This CEO Does $50m/yr and is moving to a Flat Org Structure, ChiliPiper CEO

You are listening to Conversations with Nathan Latka, where I sit down and interview the top SaaS founders like Eric Wan from Zoom. If you'd like to subscribe, go to GetLatka.com. We've published thousands of these interviews. And if you want to sort through them quickly by revenue, or churn, CAC, valuation, or other metrics, the easiest way to do that is to go to GetLatka.com and use our filtering tool. It's like a big Excel sheet for all of these podcast interviews. Check it out right now at GetLatka.com.

Over the next 20 minutes, she's going to walk you through all of this. Please help me welcome to the stage, Ms. Alina Vandenberg of Chili Piper.

Have fun, enjoy. I got all that right, right? Point solution day one, right? Okay, all right.

All right, I have to ride the wave of the beautiful demo that Monday.com, ClickUp, and GoodSud have in common. Do you know what they all have in common? Why their demo process is so good? They use Chili Piper.

All right. Irina talked to you about Gen Z buying differently. I'm going to talk to you about the change that we're making in our organization so that the Gen Zs can have the best experience working in a SaaS company, but also buying from a SaaS company. Because, as she pointed out, the traditional playbooks of entrepreneurship don't work anymore. And you don't have to do things like me. This is just what has worked for us at Chili Piper. It was what's authentic to us. And I think that's one of the biggest lessons is that you can listen to how people have done it in the past, you can listen to crowd knowledge, but what really can work is what

adapts to your values and your beliefs. In my case, what I've experienced is that in entrepreneurship, we only have two modes. Either we're in terror or we're in euphoria. And if we have lack of sleep, both of them get accelerated. I am running on very few hours of sleep because last night we went to play poker and we kept going. However, there's something that I really want to optimize for, which is having fun and having euphoria at work because that's what motivates me, that's what drives me, that's what keeps me going. I do not want to run a company by being miserable.

And the most important part by building a company is creating a culture that you want to live on forever, that you want to live to your grandchildren, to your children. And that's what I call the company of the future. And the structure of such a company, it comes a lot down to how systems are set up, how employees are being helped to thrive, and how growth happens. This is our ARR to date. There are a lot of things that have happened this year, but we're cash breakeven and we're continuing to grow. And our modeling is courtesy of a famous person in this room, our fractional CFO, Josh. This meme was not created by him,

but go listen to him speak about how he accumulated 400,000 followers. But as you know, we're all kind of delusional sometimes and that's how we're projecting our numbers.

And in my delusion, I think that there's a better way to do companies. There's a better way to run a company that prepares you for the future. And that is the traditional org chart in which we all have an SVP, a VP, a director, an IC is broken. I believe that the best way to run a company is by having a flat structure. Some of you might have read Paul Graham's essay with Founder Mode, Brian Chesky, Airbnb. Did anyone read it this week? Yes, a couple of you. So what he's referring to by Founder Mode is that we're told that we can run our company by hiring great people and get outside of their way. Senior, great people. That sounds lovely in theory.

In practice, because we're founders and we're very particular about things and because we see a lot of things differently, that doesn't really work. So what has worked for me is by creating a structure where there's self-management. People can create plans together. We're all seeing things that I might not be able to. People on the front line see things that are different. We all have a purpose and the purpose matters a lot. The decision-making is not made at the top. I gave out control a long time ago. The decision-making is made together. That relieves me of a lot of stress. We bring ourselves fully as we are to work, not with masks, not with things that we don't believe in. And there's fluidity in how we actually take action.

But in order to execute, I believe that you have to hire a certain kind of people that believe they can. If somebody comes to work just because they have to do their job, if they do not have a desire to win, they're not going to win. As a result, the most important thing for me when I hire someone in my company is that they have the belief that we can achieve the kind of crazy numbers together, that they believe that we can do it. And this is a hard one to spot in the hiring process. The belief is not enough. The system is not enough. What is critical is a game plan. Like in sports, if you don't have a game plan, you do not win.

And that game plan has to be based on numbers. Numbers can sometimes hide reality. But there are numbers that you can rely on in your pipeline that allow you to play the game better than others. And the pipeline numbers do not lie, especially as you're looking at the funnel progression and as you're looking at demand conversion, you can create game plans and activities that impact those numbers. And I gave you an example here from marketing, because I took over marketing about two years ago as an acting CMO. And I started getting obsessed with my ICPs, getting obsessed with my targeting, with my account touches, with my velocity, my first engagements. And as Irina was saying, there are 16 touches before somebody comes and buys.

And you want to optimize for all of these impressions that your customers are going to see. And as a result, in our marketing plan, we have very precise activities that are going to influence and that we're tracking towards our pipeline conversion.

And yes, we started with one product, the one that's used by monday.com and ClickUp and HoodSud. But there were a lot of other products that the market never saw. We actually had at some point an inbox as well. And the inbox was allowing buyers to see their entire buyer's journey and see who at the company emailed, what they did and so forth. We killed it because we realized that it's going to be so hard to get people to switch from Gmail or Microsoft to another inbox. In the end, we went a DSN to our space. We called the platform Demand Conversion. We focused on what we know, which is pipeline conversion. And we created five SKUs that you can see here.

Form routing, chat, team handoff, scheduling and lead distribution.

