Rewriting Corporate Culture: How Chili Piper Scales with Humans, AI Agents, and Radical Decision-Making w/ Alina Vandenberghe, Co-Founder at Chili Piper

What happens when an engineer-turned-entrepreneur brings B2C energy to B2B enterprise software and a borderline obsession with fixing broken meetings? You get Alina Vandenberghe—co-founder and Co-CEO of Chili Piper, the woman who turned scheduling software into a billion-dollar empire while managing teams across 38 countries (and somehow still finds time to make her employees build AI agents).

From starting work at 8 years old to building stealth iPad apps that caught Steve Jobs' attention, Alina's journey is equal parts inspiring and remarkable. In this episode, Becca sits down solo with one of enterprise software's most magnetic leaders to discuss how she turned corporate culture on its head.

You'll discover:
— Her early career wins (including a New York Times interview before she could barely speak English)
— Chili Piper's radical approach to decision-making and culture design
— Why every employee is required to build AI agents
— How LinkedIn became her unexpected writing school
— Why parenting, product-building, and personal growth are all connected by the same thread: curiosity

This episode is packed with tactical ideas and vulnerable reflections—from the power of documentation to the messiness of leadership to what it means to find joy while you're building something hard. Stick around for walkout songs, emoji debates, and a rapid-fire round featuring your favorite unhinged “hiccups or pinkies” question.

Transcript

[00:01:14] Becca: Welcome to the Under Embargo Podcast. I am your host, Becca Chambers. I'm the CMO of Scale Venture Partners. My co-host, Perry Hedrick, who you will. Uh, notice is absent today. Um, so I'm doing this solo [00:01:30] for the first time ever. Um, although I have an excellent, um, I guess we can call Alina my co-host today, although she is also my guest, so no judgment of, of me trying to host.

Did the show alone. But I am super excited for today's guest. She has one of the most compelling founder journeys that I've heard, um, and I've actually heard a lot of founder journeys. So Alina Vandenberg is the co-founder and Co CEO of Chili Piper. And her [00:02:00] path to building, um, a very respected, one of the most respected names in revenue tech is pretty amazing.

So I will dig into some of her background in the podcast. So I'm no spoilers now. Alina's been hustling since she was eight years old. She's an immigrant with a master's in computer science and she's had her apps featured by the likes of Steve Jobs himself. And she's founded a company with her husband and they're now re-imagining how B2B revenue teams are operating and solving really [00:02:30] complicated business problems.

And if you've been on LinkedIn for any amount of time, you're sure to have seen Alina there because she's building a super authentic brand that I love, and that's. How I found her and started following her. So I'm really happy to have her here. Welcome to Under Embargo. 

[00:02:46] Alina: Thank you, Becca. It, uh, feels a privilege for a nerd like me to be invited on a communication podcast.

[00:02:53] Becca: Ah, no, it's my privilege. I'm so happy to have you here. Um, well, let me just, can I just have you kind [00:03:00] of introduce yourself and Chili Piper and, you know, maybe just a little bit about your journey. 

[00:03:07] Alina: Uh, as you said, I started, uh, working ever since I can remember. And, um, I didn't know that I wanted to become an entrepreneur, but I, uh, started working because I had to.

And, um, I thought my dream would be to climb, uh, the ladder in corporate America, which I did. Um, I started working as an intern at, uh, Thomson Reuters and [00:03:30] I worked for Bloomberg and some other, uh, publicly traded company. Um. And I realized that what I really love is building things. Um, and uh, I wanted to see if I can start a company where I can just do that.

So it's an ongoing experiment. 

[00:03:48] Becca: What was the first thing that you built? 

[00:03:51] Alina: Um, when I started the, my first job here in America at Thomson Reuters, um, it was an application for news, [00:04:00] uh, for Thomson Reuters on the iPad. It was before the iPad was launched. There was a guy with a turtleneck that came into our office and, um, it was in a room with no windows, no, uh, access to anybody.

I, I was the only one with a key. He had, uh, chained the device to a table that, um. I couldn't move and I wasn't supposed to show what I was working on to anyone, not even to talk about it with my husband. And, uh, about few weeks after I finished it, um, it [00:04:30] turns out that, uh, that's the app that got keyed by Steve Jobs on, on stage.

And all of a sudden Tom Reuters got 30 new 30 million new, um, users because they've decided to pre-install, uh, the app on iPads. 

[00:04:44] Becca: That is amazing. Okay, so I need to know more about this. So you, you were building it for the iPad, but you didn't really know that you were building it for the iPad. You just knew you were building it for this kind of secret thing.[00:05:00] 

Did you know it was going, it was kind of, sorry, go ahead. 

[00:05:03] Alina: It was like the, it was like in a, in a metal chain so I could see the device, but I, we didn't know the name of it. We didn't know what's gonna happen to it. It was, uh, under, uh, yeah. 

[00:05:13] Becca: Well, as Apple always is, right, everything is like super secretive.

Did you, so you had just kind of like working specs that you needed to work like with Right? To be able to create the thing. 

[00:05:26] Alina: Well, it was the beginning, right? So they didn't really have like, uh, guidelines for [00:05:30] it. Uh, they didn't quite know what precisely the apps on, on it would look like, but we did have the iPhone as an example.

And so it was somewhat easier imagining how to take that to a larger screen. Um, but still it was a lot of fun to kind of develop without much instruction. Yeah. 

[00:05:48] Becca: Yeah. That's super cool. And did you have any idea it was gonna be on the stage or was that a surprise? No 

[00:05:52] Alina: idea. No. No idea. 

