Alina Vandenberghe built Chili Piper to $20 million by testing willingness to pay before writing code. She landed a $14-15k contract in 2016 using a Keynote prototype, then iterated on lead routing logic based on segment, region, and rep expertise as customers demanded more sophistication.
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Sales, marketing, and RevOps. It's sink or swim out there, and yesterday's strategies and tactics won't help you today. This is Revenue Today, and I'm your host, Jared Robin. Join me as we interview revenue leaders in our community to learn what steps we could take right now to help you scale yourself and your company. Revenue Today is sponsored by Rev Genius, and we're on a mission to bring inspiration and creativity to all revenue professionals in the world. Want to shout out our sponsor, Demandbase. Demandbase is smarter GTM for B2B brands. They help marketing and sales teams spot the juiciest opportunities earlier and progress them faster by injecting account intelligence into every step of the buyer journey and orchestrating every action. For more information about Demandbase, visit demandbase.com.
Now we have an incredible talk between Jared Robin, our founder here at Rev Genius, and Alina Vandenberg. She's going to be speaking today about— she is the CEO, co-founder of Chili Piper, how she went from $0 to $16 million. Alina Vanderberg— I'm saying that wrong— Vandenberg. She was the co-founder of Chili Piper and GypsyBot. You read that correctly. She has founded 2 startups at the same time, which is absolutely incredible. I love seeing women in business who are achieving so much. Chili Piper is an incredibly powerful sales tool for enterprises, and her second startup is GypsyBot. So Jared, please take it away. And Alina, I hope that you two enjoy.
Thank you, Anna.
So I couldn't be more excited to be with you today. And it was funny, we were joking backstage because it was $0 to $16 million, now it's $0 to $20 million. You don't do that without product-market fit, right? And that's the name of the game today. And I'm just so humbled and grateful to be in your presence, Alina. Welcome.
I'm very excited to be talking to you, Jared. I'm as in awe of what you guys have done at Rev Genius
You're, you're too kind. But so $0 to $20 million doesn't happen overnight. Product market fit for 99.99% of people doesn't happen that fast. So would love to like understand your story. Can you tell us a bit about your journey at Chili Piper?
So I've always been in product. So for me, product market fit is part of my DNA, part of my neurons, my, my entire being. thing. I've, uh, in school I've studied computer science. I actually did a master's in computer science. And, um, I coded in Java and C++ and Pascal back in the day. But I wasn't a very good, uh, engineer per se, because I had, um, I didn't have enough patience inside of me. Patience is not one of my best character trait to debug and to know how to solve certain bugs that were coming up in my code. But what I loved instead was to observe human behavior. I loved the understanding of psychology on why people do what they do, what drives them, what motivates them. And that for me was fascinating. And even more fascinating was how to look at that behavior and optimize for a better whatever that thing that I was observing was, a better process, a better decision-making, a better solution to come to solve that particular problem that I was seeing. And I've been doing that ever since I came out of school for various startups and for various companies in various industries, including Bloomberg in the financial world, for media, for Reuters, for a health tech company that was started by Oprah. So I've dabbled with a lot of industry and I've done a lot of product market fit as I went along. And I decided to just do it on my own. It was just too exciting not to try without having people to tell me what to do.
I, I love that. It's so fascinating. Now, in Chilipiper, you decide to do it on your own. Walk me through finding product-market fit. Did it come easily for you here?
So because I've done it so many times, I don't know, 50 times for 50 different industries, for 50 different personas, I feel like that part was not as hard as the other parts that are, um, that I'm discovering as we're funding Chili Piper. But as we're launching new products, even within Chilly Piper, and as we're targeting different personas with different specifics of our product, you always start from scratch. So it never quite ends. And for me, it's a fun process. I would not think of it as a difficult process, more as a fun process and different every single time.
