Scale Like a CEO

From Google Engineer to $4.3M ARR: Building Mexico's Next Tech Giant | Roby Peñacastro

• Justin Reinert • Season 1 • Episode 44

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What if your CRM started where your customers actually are—inside WhatsApp and social DMs? We sit down with Robbie Peña Castro, founder and CEO of Lead Sales, to unpack how a chat-native platform scaled to 3,000+ companies across 20 countries and reached $4.3M ARR by turning conversation chaos into predictable revenue. Robbie shares why email feels too slow for modern buying moments, how SMS breaks collaboration, and why centralizing WhatsApp threads under an official company channel unlocks speed, context, and trust.

We explore the early grind—funding hires with Google bonuses when no one believed in the idea—and the pivotal shift at UC Berkeley’s SkyDeck that led to a $400k pre-seed and a $3.7M raise to recruit top talent. Robbie explains how market pull dictated hiring, how infrastructure bottlenecks forced senior engineering, and why culture interviews ensure engineers, support, sales, and marketing actually talk to each other. He also breaks down the playbooks that freed his time: CEOs Are Lazy for switching leadership “hats,” and Buy Back Your Time for SOPs, executive assistants, and outcome-based delegation.

On product, we dig into Lead Sales’ smart AI assistant that learns directly from customer chats to answer FAQs, triage requests, and even help close deals—without feeling bolted on. We talk decision overload, brain-dump prioritization, and looping in leadership and investors early to avoid preventable mistakes. Finally, Robbie lays out a bold vision: build one of Mexico’s biggest tech companies and go head-to-head with Salesforce and HubSpot by owning conversational CRM on a global stage.

If you care about conversational commerce, AI in customer service, or scaling teams across the Americas, this one’s packed with hard-won insights and practical steps you can use today. Subscribe, share with a founder who needs it, and leave a review with your biggest takeaway.

Roby:

So the first challenge was being bootstrapped and tried to raise funds and nobody believing in this idea at the beginning. So I said, fuck it, I'll just do it myself and I'll win every single quarterly bonus at Google and use that as my fuel to be able to hire people. So at the beginning it was that being bootstrapped. And eventually we ended up landing into Silicon Valley through an accelerator from the University of Berkeley called Skydeck. And that's where we basically opened our minds to fundraising properly from VCs in the Valley. And we raised 400K as a pre seed, and we ended up raising 3.7 million from VCs to really hire top quality talent. And the challenges at the beginning is you don't have any brand. So people are just hopping into a baseless dream, probably.

Speaker:

So that was the major challenge at the beginning. In this episode of Scale Like a CEO, host Justin sits down with Robbie Peña Castro, founder and CEO of Lead Sales. Robbie shares his remarkable journey building a conversational commerce platform for WhatsApp and social media that's transforming how businesses communicate with customers. Lead sales is now scaling rapidly across Latin America and expanding into global markets.

Justin:

Robbie, thank you so much for taking some time to join me on Scale like a CEO, just to get us started. If you wouldn't mind just giving us a 90-second intro to you and your business.

Roby:

Yeah, so my name's Robbie Venacastro. I am from Mexico, born and raised. Basically, I decided to become a tech entrepreneur because of my mom, who was one of the first software engineers in Mexico. And through life being in Helsinki at one of the biggest tech conferences there, I decided to pursue a career in tech working at Google. And during pandemic, I started Lead Sales, which is a conversational commerce platform, basically a CRM for WhatsApp and social media that helps businesses scale their sales and support via conversations, basically. That's what we do. And as of today, we have over 3,000 companies across 20 countries making around 4.3 million in ARR. And yeah, we're still growing.

Justin:

Well, that's incredible. So I'm sure there's an amazing story around your mother and how she got into computer programming. But I'd love to hear, you know, what is the biggest problem that you see in your industry and how are you solving it?

Roby:

I mean, at least in Latin America and a lot of countries, it's still working in progress in the US, but I see that in our industry, the de facto operating system for customers to communicate with businesses is through WhatsApp, right? It is a communications tool that it's being used by billions of people, mostly outside of the US, but it's slowly growing. There's over 100 million users actively in the United States, mostly by foreigners, but also people from the US that go out and explore the world. They realize what a handy tool WhatsApp is. But the biggest problem is how do you scale that, right? Because it's a communications tool. So when people are starting to use it to communicate with businesses, businesses have this problem of how can I scale? How can I handle all these conversations? And usually they end up questioning if there's a CRM with a native integration for this type of channels. And they bump into the problem that there's not quite a solution up until now that lead sales is slowly starting to get into this um big problem that is happening across the globe. And we're solving it by making very accessible technology. We made it so simple that you could be on boarded in five minutes and connect your social media and your WhatsApp account and be set to go in five minutes. So that's how we solve it.