[00:05:55] Becca: That's so cool. It was de 

[00:05:56] Alina: surprise.

Hmm. 

[00:05:58] Becca: What was your reaction when that [00:06:00] happened? 

[00:06:01] Alina: Oh my gosh. I thought that I made it to America. You know, it was, I was interviewed by the New York Times. We were in, uh, times Square, or the app was everywhere. I, I even have a picture of it and, uh, I, I couldn't believe my luck. I could barely speak English, but I, here I was in New York Times, you know?

[00:06:19] Becca: No, totally. Did that have like a profound impact on your career? Like just that? Moment, kind of, did that help launch you? 

[00:06:28] Alina: It gave me a lot of, uh, [00:06:30] confidence for sure. If I could, uh, do this, uh, fast. I, what else did I have in me? 

[00:06:36] Becca: Totally. How, what a cool moment. Um, so you are from Romania. How did, how did you make your way here?

[00:06:47] Alina: Uh, my husband imported me. That's the short answer. 

[00:06:52] Becca: Where's your husband from? 

[00:06:54] Alina: He is French, but he had the, he, he was living here for a long time and he had the American citizenship. 

[00:06:59] Becca: [00:07:00] Nice. Did you meet him here? 

[00:07:02] Alina: Uh, no. I met him in Romania. 

[00:07:04] Becca: Oh, okay. All right. Very nice. And did you guys found your company in the US or in Romania?

[00:07:13] Alina: Uh, so the company we started together in 2016, and he was a serial entrepreneur, so he started many companies. Some of them went bankrupt, some of them did well, and uh, he said, you know, with this talent that you have in product, you should start a company. You should try to start a company with [00:07:30] me. And he kept insisting and insisting and insisting, and eventually I said, fine, I'll do it, but only I'm the CEO.

[00:07:37] Becca: Nice. So how did Chili Pipe come to be? Like why, why that business?

[00:07:46] Alina: I didn't quite know what, um, what we will do. Like I didn't have like a master plan, like most entrepreneurs. I just knew that I loved building things and especially my. Brain works best when [00:08:00] the complexities of the software are, are hard to crack. In this case, enterprise software is really, really complicated to figure it out.

And I was seeing at, at the time I was working with, uh, Oracle, I was working with Salesforce and I felt, you know, in, in B2B software is usually boring. I don't want to build boring software, but I want to see if I can use my B2C kind of. Talent and, and applied to the boring software. And I was just curious.

I I, I really was just curious to see what can be [00:08:30] done and if I can use my talent there. 

[00:08:33] Becca: And what do you think the biggest, kind of like, technical challenges have you helped? Overcome in that space using your B2C minded brain. 

[00:08:48] Alina: I, I literally went and I applied, uh, principles from B2C buying experience into the B2B world and made sure that, um, you know, when, [00:09:00] when we want something as consumers, we press a button on Promise Amazon Prime in three seconds is, uh, at our door.

And B2B is a lot more complicated. You go to somebody's website to have to figure out who you're supposed to talk to. You have to wait for them. Um, on the seller side, there's a buying group, which is harder to, uh, wrangle and then move towards the right, uh, parts of the funnel. So it's a lot more complicated and I figured that there's a way to.

Improve that buying experience and that's, uh, that there are still a lot of things that can [00:09:30] be improved even nine years into it. Uh, I I still think that there, there are a million ways to improve it 

[00:09:37] Becca: for sure. I mean, I have an example just from this week, I am evaluating some vendors for some software that I want and.

One of the vendors, I was able to get a demo immediately. Great. The other one, I've, I just want a demo. You know, I just wanna see it so that I can evaluate and I haven't been able to get an email back and it's like, I just wanna see the, the damn product. [00:10:00] You know? I don't wanna wait, I don't wanna talk. I don't even wanna talk to somebody.

I just wanna play with it myself, you know? And instead I have to wait. Am I gonna be able to talk to somebody? I don't know. It's like. I'm gonna end up abandoning even the, like seeing that product just because it's this whole long process and dance and whatever, and I just want to maybe buy the product.

But no, it's a whole thing. But I totally agree. I have to call them 

[00:10:25] Alina: after, after our conversation to make sure that they buy chili pipe. 

[00:10:28] Becca: Seriously. I know [00:10:30] I'm gonna be like, Hey, I've got somebody for you. Maybe improve your buying process. Um, but I feel the same way actually about. Marketing in B2B. Like I think the way that people market B2B products is this like very stiff whatever, and it doesn't need to be it.

We can, we can do consumer marketing, we can take principles from consumer marketing and use that in B2B marketing, you know, we can have a more [00:11:00] human-centric marketing. Um, I don't know what the word I'm looking for is, but, uh, the way that we talk to people doesn't need to be this very, like, business stuffy, um, thing that we've always.

Done. I don't know the enterprise voice that we're used to. I'm so over it and I wish that more enterprises would take, um, take a lesson from the, from the consumer brands that are just having more fun with their marketing. You know, I think we could all allow 

[00:11:27] Alina: Mm, a hundred percent agree [00:11:30] with you. 

[00:11:31] Becca: Um, so you have described yourself as a miserable employee.

What are red flags that told you that you needed to build your own thing? 

[00:11:44] Alina: A couple of things. One is I love traveling and I couldn't stand being stuck in one location, uh, under a neon light without, uh, any access to, uh, nature or any of those things. I think that. When you are [00:12:00] more of a creative type and you get your ideas when you walk or when you're changing environment, it's a lot more conducive to to better work.

