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Podcast Pit Stop: Alina Vandenberghe on Building A Billion Dollar Company From Scratch

Building A Billion Dollar Company From Scratch

In episode 81 of Pit Stops to Podium, we sit down with Alina Vandenberghe, Co-Founder and Chief Experience Officer of Chili Piper. Alina shares her entrepreneurial journey, starting with the creation of Chili Piper, the leading scheduling and routing software for B2B revenue teams. She provides valuable insights on standing out in a crowded market, acquiring early customers, and driving long-term success through effective marketing strategies.

Additionally, Alina delves into the challenges and rewards of building and maintaining a strong company culture in a remote-only environment. With her experiences at Chili Piper and her AI-powered productivity startup, KosmoTime, Alina offers valuable perspectives on the art of building a billion dollar company from scratch while prioritizing customer acquisition, differentiation, and cultivating a thriving organizational culture.

If you’re ready to learn from one of the best, then buckle up and hold on!


Pitstop Highlights

Lessons from Chili Piper's Founding Success

Initially, Chili Piper acquired their customers through events, not inbound or outbound.  Later, LinkedIn was used as a strategy to voice opinions regarding marketing trends and problems prospects may have.  After 50M in ARR the strategies became a lot broader in nature.

Strategies for Success in the Post-COVID Digital Landscape

Online events are tough because you need to be really prepared, get good audience attendance, and have a guest who's also very prepared and interactive with the audience.

You tend to see better results from smaller, targeted audiences as opposed to large events.  The key is to bring value.

When attempting to reach large audiences, it's important to remember that personal LinkedIn accounts perform a lot better than company ones.

Nurturing a Thriving Culture at Chili Piper

The growth of employees is more important than the retention of them. 

It's important to match people with projects that highlight their passions.  Ultimately, a company should be seeking to understand the passions of each employee so that they can offer the environment to unlock it.

Connect with Alina



Full Transcript

Brendan:  Hey everyone. Welcome to Pit Stops to Podium, the RevPartners podcast where we talk to execs who have competed and won in taking companies from high growth to high scale. My name is Brendan Tolleson and I serve as the Co-founder and CEO of RevPartners, and I'm delighted to have with me today, Alina Vandenberghe for this episode, welcome Alina.

Alina:  Thank you, Brandon, for having me.

Brendan:  You know, this is a fun one. I mean, we've worked with Chili Piper for the last few years. And so to get the opportunity to speak with the founder and the CEO, it truly is a delight. So thank you for coming on for this episode.

Alina:  I'm very happy to have you as a partner as well.

Brendan:  Well, hey, for those that may not know who Chili Piper is, if they live under a rock, I think this would be a great opportunity for you just to give a little bit of perspective on who Chili Piper is, and a little bit of the origin story. How did you come up with the idea? And yeah, what led you to build this company?

Alina:  I have a background in computer science. So I did a master's in computer science, started as a programmer and then as a product manager, building products for companies like Bloomberg and Pearson, so finance, ed tech, media. I loved building products and I got some of my products keynoted by Steve Jobs, but I was completely ill fitted for the corporate environment and I was destined to be an entrepreneur. I started Chili Piper in 2016. Right now, I am the co-founder and the co-CEO of the company. And we started with the premise that revenue teams have it hard as it is. There's a pressure of meeting the quota in every environment. Tech tools should not make it harder for them to win. It should make it easier. And we went on solving all sorts of hard problems behind the scenes to make sure that they get to talk to prospects, that they book more meetings, that they route you to the right reps. And all that nitty-gritty to these sales that make a revenue engine work seamless across from one team to another.

Brendan:  That's great. And just for our audience to have perspective, what's kind of the size and scale of Chili Piper now?

Alina:  So we're a 30 million in ARR and we are covering a lot of, so we have a lot of teams within Chili Piper, product engineering, sales marketing, customer success, we're 200 employees and we're in 40 countries.

Brendan:  That's great. Well, congrats on the success you've had. I know that's not an easy road and we'll talk a little bit more about how you've been able to scale it to 30 million in just a second. But before we do that, Alina, we have a tradition here at Pit Stops to Podium and that's to get to know our guests outside of work. So, you know, when you're not building Chili Piper, which you probably don't have a ton of margin, but if you do or did, how would you spend that time with, you know, friends, family, hobbies, whatever?

