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

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Because as she pointed out, the traditional playbooks of entrepreneurship don't work anymore. 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 lesson is that you can listen to how people have done it in the past.

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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.

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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.

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And the most important part by building a company is creating a culture that you want to live on forever, that you want to leave 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.

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There are a lot of things that have happened this year, but we're cash break even, 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.

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There are a lot of touch points that can be optimized in the funnel without compromising on authenticity. You don't have to send robocallers 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.

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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 G3 reviews. And it's hard to qualify all these 300 touch points in order to reach out to your best accounts with your best messages.

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So we created all sorts of bots to ensure that our data points are correct. We also observed that we're going to sell less well if, sorry, 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.

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And I just want to give a shout out for all this AI work that we're doing to Barts AI for our friend here, who has helped us create some of these autonomous AI bots. He's also speaking tomorrow, yeah? 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.

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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.