Um, the second. One was related to decision making in large corporations. You get to climb the ladder if you really good at, get good at politics, and I started getting good at that, but I didn't like that that was the case. I felt that there has to be a better way where talent is the one that gets at the top, and that's what I am aiming to do at Chili [00:12:30] Piper as well, where all decisions are transparent.

Um. Everyone can make a decision that changes the business. Ev anyone can contribute. It doesn't matter where you are in the ladder and everything is transparent, so everybody sees everything. Um, and it's uh, it's one big experiment, but I do believe that it's a lot more. It's a better system in which everybody feels like they're contributing as opposed to just people who are louder or who are more astute, uh, from a political standpoint.

[00:12:59] Becca: For [00:13:00] sure. I mean, oftentimes the quiet, thoughtful people are the ones who don't have their voices heard, but are the ones who have like super important perspectives. But how are you fostering that? Culture and making sure that those quieter voices are having their voices heard as part of this. 

[00:13:22] Alina: We have, uh, it's actually documented it in a notion doc because, uh, all my CEO friends ask me about how we make decisions.

'cause it's very unusual [00:13:30] and we. Have this thing, we call it a decision memo. So it's a Google Doc, and we have thousands of thousands of such documents and everyone can create a decision about anything. Could be our pricing, could be who we're going after. So our, our segments, our SCP, it could be, uh, what's the right org structure for their particular team.

Um, so they start with a problem statement and then they start why they need to fix that problem now and then. Potential options on how to solve that problem. [00:14:00] And those documents, like they, nobody in the company can make a decision without starting such a document. And those, uh, documents are open to anyone, anyone can contribute with options and, and thoughts.

Um, for each one of these decisions, we have what, what's called a consensus scholar. So it's not. That it's a vote, but everybody get gets input back into the decision, and then there's a consensus that needs to happen. So if you have voices that are completely against the solution, then you have to make sure that their view is [00:14:30] respected and that you include the um.

Uh, their data, et cetera, so that the decision can, can move in the best direction. And we have deadlines. 'cause otherwise the decision can stall forever. Yeah. And you can put like a two hour deadline or 30 minutes deadline, like a few minutes, a few hour, a few days deadline. Um, and, uh, we, we've got used to documenting everything, rationalizing everything, um, and seeing more options than maybe it's possible at the first glance.[00:15:00] 

[00:15:00] Becca: That's super interesting. Um, do, do, when you bring new employees on, how do you like onboard them into this system? 

[00:15:10] Alina: At the beginning it is very overwhelming because you have all sorts of decisions kind of flying everywhere all the time, and you feel like things are moving very fast. But, um. After a while, they get used to it and they contribute and they can start their own decision making.

And it's very empowering because usually you join a company and you feel like you're just [00:15:30] a, a cog in the machine. And actually, Piper, everybody takes like, ownership over things. And not everybody survives. Not everybody survives, but, but, uh, those that do are very resilient and, uh, action oriented. 

[00:15:43] Becca: How large is Chili Piper?

How many people. 

[00:15:47] Alina: So we're in 38 countries. And so that's why the decision making process has to be written. Um, we're in different time zones and we're very different culturally. Uh, and that's kind of the beauty of, of it. [00:16:00] Um, right now we have 140 employees, uh, that are human and then thousands of AI agents.

[00:16:06] Becca: That's, yeah, that's, I like that you. That you, um, couched it like that, that you have the human employees and then you have your agents as well. And do you have running, running the agents? 

[00:16:19] Alina: We have agents running the humans, human agents. 

[00:16:24] Becca: It's, it's all included. Where, where do you have the ai? What parts of your business do [00:16:30] you have AI most?

Um, where are the agents most automating, I guess right now? What part of the business? 

[00:16:39] Alina: Uh, it's a lot on the GTM, uh, functions. I actually wrote another notion Doc Exactly. With examples of all the agents that we've built. Really, 

[00:16:48] Becca: are you gonna, can you share it? Is it shareable or is it an informal? I can share, I can share 

[00:16:51] Alina: both notions.

Okay. No, no, no. It's, I would love to and I keep, keep updating them. Yeah. Um, we have, um. [00:17:00] Uh, a slack channels where everybody can build agents. Um, and it's actually part of the, part of the promotion process if you want to get promoted, that's Chili Piper. You have to show that you've built agents, that you're innovative, that you're thinking about, uh, how to improve productivity.

Um, and everybody, anybody can volunteer. Anybody can volunteer for ideas and uh, yeah, it's, it's, it's very organic and a little bit chaotic, but it's also fun. 

[00:17:24] Becca: I love that though, because. You know, if you work somewhere that that [00:17:30] AI is just not in the DNA of the company, and you'd start, like if I were to start building agents or a team at a company, were to start building agents and you were to start saying, this is how people are getting promoted, or this is a way that is, this is a path towards promotion.

It really does create, I don't know. It gives people something that they can tangibly do that's adding value to the business that they can go do and learn on their own. [00:18:00] That isn't something, they don't have to go take a class, right? They don't have to go take a leadership course, or they don't have to hope that, that their boss is gonna give them a promotion because they've hit some, you know, maybe they hit, uh, a goal that is potentially tangible or intangible.

It's like there are some real things that. You're saying these are value adds to the, to the business and all of the people are going and doing it. And like you said, it creates this kind of organic movement of people adding value for each [00:18:30] other and everybody's learning from it. It's not just like, oh, I did one thing That's creating a better process.