Alina:  I obviously enjoy connecting with friends and I love my family to know margins on our returns. I think that my boys are my biggest creation. But if I weren't to have Chili Piper, I don't know what I would be doing with my skills because I'm really destined to build a SaaS company. I do spend a lot of time on our foundation as well. I have a strong need to stop violence in the world of any kind, not only between countries that are at war, but also between political parties and even people at home, even people with their children, even interior violence. And that's a mission that I keep working towards as well.

Brendan:  That's great. Well, appreciate the work that you do there. And how old are they? You said you had some boys?

Alina:  Four and two.

Brendan:  OK, great. Yeah, I have three kids under the age of nine, so I can relate to that that season of life. It's a fun time.

Alina:  They've been my greatest source of inspiration and of learning.

Brendan:  That's great. Well, let's transition a little bit into your point of you were destined to build a software company. And as you described earlier, you've been pretty successful at that as you've built Chili Piper. I'd love to just kind of take a, I don't call it post-mortem, that's too, that's a wrong word. But as we think about how you've been successful at building Chili Piper, as we think through how to really build a billion dollar type company from scratch, I think there's a progression here, right? Chili Piper, in those early days, as we have founders or we have early stage companies, they're looking to acquire, they have an idea and they're trying to acquire those first few customers. What can they learn from you as to how do you stick out and how do you really break through that noise?

Alina:  At the beginning, we acquired our first customers all the way to 3 million in ARR only through events, so field events, no outbound, no inbound. We would just attend or organize events and we would meet people and we'd talk about their problems and we'd offer a solution to the problem. Oftentimes we'd build it with them. That was our early strategy. benefited a lot from LinkedIn as a strategy, and we would empower all our employees to be on LinkedIn and talk about the problems that our prospects would have and just have an opinion on market trends and things of this nature. Not every company feels comfortable with that strategy, but we took it. And now it's really a lot of strategies. We have so many tools in the toolbox to grow after that. After... After 15 million ARR or so, the strategies became a lot broader in nature.

Brendan:  Yeah, it's interesting when you talk about events being the driver. I think you set up about three million. That's really what you focused on. Um, do you feel like for, you know, events have changed dramatically or not dramatically, but just the way that people approach it, you know, pre COVID, post COVID digital versus live, you know, we're, I guess, what are you seeing in terms of trends that you'd say, Hey, if, if you're looking to do an event strategy here, here's what we've seen be successful or here's how you can pivot. to really attack that type of strategy.

Alina:  I think online events are tough. You have to be really prepared and you have to have an amazing guest that is really prepared and be interactive with your audience and spend a lot of time for making sure that you get attendance to really have engagement. I rarely see successful events these days online, rarely, that I attend. I also am not very bullish on large events to really book a business there. Like a where you have a million booths and a million people trying to pitch something. And it's really hard to process the keynotes.  I'm not keen on that. I'm it was a strategy early on and it's a strategy that we still continue to believe in is that smaller targeted audiences where you bring a lot of value in person. You see a lot more results from that. But again, it's down to bringing a lot of value in those events, not just drinks and food. People don't want to be on a list just because you pay for their lunch, right? And you have to think long and hard about your audience and what's helpful to them to be able to attract them, for them to connect with peers and be learning from you.

Brendan:  Yeah, I think, you know, it's interesting. We, we actually did an event with your team and, um, it was, it was very creative. It was very specific in terms of the audience. Um, and it was a, it was like a wine and cheese night. Uh, and you invited a sommelier to kind of, uh, be that facilitator, but also have the opportunity to share a little bit about Chili Piper. I thought it was a really, uh, unique experience, um, that your team was able to create and curate. for a very small audience and not this very broad. So your team is doing what you said. So I think that's a fun one to call out. And then to your point about events, it's almost creating events inside an event. And like, how do you think through, really these large opportunities, how do you do something a little bit different? So I love how you guys are on the cutting edge of that. And then as you described, I think what I heard you say is really leveraging your, leveraging is the wrong word, but. giving your people a platform on social channels to really talk about the problems and the solutions that they're seeing because that allows you to have access to a broader network than you otherwise would with like a LinkedIn, for example, if you're in the B2B category.

Alina:  Of course, my personal LinkedIn or our employees LinkedIn performs 10 times better in terms of engagement than a company account, even with the same content, because it's very hard to engage with the logo. It's a lot easier to engage with a person. So I'm a lot more cognizant that people are a lot more efficient at reaching other people than an abstract logo.

Brendan:  So for those that say, hey, that's great. You've been able to grow a lot through marketing. At what point does the sales function come into play for Chili Piper? Did you eventually say, hey, we need to get in a prospecting motion or is it still very much marketing led and the reps take it once those deals are coming in?

