00:00:54 · S2, S3, S4
Ad[00:00:54] S2: What will you Canva today? What will you brainstorm, collaborate on, present today? What will you resize, post, edit? Imagine. What will you research, test, switch, and finally have the courage to pitch? You got this. What will you visualize, design, brand, animate, create, generate? What will you translate, pour your heart into, or have a laugh doing? Whatever you wanna make, it's possible. So what will you Canva today? Ad[00:01:24] S3: This episode is brought to you by Indeed. You're ready to level up your business, but the pressure to find the right person to make that happen is intense. Indeed Sponsored Jobs can help carry the load. Ad[00:01:35] S4: It boosts your job post Ad[00:01:36] S3: to help it reach quality talent fast. Cut through the chaos with Indeed sponsored jobs. Get a $75 sponsored job credit at indeed.com/podcast. Terms and conditions apply. Hiring now? Then this is a job for Indeed sponsored jobs.
00:01:53 · Peter Ahn
[00:01:53] S5: One of the things that is really important to understand in sales, it's a give and take relationship. Give something of value first before you ask for a meeting. Gain their trust first. Oftentimes, a lot of founders, they go way too broad, and you can't sell the world if you're a startup. 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. 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. 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, was able to close their first 10 large enterprise deals. I've coached over a 100 startups, and 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 three d design space. And there's then companies like Twingate, who started off as a client of mine when... 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's 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 a 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 2,000 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.
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.