Like everybody is learning how to be better at their jobs and then they'll be better at their jobs and their next job too. Right? Because they're all learning how to build a better plane, I guess, for lack of a better analogy. 

[00:18:49] Alina: And we'll learn a lot better by doing than by reading about it, you know? So it's a lot more actionable.

Hmm, 

[00:18:55] Becca: totally. I'm particularly, I would love to see all of the ways that you're [00:19:00] using AI in your go-to market. Can you share a couple examples? Like what are some interesting or like maybe some recent examples of, of automation that you've done in your go-to-market Motions. 

[00:19:12] Alina: So we have something unusual in that we put push all our data from our Salesforce, from our marketing automation and from our product all in one place.

We use Snowflake and as a result we can make a lot of inheritances around what makes for a great customer, what makes for a great customer that sticks, what are the characteristics? And we always [00:19:30] feedback that back to the top of the funnel to the accounts that we, uh, target. So there are a lot of data components that we gather with AI agents to make sure that the scoring is correct and that.

Um, we, it, it keeps evolving with the right kind of accounts, and right now something that I'm working on is making sure that, uh, for, we have a lot of partners, so we work with a lot of agencies and we work a lot with a lot of product partners as well. Whenever in our ecosystem there are new prospects or new customers, make sure that they're nurtured, like the [00:20:00] right buyer in the right company is nurtured with.

Um, them understanding how like Chili Piper and Gong work together, or Chili Piper and G two work together. And that also happens with AI agents because we identify which persona could be best suited for a nurture campaign. And we automate the process like with Evergreen, um, uh, automatic campaigns as well on that front.

That's something that I'm working on myself right now. 

[00:20:24] Becca: That's very cool. I, um, yeah, I really wanna see your notion. I'm, I'm [00:20:30] particularly interested right now. It just feels like every day I see some new go to market use case that somebody's do some, you know, CMO is coming up with an interesting way of, um, automating a different part of go to market.

And so I'm, I love that people are starting to create lists of this and I. Eager to start taking, I don't know, smart people classes because I'm not nearly as smart as other people that are figuring this out. 

[00:20:56] Alina: Um, we're all trying to figure it out, Becca. We're all trying to figure it out, 

[00:20:59] Becca: but I [00:21:00] actually think that's the beauty of right now is I see people online who are like, take my course, I'm an expert.

And I'm like, you're a liar. Nobody's an expert expert right now. You're literally nobody. And that's why it's so beautiful right now, because exactly, nobody knows what they're doing and everyone is just trying to figure it out. And in two years we're gonna look back and be like, wow, we had no idea what we were doing, but like.

The people who are playing with it right now are gonna be the ones who are experts in five years, just because mm-hmm. They're tinkering. [00:21:30] Right. We're trying to figure it out. We're like getting into the weeds and starting to learn how the pieces fit together, and I don't know, I think it's as a, as a, like, I'm not nearly as big of like a tech nerd as you are, but like, I like getting into the, like, how does it work?

Part of it, not just into the. Put an input in, get an input out piece of it because it helps me, I guess, with my process. So. [00:22:00] Mm-hmm. I love this 

[00:22:00] Alina: space. 

[00:22:03] Becca: Um, so let me ask you, since I found you on LinkedIn, I will pivot there a little bit. How did you start? LinkedIning and building your LinkedIn presence. And was that just kind of an organic thing, like you just like it?

Or was that a business decision? Um, tell me about that. 

[00:22:26] Alina: I very much like three years or four years ago, I was your [00:22:30] typical tech founder that would, uh, avoid eye contact and would not want to be in front of press or in front of journalists or anything really. Very much so, very much so. I was terrified of any kind of, uh, being on stages or anything like that.

Um, first I felt like my English was awkward. Second, I felt like my, the words that I was using were limited. Um, I just didn't feel like I had anything to say really. Um, so as a result, I was just terrified of social media. Until I decided that I'm just gonna force myself, [00:23:00] I'm gonna force myself and just feel comfortable with pressing the publish button, uh, until just that felt less terrifying and I learned a lot more by just posting every day and feeling uncomfortable.

Then I did from reading any other books on communication on social media, um, until I finally found my voice and I finally found, um, the. The courage, but it, but it took a, it took, uh, about [00:23:30] 12 months or so everyday posting. 

[00:23:33] Becca: I feel like I wanna just like clip that clip right there because that is like the perfect, like, I don't know, 30, 60 seconds of everyone I ever try to convince to start posting on LinkedIn.

They give me the whole like, yeah, but like you're so comfortable writing or showing up on camera or whatever, and I'm like, no. No, like I was, I'm a, I'm a comms lady. I'm a behind the scenes comms lady. Like, I don't like being on camera. I don't like doing podcasts. Like I don't, [00:24:00] I never liked doing this stuff.

I think LinkedIn is cringey too, or I used to think LinkedIn is cringey, but like, to your point, you just have to start, right? Like there is a reason to do it. We all know that there is a benefit to being out there and doing it. So once you start doing it, it. Becomes a little bit easier and it becomes a little bit easier and you get positive back in like right.

People start to reflect back to you that there is, um, there is, [00:24:30] people are getting something out of it. When you are putting something out there and when you start to hear from them, oh, I'm getting value out of what you're putting out there that's giving you the. Encouraged to do more of that, and then you start to realize I don't have to be some polished, perfect, whatever.