Alina:  Sales has always been a great asset for Chili Piper and outbound motion is very effective, very profitable motion. And our SDR team is great, our account executives are great, and the numbers that are published everywhere tell that story. Our account executive reached their quota, our SDRs reached their quota. And the reason why that is happening is because we've spent so much time investing in our brand. that our brand is recognized. So it's a lot easier when an SDR reaches out from a brand that you've seen everywhere. So you recognize the name, but you don't really know what they're doing. And then an SDR points out a problem that it's solving for. So it's a lot easier, the outbound effort.

Brendan:  Yeah, I think one of the things that Chili Piper have done a really good job of, is that we talk a lot about how do you make prospecting successful. And a lot of the guests we've had in the past are being timely and relevant. And one of the things that I've, even actually I did a screen share of a Chili Piper outreach to me during a webinar to show like an effective way to prospect. And it's the whole, like what I saw was, hey, it wasn't a spray and pray approach. It was very personalized. It was to me, a video of my website and showing the problems that exist within our technical issues with our website. And it was a great, to me, it was like, hey, you actually did your homework. And now I actually want you to take action because I see I do have a problem that I need to solve for. And so I think it's just a testament to the work that your team is doing. Let's transition a little bit into kind of the last point, Alina, which gets into the culture. And so we talked a little bit about the go-to-market. But if you don't have a culture that retains that talent, that they actually want to be there, that can be really disruptive. And so how have you done, or how have you managed through a COVID climate and as you continue to scale, you mentioned 30 million to keep your people there and keep them excited and motivated and feel like they're part of a movement that you created at Chili Piper.

Alina:  It's an interesting question because I've never thought about it this way, in that my goal is to retain people at Chili Piper. And the last thing I want to do is keep people captive somewhere, they would not be happy. My goal is to create the kind of environment where people find most growth. And the way I'm thinking about that is... unearthing the passions and the joys in every person that works at Chili Piper to make sure that the actions and activities that they're being assigned to are going to ramp that into your intrinsic motivation. Because if someone is taking the job just to pay the bills, it's really, really hard to make it work. And it's really demotivating to just come from a nine to five job and crank to the tasks, but if you're really passionate about solving that particular problem because you see a future in it and maybe you want to be an entrepreneur one day or maybe you want to be a CMO or you want to be a CRO, whatever that dream that you might have, maybe you just want to triple your salary, whatever your dream might be, it's very important for us to know and unearth that passion to be able to then offer the environment that lets you unlock it. That's been a focus for us.

Brendan:  I like that, we had Horst Schulze, who was the, you know, one of the co-founders and CEO of the Ritz-Carlton from a hospitality perspective. And one of the things he talked about, um, it's like the paycheck is like, people think that as a driver and often, like it's actually like number seven, like the top 10 reasons why people stay. And it speaks a lot to what you just described, which gets into like passion and purpose and a sense of belonging. And so that speaks out broader narrative, like How do you retain people is actually inviting them into something bigger than themselves and how they fit into that core narrative. And so unlocking that passion or understanding what that is allows you to create the space and the opportunities for your people, which I think is really, really powerful.

Alina:  It's hard because for tech company like ours in the B2B space, you're not curing cancer. You're not going to create peace on the planet, right? So the purpose is not hyper palpable in changing to the world. So it gets down to the things that bring you joy at work, that makes you feel that you're in the flow. And it's really hard to interview for that because... It's hard to identify what really gets people excited, but that's what I focus a lot on in all our interviews.

Brendan:  Yeah, I like that. It's that whole connection. And you're kind of what you're saying, it's your role is connecting what they're passionate about to what Chili Piper can facilitate from a work perspective. So it's not just a transaction. It really is, or they feel like they can make a career or at least have that path by which to fulfill that desire that they do have.  Well, hey, as we as we wrap up, I really appreciate your time and giving you your perspective on, you know, what's been successful for Chili Piper as you've grown to where you are today. If our audience wants to connect with you or learn more about Chili Piper, what's the next step they can take?

Alina:  You can just follow me on LinkedIn. I post a lot of things that we're going through, a lot of mishaps and successes and all sorts of learnings that I have throughout the way.

Brendan:  Well, I'm sure you'll get some more followers after this podcast interview. And to your point, I've always appreciated your willingness to be open and vulnerable and use that channel for those type of lessons. So thank you so much for your time. Thanks for the opportunity to connect with you and to have this interview and let's stay in touch.

Alina:  Thank you for having me.

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