Yeah. I mean, help, help everybody understand your process because 50 go-rounds helped it become second nature to you. But if you had to like unpack it, what, what's, what's the process for finding product market fit that now is like rinse and repeat for you? And as, as you're launching new evolutions of Chili Piper going through it,
So the first and foremost that I look at is the motivation for somebody to buy a product. Why would they go and purchase the tool? And if that motivation is not strong, then obviously I'm on the wrong path. So I would say that motivation is the number one thing that I search for. Once I understand that motivation, I probe it very, very hard with dollar signs behind it. So I know that somebody's motivated, but would they pay money to solve for that motivation? So let's say that you say, Jared, I'm really motivated to optimize for my productivity, and I would love to try your tool to do that. And I would say, well, before you try my tool, would you pay $50 to try it? And if you say, well, I want to try it first, and I know that I've not been able to at least visually convince you that the product matches your motivation. So I always probe with that. And I don't rely on so much on the words that I hear from that person of whether they're going to buy my product or not, until I know that they can make a commitment. So when we started Chilly Piper in 2016, we actually did not build a product. we actually signed the contract first. We didn't build the product, was not built. We had the company pay, I think at that time it was like $14,000 to have the product built. And once I did a small thing for them, I went to another company and I say, are you willing to pay $15,000, $16,000 to have the same product? And so forth until I made sure that Um, all the features that I was building made sense for my buyer and that buyer had a repeatable, uh, need and repeatable motivation as well.
That, that's amazing. And this is the perfect world. Like we were in a session earlier where they alluded to, yeah, find product market fit before you put money and resources into figuring it out. For that $14,000-$15,000+ product, how did that look at the time? Because I'm sure it's evolved quite a bit. Like what was your— It was very rough.
It was very rough.
Your MVP to get money.
The MVP to the money. Yeah. It was very rough. I did not have money to hire the right people to build it, obviously, at that time. And we were all on our own bootstrapped resources. So, I put a prototype together in Keynote. And it was a very rough prototype. I think it had like 3 screens in it. And it was kind of solving the problem that This company needed us to solve for, but it wasn't, uh, any close to what we have right now. It was just, you click 3 screens and you get something happening in Salesforce. And that was about it. It was very rough, but it still solved for the need and it was still a product that they were very happy with.
So was the lead routing part of the original or is that, did that come later? Was it just like an integrated calendar into the CRM?
The first use case for us was the account executives that were closing a deal, then wanting to immediately give that closed deal to somebody to onboard them so that they don't lose them in that process because they had a problem that if they would schedule it after the deal was closed, there was a high likelihood that that person would never onboard and they would lose them because it was a small— a low ACV and a monthly ACV. So, you know, if you don't get people onboarding on a low ACV and on a monthly contract, then you lost. So they wanted to have that real time. And to have that real time, they wanted to make sure that the onboarding specialists were available and it was an equitable distribution of that real-time passing of that customer. And At that time, they would— I don't even remember how it worked, but I think it would just show who was available next. And after you show who was available next, we would just display their calendar and that was it. It was like nothing fancy, um, in those early days. But, uh, as, as the product developed, we realized that was not sufficient to solve anybody's needs and we needed to get a lot more advanced with our routing and all sorts of conditions in who actually gets it, whether they're in a specific segment, in a specific region. And then certain reps were more efficient at closing specific kind of accounts and putting that all up front, as well as taking into consideration vacations and other rules around engagement as well that were important in the process. But it was still a product that was working for 50 or so reps that were handling over to 50 or so other reps.
Whoa, another great episode of Revenue Today. For show notes, links, and mentions, visit revenue today dot live. For all my friends in the Rev Genius community, thank you. It's been awesome to spend this time with you. Please DM me any feedback and ideas in our Slack channel or on LinkedIn. If you're not in Rev Genius, join us at revgenius.com. It's free and it only takes like 2 seconds and you'll be joining a group of 27,000 revenue professionals strong. We've got it all. Looking forward to seeing you there. Catch you on the flip side. Thank you.