They like the flawed version or they like the, you know, I have, I, I have, they like the immigrant story, right? Or they like the tech founder story or they like whatever version of you you were worried to share [00:25:00] in the first place. And I just think that people need to get past the worry about cringe and just start doing it because after 12 months.

There you are. Suddenly you are. You are full of courage and full of new communication skills and poised in a way that you never thought you would be. And I never would've guessed that you were not comfortable doing this because you seem like such a natural and like a content creator at heart online to me.

I thought you were like all [00:25:30] in on all of that. Seriously. 

[00:25:34] Alina: No, no, no. Just, uh, posting every day, uh, was the best, uh, writing course. And right now I do find joy in it right now. I, I actually enjoy it. Um, but yeah, I was completely terrified and, uh, now it's more automatic. One thing that helped me a lot at the beginning was, um, and I don't know how I came up with it.

I think, uh, I don't think I read it anywhere. I came up with it on, on, uh. And, and helped me a [00:26:00] lot was to imagine myself a few years back and just write to myself. And I knew myself pretty well and I would know that I don't like to read fluffy things, um, egocentric things, more things that would've been helpful to me, uh, in that stage of my life.

And that made it a lot easier. It felt like I was writing letters to myself. 

[00:26:21] Becca: That is such good advice. And I also tell people, like when I write, like pick one person to write to, like you said, like you're writing to your former self. I [00:26:30] would write to somebody on my team, right? Like if I'm writing to somebody who needs advice from a leader, there you go.

That's a person not to the entire world. Um, do you write all of your own content? 

[00:26:44] Alina: Yes. I've never had anybody editing or write help me with content. And 

[00:26:48] Becca: I dunno if it 

[00:26:49] Alina: was a good idea or not. Uh, 

[00:26:50] Becca: no, it's totally authentic. That's why. I mean, that's why it works, really, truly. Um, but you know, I always ask CEOs, I've spent my career writing [00:27:00] content for CEOs, so I'm always curious, um, when CEOs do their own content.

I think it's such an interesting, um, uh, it, you know, it takes time, right? Content is a labor of love. Do you use AI to create content? 

[00:27:16] Alina: So here's my process is very, very strange. Every evening when I put my kids to sleep around eight o'clock, I sometimes fall asleep with them and I don't have any content.

Or if I don't fall asleep, then I [00:27:30] re I just think about something that has happened that day and write it in my, uh, apple notes. And then in the morning I. Reread 'cause I have like an ongoing set of notes, which one feels more alive in me that particular morning and I just take my notes and I post it.

[00:27:46] Becca: Your process is almost exactly the same as mine. Almost exactly the same. I have an ongoing Apple note that is just like full of random ideas. I call them my shower thoughts because it's like they come the most inopportune times when I [00:28:00] can't write a whole post. So I'll just like throw some of my thoughts in there and then.

I'll go scroll through them and be like, which one can I build out the rest of the ideas around right now? And then I'll post it. So that's funny. I love that. How old are your kids? 

[00:28:15] Alina: Uh, they're six and four. 

[00:28:17] Becca: Okay. Yeah. I have a 10 and 8-year-old, so I'm just ahead of you, but six and four. You're still in the, in the young, young era.

Fun. I don't know how you do it as a, as a CEO. [00:28:30] I'm hanging on, I dunno 

[00:28:31] Alina: either. It's just complete chaos at all times. 

[00:28:35] Becca: That's how, that's how you do it. It's just chaos at all times. All the time. 

[00:28:39] Alina: I'm embracing it. 

[00:28:40] Becca: Yeah. Well, okay, so that actually brings me to another question. Like as a founder and your husband, also a founder and CEO Co.

CEO, is there ever like. Moments where you're just like, this isn't gonna work. Like, what are we, like, we can't do this. You know, like, what have we gotten ourselves into? Do [00:29:00] you ever feel like that? 

[00:29:02] Alina: In my case, it's a little bit different because unlike other, I, I think that I talk to a lot of founders and in our case, because we had a beautiful exit, uh, cash wise, I don't feel like the pressure of, um.

Of, of finances or anything like that. And I just focus on the joy of building. Um, and he loves it a lot as well. We can't imagine doing anything else. So I think I'm gonna do this until I'm 150 [00:29:30] years old, which I know sounds weird, but I really, really like it. So. 

[00:29:36] Becca: Um, that is the, that's the dream, right? Is like finding the thing that you love to do so much that you just wanna do it forever.

That, 

[00:29:46] Alina: mm, it doesn't sound weird. 

[00:29:47] Becca: That sounds ideal. So good on you. Congratulations for finding that thing in life. 

[00:29:53] Alina: I'm happy I found what brings me the joy. Yeah, 

[00:29:57] Becca: for real though. Especially. Especially when [00:30:00] you are grinding in it, but you still love it, right? Like, I think that's when you know that you found the thing that you love is when you can, when you have to grind sometimes to the point that you're like exhausted and are giving up things in your life that you also love, but you're still doing it because you love to do it.

That's, that's the joy 

[00:30:23] Alina: I do. I don't want to caution it because I don't want to sound, uh, like. Uh, not in [00:30:30] touch with reality. It's hard. Like I have rollercoasters every day and they're like hard things happening every day, um, that take me down and make me doubt on, on my capacity to handle it all. But even when those hard moments come, I just know that it's a signal that I'm learning something new and it's a painful moment, but I'm learning something.

So I approach it with curiosity. It, it is a, it is a rollercoaster with, with emotional, uh, ups and downs. Um, but, but I still lean in with curiosity even when it's hard. 