Justin:

I love that. And you know what makes you unique in the way that you're helping others?

Roby:

I mean, what makes us unique is that we're solely focused on this type of channels, which are conversations, chats. We don't integrate email. I tend to say that email it's obsolete and the same goes through SMS, right? Because you cannot scale those in a way that centralizes the conversation. So the way we do it is you need to centralize to your business because it's your business talking with customers and through an agent, right, or a rep that talks with the customers, but usually it needs to go through an official channel of your company, and that's how we differentiate ourselves. And how we're making it more unique is that we're consolidating this information of all these chats and giving you access to AI tools that can get a knowledge base from your conversations and start operating as one another another teammate, right? So that's what we are building with our smart lead bug that can take all that information and start answering FAQs to your customers and pretty much doing the sale for you.

Justin:

Oh, that's great. And so you've been building the business since around 2020, is that right? Correct. And so I'd love to hear a little bit about some of the challenges you faced as you transition from, I'm sure you were a founding team of one, two, three people, but then starting to grow and build your team to where it's at today. What are some of the challenges you faced as you navigated that transition of growth?

Roby:

So the first challenge was being bootstrapped and tried to raise funds and nobody believing in this idea at the beginning. So I said, fuck it, I'll just do it myself and I'll win every single quarterly bonus at Google and use that as my fuel to be able to hire people. So at the beginning, it was that being bootstrapped. And eventually we ended up landing into Silicon Valley through an accelerator from the University of Berkeley called Skydeck. And that's where we basically open our minds to fundraising properly from VCs in the valley. And we raised 400k as a pre seed, and we ended up raising 3.7 million from VCs to really hire top quality talent. And the challenges at the beginning is you don't have any brand. So people are just hopping into a baseless dream, probably. So that was the major challenge at the beginning. And usually the people who hop into that are students still at the uni. So that was the first. And now the challenge is how we can sell this big vision of becoming bigger than Salesforce, big in their hop spot, in order to bring the most talented people outside from Google, come back to the startup world or come back from Amazon. That's the type of people that I'm bringing in, and also other really successful startups like Stripe, like New Bank. I'm trying to bring those people in so they can hop into our into our project. And the challenge now is those people are expensive. So we need to calculate as well.

Justin:

Yeah, and so you know how what was the pivot point of you know when you knew you were ready to start hiring? I'm assuming the funding had a big part of that. Um, but you know, what was that one of the turning points there?

Roby:

The first turning point while we were bootstrapped was the pull of the market. We were receiving so many leads that we couldn't keep up. So that really pushed us to we need one more people because there's a lot of leads and we're leaving money on the table, right? And then as we started scaling, we bumped into infrastructure problems. So we decided that, hey, we need more experienced developers, so we need to hire someone who's got more experience working complex infrastructure, right? So every single stage of the business has bringed us to a different problem, and from there, we always think, okay, who's the who's the best person to solve this problem? And usually that's how we decide or identify the moment, the right moment to bring another person in.

Justin:

Yeah. And how do you go about identifying people? What are some of the key qualities that you're looking for when you're hiring?

Roby:

So I tend to find people with similar values as me and my co-founder, right? Fumble enough to know that we don't know everything, with a hunger to learn more and try new things, and also being open to things being fucked up and no processes. Startup world, usually we do a process just like Google. We try to really be really diligent when we're hiring people, and we go through a process of over four to five interviews. So we really know that that person is the right fit. And especially in our last interview, which is a cultural fit, right? We want to bring people in that can connect with other team members, regardless if they're in the same department, right? If you're gonna be coding, you should also be open to talk with customer success or support or sales or marketing, right? And we look to find those people. And I've seen that if you adjust the process well and you share all the values of the company, it's very easy to see who is really in for that and who is not for that. And usually that filters out people that won't be a right fit. And starting from being a startup, right? I tend to say people, hey, you're you might be working Saturdays and Sundays. This is not a place for work-life balance. Are you agreeing with that? And that just filters out people.

Justin:

Yeah. And I'm curious, so you're in Mexico, right? In Mexico City? In Queretaro, two hours away from Mexico City. Oh, wow. Incredible. And is that have you are you building most of your team in Mexico? Or you know, you you had done some, you were part of the accelerator in the Bay Area. You know, how are you growing, like where are you growing your team geographically?