With the goal of cross-selling and creating a machine that creates pipeline from these other products. My co-founder, who happens to be my husband and also has fancy pants, is going to speak next after me, so he can talk to you more about how those multi-product strategy works. I'm going to focus on the things that I have split with him, which is operational excellence. And the best way to achieve operational excellence is, I found, using AI. There are a lot of touchpoints that can be optimized in the funnel without compromising on authenticity. You don't have to send robot callers to book business. You don't have to send fake emails, a million of them, that sound all the same.

But you can use AI in the process. And we use it for identifying our ICP. We use it for account scoring, for targeting. To give an example, we have a propensity to sell to our companies if they have some of these criteria here, if they have more than 10 sales rep, if they have a high influx of leads, if they have a complex sales cycle, are in good standing, have good GTRs. And it's hard to qualify all these 300 touchpoints in order to reach out to your best accounts with your best messages. So we created all sorts of bots to ensure that our data points are correct.

We also observe that we're going to sell less well if, sorry, if they're based in Europe, they take forever to close. If they're on Outlook, for some reason, people that use Outlook, they're a lot slower to make decisions as well. And if they're a traditional company. That's how we managed to book 500 meetings a quarter. And I just want to give a shout out for all this AI work that we're doing to Bard's AI, for our friend here, who has helped us create some of these autonomous AI bots. He's also speaking tomorrow, you know? All right. All right, you can just go and chase him, and he can tell you how he does it with his magical team.

On top of it, our GTM strategy is probably a lot more unusual. Because it's the same as day one when we had the point solution. I have not changed any of it. And it comes down to our values, to the way we empower our employees to go to market and the way we work with the ecosystem. Because by now you all know, all your products are super easy to copy. Anybody can just go on and copy your products. Autonomous AI bots are gonna be here, they're gonna act as your employees, they can act as as salespeople. But, there's something that remains, which is our humanity and our ability to connect with others.

And that's so much harder to scale and so much harder to fake. And let me tell you how we do it. We have a desire to create a community around us. And I'm not talking about Zendesk or Slack, though we have that too. That's not what I mean by "community". What I mean is by having a true, true value of helping people around us. When we hire, when we work with partners, when we work with prospects, when we work with customers, help is really important. When we recruit, I told you that I look at how much they believe that they can succeed. Well, I also look how much they care about helping those around them. Because not everybody has the same value.

I cannot teach these values. I cannot teach people how to believe and I cannot teach people how to care about others. But I can hire people that have these characteristics. And hiring people that generally, but generally care about others is very important to me.

Because, when I look at my employees, I generally care about growing them as well. And I do unusual things. Like, if I can't find a job in our company that makes them happy, if I don't find the path for them to grow them in my company, I'm gonna find them a job outside. And I really go outside of my way to find them a perfect fit.

With prospects, I go the same length. I don't trick them into funnels. I don't trick them into downloading some ebooks that nobody reads. I do not trick them with creating content that's fake. I go above and beyond to help them with sharing my experiences, sharing what I found, sharing things that I know that they care about.

With our customers, we do not stop at customer deployment. We help them with tactics. And what do people really care about? Succeeding in their job, getting promoted. We help them with their success metrics. We make them so that they're superheroes inside of their organization, so that when others talk about them on stage, they're proud about it. We get them on stage. We get them all sorts of opportunities in which they're shining. We also care for them when they're in trouble. If they're sick, we send them chicken soup. If they're giving birth to a new baby, we help them celebrate that as well. Similarly, when we have a partner on board, we don't just do our playbooks with partners. We become creative with how we're going to help them. And this is an example of something that we've done with Mutiny,

an event for marketers together. With our influencers, we also look at being creative beyond cash. Because influencers, they care as much of audience as we all do. And yes, cash is nice, it helps them survive. But being creative and helping them get more rich is a lot more important. Just an example of impressions of one influencer in Q1, to show you the kind of results you can get without spending too much money, without spending too much effort as well. Outside of that, because now we have a lot of products that have important cross-sells and triggers for us to sell,

we work a lot with Crossbeam. And this is a book from Bob Moore. If you haven't read it yet, it's a pretty damn book. It's pretty damn good. We're actually part of the book as well. And it shows some of the playbooks that are used to do integrations with partners and how to elevate partners around you to win together. The end result of our efforts to elevate the community around us. This is an example for Nicola. Do any of you know him? He publishes these metrics with Mark Sales Tech.

No? He actually said it to me: "Alina, you didn't build a product. You've created an entire industry because it's an ecosystem. It's a community that people crave to be part of. And that's very, very unique. That's very, very unique. Because you know that everybody around you is an advocate. You don't have to go outside of your way. You don't have to be on stage to evangelize for your product because everybody else does it on your behalf. And who is better to advocate on your behalf then? Your customers, your employees. They're going to do it better than you. And it's a lot easier if you empower the right nodes in the ecosystem to get the results you want. And in our case, an important piece of the puzzle...

Let me see if I see... For some reason, it doesn't load. Anyway, an important piece of the puzzle is creating these relationships in person. Because in the digital realm, there's some fakeness around it. Yes, you can exchange some nodes, but they don't really know who you are. You become a lot more real when you meet people in person. And that's why I think that there's a lot of power at SaaS Open because you can create a lot of partnerships here. You can create a lot of relationships that are going to last a long time after this event. And hopefully, you can create business opportunities out of it as well. And that's been my playbook since day one.

And because I'm also on social media like Irina, this is my QR code. You can connect with me only then. And I promise that I will connect as long as you write SaaS Open when you connect with me. So when you send me a request to connect, just write SaaS Open so that I know where we have created this relationship together.