[00:30:57] Becca: Well, yeah. And it's worth it for you, right? Because [00:31:00] like, like you said, like it brings you joy and it's fulfilling. So again, it's like the, at the end of the day, that's what matters.

Um, so what is the future of Chili Piper? You know, if you had your Magic eight ball, like what's the, what's the next five years? 

[00:31:21] Alina: So, as I was telling you, for me it's uh, one big experiment. I wonder, um, if we can make this company work where everybody's striving and everybody has as much [00:31:30] fun as me and my co-founder in it.

And we try to get the employees that find that, but they love working remote on hard problems and it's their passion that, that they're working on and that they're growing and, and thriving. Um, that's like my main priority. And then of course, on the revenue front, we want to, um, in, in five years, probably like 400 million in AR or so, and employ as many happy employees as we can, doing cool things in the agent [00:32:00] orchestration space.

Um, right now we're focusing on marketing and it's a lot of fun. 

[00:32:04] Becca: That's so cool. Well, okay, so this is a communications podcast and what you're doing internally with your culture, this experiment that you talk about is like an internal communications case study in the making. Like this is an amazing thing that you're doing.

So my first question is, do you have an internal communications person at your company who is helping you manage all of this? Or who [00:32:30] is doing internal communications? Does that come from you? 

[00:32:34] Alina: It's very, uh, funny, but I have a notion, doc. 

[00:32:38] Becca: The Notion Doc is your internal communications person. 

[00:32:43] Alina: No, I, I have a notion doc that explains how we do this kind of, uh, stuff as well.

'cause our culture is very unusual. We're very flat, so there's no need for an executive to communicate something because we're all kind of working together and, um. We kind of, our roles [00:33:00] are quite fluid as well. So our alignment is, is fluid. And I wrote a about it in a culture doc in the Notion Culture doc on how we kind of make it work because it's kind of, it's unusual.

We, we spend tons of training 'cause tons of time on training because of, uh, on communication, specifically because we believe that. Very much so. We believe that, uh, the reasons why, uh, companies break is because of lack of communication and uh, also [00:33:30] because there's conflict. And when conflict is uncomfortable, most people choose not to go and, and have a different opinion or butt heads, and we kind of.

Eliminated that with, because we do the decision memos, but there's still people that have a very strong, uh, opposing voice and you still want to make sure that the, the, that they feel heard and that everybody's understood and everybody kind of understand the different points of view. So we do tons of training on it, tons of it.

[00:33:56] Becca: What does that training look like? 

[00:33:59] Alina: Um, it [00:34:00] is based off of, um, book, so you probably heard of it. It's Marshall Rosenberg called, uh, wrote a book that's called, uh, nonviolent Communication. Uh, it's one of like bestselling and he left behind him. Uh, a non-profit that also helps with, uh, nonviolent communication.

Not that we're all violent with in our, in our words, but more helping with. Um, conflict of opinion, difference of opinions. And, uh, we have their coaches that are part of that foundation kind of coming [00:34:30] with us and helping us with the systems, helping us with the groups. Um, even though we're remote, we do these trainings in person, we find that there it's a lot more productive.

And quarterly we get together and, and train our team on trust, building on connection, um, conflict management and all of those things. 

[00:34:47] Becca: I love this. I mean, I really do. You know, I've talked to a lot of companies and I've seen a lot of cultures, and I've seen, I, I could not agree with you more that the breakdown of culture comes from com, communication [00:35:00] breakdown, lack of trust, lack of lack of psychological safety, lack of empowerment, and you are.

[00:35:06] Alina: Head on 

[00:35:07] Becca: addressing those specific issues. Before people even get into their roles, you are literally like, hi, day one. Welcome to the company. We're gonna train you on how to mitigate these problems. Oh, and also we're gonna empower you with this decision making process that we have. Oh, and by the way, we're a flat organization, so your opinion [00:35:30] matters and you know, if you need to.

You know, talk to the people you need to talk to. You're able to talk to them. Like, this is a, it's an important, I think, um, experiment that you're running. And frankly, I think, um, I would be very interested to see the results in a couple of years to see, you know, as you scale, as you become a 500 person company, thousand person company, 5,000 person company.

Um, how these processes start [00:36:00] to, you know, how they stretch, how they start to change or evolve as more people come into the mix. Do you think, you know, does that scare you? Does that excite you? Like what, what do you think about that? 

[00:36:15] Alina: The scaling question is a very one that's on my mind a lot because I'm building out of AI agents and I just don't know what the.

Like how far the agents, AI agents can go [00:36:30] on, what a human can do. And um, I actually wrote, uh, I, I did, um, I was invited at Oracle two days ago to do a com to do a speech around AI agents in the org chart because mid journeys at 300 million with 60 employees, cursor has 30 employees, and they're also, I don't know, like 60 million now in ar.

And like companies need less and less head count. And on one side that's terrifying because what does that even look like? [00:37:00] Um, like where are humans kind of playing in that, uh, ecosystem On the other side, I think there are a lot of exciting, um, outcomes from it. I think that the companies I. Uh, will get smaller, but we will have more companies in the ecosystem.

So I think that a lot more people will start their own companies. They will not have to be bogged down with like a overhead with having a hundred people to work for them, and they will just like administer the, um, orchestration of agents and so forth. It's just so hard to predict. [00:37:30] What the world is gonna look like with this kind of new structure in place.