Roby:

All across the Americas. So we have people in Mexico, we got team in Colombia, in Argentina, in Chile, in the States, we had some people. So it's multicultural and very diverse and all across the globe. And sometimes I'm working from Finland uh in the years, so we could say I'm also in Europe.

Justin:

Wow, that's so very spread out. I love that. And so as you grew, as you went from that founding team of two, and now you've got a much larger team. How big is your team today? We're 80 people now. 80. Yeah. So that's some incredible growth, especially in less than five years. One of the biggest challenges that a lot of founders face is knowing when and how to delegate as the team gets bigger, so that you're not creating a bottleneck for the organization. I'm curious how you went through that and how you've learned to delegate down in the organization.

Roby:

There's two books that really help be into that mindset. The first one is CEOs are lazy. It's a book that tells you about how as a CEO you need to be pulling in different hats, sometimes the architect, sometimes the strategist, and sometimes the operator. And as you want to pull into a different, you need to find someone to litigate that role that you've been doing, right? And you go first because you're the CEO and you understand how things should run. And once you understand it, maybe then you can systemize that. That is really the key. And the second book is from one of my mentors, Dan Martel, who's a very seasoned coach and mentor, and he wrote this book called Buy Back Your Time. And in this book, basically, it's just the methodology on how to buy back your time. And exactly is basically hiring the right people to do the certain tasks that have very low return on value for a CEO, right? So it starts from CEOs need to have an executive assistant to run their inbox because if not, they're gonna be wasting their full time on the mornings just going through your infinite inbox list, right? So those two books I think that that made me really learn and have a playbook on how to delegate and how to create standard operating procedure playbooks. That is also from Buy Back Your Time. It helps you to write an SOP really structured so you can write it down, give it to your team. This is how the show needs to run, and you just give it to them and give them the objectives. And usually with the right talent with the A players, you can delegate very efficiently.

Justin:

Yeah, that's great. That's great. So you can you think about a time when maybe you were overwhelmed by decision making, and what strategies did you implement to overcome it?

Roby:

I say there are times when we are constricted by deadlines, there's a lot of things going on, and you just your head cannot handle so much information. I usually tend to go down into my notebook, write it down, write everything that is on your brains at brain dump. And once you do that, you start seeing clarity into things that are here in your brain, and you just by writing them down, you prioritize when you see, hey, maybe this is not such a big problem. I could do this or that. So you tend to do that, and also knowing that you don't need to do everything. I tend to do round meetings with my leadership team in order to share the problems that are going on in my head, and usually that helps me also to find a different perspective from one of my team members, and they can tell you, hey Robbie, but you can solve it this way. And it's like, oh yeah, I didn't thought about that. Let's do it. You know, not keeping everything to yourself really helps, and not only with your team members. No, in our case, I tend to share those problems with my VCs, no, which gets sometimes people think like, Hey, well, why would you tell your VCs that things are not going well? Well, if you don't say it, maybe you will be too late into raising your hand and asking for some help to your investors.

Justin:

Yeah, well, that's I think that's great. You know, kind of escalating early can help you get ahead of things before they snowball into something bigger and worse. So looking forward, what's the future of your company look like?

Roby:

Looking forward, well, I'm trying to build one of the biggest tech companies from Mexico, right? And that is a bold statement. I say that we're the Salesforce killer and we're going in for that level of tech company. So we need to keep bringing on the best people. We need to develop leaders from within and bring other leaders from tech startups. Uh and in culture, we need to maintain that culture as we grow from 80 to 160, maybe 500 people, which is what it's going to take to go global, because we don't want to end up just playing in Latin. I see the opportunity as being global, and more and more we see evidence of other markets adopting these types of conversational commerce, which are paired up with AI, right? Because that's where it's easier for AI to fill in some gaps of serving customers 24-7. And the steps critical to do this is like another book I really like. It's The Road Less Stupid by Keith Cunningham. It's just about taking the less stupid decisions, you know, like not trying to avoid uh errors, but just seeing my next decisions coming in for the next year and planning out everything to commit as least stupid decisions in the future.

Justin:

That's great. Well, Robbie, thank you so much for joining me today. If folks want to get in touch with you, what's the best way to do so?

Roby:

The best way is on LinkedIn. I'm always posting there every single day, and I always happy to share experiences and have a virtual coffee. If you find me there, just send me over a DM and I'll be happy to talk.

Justin:

Great. Well, thank you so much for your time today, Robbie.

Roby:

Thank you, Justin.