34if you're a surface level or if
11:36you're not able to show that you know what you're talking about
11:39or that you're an expert in your field,
11:41those are like three tangible things.
11:42The other thing I would say about building EQ is you just have to be around
11:45people a lot in different environments.
11:47So if I were just on zoom calls all day, like it probably wouldn't help me with EQ,
11:51but I try to meet people for coffee.
11:53Like I try to vary things, you know, like text people go to bars
11:57or dinners with people and, you know,
11:59like spend time around people and really understand what makes people tick,
12:04what gives them motivation, both on the personal and professional side.
12:08That's the other thing I think with EQ is if you're in sales, you can't always be
12:11talking about your product or business.
12:13You have to have a genuine interest in the other person as a person.
12:16And if you don't have a genuine interest, that shows if you're just asking
12:20a set of questions about the weather or where they're from or how many kids
12:23they have, like those are very trained.
12:25But the question is, what do you do with that information?
12:28And how do you actually remember people's kids names, or remember people's hobbies
12:33and ask more about their interests?
12:38I think the reason why I was successful at sales is because, one,
12:41I have a genuine passion for technology and understanding more about
12:45the technology than my competition.
12:47And then the second thing is I'm a hard worker.
12:49You know, Dropbox had ping pong tables, they had a cafeteria.
12:52And I never played a game of ping pong at Dropbox.
12:55Maybe I did, actually once or twice.
12:56But I always pride myself on being the hardest worker in the room.
13:00And clients notice that if you're the fastest person to reply to an email,
13:04if you're the fastest person to get back to somebody or find a solution,
13:07that is a lot of what customers are looking for because they want
13:10to understand that when there's a problem, you're going to be there.
13:13So the other reason why I was successful in sales
13:16is because I took outlier characteristics and what I perceived to be weaknesses of myself
13:22and turned them into superpowers.
13:24I'll give a very tangible example. English was my second language.
13:28Initially, as a kid growing up, I had a stuttering problem.
13:31I was not very confident speaking English. But fast forward to today.
13:35I teach people how to communicate, and I think I'm more effective at it
13:38because I've actually created phrases that help slow down the conversation.
13:42So when I need to buy more time to think, I have phrases like let me think about
13:46that or that's a great question, but I don't know the exact answer right now.
13:50Or can we go back to what you said in the beginning of the conversation?
13:54A lot of these phrases were designed to help me slow the conversation down,
13:57and I think it resonates with a lot of people who are not natural communicators,
14:01because they can imagine how to authentically slow the speed
14:06of the conversation down for them.
14:08So turning something like that into a superpower.
14:10The other thing, too, is I thought it was going to be a weakness
14:12to be an Asian salesperson because there weren't that many Asian salespeople.
14:16But then I decided to actually lean into that and take people to Korean barbecue
14:21or karaoke bars instead of steakhouses and stuffy bars, right?
14:25So I think a lot of like putting my personality into the sales process
14:29also made me successful because it made me memorable as a seller.
14:33My vision is to teach sales to as many people who think that sales is
14:39not for them, and to get them confident in the craft, and then for existing sellers
14:44or existing sales teams,
14:45change the focus not just only on numbers and results, but also empowering
14:50individuals to feel like they have their own personality in the deal.
14:54And so I'd love to start to educate people more on the art of sales
14:58and how important that is,
15:00and the nuance of communication in a way where people see sales
15:05as an example of how to do great business, not as an example of stereotypes
15:10or sales bro culture or something else.
15:13I do believe sales can change the world.
15:15I think right now there's a lot of waste in technology spend,
15:19and I think a lot of people are getting convinced of the wrong things.
15:22And so I think a great way sales can change the world
15:25is if we can start making a dent in that,
15:27where people feel like salespeople are trustworthy people and not people
15:31who are trying to buy their next Ferrari.
15:34The other way I think sales can change the world is that I do think the best
15:37salespeople are the best communicators.
15:39When you're trying to give your next speech or you're trying to connect
15:43as a diplomat with another country.
15:45I think it's sales.
15:46Like if you're good at sales, you can understand how to negotiate
15:50with countries as well, right?
15:51If you're a diplomat.
15:52So I think like my dream would be like if other industries look at salespeople
15:56and they're like, wow, I don't want to just learn sales from this salesperson.
15:59I want to learn how to communicate, or I want to learn how to bridge the gap.
16:03I want to learn how to bridge misunderstandings.
16:06That would be like a dream. So bringing sales into a noble profession.
16:10I think the most important thing in sales is to have a confident mentality.
16:14If you're not confident, people are gonna sense that right away.
16:18And then the other thing with sales and technical sales is you have to be as close
16:22of a thought leader expert as possible to the product that you're selling,
16:26because sales is a lot about education as well.
16:29So if you're able to confidently educate your prospects,
16:32you'll do very well in sales.