[00:37:34] Becca: And I think a lot about how I would very much not want to be like a 22-year-old straight out of college right now. Because like on the one hand, yeah, it's exciting. Everything's new and you have an opportunity to kind of shape the next trend. But at the, on the other hand, it's like. How do you even decide what to do knowing that all of the skills that you've just [00:38:00] acquired over the last four years might be completely meaningless in two years?

I don't know. It's such a weird, weird place to be in the world right now. Like at least with us, like we have years of experience, work experience that. Matters, right? Like the experience counts for something new grads are like, they don't have experience. And the fut, I don't know. It's such a weird, such a weird time.

Like you said, we can't predict what's coming and I don't even know what it's, 

[00:38:27] Alina: it's definitely, it's definitely on my mind for my [00:38:30] kiddos to, uh, prepare them for real life. And, uh, it's, it's hard to pick the type of things we put emphasis on. Um, but I still get back to. Teaching them how to build trust and how to learn to, uh, create their own.

Mm. Compass of wisdom that allows them to kind of pivot and a adapt. 'cause the only thing that's certain is that everything will be uncertain ahead of them. 

[00:38:56] Becca: Totally. I've decided that the only thing that matters is being a good [00:39:00] person and being adaptable. So those are the things in life that we can control.

Right. Um, okay, well I'm gonna go to our rapid fire questions since we're getting, um, close to time. So let me pull these up. 

[00:39:15] Alina: Okay. 

[00:39:16] Becca: Alright, so first rapid fire question, what is a myth or misconception about marketing or communications that drives you crazy? I. 

[00:39:27] Alina: Well, when I started [00:39:30] working in large co corporations, I thought that I would only get good at communication if I read a lot of books on it.

Um, and I learned to use fancy words. Turns out the opposite was true. I don't need to use any fancy words and all I have to do is keep practicing. So, yeah, 

[00:39:44] Becca: very true. I actually think. People who use fancy words tend to sound like they're just trying to overcompensate for not really being great communicators.

So yeah, that's funny. 

[00:39:54] Alina: I'm not saying much. Yeah, 

[00:39:56] Becca: yeah. Okay. You get to erase one corporate [00:40:00] buzzword from existence. What is it? 

[00:40:05] Alina: So, it's not a word, but it's a structure that I see a lot and I hate it, hate it. Uh, and it says in today's fast-paced world. That's something that I hate. 

[00:40:14] Becca: Well, it's the AI speak, right?

It's like the, the beginning of every AI sentence in today's blah, blah, blah, in today's evolving, blah, blah. Yeah, totally agree. And every time I see it now, I'll just immediately like ignore whatever comes after. 

[00:40:29] Alina: Dismiss it. [00:40:30] 

[00:40:30] Becca: Totally. Okay. You're about to give a presentation in front of 50,000 people, and maybe you've actually done this before.

What is your walkout song? 

[00:40:41] Alina: They never ask me what workout sound I walk, I want, I, I just, I do speak a lot, but I would love to have the She's got it. Uh, baby. She is. Got it. 

[00:40:51] Becca: Oh, that's a good one. Uh, um, your Venus? Uh, yeah, that one. Yeah, that's the one. Nice. I like [00:41:00] that one. And they don't ask you what song you want.

[00:41:03] Alina: They don't put the song, I dunno why, and I've spoke so many times and I never get the song. 

[00:41:08] Becca: Well, if you're ever at one of my conferences, you can pick your walkout song. There you go. And you can pick your walk off song too. So really you could have two songs.

Okay. Speaking of speaking, if you had mm-hmm. To do a TED Talk on anything but marketing or communications, what would [00:41:30] your topic be? 

[00:41:32] Alina: Well, I think I'm gonna do it Ted Talk soon. And, um, my topic for sure, it would be around, uh, rebranding happiness. How a mom who built a billion dollar company hacks joy at scale.

That's talk to, that's my talk a 

[00:41:45] Becca: little bit more about that. I wanna hear more. 

[00:41:49] Alina: So it's, um, I, I'm writing now my biography and my book and, um, that's kind of been my theme throughout is how to find joy in everything that [00:42:00] I do and in the worst possible circumstances. I've had a super weird upbringing and, um, how that, uh, lift me up from what I was told that I can do or can't do.

Mm. So it's a topic that's dear to my heart. 

[00:42:18] Becca: Okay, so like nobody tells you that a, um, a 

[00:42:20] Alina: woman with two kids can run a company that the tech company and nobody tells you that, uh, a kid that has nothing, had nothing to eat as a child can build, come to us and, and do all these [00:42:30] crazy things. So I, I just don't believe in limitations.

I believe in finding joy. 

[00:42:35] Becca: So what's like one tip you give you would give to somebody to help them find joy in everyday moments? 

[00:42:48] Alina: It's, it's complicated 'cause I'm writing an entire book around it, but if I were just to sum it up to, uh, one thing, it would be to find self-compassion. A lot more [00:43:00] self-love and self-compassion.

[00:43:02] Becca: I could not agree more. I always talk about how like my biggest gift to myself was giving myself more grace to just like be right, like we are humans and self-compassion is such an important part of who we are. If we don't have compassion for ourselves, why would we expect other people to have compassion for us?

So I love that. 

[00:43:24] Alina: Mm. 

[00:43:25] Becca: And I can't wait to read your biography. So what, what's the timing on that? What, [00:43:30] when are you planning to finish writing it? 

[00:43:31] Alina: Uh, I wrote it, but I'm just afraid to, to, uh, publish it. And I think that my fear on, on publishing comes from the fact that I've never written a book. I've never written anything.

I've only started writing two years ago, and I wonder if I let it match it for one more year, can I make it better? So. That's where I am. I would be happy 

[00:43:51] Becca: to read a draft. If you want somebody to give you an opinion. Seriously, 

[00:43:56] Alina: you 

[00:43:56] Becca: don't 

[00:43:56] Alina: please it. You don't have to insist. 

[00:43:59] Becca: I would [00:44:00] love to, but if you want an unfiltered opinion, I have no filter and I would be happy to share my thoughts.

So just bring that out. 

[00:44:07] Alina: There's the best, that's the best type of communication. The one where you don't hold anything back. 

[00:44:11] Becca: I, I have, I do not have the ability to hold things back. Unfortunately. That is both a flaw and a uh. A good thing about me. I guess I know what that looks like. Yeah. 

[00:44:21] Alina: I have the same problem.

So I know 

[00:44:23] Becca: my mom used to joke that like, if you wanted to find out, you know, if the neighbors have something going on, it's like, just send Becca in. [00:44:30] She'll find out all of the information. 'cause I have no filter and I'll ask all of the inappropriate questions, but you know, it's a good thing. Um, okay, two more questions.

You get to use one emoji for the rest of your life. Which one? 

[00:44:46] Alina: It's the thinking one. That's what I use all the time. 'cause I'm always in deep thought. Yeah, 

[00:44:53] Becca: it's that one. Because I feel like there's two thinking ones. There's that one, and then there's like the mono. No, there's like a 

[00:44:58] Alina: The monocle. The [00:45:00] monocle one is the monocle.

Yeah. 

[00:45:01] Becca: Okay. Yep. I like the thinking. I like the thinking one. I use that one frequently. Okay. 

[00:45:06] Alina: But I think we can't use emojis anymore. 'cause then people will think that we wrote it with ai. So I don't think we can use emojis. I use them all the time. 

[00:45:13] Becca: And M dashes and Oxford commas. Everyone be damned. I refuse to let AI ruin my writing.

AI has stolen my writing style, not the other way around. 

[00:45:26] Alina: I think 

[00:45:27] Becca: that's 

[00:45:27] Alina: the case. Yeah. 

[00:45:28] Becca: That is totally the case. I take, I [00:45:30] take offense by everybody. Uh, mocking the ai. Actually, I wrote about this today. What it really comes down to is people who have pattern recognition can, can recognize AI writing because of the patterns.

It's not the M dashes or the emojis, it's the like. The cadence of the writing, but, but it's 

[00:45:48] Alina: the cadence 

[00:45:48] Becca: people, people who don't recognize patterns in the same way need to have the tells. Right? They need to know it's the m dashes, it's the emojis. It's the commas. But really it's not [00:46:00] those things. It's the cadence and the patterns, the 

[00:46:02] Alina: whole thing.

Yeah. 

[00:46:03] Becca: Wax on about this all day, but I will not, I will ask you Perry's unhinged question in the absence of Perry, because this is the question that we ask everybody at the end of our show. But I will caveat this with this Perry's unhinged question, which is you can either have hiccups 24 7 for three months, so while you're sleeping, while you're eating, while you're trying to work hiccuping [00:46:30] nonstop, or.

You can chop off your own pinky, either Pinky, your choice.

[00:46:38] Alina: So the hiccupping is super, um, pleasant, but it goes away. And it kind of reminds me from when I was pregnant and I was always awake at all times. 'cause I felt like, uh, all sorts of things were happening inside of my body. So I lived through it. I know I can do it, it turns, and then I keep my fingers. 

[00:46:56] Becca: Perry would be so happy that you said that.

He would be like, see, I told [00:47:00] you Becca. See? Alina's not crazy. 'cause I would, I would cut off my pinky. There you go. I'm the unhinged nuts one who would cut off my pinky. And I will say it's because I have had hiccups for multiple days at a time and it really hurts and I cannot sleep. And I would rather, I would lose my mind after three months of having hiccups and I would have jumped off a bridge at that point.

And so by that point, who needs a pinky if you've already jumped off a bridge? So there you go. 

[00:47:28] Alina: That's true. That's [00:47:30] true. 

[00:47:30] Becca: Um, okay with, before we sign off, I would love to give you an opportunity. Is there anything that you would like to share, pitch, whatever, send people to before? Um, we log off for the day.

[00:47:48] Alina: I, uh, don't have any pitches, but I do have a deep desire to help with all my crazy experiments because whenever I share, um, the type of things that I'm working on, someone always gives me [00:48:00] feedback on what's working and what's not working, and that's my best way of learning. So I do have a notion docs around all the things that I've spoken about and also around how we do our.

Strategy for social media and deeper into my process for writing, and I can share all of that with you and we can put it in the description and maybe it helps someone. 

[00:48:20] Becca: I would love that. So yes, please share with me and audience, I will add the links into the show notes so that you can go see Alina's [00:48:30] Jillions of notions because she is apparently the notion queen.

And I am super excited to dig into these myself 'cause I think we all have a lot to learn here. Thank you so much for coming on the show. Sorry. 

[00:48:41] Alina: Thank, thank you, Becca. And for those that are listening and do not see, like in YouTube, uh, if you come find me on LinkedIn, I have it on the, at the top of my profile, it says, visit my website, and it goes deep into my notions as well.

So if you are listening and you don't have the link, there's that option. So 

[00:48:58] Becca: there you go. Thank you so [00:49:00] much. It's been great having you. 

[00:49:02] Alina: Thank you, Becca. It was a pleasure.